KR840008319A - 시클로헥산디온 유도체의 제조방법 - Google Patents
시클로헥산디온 유도체의 제조방법 Download PDFInfo
- Publication number
- KR840008319A KR840008319A KR1019840002146A KR840002146A KR840008319A KR 840008319 A KR840008319 A KR 840008319A KR 1019840002146 A KR1019840002146 A KR 1019840002146A KR 840002146 A KR840002146 A KR 840002146A KR 840008319 A KR840008319 A KR 840008319A
- Authority
- KR
- South Korea
- Prior art keywords
- cycloalkyl
- alkyl
- dialkylmalonate
- malonate
- unsubstituted
- Prior art date
Links
- OILAIQUEIWYQPH-UHFFFAOYSA-N cyclohexane-1,2-dione Chemical class O=C1CCCCC1=O OILAIQUEIWYQPH-UHFFFAOYSA-N 0.000 title 1
- 150000002576 ketones Chemical class 0.000 claims 4
- OFOBLEOULBTSOW-UHFFFAOYSA-L Malonate Chemical compound [O-]C(=O)CC([O-])=O OFOBLEOULBTSOW-UHFFFAOYSA-L 0.000 claims 2
- 230000010933 acylation Effects 0.000 claims 2
- 238000005917 acylation reaction Methods 0.000 claims 2
- 125000000217 alkyl group Chemical group 0.000 claims 2
- 125000004432 carbon atom Chemical group C* 0.000 claims 2
- 125000005842 heteroatom Chemical group 0.000 claims 2
- 125000004648 C2-C8 alkenyl group Chemical group 0.000 claims 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims 1
- 239000002253 acid Substances 0.000 claims 1
- 150000001266 acyl halides Chemical class 0.000 claims 1
- 125000003158 alcohol group Chemical group 0.000 claims 1
- 150000001298 alcohols Chemical class 0.000 claims 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims 1
- 239000003054 catalyst Substances 0.000 claims 1
- 238000006243 chemical reaction Methods 0.000 claims 1
- 150000001875 compounds Chemical class 0.000 claims 1
- 238000006114 decarboxylation reaction Methods 0.000 claims 1
- 238000004821 distillation Methods 0.000 claims 1
- 125000001072 heteroaryl group Chemical group 0.000 claims 1
- 230000007062 hydrolysis Effects 0.000 claims 1
- 238000006460 hydrolysis reaction Methods 0.000 claims 1
- 230000003301 hydrolyzing effect Effects 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 claims 1
- 229910052757 nitrogen Inorganic materials 0.000 claims 1
- 229910052760 oxygen Inorganic materials 0.000 claims 1
- 150000003839 salts Chemical class 0.000 claims 1
- 229920006395 saturated elastomer Polymers 0.000 claims 1
- SNOOUWRIMMFWNE-UHFFFAOYSA-M sodium;6-[(3,4,5-trimethoxybenzoyl)amino]hexanoate Chemical compound [Na+].COC1=CC(C(=O)NCCCCCC([O-])=O)=CC(OC)=C1OC SNOOUWRIMMFWNE-UHFFFAOYSA-M 0.000 claims 1
- 239000002904 solvent Substances 0.000 claims 1
- 125000003107 substituted aryl group Chemical group 0.000 claims 1
- 229910052717 sulfur Inorganic materials 0.000 claims 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
- C07C49/587—Unsaturated compounds containing a keto groups being part of a ring
- C07C49/703—Unsaturated compounds containing a keto groups being part of a ring containing hydroxy groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/61—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups
- C07C45/67—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton
- C07C45/673—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton by change of size of the carbon skeleton
- C07C45/676—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton by change of size of the carbon skeleton by elimination of carboxyl groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C319/00—Preparation of thiols, sulfides, hydropolysulfides or polysulfides
- C07C319/14—Preparation of thiols, sulfides, hydropolysulfides or polysulfides of sulfides
- C07C319/20—Preparation of thiols, sulfides, hydropolysulfides or polysulfides of sulfides by reactions not involving the formation of sulfide groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/24—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D213/44—Radicals substituted by doubly-bound oxygen, sulfur, or nitrogen atoms, or by two such atoms singly-bound to the same carbon atom
- C07D213/46—Oxygen atoms
- C07D213/50—Ketonic radicals
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D309/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings
- C07D309/02—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings having no double bonds between ring members or between ring members and non-ring members
- C07D309/04—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings having no double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
- C07D309/06—Radicals substituted by oxygen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D309/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings
- C07D309/16—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
- C07D309/20—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with hydrogen atoms and substituted hydrocarbon radicals directly attached to ring carbon atoms
- C07D309/22—Radicals substituted by oxygen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D335/00—Heterocyclic compounds containing six-membered rings having one sulfur atom as the only ring hetero atom
- C07D335/02—Heterocyclic compounds containing six-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2601/00—Systems containing only non-condensed rings
- C07C2601/12—Systems containing only non-condensed rings with a six-membered ring
- C07C2601/14—The ring being saturated
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2601/00—Systems containing only non-condensed rings
- C07C2601/12—Systems containing only non-condensed rings with a six-membered ring
- C07C2601/16—Systems containing only non-condensed rings with a six-membered ring the ring being unsaturated
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2601/00—Systems containing only non-condensed rings
- C07C2601/18—Systems containing only non-condensed rings with a ring being at least seven-membered
- C07C2601/20—Systems containing only non-condensed rings with a ring being at least seven-membered the ring being twelve-membered
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2602/00—Systems containing two condensed rings
- C07C2602/36—Systems containing two condensed rings the rings having more than two atoms in common
- C07C2602/42—Systems containing two condensed rings the rings having more than two atoms in common the bicyclo ring system containing seven carbon atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Pyrane Compounds (AREA)
- Heterocyclic Compounds Containing Sulfur Atoms (AREA)
- Pyridine Compounds (AREA)
- Steroid Compounds (AREA)
Abstract
내용 없음.
