JPH02290883A - Organosilicon compound and its production - Google Patents
Organosilicon compound and its productionInfo
- Publication number
- JPH02290883A JPH02290883A JP1111590A JP11159089A JPH02290883A JP H02290883 A JPH02290883 A JP H02290883A JP 1111590 A JP1111590 A JP 1111590A JP 11159089 A JP11159089 A JP 11159089A JP H02290883 A JPH02290883 A JP H02290883A
- Authority
- JP
- Japan
- Prior art keywords
- group
- substituent
- phenyl
- compound
- pyrimidine
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
Links
- 150000003961 organosilicon compounds Chemical class 0.000 title claims description 9
- 238000004519 manufacturing process Methods 0.000 title claims description 7
- -1 silane compound Chemical class 0.000 claims abstract description 20
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 13
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 13
- 229910000077 silane Inorganic materials 0.000 claims abstract description 11
- 125000005843 halogen group Chemical group 0.000 claims abstract description 9
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract description 8
- 239000000126 substance Substances 0.000 claims abstract description 5
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims abstract description 5
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims abstract description 3
- 125000001424 substituent group Chemical group 0.000 claims description 13
- 125000004438 haloalkoxy group Chemical group 0.000 claims description 7
- 125000003545 alkoxy group Chemical group 0.000 claims description 6
- 125000001188 haloalkyl group Chemical group 0.000 claims description 6
- 125000004432 carbon atom Chemical group C* 0.000 claims description 4
- 150000001875 compounds Chemical class 0.000 abstract description 12
- 238000003786 synthesis reaction Methods 0.000 abstract description 8
- BLRPTPMANUNPDV-UHFFFAOYSA-N Silane Chemical compound [SiH4] BLRPTPMANUNPDV-UHFFFAOYSA-N 0.000 abstract description 7
- 230000015572 biosynthetic process Effects 0.000 abstract description 7
- 239000003963 antioxidant agent Substances 0.000 abstract description 2
- 229940079593 drug Drugs 0.000 abstract description 2
- 239000003814 drug Substances 0.000 abstract description 2
- 239000003795 chemical substances by application Substances 0.000 abstract 2
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 abstract 1
- 239000000853 adhesive Substances 0.000 abstract 1
- 230000001070 adhesive effect Effects 0.000 abstract 1
- 230000000975 bioactive effect Effects 0.000 abstract 1
- 229910052736 halogen Inorganic materials 0.000 abstract 1
- 229910052744 lithium Inorganic materials 0.000 abstract 1
- 239000000463 material Substances 0.000 abstract 1
- 239000000575 pesticide Substances 0.000 abstract 1
- 238000002360 preparation method Methods 0.000 abstract 1
- 230000001105 regulatory effect Effects 0.000 abstract 1
- 229920002554 vinyl polymer Polymers 0.000 abstract 1
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 9
- 239000000243 solution Substances 0.000 description 9
- 238000006243 chemical reaction Methods 0.000 description 7
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 6
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 6
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 5
- 238000001819 mass spectrum Methods 0.000 description 5
- 239000000047 product Substances 0.000 description 5
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical group [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 4
- QZRWJJLUUOMZIT-UHFFFAOYSA-N chloro-dimethyl-pentylsilane Chemical compound CCCCC[Si](C)(C)Cl QZRWJJLUUOMZIT-UHFFFAOYSA-N 0.000 description 4
- 239000003960 organic solvent Substances 0.000 description 4
- 239000002994 raw material Substances 0.000 description 4
- 229910052710 silicon Inorganic materials 0.000 description 4
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- 239000011261 inert gas Substances 0.000 description 3
- 239000000543 intermediate Substances 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 3
- 150000003230 pyrimidines Chemical class 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 3
- 238000005160 1H NMR spectroscopy Methods 0.000 description 2
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 2
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 2
- 238000005481 NMR spectroscopy Methods 0.000 description 2
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 2
- 239000012298 atmosphere Substances 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 2
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 2
- 150000004756 silanes Chemical class 0.000 description 2
- 238000001308 synthesis method Methods 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- WVHAIMKMNMGHMX-UHFFFAOYSA-N (4-fluorophenyl)-methylsilane Chemical compound FC1=CC=C(C=C1)[SiH2]C WVHAIMKMNMGHMX-UHFFFAOYSA-N 0.000 description 1
- 125000001340 2-chloroethyl group Chemical group [H]C([H])(Cl)C([H])([H])* 0.000 description 1
- 125000004777 2-fluoroethyl group Chemical group [H]C([H])(F)C([H])([H])* 0.000 description 1
- 125000004204 2-methoxyphenyl group Chemical group [H]C1=C([H])C(*)=C(OC([H])([H])[H])C([H])=C1[H] 0.000 description 1
- 125000004211 3,5-difluorophenyl group Chemical group [H]C1=C(F)C([H])=C(*)C([H])=C1F 0.000 description 1
