KR960704841A - 옥시란, 아지리딘 또는 싸이클로프로판 제조방법 (process for the preparation of an oxirane, aziridine or cyclopropane) - Google Patents
옥시란, 아지리딘 또는 싸이클로프로판 제조방법 (process for the preparation of an oxirane, aziridine or cyclopropane)Info
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- KR960704841A KR960704841A KR1019960701990A KR19960701990A KR960704841A KR 960704841 A KR960704841 A KR 960704841A KR 1019960701990 A KR1019960701990 A KR 1019960701990A KR 19960701990 A KR19960701990 A KR 19960701990A KR 960704841 A KR960704841 A KR 960704841A
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- 238000000034 method Methods 0.000 title claims abstract 8
- JECYNCQXXKQDJN-UHFFFAOYSA-N 2-(2-methylhexan-2-yloxymethyl)oxirane Chemical compound CCCCC(C)(C)OCC1CO1 JECYNCQXXKQDJN-UHFFFAOYSA-N 0.000 title claims abstract 3
- NOWKCMXCCJGMRR-UHFFFAOYSA-N Aziridine Chemical compound C1CN1 NOWKCMXCCJGMRR-UHFFFAOYSA-N 0.000 title claims abstract 3
- LVZWSLJZHVFIQJ-UHFFFAOYSA-N Cyclopropane Chemical compound C1CC1 LVZWSLJZHVFIQJ-UHFFFAOYSA-N 0.000 title claims abstract 3
- 125000000217 alkyl group Chemical group 0.000 claims abstract 19
- 125000003118 aryl group Chemical group 0.000 claims abstract 17
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract 16
- 239000001257 hydrogen Substances 0.000 claims abstract 16
- 150000001875 compounds Chemical class 0.000 claims abstract 12
- 125000001072 heteroaryl group Chemical group 0.000 claims abstract 12
- 125000000753 cycloalkyl group Chemical group 0.000 claims abstract 10
- 150000002431 hydrogen Chemical class 0.000 claims abstract 10
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract 6
- 239000003153 chemical reaction reagent Substances 0.000 claims abstract 6
- 239000002184 metal Substances 0.000 claims abstract 6
- 125000000623 heterocyclic group Chemical group 0.000 claims abstract 4
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical class C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 claims abstract 4
- 125000002524 organometallic group Chemical group 0.000 claims abstract 4
- 125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 claims abstract 4
- KPPVNWGJXFMGAM-UUILKARUSA-N (e)-2-methyl-1-(6-methyl-3,4-dihydro-2h-quinolin-1-yl)but-2-en-1-one Chemical compound CC1=CC=C2N(C(=O)C(/C)=C/C)CCCC2=C1 KPPVNWGJXFMGAM-UUILKARUSA-N 0.000 claims abstract 2
- 125000003710 aryl alkyl group Chemical group 0.000 claims abstract 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims abstract 2
- 125000005842 heteroatom Chemical group 0.000 claims abstract 2
- 239000000203 mixture Substances 0.000 claims abstract 2
- UUEVFMOUBSLVJW-UHFFFAOYSA-N oxo-[[1-[2-[2-[2-[4-(oxoazaniumylmethylidene)pyridin-1-yl]ethoxy]ethoxy]ethyl]pyridin-4-ylidene]methyl]azanium;dibromide Chemical compound [Br-].[Br-].C1=CC(=C[NH+]=O)C=CN1CCOCCOCCN1C=CC(=C[NH+]=O)C=C1 UUEVFMOUBSLVJW-UHFFFAOYSA-N 0.000 claims abstract 2
- 229910052760 oxygen Inorganic materials 0.000 claims abstract 2
- 239000001301 oxygen Substances 0.000 claims abstract 2
- UCKMPCXJQFINFW-UHFFFAOYSA-N Sulphide Chemical compound [S-2] UCKMPCXJQFINFW-UHFFFAOYSA-N 0.000 claims 7
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims 3
- 229910052799 carbon Inorganic materials 0.000 claims 3
- 238000004519 manufacturing process Methods 0.000 claims 1
- 229910052976 metal sulfide Inorganic materials 0.000 abstract 1
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D203/00—Heterocyclic compounds containing three-membered rings with one nitrogen atom as the only ring hetero atom
- C07D203/04—Heterocyclic compounds containing three-membered rings with one nitrogen atom as the only ring hetero atom not condensed with other rings
- C07D203/06—Heterocyclic compounds containing three-membered rings with one nitrogen 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
- C07D203/22—Heterocyclic compounds containing three-membered rings with one nitrogen 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 hetero atoms directly attached to the ring nitrogen atom
- C07D203/24—Sulfur atoms
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D203/00—Heterocyclic compounds containing three-membered rings with one nitrogen atom as the only ring hetero atom