Description
본 내용은 요부공개 건이므로 전문내용을 수록하지 않았음
Claims (1)
- 다음 일반식(Ⅱ)의 α,β-불포화케톤을 염기의 존재하에 디알킬말로네이트와 반응시켜 다음 일반식(Ⅲ)의 알콕시카보닐시클로헥세놀론 또는 그것을 염을 얻고 얻어진(Ⅲ)의 화합물을 아실화, 가수분해 및 탈카복실화시키며, 여기서 1) α,β-불포화케톤(Ⅱ)을 염기의 존재하에 말로네이트를 증류해 낼 수 있는 것으로부터 유리된 알코로부터 선택한 용매중에서 디알킬말로네이트와 반응시키고, 2) 알콜을 공비물이 되기에 적당한 단계에서 증류해내고, 3) R2가 탄소원자이상이 아닌 알킬을 나타내는 R2COHal식의 카복실린산할리드로 알콕시카보닐시클로핵세놀론의 염을 반응시키고, 4) 과량의 아실할리드의 제거후 적당한 단계에서 생성물질을 아실화촉매로 처리하고, 그리고 5) 이 생성물을 가수분해하고 탈탄산화시킴을 특징으로 하는 다음 일반식(Ⅰ)의 시클로헥산디온 유도체의 제조방법.상기식에서 R1C2-C8-알킬, C2-C8-알케닐, C3-C12-시클로알킬, 0-4개의 올레핀적으로 불포화 결합을 한 C5-C12-시클로알킬, C2-C8-알킬티오알킬, 0-3계의 올레핀적으로 불포화결합하거나, 치환하지 않은 또는 치환된 또는 헤트아릴로 된 C6-C12-비시클로 또는 포하되거나 올레핀적으로 포화되지 않은 기로 3이상이 아닌 O, S 및 N로부터 선택된 헤테로-원자일 수 있는 4 내지 7원자의 헤테로 고리를 나타내며 R2는 6탄소원자이상이 아닌 알킬기이며 R은 말로네이트의 알콜기이다.※ 참고사항 : 최초출원 내용에 의하여 공개하는 것임.
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DE19833314816 DE3314816A1 (de) | 1983-04-23 | 1983-04-23 | Verfahren zur herstellung von cyclohexandionderivaten |
DEP3314816.3 | 1983-04-23 |
Publications (2)
Publication Number | Publication Date |
---|---|
KR840008319A true KR840008319A (ko) | 1984-12-14 |
KR910004134B1 KR910004134B1 (ko) | 1991-06-22 |
Family
ID=6197224
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
KR1019840002146A KR910004134B1 (ko) | 1983-04-23 | 1984-04-23 | 시클로헥산디온 유도체의 제조방법 |
Country Status (13)
Country | Link |
---|---|
US (1) | US5118856A (ko) |
EP (1) | EP0124041B2 (ko) |
JP (1) | JPH064556B2 (ko) |
KR (1) | KR910004134B1 (ko) |
AT (1) | ATE16587T1 (ko) |
BR (1) | BR8401860A (ko) |
CA (1) | CA1280756C (ko) |
DD (1) | DD215529A5 (ko) |
DE (2) | DE3314816A1 (ko) |
ES (1) | ES531835A0 (ko) |
IL (1) | IL71585A0 (ko) |
SU (1) | SU1450733A3 (ko) |
UA (1) | UA7020A1 (ko) |
Families Citing this family (8)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE3543447A1 (de) * | 1985-12-09 | 1987-06-11 | Basf Ag | Cyclohexenonderivate, verfahren zu ihrer herstellung und ihre verwendung als herbizide und das pflanzenwachstum regulierende mittel |
DE3600642A1 (de) * | 1986-01-11 | 1987-07-16 | Basf Ag | Cyclohexenonderivate, verfahren zu ihrer herstellung und ihre verwendung als herbizide mittel |
US4945178A (en) * | 1986-02-03 | 1990-07-31 | Eastman Kodak Company | Preparation of 4-carboalkoxy-1,3-cyclohexanedione type compounds |
EP0233117B1 (en) * | 1986-02-03 | 1992-01-29 | EASTMAN KODAK COMPANY (a New Jersey corporation) | Preparation of 4-carboalkoxy-1,3-cyclohexanedione type compounds |
CN101205207B (zh) * | 2006-12-18 | 2010-12-15 | 中国石油天然气集团公司 | [6-(2-乙硫基丙基)-2,4-二氧代-3-丙酰基]环己基甲酸乙酯的合成方法 |
WO2011062964A1 (en) * | 2009-11-17 | 2011-05-26 | University Of Rochester | Compounds and methods for altering lifespan of eukaryotic organisms |