- 125000004179 3-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(Cl)=C1[H] 0.000 description 1
- 125000004180 3-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(F)=C1[H] 0.000 description 1
- 125000004207 3-methoxyphenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(OC([H])([H])[H])=C1[H] 0.000 description 1
- 125000004860 4-ethylphenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 description 1
- 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 description 1
- 125000000590 4-methylphenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 description 1
- 125000004199 4-trifluoromethylphenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C(F)(F)F 0.000 description 1
- 101150041968 CDC13 gene Proteins 0.000 description 1
- 239000004215 Carbon black (E152) Substances 0.000 description 1
- 239000005046 Chlorosilane Substances 0.000 description 1
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
- NHTMVDHEPJAVLT-UHFFFAOYSA-N Isooctane Chemical compound CC(C)CC(C)(C)C NHTMVDHEPJAVLT-UHFFFAOYSA-N 0.000 description 1
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- 239000013543 active substance Substances 0.000 description 1
- 239000002318 adhesion promoter Substances 0.000 description 1
- 239000003905 agrochemical Substances 0.000 description 1
- 235000019270 ammonium chloride Nutrition 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 229910052786 argon Inorganic materials 0.000 description 1
- 125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 description 1
- 239000012681 biocontrol agent Substances 0.000 description 1
- 125000001246 bromo group Chemical group Br* 0.000 description 1
- OEERIBPGRSLGEK-UHFFFAOYSA-N carbon dioxide;methanol Chemical compound OC.O=C=O OEERIBPGRSLGEK-UHFFFAOYSA-N 0.000 description 1
- 125000001309 chloro group Chemical group Cl* 0.000 description 1
- ZLZGHBNDPINFKG-UHFFFAOYSA-N chloro-decyl-dimethylsilane Chemical group CCCCCCCCCC[Si](C)(C)Cl ZLZGHBNDPINFKG-UHFFFAOYSA-N 0.000 description 1
- GZGREZWGCWVAEE-UHFFFAOYSA-N chloro-dimethyl-octadecylsilane Chemical group CCCCCCCCCCCCCCCCCC[Si](C)(C)Cl GZGREZWGCWVAEE-UHFFFAOYSA-N 0.000 description 1
- KOPOQZFJUQMUML-UHFFFAOYSA-N chlorosilane Chemical compound Cl[SiH3] KOPOQZFJUQMUML-UHFFFAOYSA-N 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 125000004786 difluoromethoxy group Chemical group [H]C(F)(F)O* 0.000 description 1
- 125000001028 difluoromethyl group Chemical group [H]C(F)(F)* 0.000 description 1
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 1
- JVSWJIKNEAIKJW-UHFFFAOYSA-N dimethyl-hexane Natural products CCCCCC(C)C JVSWJIKNEAIKJW-UHFFFAOYSA-N 0.000 description 1
- 239000004210 ether based solvent Substances 0.000 description 1
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 125000001153 fluoro group Chemical group F* 0.000 description 1
- 125000004216 fluoromethyl group Chemical group [H]C([H])(F)* 0.000 description 1
- 125000000524 functional group Chemical group 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- DKAGJZJALZXOOV-UHFFFAOYSA-N hydrate;hydrochloride Chemical compound O.Cl DKAGJZJALZXOOV-UHFFFAOYSA-N 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 239000012263 liquid product Substances 0.000 description 1
- 150000002642 lithium compounds Chemical class 0.000 description 1
- 125000000040 m-tolyl group Chemical group [H]C1=C([H])C(*)=C([H])C(=C1[H])C([H])([H])[H] 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
- 239000012046 mixed solvent Substances 0.000 description 1
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- TVMXDCGIABBOFY-UHFFFAOYSA-N octane Chemical compound CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- 238000010898 silica gel chromatography Methods 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000012756 surface treatment agent Substances 0.000 description 1
- 239000013076 target substance Substances 0.000 description 1
- 125000004213 tert-butoxy group Chemical group [H]C([H])([H])C(O*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 description 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
- QNALEQFOLRRVQI-UHFFFAOYSA-N trimethyl(pyrimidin-2-yl)silane Chemical compound C[Si](C)(C)C1=NC=CC=N1 QNALEQFOLRRVQI-UHFFFAOYSA-N 0.000 description 1
- 125000002948 undecyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 238000005292 vacuum distillation Methods 0.000 description 1
Abstract
Description
【発明の詳細な説明】
（産業上の利用分野）
本発明は文献未載の新規な有機けい素化合物、及びその
製造方法に係り、詳しくは、医薬、農薬用の中間体など
として有用とされる１．３−ビリミジン−５−イルシラ
ン化合物、及び八ロシランに１．３−ビリミジンー５−
イルリチウムを反応させることを特徴とするその製造方
法に関するものである。Detailed Description of the Invention (Field of Industrial Application) The present invention relates to a novel organosilicon compound that has not yet been published in any literature, and a method for producing the same. 1,3-pyrimidin-5-ylsilane compound, and 1,3-pyrimidin-5-ylsilane compound
The present invention relates to a method for producing the same, which is characterized by reacting illithium.
（従来の技術）
従来、ビリミジン核とけい素原子が結合した化合物とし
ては、ビリミジン核の２または４位に置換基として、ク
ロロ、メトキシ、２−メトキシエトキシ、ヒドロキシ、
ベンジルオキシなどの官能基を有するトリメチルシリル
ビリミジンまたはトリエチルシリルピリミジンしか知ら
れていなかった。(Prior Art) Conventionally, compounds in which a pyrimidine nucleus and a silicon atom are bonded include chloro, methoxy, 2-methoxyethoxy, hydroxy,
Only trimethylsilylpyrimidine or triethylsilylpyrimidine with functional groups such as benzyloxy were known.
