SU719491A3 - Способ получени оптически активных алкилхризантемата - Google Patents

Способ получени оптически активных алкилхризантемата Download PDF

Info

Publication number: SU719491A3
Authority: SU; USSR - Soviet Union
Prior art keywords: optically active; formula; butyl; dimethyl; amino
Prior art date: 1975-08-01

Application number

SU762387252A

Other languages

English (en)

Russian (ru)

Inventor

Аратани Тадатоси

Ениеси Юкио

Фудзита Фумио

Нагасе Цунеюки

Original Assignee

Сумитомо Кемикал Компани Лимитед (Фирма)

Priority date (The priority date 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 date listed.)

1975-08-01

Filing date

1976-07-30

Publication date

1980-02-29

1976-07-30 Application filed by Сумитомо Кемикал Компани Лимитед (Фирма) filed Critical Сумитомо Кемикал Компани Лимитед (Фирма)

1980-02-29 Application granted granted Critical

1980-02-29 Publication of SU719491A3 publication Critical patent/SU719491A3/ru

Links

238000000034 method Methods 0.000 title claims description 12
-1 diazo acetate Chemical compound 0.000 claims abstract description 14
230000003287 optical effect Effects 0.000 claims abstract description 9
150000004753 Schiff bases Chemical class 0.000 claims abstract description 6
150000004699 copper complex Chemical class 0.000 claims abstract description 6
239000002262 Schiff base Substances 0.000 claims abstract description 5
125000000217 alkyl group Chemical group 0.000 claims abstract description 5
BXEFQPCKQSTMKA-UHFFFAOYSA-N OC(=O)C=[N+]=[N-] Chemical compound OC(=O)C=[N+]=[N-] BXEFQPCKQSTMKA-UHFFFAOYSA-N 0.000 claims description 4
125000004432 carbon atom Chemical group C* 0.000 claims description 4
125000003545 alkoxy group Chemical group 0.000 claims description 3
DTGKSKDOIYIVQL-WEDXCCLWSA-N (+)-borneol Chemical group C1C[C@@]2(C)[C@@H](O)C[C@@H]1C2(C)C DTGKSKDOIYIVQL-WEDXCCLWSA-N 0.000 claims description 2
125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 2
125000001424 substituent group Chemical group 0.000 claims description 2
125000003118 aryl group Chemical group 0.000 claims 2
239000003849 aromatic solvent Substances 0.000 claims 1
125000003710 aryl alkyl group Chemical group 0.000 claims 1
239000002585 base Substances 0.000 claims 1
229910052799 carbon Inorganic materials 0.000 claims 1
150000001875 compounds Chemical class 0.000 claims 1
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 1
230000003340 mental effect Effects 0.000 claims 1
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims 1
239000003054 catalyst Substances 0.000 abstract description 10
XLOPRKKSAJMMEW-SFYZADRCSA-N Chrysanthemic acid Natural products CC(C)=C[C@@H]1[C@@H](C(O)=O)C1(C)C XLOPRKKSAJMMEW-SFYZADRCSA-N 0.000 abstract description 7
XLOPRKKSAJMMEW-UHFFFAOYSA-N chrysanthemic acid Chemical class CC(C)=CC1C(C(O)=O)C1(C)C XLOPRKKSAJMMEW-UHFFFAOYSA-N 0.000 abstract description 7
DZPCYXCBXGQBRN-UHFFFAOYSA-N 2,5-Dimethyl-2,4-hexadiene Chemical compound CC(C)=CC=C(C)C DZPCYXCBXGQBRN-UHFFFAOYSA-N 0.000 abstract description 2
VEMKTZHHVJILDY-UXHICEINSA-N bioresmethrin Chemical compound CC1(C)[C@H](C=C(C)C)[C@H]1C(=O)OCC1=COC(CC=2C=CC=CC=2)=C1 VEMKTZHHVJILDY-UXHICEINSA-N 0.000 abstract 1
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 9
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
238000006243 chemical reaction Methods 0.000 description 6
238000004817 gas chromatography Methods 0.000 description 6
239000000203 mixture Substances 0.000 description 6
BDERNNFJNOPAEC-UHFFFAOYSA-N 1-propanol Substances CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 4
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
150000001879 copper Chemical class 0.000 description 4
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 3
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
239000011541 reaction mixture Substances 0.000 description 3
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
241000723353 Chrysanthemum Species 0.000 description 2
235000007516 Chrysanthemum Nutrition 0.000 description 2
LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
238000004458 analytical method Methods 0.000 description 2
230000000052 comparative effect Effects 0.000 description 2
229910052802 copper Inorganic materials 0.000 description 2