CN111233720A (zh) * | 2018-11-28 | 2020-06-05 | 沈阳科创化学品有限公司 | 一种丙三酮的提纯方法以及烯草酮的制备方法 |
CN112679330B (zh) * | 2020-12-24 | 2022-07-05 | 西安向阳航天材料股份有限公司 | 一种丁二酰丁二酸二甲酯的水解工艺 |
Family Cites Families (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3950420A (en) * | 1973-08-15 | 1976-04-13 | Nippon Soda Company, Ltd. | Cyclohexane derivatives |
JPS51125738A (en) * | 1974-08-30 | 1976-11-02 | Nippon Soda Co Ltd | Cyclohexene insecticides and tickicides |
US4115204A (en) * | 1977-07-21 | 1978-09-19 | Phillips Petroleum Company | Separation of phenol-, cyclohexanone-, and cyclohexylbenzene-containing mixtures employing an N,N-disubstituted amide |
US4281204A (en) * | 1979-10-05 | 1981-07-28 | Fritzsche Dodge & Olcott Inc. | Substituted spirocyclic derivatives |
US5006158A (en) * | 1984-12-20 | 1991-04-09 | Ici Americas Inc. | Certain 2-(2-substituted benzoyl)-1,3-cyclohexanediones |
-
1983
- 1983-04-23 DE DE19833314816 patent/DE3314816A1/de not_active Withdrawn
-
1984
- 1984-04-19 EP EP84104475A patent/EP0124041B2/de not_active Expired - Lifetime
- 1984-04-19 IL IL71585A patent/IL71585A0/xx unknown
- 1984-04-19 CA CA000452369A patent/CA1280756C/en not_active Expired - Lifetime
- 1984-04-19 DE DE8484104475T patent/DE3460015D1/de not_active Expired
- 1984-04-19 AT AT84104475T patent/ATE16587T1/de not_active IP Right Cessation
- 1984-04-23 KR KR1019840002146A patent/KR910004134B1/ko not_active IP Right Cessation
- 1984-04-23 UA UA3728541A patent/UA7020A1/uk unknown
- 1984-04-23 ES ES531835A patent/ES531835A0/es active Granted
- 1984-04-23 SU SU843728541A patent/SU1450733A3/ru active
- 1984-04-23 BR BR8401860A patent/BR8401860A/pt not_active IP Right Cessation
- 1984-04-23 DD DD84262215A patent/DD215529A5/de not_active IP Right Cessation
- 1984-04-23 JP JP59080363A patent/JPH064556B2/ja not_active Expired - Lifetime
-
1990
- 1990-08-02 US US07/562,445 patent/US5118856A/en not_active Expired - Lifetime
Also Published As
Publication number | Publication date |
---|---|
KR910004134B1 (ko) | 1991-06-22 |
ATE16587T1 (de) | 1985-12-15 |
SU1450733A3 (ru) | 1989-01-07 |
DD215529A5 (de) | 1984-11-14 |
JPH064556B2 (ja) | 1994-01-19 |
EP0124041B1 (de) | 1985-11-21 |
JPS601150A (ja) | 1985-01-07 |
IL71585A0 (en) | 1984-07-31 |
DE3460015D1 (en) | 1986-01-02 |
EP0124041A1 (de) | 1984-11-07 |
BR8401860A (pt) | 1984-11-27 |
ES8502966A1 (es) | 1985-02-01 |
CA1280756C (en) | 1991-02-26 |
DE3314816A1 (de) | 1984-10-25 |
EP0124041B2 (de) | 1991-11-06 |
ES531835A0 (es) | 1985-02-01 |
UA7020A1 (uk) | 1995-03-31 |
US5118856A (en) | 1992-06-02 |
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