以上、｝ＩＥＴＥＲＯＣＹＣＬＥＳ ，碁， ５８５
（１９８７）参照以上、ＩＺＶ． ＳＩＢ． ＡＫＡＤ
． ＮＡＵＫ． ＳＳＳＲ， ＫＨＩＭ． ＮＡＵＫ．
，９２ （１９７６１参照
Ｕ
以上、ＢＩＯＯＲＧ． ＫＨＩＭ、．功， １６４５
（１９８４１参照以上、Ｊ． ＣＨＥＭ． ＳＯＣ．
， ＣＨＥＭ． Ｃｏ曲ＵＮ． ，６９ ｆ１９７６１
参照また、けい素原子に結合したビリミジン核に置換基
を有さず、けい素原子に結合した残りの基として多様な
基を有するシランについては、これまでその合成法が知
られていなかった。Above, }IETEROCYCLES, Go, 585
(1987) see above, IZV. SIB. AKAD
．． NAUK. SSSR, KHIM. NAUK.
, 92 (19761 reference U above, BIOORG. KHIM,.Isao, 1645
(See 19841, J. CHEM. SOC.
, CHEM. Co song UN. ,69 f19761
Reference Also, until now, no synthesis method has been known for silanes which have no substituents on the pyrimidine nucleus bonded to the silicon atom and have various groups as the remaining groups bonded to the silicon atom.
（発明の構成）
本発明者らは、新規な化合物であるところの置換基を有
しないピリミジン核がけい素原子に結合したシラン化合
物について、その合成法を鋭意研究した結果、けい素原
子に結合した脱離基を有する各種のシラン化合物をビリ
ミシンのリチウム化物と反応させることにより、目的物
が収率よく得られることを見出し、さらに検討を重ねて
本発明を完成するに至ったものである。(Structure of the Invention) As a result of intensive research into a synthesis method for a new compound, a silane compound in which a pyrimidine nucleus without a substituent is bonded to a silicon atom, the present inventors found that The inventors discovered that the desired product can be obtained in good yield by reacting various silane compounds having a leaving group with a lithium compound of birimicin, and after further studies, the present invention was completed.
この出願の第一の発明は、一般式１
Ｒ３
［式中、Ｒ１は炭素数１〜１８のアルキル基、ビニル基
またはシクロプロビル基を、Ｒ２およびＲ３は独立に、
メチル基、フェニル基または置換基を有するフェニル基
（ただし該置換基はハロゲン基、低級アルキル基、低級
アルコキシ基、低級ハロアルキル基および低級ハロアル
コキシ基から選ばれる基）をそれぞれ表す。１で示され
る有機けい素化合物を要旨とするものであり、
第二の発明は前記の有機けい素化合物を製造する方法の
発明であって、一般式２
Ｒ’
Ｒ”−Ｓｉ−Ｘ
Ｒ３
［式中、Ｒ１は炭素数１〜１８のアルキル基、ビニル基
またはシクロプロビル基を、Ｒ２およびＲ３は独立に、
メチル基、フェニル基または置換基を有するフエニル基
（ただし該置換基はハロゲン基、低級アルキル基、低級
アルコキシ基、低級ハロアルキル基および低級ハロアル
コキシ基から選ばれる基）を、Ｘはハロゲン基をそれぞ
れ表す。］で示されるシラン化合物に、１．３−ピリミ
ジン−５−イルリチウムを反応させることを特徴とする
、一般式１
Ｒ１
Ｒ３
（式中、Ｒｌ．Ｒ２、Ｒ３は前記に同じ。）で示される
有機けい素化合物の製造方法を要旨とするものである。The first invention of this application is based on the general formula 1 R3 [wherein R1 is an alkyl group having 1 to 18 carbon atoms, a vinyl group or a cycloprobyl group, and R2 and R3 independently,
Each represents a methyl group, a phenyl group, or a phenyl group having a substituent (wherein the substituent is a group selected from a halogen group, a lower alkyl group, a lower alkoxy group, a lower haloalkyl group, and a lower haloalkoxy group). 1, and the second invention is an invention of a method for producing the organosilicon compound, which has the general formula 2 R'R"-Si-X R3 [ In the formula, R1 is an alkyl group having 1 to 18 carbon atoms, a vinyl group or a cycloprobyl group, and R2 and R3 are independently,
A methyl group, a phenyl group, or a phenyl group having a substituent (wherein the substituent is a group selected from a halogen group, a lower alkyl group, a lower alkoxy group, a lower haloalkyl group, and a lower haloalkoxy group), and X represents a halogen group, respectively. represent. ], characterized in that 1,3-pyrimidin-5-yllithium is reacted with the silane compound represented by the general formula 1 R1 R3 (wherein Rl.R2 and R3 are the same as above). The gist of this paper is a method for producing organosilicon compounds.
以下に本発明を詳しく説明する。The present invention will be explained in detail below.
本発明の有機けい素化合物は、 一般式１ Ｒ１ Ｒ３ で示される。The organosilicon compound of the present invention is General formula 1 R1 R3 It is indicated by.
式中のＲ１は炭素数１〜ｌ８のアルキル基、ビニル基ま
たはシクロプロピル基であるが、このアルキル基として
は例えばメチル基、エチル基、ｎープロビル基、ｎ−ブ
チル基、ｉｓｏ−ブチル基、ｎ −ペンチル基、ｎ−ヘ
キシル基、２−エチルヘキシル基、ｎ−デシル基、ｎ−
ウンデシル基、ｎ−ドデシル基、ｎ−才クタデシル基な
との直鎖状または分枝状アルキル基が挙げられる。R1 in the formula is an alkyl group having 1 to 18 carbon atoms, a vinyl group, or a cyclopropyl group, and examples of this alkyl group include a methyl group, an ethyl group, an n-probyl group, an n-butyl group, an iso-butyl group, n-pentyl group, n-hexyl group, 2-ethylhexyl group, n-decyl group, n-
Examples include straight-chain or branched alkyl groups such as undecyl, n-dodecyl, and n-tadecyl groups.