239000010949 copper Substances 0.000 description 2
150000001993 dienes Chemical class 0.000 description 2
150000002148 esters Chemical class 0.000 description 2
229910052739 hydrogen Inorganic materials 0.000 description 2
239000001257 hydrogen Substances 0.000 description 2
230000007062 hydrolysis Effects 0.000 description 2
238000006460 hydrolysis reaction Methods 0.000 description 2
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
229910052698 phosphorus Inorganic materials 0.000 description 2
239000000243 solution Substances 0.000 description 2
239000002904 solvent Substances 0.000 description 2
BJESMBBTQNGLAB-UHFFFAOYSA-N 2-[[1,1-bis(2-butoxy-5-phenylphenyl)-1-hydroxy-3-phenylpropan-2-yl]iminomethyl]phenol Chemical compound CCCCOC1=CC=C(C=2C=CC=CC=2)C=C1C(O)(C=1C(=CC=C(C=1)C=1C=CC=CC=1)OCCCC)C(N=CC=1C(=CC=CC=1)O)CC1=CC=CC=C1 BJESMBBTQNGLAB-UHFFFAOYSA-N 0.000 description 1
KPNZZCZTBVDMEA-UHFFFAOYSA-N 2-[[1-hydroxy-3-phenyl-1,1-bis(2-propan-2-yloxyphenyl)propan-2-yl]iminomethyl]phenol Chemical compound CC(C)OC1=CC=CC=C1C(O)(C=1C(=CC=CC=1)OC(C)C)C(N=CC=1C(=CC=CC=1)O)CC1=CC=CC=C1 KPNZZCZTBVDMEA-UHFFFAOYSA-N 0.000 description 1
JEYCPFDCZQPYBL-UHFFFAOYSA-N 2-diazo-2-phenylacetic acid Chemical compound OC(=O)C(=[N+]=[N-])C1=CC=CC=C1 JEYCPFDCZQPYBL-UHFFFAOYSA-N 0.000 description 1
HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 description 1
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 1
229910002480 Cu-O Inorganic materials 0.000 description 1
JPVYNHNXODAKFH-UHFFFAOYSA-N Cu2+ Chemical compound [Cu+2] JPVYNHNXODAKFH-UHFFFAOYSA-N 0.000 description 1
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
239000002253 acid Substances 0.000 description 1
239000012670 alkaline solution Substances 0.000 description 1
150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
229910001431 copper ion Inorganic materials 0.000 description 1
238000000354 decomposition reaction Methods 0.000 description 1
150000008049 diazo compounds Chemical class 0.000 description 1
229910001873 dinitrogen Inorganic materials 0.000 description 1
YVPJCJLMRRTDMQ-UHFFFAOYSA-N ethyl diazoacetate Chemical compound CCOC(=O)C=[N+]=[N-] YVPJCJLMRRTDMQ-UHFFFAOYSA-N 0.000 description 1
238000002474 experimental method Methods 0.000 description 1
239000011521 glass Substances 0.000 description 1
229910052736 halogen Inorganic materials 0.000 description 1
150000002367 halogens Chemical class 0.000 description 1
230000000749 insecticidal effect Effects 0.000 description 1
239000002917 insecticide Substances 0.000 description 1
239000003446 ligand Substances 0.000 description 1
239000007788 liquid Substances 0.000 description 1
238000002844 melting Methods 0.000 description 1
230000008018 melting Effects 0.000 description 1
238000012986 modification Methods 0.000 description 1
230000004048 modification Effects 0.000 description 1
230000007935 neutral effect Effects 0.000 description 1
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
239000012044 organic layer Substances 0.000 description 1
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
239000002244 precipitate Substances 0.000 description 1
239000000047 product Substances 0.000 description 1
238000000926 separation method Methods 0.000 description 1
238000003756 stirring Methods 0.000 description 1
239000008096 xylene Substances 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C245/00—Compounds containing chains of at least two nitrogen atoms with at least one nitrogen-to-nitrogen multiple bond
- C07C245/12—Diazo compounds, i.e. compounds having the free valencies of >N2 groups attached to the same carbon atom
- C07C245/14—Diazo compounds, i.e. compounds having the free valencies of >N2 groups attached to the same carbon atom having diazo groups bound to acyclic carbon atoms of a carbon skeleton
- C07C245/18—Diazo compounds, i.e. compounds having the free valencies of >N2 groups attached to the same carbon atom having diazo groups bound to acyclic carbon atoms of a carbon skeleton the carbon skeleton being further substituted by carboxyl groups
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F1/00—Compounds containing elements of Groups 1 or 11 of the Periodic Table
- C07F1/005—Compounds containing elements of Groups 1 or 11 of the Periodic Table without C-Metal linkages