Ｒ２およびＲ３は独立に、メチル基、フエニル基または
置換基を有するフエニル基であるが、フェニル基が置換
基を有する場合の置換基は、ハロゲン基、低級アルキル
基、低級アルコキシ基、低級ハロアルキル基および低級
ハロアルコキシ基から選ばれる基である。上記のハロゲ
ン基としては、例えばフルオロ基、クロロ基、ブロモ基
が挙げられ、低級アルキル基としては、例えばメチル基
、エチル基、ローブロビル基、ｉｓｏ−プロビル基、ｎ
−ブチル基． ｉｓｏ−ブチル基、 ｔｅｒｔ−ブチル
基、ｎ＝ペンチル基、ｎ−ヘキシル基が挙げられ、低級
アルコキシ基としては、例えばメトキシ基、エトキシ基
、ｎ−ブロボキシ基、０−ブトキシ基、 ｔｅｒｔ−ブ
トキシ基が挙げられ、低級ハロアルキル基としては、例
えばフルオロメチル基、ジフルオ口メチル基、トリフル
オロメチル基、２−クロロエチル基、２−フルオロエチ
ル基、２，２．２−トリフル才ロエチル基、３，３．３
−１−リフル才口プロピル基が挙げられ、低級ハロアル
コキシ基としては、例えばジフルオ口メトキシ基、トリ
フル才ロメトキシ基が挙げられる。このような置換フェ
ニル基としてのＲ１には、例えば４−フル才ロフエニル
基、３−フル才ロフェニル基、４−クロロフェニル基、
３−クロロフェニル基４−プロモフェニル基、３．４−
ジフルオ口フエニル基３．５−ジフル才口フエニル基、
３．４−ジクロ口フエニル基、３．５−ジクロ口フェニ
ル基、４−メチルフェニル基、３−メチルフェニル基、
３．４−ジメチルフエニル基、３．５−ジメチルフエニ
ル基、４−エチルフェニル基、４−プロビルフェニル基
、４−ｔ−プチルフエニル基、４−クロロ−３−メチル
フェニル基、３−クロロ−４−メチルフエニル基、４−
メトキシフエニル基、３−メトキシフエニル基、２−メ
トキシフエニル基、４−エトキシフェニル基、４−ｎ−
プロボキシフエニル基、４−ｎ−ブトキシフエニル基、
４−トリフルオロメチルフェニル基、３−トリフルオロ
メチルフエニル基、４−トリフエニルメチルフエノキシ
基等が挙げられるが、これらに限定されるものではない
．
本発明の有機けい素化合物は、
前記の一般式２
Ｒ１
Ｒ２−ＳＬ−Ｘ
Ｒ３
（式中、Ｒ’，Ｒ”、Ｒ”、Ｘ は前記に同じ。）で
示されるシランと１，３−ビリミジン−５−イルリチウ
ムとを反応させることによって合成されるが、原料の一
般式２で示されるシランは公知の方法によって製造した
ものを用いることができ、１．３−ビリミジン−５−イ
ルリチウムは、５−ハロー１．３−ピリミジンに有機溶
媒の存在下、不活性気体雰囲気中でアルキルリチウムを
反応させることによって合成することができる。R2 and R3 are independently a methyl group, a phenyl group, or a phenyl group having a substituent, and when the phenyl group has a substituent, the substituent is a halogen group, a lower alkyl group, a lower alkoxy group, a lower haloalkyl group. and a lower haloalkoxy group. Examples of the above halogen group include fluoro group, chloro group, and bromo group, and examples of lower alkyl groups include methyl group, ethyl group, loebrovir group, iso-probyl group, n
-Butyl group. Examples include iso-butyl group, tert-butyl group, n=pentyl group, and n-hexyl group, and examples of lower alkoxy groups include methoxy group, ethoxy group, n-broboxy group, 0-butoxy group, and tert-butoxy group. Examples of lower haloalkyl groups include fluoromethyl group, difluoromethyl group, trifluoromethyl group, 2-chloroethyl group, 2-fluoroethyl group, 2,2.2-trifluoroethyl group, 3,3 .3
Examples of the lower haloalkoxy group include a -1-riflepropyl group, and examples of the lower haloalkoxy group include a difluoromethoxy group and a trifluoromethoxy group. R1 as such a substituted phenyl group includes, for example, a 4-fluorophenyl group, a 3-fluorophenyl group, a 4-chlorophenyl group,
3-chlorophenyl group 4-promophenyl group, 3.4-
difluorophenyl group, 3,5-difluorophenyl group,
3.4-dichlorophenyl group, 3.5-dichlorophenyl group, 4-methylphenyl group, 3-methylphenyl group,
3.4-dimethylphenyl group, 3.5-dimethylphenyl group, 4-ethylphenyl group, 4-propylphenyl group, 4-t-butylphenyl group, 4-chloro-3-methylphenyl group, 3- Chloro-4-methylphenyl group, 4-
Methoxyphenyl group, 3-methoxyphenyl group, 2-methoxyphenyl group, 4-ethoxyphenyl group, 4-n-
Proboxyphenyl group, 4-n-butoxyphenyl group,
Examples include, but are not limited to, 4-trifluoromethylphenyl group, 3-trifluoromethylphenyl group, and 4-triphenylmethylphenoxy group. The organosilicon compound of the present invention comprises a silane represented by the general formula 2 R1 R2-SL-X R3 (wherein R', R", R", and X are the same as above) and a 1,3- It is synthesized by reacting 1,3-pyrimidin-5-yllithium with 1,3-pyrimidin-5-yllithium. can be synthesized by reacting 5-halo1,3-pyrimidine with an alkyllithium in an inert gas atmosphere in the presence of an organic solvent.
この合成反応に用いる５−ハローｌ，゛３−ピリミジン
としては５−クロロ−１．３−ピリミジン、５−ブロモ
ー１．３−ビリミジン、５−ヨード−１．３ピリミジン
が挙げられ、アルキルリチウムとしてはｎ−ブチルリチ
ウムが挙げられる。Examples of 5-halo-1,3-pyrimidine used in this synthesis reaction include 5-chloro-1,3-pyrimidine, 5-bromo-1,3-pyrimidine, and 5-iodo-1,3-pyrimidine, and examples of alkyllithium include Examples include n-butyllithium.
有機溶媒としては、エチルエーテル、テトラヒド口フラ
ン、ジメトキシエタン等のエーテル系溶媒やペンタン、
ヘキサン、ヘプタン、オクタン、イソオクタン等の炭化
水素系溶媒およびこれらの２種以上の混合物を用いるこ
とができ、不活性気体としては窒素、アルゴン等を用い
ることができる。Examples of organic solvents include ether solvents such as ethyl ether, tetrahydrofuran, dimethoxyethane, pentane,
Hydrocarbon solvents such as hexane, heptane, octane, and isooctane, and mixtures of two or more thereof can be used, and nitrogen, argon, etc. can be used as the inert gas.
反応は上記のアルキルリチウムを溶液、例えばｎ−ブチ
ルリチウムのヘキサン溶液とし、これを５−ハロー１．
３−ピリミジンの有機溶媒溶液に滴下して行う。滴下時
間は１０分〜１時間とし、滴下終了後、さらに１〜８時
間、望ましくは１〜３時間反応させるとよい。反応温度
は、滴下開始から反応終了までを通して−１００〜０℃
、望まし《は−７８〜−６０℃とすればよい。In the reaction, the above alkyllithium is used as a solution, for example, n-butyllithium in hexane, and this is converted into 5-halo1.
This is carried out by dropping it into a solution of 3-pyrimidine in an organic solvent. The dropping time is 10 minutes to 1 hour, and after the dropwise addition is completed, the reaction is preferably allowed to continue for 1 to 8 hours, preferably 1 to 3 hours. The reaction temperature was -100 to 0°C from the start of dropping to the end of the reaction.
, preferably -78 to -60°C.
このようにして得られた１．３−ピリミジン−５−イル
リチウムの溶液は、このままの状態で次の反応に用いら
れる。すなわち、この低温の溶液に不活性気体の雰囲気
下、前記の一般式２で示されるシランを１０分〜１時間
で滴下し、同条件下にさらに１〜３時間保った後、室温
まで昇温させれば本発明の化合物が溶液として得られる
。The solution of 1,3-pyrimidin-5-yllithium thus obtained is used as is in the next reaction. That is, the silane represented by the general formula 2 above is added dropwise to this low-temperature solution under an inert gas atmosphere over 10 minutes to 1 hour, kept under the same conditions for an additional 1 to 3 hours, and then heated to room temperature. By doing so, the compound of the present invention can be obtained as a solution.
このようにして合成された１，３−ピリミジン−５−イ
ルシラン化合物はつぎのようにして単離することがでさ
る。まず上記の目的物を含む反応液に水、希塩酸または
塩化アンモニウム水溶液を加えて撹拌した後、水と混じ
り合わない有機溶媒で抽出し、抽出液を乾燥し、減圧下
に溶媒をストリップして残渣を得、これを必要に応じて
減圧蒸留やクロマトグラフィーで精製する。The 1,3-pyrimidin-5-ylsilane compound thus synthesized can be isolated as follows. First, water, dilute hydrochloric acid, or ammonium chloride aqueous solution is added to the reaction solution containing the above-mentioned target substance, and the mixture is stirred, extracted with an organic solvent that is immiscible with water, the extract is dried, and the solvent is stripped under reduced pressure to remove the residue. This is purified by vacuum distillation or chromatography as necessary.
本発明の有機けい素化合物は新規な化合物であり、これ
らの化合物自体が酸化防止剤、表面処理剤、接着促進剤
、生物制御剤として有用であるほか、他の有用物質用の
中間体、例えば医薬、農薬などの生理活性物質の合成の
ための中間体及びこれらのビルディングブロック合成の
ための中間体として有用である。The organosilicon compounds of the present invention are novel compounds, and these compounds themselves are useful as antioxidants, surface treatment agents, adhesion promoters, and biocontrol agents, as well as intermediates for other useful substances, such as It is useful as an intermediate for the synthesis of physiologically active substances such as medicines and agricultural chemicals, and as an intermediate for the synthesis of building blocks thereof.
また、本発明の製造方法によればきわめて高収率で１．
３−ビリミジンー５−イルシラン化合物を合成すること
ができるので、その実用的価値は大きい。Furthermore, according to the production method of the present invention, 1.
Since a 3-pyrimidin-5-ylsilane compound can be synthesized, its practical value is great.