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Catalysts (AREA)

SU762387252A 1975-08-01 1976-07-30 Способ получени оптически активных алкилхризантемата SU719491A3 (ru)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
JP50094349A JPS5910336B2 (ja)	1975-08-01	1975-08-01	第一菊酸エステルの不斉合成法

Publications (1)

Publication Number	Publication Date
SU719491A3 true SU719491A3 (ru)	1980-02-29

Family

ID=14107796

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
SU762387252A SU719491A3 (ru)	1975-08-01	1976-07-30	Способ получени оптически активных алкилхризантемата

Country Status (12)

Country	Link
JP (1)	JPS5910336B2 (ja)
BE (1)	BE844631A (ja)
CA (1)	CA1121813A (ja)
CH (1)	CH621767A5 (ja)
DE (1)	DE2634663C3 (ja)
DK (1)	DK142765B (ja)
FR (1)	FR2319623A1 (ja)
GB (1)	GB1499094A (ja)
IL (1)	IL50100A (ja)
IT (1)	IT1070323B (ja)
NL (1)	NL7608508A (ja)
SU (1)	SU719491A3 (ja)

Families Citing this family (14)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
DE2919820A1 (de) *	1979-05-16	1980-11-20	Bayer Ag	Fluor-substituierte oxyalkenyl-cyclopropancarbonsaeureester, verfahren zu ihrer herstellung sowie ihre verwendung als insektizide und akarizide
EP0023075A1 (en) *	1979-07-13	1981-01-28	Imperial Chemical Industries Plc	Process for the preparation of cyclopropane carboxylic acid esters
EP0024796A1 (en) *	1979-07-13	1981-03-11	Imperial Chemical Industries Plc	Chiral amino-alcohol complexes and process for their preparation
EP0024797A1 (en)	1979-07-13	1981-03-11	Imperial Chemical Industries Plc	Chiral sugar complexes and process for their preparation
DE3064018D1 (en) *	1979-07-13	1983-08-11	Ici Plc	Process for the preparation of cyclopropane carboxylic acid esters
EP0024795A1 (en) *	1979-07-13	1981-03-11	Imperial Chemical Industries Plc	Chiral compounds and process for their preparation
JPS59158260A (ja) *	1983-02-28	1984-09-07	Seikei Giken:Kk	転写装置
JPS59158261A (ja) *	1983-07-19	1984-09-07	Seikei Giken:Kk	転写装置
JPH01232619A (ja) *	1988-03-11	1989-09-18	Toska Co Ltd	キートップの印字方法
JPH0671852A (ja) *	1992-08-31	1994-03-15	Shizuoka Giken Sanki Kk	曲面真空プレス熱転写方法及びその装置
JP4576642B2 (ja) *	1998-01-29	2010-11-10	住友化学株式会社	光学活性な菊酸の製造方法
ITMI20041211A1 (it) *	2004-06-16	2004-09-16	Endura Spa	Catalizzatori a base di complessi metallici per la sintesi di acido crisantemico otticamente attivo
CN103789789B (zh) *	2014-02-11	2016-06-29	华东师范大学	电化学合成具有光学活性的苯乙烯环状碳酸酯的方法
CN103789791B (zh) *	2014-02-12	2016-08-17	华东师范大学	一种电化学合成具有光学活性的2-苯丙酸方法

Family Cites Families (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
IL44167A (en) *	1973-02-14	1979-09-30	Sumitomo Chemical Co	Chiral copper-complex catalyst