次に、本発明の実施例を挙げる。Next, examples of the present invention will be given.
実施例１
５−ブロモー１，３−ピリミジン１．５９ｇ （ｔｏミ
リモル）をエチルエーテルｌＯｍｆｆとテトラヒド口フ
ランｌＯｍＩ２の混合溶媒の溶液とし、窒素雰囲気下、
ドライアイスーメタノール浴で−７０℃に冷却した。こ
れに、攪拌しながら１．６Ｍ濃度のｎ−ブチルリチウム
のヘキサン溶液６． ２３ｍ！２（ １０ミリモル）を
反応液の温度が−６０℃を越えないようにして３０分間
で滴下した。滴下後−６０から−７０℃に２時間保った
後、ジメチルーｎ−ペンチルクロロシラン１．６４ｇ（
１０ミリモル）をテトラヒド口フラン１０ｍｌ２に溶解
した溶液を１５分間で滴下した。同条件下にさらに３０
分間保った後、そのまま撹拌な続けて２時間の間に室温
まで昇温させた。０，５モル／Ｉ２の塩酸水５０ｍβを
加えた後、５０ｍｊ２の酢酸エチルで２回抽出し、抽出
液を無水硫酸ナトリウムで乾燥し、減圧下に溶媒をスト
リップすると、２． ７２ｇの赤桧色を帯びた油状物が
得られた。これをシリカゲル力ラムクロマトグラフィー
で分離して、無色液状の生成物１．５３ｇを得た。この
生成物は下記の質量スペクトル及び核磁気共鳴スペクト
ル分析から、ジメチルーｎ−ペンチル（１．３−ビリミ
ジンー５−イル）シラン
ＣＨ．
であることが確かめられた。（収率７４％）質量スペク
トル（ＩＩＩ／ｅ）
２０８ （Ｍ”） ， １９３， １６５， １５２．
１３７ ｆｂａｓｅｌ核磁気共鳴スペクトル： ’Ｈ
−ＮＭＲ （ＣＤＣｌ３，δ，ｐｐｍ）０．２９ （６
Ｈ，Ｓｌ ，０．８２ （５Ｈ，ｍｌ ，１．２６ （
６Ｈ，ｍｌ ，８．７２（２Ｈ，Ｓ），９．１５（ＩＨ
，Ｓｌ実施例２
原料のジメチル一〇一ペンチルクロロシランをジメチル
ーｎ−デシルクロロシランに代えたほかは，実施例１と
全く同様にして合成を行った。得られた生成物は下記の
分析結果からジメチルーｎ一デシル（ｌ，３−ピリミジ
ン−５−イル）シラン
ＣＩ．
であることが確かめられた。Example 1 1.59 g (to mmol) of 5-bromo-1,3-pyrimidine was dissolved in a mixed solvent of ethyl ether lOmff and tetrahydrofuran lOmI2, and under a nitrogen atmosphere,
It was cooled to -70°C in a dry ice-methanol bath. Add to this a 1.6M hexane solution of n-butyllithium while stirring.6. 23m! 2 (10 mmol) was added dropwise over 30 minutes while ensuring that the temperature of the reaction solution did not exceed -60°C. After dropping and keeping at -60 to -70°C for 2 hours, 1.64 g of dimethyl-n-pentylchlorosilane (
A solution of 10 mmol) dissolved in 10 ml of tetrahydrofuran was added dropwise over 15 minutes. 30 more under the same conditions
After maintaining the temperature for 2 minutes, the mixture was continued to be stirred and the temperature was raised to room temperature over a period of 2 hours. After adding 50 mβ of 0.5 mol/I2 hydrochloric acid water, extraction was carried out twice with 50 mj2 of ethyl acetate, the extract was dried over anhydrous sodium sulfate, and the solvent was stripped under reduced pressure.2. 72 g of a reddish oil was obtained. This was separated by silica gel column chromatography to obtain 1.53 g of a colorless liquid product. This product was found to be dimethyl-n-pentyl(1,3-pyrimidin-5-yl)silane CH. It was confirmed that. (Yield 74%) Mass spectrum (III/e) 208 (M”), 193, 165, 152.
137 fbasel nuclear magnetic resonance spectrum: 'H
-NMR (CDCl3, δ, ppm) 0.29 (6
H, Sl, 0.82 (5H, ml, 1.26 (
6H, ml, 8.72 (2H, S), 9.15 (IH
, Sl Example 2 Synthesis was carried out in exactly the same manner as in Example 1, except that the raw material dimethyl-101pentylchlorosilane was replaced with dimethyl-n-decylchlorosilane. The obtained product was found to be dimethyl-n-decyl(l,3-pyrimidin-5-yl)silane CI. It was confirmed that.
質量スペクトル（ｍ／ｅ）
２７８ （Ｍ”ｌ ． １６３， ２４９， ２３５，
２２１， ２０７， １９３， １７９， １６５，
１５２． １３７ （ｂａｓｅ）
核磁気共鳴スペクトル： ｌ Ｈ−ＮＭＲ ｆｃＤｃｌ
３ ，δ， ｐｐｍ）０． ３０ （６Ｈ， Ｓ） ，
０． ８２ （５Ｈ， ｍｌ ， １． ２３ （１
６Ｈ， ｍ） ．８． ７３ （２Ｈ， Ｓ） ， ９
． １６ （ＩＨ， Ｓｌ実施例３
原料のジメチルーｎ−ペンチルクロロシランをジメチル
ーｎ−オクタデシルク口ロシランに代えたほかは、実施
例１と全《同様にして合成を行った。得られた生成物は
下記の分析結果からジメチルーｎ−オクタデシル（１，
３−ビリミジンー５一イル）シラン
ＣＨ．
であることが確かめられた。Mass spectrum (m/e) 278 (M”l. 163, 249, 235,
221, 207, 193, 179, 165,
152. 137 (base) Nuclear magnetic resonance spectrum: l H-NMR fcDcl
3, δ, ppm) 0. 30 (6H, S),
0. 82 (5H, ml, 1.23 (1
6H, m). 8. 73 (2H, S), 9
．． 16 (IH, Sl Example 3 Synthesis was carried out in the same manner as in Example 1 except that dimethyl-n-pentylchlorosilane as a raw material was replaced with dimethyl-n-octadecylchlorosilane. The obtained product was as follows. From the analysis results, dimethyl-n-octadecyl (1,
3-pyrimidine-5-yl)silane CH. It was confirmed that.
質量スペクトル（ｍ／ｅｌ
３９０ （Ｍ”） ， ３７５， ３６２， ３４８，
３３４， ３２０， ３０６， ２９２，２７８，
２６４， ２４９， ２３５， ２２１， ２０７，
１９３， １７９， １６５，１５２， １３７ （ｂ
ａｓｅ） ， １２３核磁気共鳴スペクトル： ’ Ｈ
−ＮＭＲ （ＣＤＣ１３ ，δ．ｐｐｍ）０．３４（６
Ｈ，Ｓｌ，０．８７（５１Ｌｍ），１．２５（３２Ｈ，
ｍ），７．２６（ＩＨ，Ｓｌ，８．８１（２Ｈ，Ｓｌ，
９．２２（ＩＨ，Ｓ）実施例４
原料のジメチルーｎ−ペンチルクロロシランをジ．メチ
ル−４−フル才ロフエニルク口ロシランに代えたほかは
、実施例ｌと全《同様にして合成を行った。得られた生
成物は下記の分析結果からジメチル−４−フル才ロフェ
ニル（ｌ，３−ビリミジン−５−イル）シラン
ＣＨ．
であることが確かめられた。Mass spectrum (m/el 390 (M”), 375, 362, 348,
334, 320, 306, 292, 278,
264, 249, 235, 221, 207,
193, 179, 165, 152, 137 (b
ase), 123 nuclear magnetic resonance spectrum: 'H
-NMR (CDC13, δ.ppm) 0.34 (6
H, Sl, 0.87 (51Lm), 1.25 (32H,
m), 7.26 (IH, Sl, 8.81 (2H, Sl,
9.22 (IH,S) Example 4 The raw material dimethyl-n-pentylchlorosilane was diluted with dimethyl-n-pentylchlorosilane. The synthesis was carried out in the same manner as in Example 1, except that methyl-4-fluorophenylsilane was used. The obtained product was found to be dimethyl-4-fluorophenyl(l,3-pyrimidin-5-yl)silane CH. It was confirmed that.
質量スペクトル（ｍ／ｅ）
２３２ （Ｍ”１ ． ２１７ （ｂａｓｅ） ， １
９９， １６３， １５３， １３９，核ｔｎ気共鳴ス
ペクトル： ’ Ｈ−ＮＭＲ （ＣＤＣｌ３ ．δ．ｐ
ｐｍ）０． ６２ （６Ｈ， Ｓｌ ， ？． １０
（２Ｈ， ｔ， Ｊ＝９． ３） ， ７． ４８ （
２Ｈ， ｄｏｄ，Ｊ＝８． ３， ５． ９１ ， ８
． ７３ （２Ｈ， Ｓ） ， ９． ２０ （ＩＨ，
Ｓ）実施例５〜３０
原料のジメチル一〇−ペンチルクロロシランに代えて、
前記一般式２においてＲ’，Ｒ”及びＲ３として第１表
に示す基を有するクロロシランを用い、実施例ｌと同様
にして、このようなＲ１，Ｒ２及びＲ３を有する１．３
−ピリミジンー５−イルシラン化合物を得た。これらの
化合物の質量スペクトルの測定結果は第１表に併記した
とおりであった。Mass spectrum (m/e) 232 (M”1.217 (base), 1
99, 163, 153, 139, nuclear tn gas resonance spectrum: 'H-NMR (CDCl3.δ.p
pm) 0. 62 (6H, Sl, ?. 10
(2H, t, J=9.3), 7. 48 (
2H, dod, J=8. 3, 5. 91, 8
．． 73 (2H, S), 9. 20 (IH,
S) Examples 5 to 30 Instead of the raw material dimethyl 10-pentylchlorosilane,
In the general formula 2, using chlorosilane having the groups shown in Table 1 as R', R'' and R3, 1.3 having such R1, R2 and R3 was prepared in the same manner as in Example 1.
-pyrimidin-5-ylsilane compound was obtained. The measurement results of mass spectra of these compounds are shown in Table 1.