1975
- 1975-08-01 JP JP50094349A patent/JPS5910336B2/ja not_active Expired
1976
- 1976-07-22 IL IL50100A patent/IL50100A/xx unknown
- 1976-07-28 BE BE6045627A patent/BE844631A/xx not_active IP Right Cessation
- 1976-07-30 FR FR7623388A patent/FR2319623A1/fr active Granted
- 1976-07-30 CA CA000258220A patent/CA1121813A/en not_active Expired
- 1976-07-30 CH CH977576A patent/CH621767A5/de not_active IP Right Cessation
- 1976-07-30 DK DK345276AA patent/DK142765B/da not_active IP Right Cessation
- 1976-07-30 IT IT68927/76A patent/IT1070323B/it active
- 1976-07-30 NL NL7608508A patent/NL7608508A/xx not_active Application Discontinuation
- 1976-07-30 SU SU762387252A patent/SU719491A3/ru active
- 1976-07-30 GB GB31985/76A patent/GB1499094A/en not_active Expired
- 1976-08-02 DE DE2634663A patent/DE2634663C3/de not_active Expired

Also Published As

Publication number	Publication date
DE2634663B2 (de)	1979-05-31
DK345276A (ja)	1977-02-02
IL50100A0 (en)	1976-09-30
CA1121813A (en)	1982-04-13
IT1070323B (it)	1985-03-29
FR2319623B1 (ja)	1979-09-28
JPS5910336B2 (ja)	1984-03-08
DE2634663C3 (de)	1980-01-17
DE2634663A1 (de)	1977-03-17
DK142765C (ja)	1981-08-17
FR2319623A1 (fr)	1977-02-25
JPS5217448A (en)	1977-02-09
CH621767A5 (en)	1981-02-27
GB1499094A (en)	1978-01-25
IL50100A (en)	1982-02-28
NL7608508A (nl)	1977-02-03
BE844631A (fr)	1976-11-16
DK142765B (da)	1981-01-19

Publication	Publication Date	Title
SU719491A3 (ru)	1980-02-29	Способ получени оптически активных алкилхризантемата
JP6101636B2 (ja)	2017-03-22	バナジウム錯体を用いたファルネサールの製造方法
EP0380463A2 (en)	1990-08-01	Method for preparing (R)-succinic acid derivatives
Takeuchi et al.	2001	Asymmetric bis (alkoxycarbonylation) reaction of terminal olefins catalyzed by palladium in the presence of copper (I) triflate and a chiral bioxazoline ligand
US6072081A (en)	2000-06-06	Optically active bisoxazoline compounds, production and use thereof
JPS6117819B2 (ja)	1986-05-09
CN114957103B (zh)	2024-06-28	一种轴手性卤代联芳基化合物及其制备方法
EP0134303B1 (en)	1988-01-27	Menthyl 2,2-dimethylcyclopropanecarboxylate and resolution of the same
EP3204356A1 (en)	2017-08-16	Method for coupling a first compound to a second compound
JP4320058B2 (ja)	2009-08-26	芳香族ニトリルの製造法
US4197408A (en)	1980-04-08	Asymmetric synthesis of alkyl chrysanthemate
WO2002072524A2 (de)	2002-09-19	Verfahren zur herstellung von vinyl-, aryl- und heteroarylessigsäuren und ihrer derivate
JP4126763B2 (ja)	2008-07-30	光学活性なビスオキサゾリン化合物、その製造法およびその用途
US20220227797A1 (en)	2022-07-21	Tungsten imido alkylidene o-bitet and o-binol complexes and use thereof in olefin metathesis reactions
US5298623A (en)	1994-03-29	Cu complexes of bis-oxazolines and their use
JP4742423B2 (ja)	2011-08-10	不斉銅錯体の製造法およびそれを用いる光学活性シクロプロパン化合物の製造法
US4493799A (en)	1985-01-15	Synthesis of succinonitriles
JP3991455B2 (ja)	2007-10-17	光学活性な菊酸エステルの製造法
US6011169A (en)	2000-01-04	Process for producing optically active cyclopropanecaboxylic acid esters
EP1385814A1 (en)	2004-02-04	Enantiomerically selective cyclopropanation
JPS5850207B2 (ja)	1983-11-09	水素添加方法
JP4257977B2 (ja)	2009-04-30	１−インダノン類の製造方法
JP3221744B2 (ja)	2001-10-22	（メタ）アクリル酸エステルの直鎖二量体の製造方法
CA1155455A (en)	1983-10-18	Intermediates in the preparation of cyclopropanecarboxylate esters and process for their manufacture
Cervantes	2011	Metal-catalyzed carbon-carbon bond forming reactions for the synthesis of significant chiral building blocks