Claims (1)
基またはシクロプロピル基を、Ｒ＾２およびＲ＾３は独
立に、メチル基、フェニル基または置換基を有するフェ
ニル基（ただし該置換基はハロゲン基、低級アルキル基
、低級アルコキシ基、低級ハロアルキル基および低級ハ
ロアルコキシ基から選ばれる基）をそれぞれ表す。］ で示される有機けい素化合物。 ２、一般式２ ▲数式、化学式、表等があります▼ ［式中、Ｒ＾１は炭素数１〜１８のアルキル基、ビニル
基またはシクロプロピル基を、Ｒ＾２およびＲ＾３は独
立に、メチル基、フェニル基または置換基を有するフェ
ニル基（ただし該置換基はハロゲン基、低級アルキル基
、低級アルコキシ基、低級ハロアルキル基および低級ハ
ロアルコキシ基から選ばれる基）を、ｘはハロゲン基を
それぞれ表す。］で示されるシラン化合物に １，３−ピリミジン−５−イルリチウムを反応させるこ
とを特徴とする 一般式１ ▲数式、化学式、表等があります▼ （式中、Ｒ＾１、Ｒ＾２、Ｒ＾３は前記に同じ。）で示
される有機けい素化合物の製造方法。[Claims] 1. General formula 1 ▲ Numerical formulas, chemical formulas, tables, etc. are included. R^3 independently represents a methyl group, a phenyl group, or a phenyl group having a substituent (wherein the substituent is a group selected from a halogen group, a lower alkyl group, a lower alkoxy group, a lower haloalkyl group, and a lower haloalkoxy group). Represent each. ] An organosilicon compound represented by 2. General formula 2 ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼ [In the formula, R^1 is an alkyl group having 1 to 18 carbon atoms, a vinyl group, or a cyclopropyl group, and R^2 and R^3 are independently , a methyl group, a phenyl group, or a phenyl group having a substituent (wherein the substituent is a group selected from a halogen group, a lower alkyl group, a lower alkoxy group, a lower haloalkyl group, and a lower haloalkoxy group), and x is a halogen group. Represent each. ] General formula 1 characterized by reacting 1,3-pyrimidin-5-yllithium with a silane compound ▲ Contains numerical formulas, chemical formulas, tables, etc. ▼ R^3 is the same as above.) A method for producing an organosilicon compound.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP1111590A JPH0772191B2 (en) | 1989-04-28 | 1989-04-28 | Organic silicon compound and method for producing the same |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP1111590A JPH0772191B2 (en) | 1989-04-28 | 1989-04-28 | Organic silicon compound and method for producing the same |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPH02290883A true JPH02290883A (en) | 1990-11-30 |
| JPH0772191B2 JPH0772191B2 (en) | 1995-08-02 |
Family
ID=14565224
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP1111590A Expired - Lifetime JPH0772191B2 (en) | 1989-04-28 | 1989-04-28 | Organic silicon compound and method for producing the same |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPH0772191B2 (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5906274A (en) * | 1995-04-13 | 1999-05-25 | Mcewan; Sturt | Compact disc case |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4138483A (en) * | 1977-11-11 | 1979-02-06 | M&T Chemicals Inc. | Insecticidal compositions containing certain tetraorganotin compounds and method for using same |
-
1989
- 1989-04-28 JP JP1111590A patent/JPH0772191B2/en not_active Expired - Lifetime
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4138483A (en) * | 1977-11-11 | 1979-02-06 | M&T Chemicals Inc. | Insecticidal compositions containing certain tetraorganotin compounds and method for using same |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5906274A (en) * | 1995-04-13 | 1999-05-25 | Mcewan; Sturt | Compact disc case |
Also Published As
| Publication number | Publication date |
|---|---|
| JPH0772191B2 (en) | 1995-08-02 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| US5420301A (en) | Process for the preparation of substituted difluorobenzo-1,3-dioxoles | |
| JPH02290883A (en) | Organosilicon compound and its production | |
| KR19990013367A (en) | Process for preparing pyrazolinone compound | |
| JPH02290885A (en) | Organosilicon compound and its production | |
| JPH02108692A (en) | Production of aryldimethyl (3-arylpropyl)silane | |
| JPH02270887A (en) | Organosilicon compound and production thereof | |
| Murai et al. | Aldol-type condensation reactions of lithium eneselenolates generated from selenoamides with aldehydes | |
| JP7158717B2 (en) | Electrophilic azidating or diazotizing agents | |
| Fataftah et al. | Preparation of dimethylsilyl bis-enol ethers | |
| SU717058A1 (en) | Method of preparing alkoxysilanes | |
| JPH05508633A (en) | Intermediates used in the preparation of deferoxamine | |
| Zhou et al. | Allylboration of some ketones and aldehydes with 2-allyl-1, 2-oxaborolane. Isolation of their intermediate adducts and synthesis of homoallylic alcohols | |
| JPH02270889A (en) | Organic silicon compound and production thereof | |
| US3219683A (en) | Dichlorocyclopropaneboronate | |
| JP2624840B2 (en) | Preparation of optically active amide compounds | |
| JPH02290884A (en) | Production of organosilicon compound | |
| JPH02240086A (en) | Production of ortholithio-substituted phenylsilane compound | |
| JPS6393774A (en) | Production of 4-amino-2(5h)-furanone derivative | |
| US5023382A (en) | Synthesis of 2,3-disubstituted-2-cyclopentenones via lithiomethylmercapto compounds | |
| JPS6219582A (en) | Production of gamma-thiobutyrolactone derivative | |
| JP3495774B2 (en) | Method for producing 1-hydroxyindoles | |
| JPH03264557A (en) | Fluorine-containing compound | |
| JPH02270886A (en) | Organosilicon compound and production thereof | |
| JPS59144794A (en) | Heterocyclic five-membered phosphorus derivative | |
| JPH07324048A (en) | Production of chlorohydrin derivative |