- C07D203/04—Heterocyclic compounds containing three-membered rings with one nitrogen atom as the only ring hetero atom not condensed with other rings
- C07D203/06—Heterocyclic compounds containing three-membered rings with one nitrogen 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
- C07D203/22—Heterocyclic compounds containing three-membered rings with one nitrogen 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 hetero atoms directly attached to the ring nitrogen atom
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2/00—Preparation of hydrocarbons from hydrocarbons containing a smaller number of carbon atoms
- C07C2/86—Preparation of hydrocarbons from hydrocarbons containing a smaller number of carbon atoms by condensation between a hydrocarbon and a non-hydrocarbon
- C07C2/868—Preparation of hydrocarbons from hydrocarbons containing a smaller number of carbon atoms by condensation between a hydrocarbon and a non-hydrocarbon the non-hydrocarbon contains sulfur as hetero-atom
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- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D203/00—Heterocyclic compounds containing three-membered rings with one nitrogen atom as the only ring hetero atom
- C07D203/02—Preparation by ring-closure
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- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D301/00—Preparation of oxiranes
- C07D301/02—Synthesis of the oxirane ring
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- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D303/00—Compounds containing three-membered rings having one oxygen atom as the only ring hetero atom
- C07D303/02—Compounds containing oxirane rings
- C07D303/04—Compounds containing oxirane rings containing only hydrogen and carbon atoms in addition to the ring oxygen atoms
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- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D303/00—Compounds containing three-membered rings having one oxygen atom as the only ring hetero atom
- C07D303/02—Compounds containing oxirane rings
- C07D303/08—Compounds containing oxirane rings with hydrocarbon radicals, substituted by halogen atoms, nitro radicals or nitroso radicals
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D303/00—Compounds containing three-membered rings having one oxygen atom as the only ring hetero atom
- C07D303/02—Compounds containing oxirane rings
- C07D303/12—Compounds containing oxirane rings with hydrocarbon radicals, substituted by singly or doubly bound oxygen atoms
- C07D303/16—Compounds containing oxirane rings with hydrocarbon radicals, substituted by singly or doubly bound oxygen atoms by esterified hydroxyl radicals
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- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D303/00—Compounds containing three-membered rings having one oxygen atom as the only ring hetero atom
- C07D303/02—Compounds containing oxirane rings
- C07D303/38—Compounds containing oxirane rings with hydrocarbon radicals, substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
- C07D303/40—Compounds containing oxirane rings with hydrocarbon radicals, substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals by ester radicals
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- C07D303/02—Compounds containing oxirane rings
- C07D303/38—Compounds containing oxirane rings with hydrocarbon radicals, substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
- C07D303/46—Compounds containing oxirane rings with hydrocarbon radicals, substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals by amide or nitrile radicals
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- C07D407/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen atoms as the only ring hetero atoms, not provided for by group C07D405/00 containing two hetero rings directly linked by a ring-member-to-ring-member bond
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- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
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Abstract
본 발명은 (i)알킬금속을 식 CHR3X′X″의 메탄 유도체(식중 R3은 수소, 알킬, 아릴, 헤테로방향족, CO2R8, R8 3Sn, CONR8R9또는 트리메틸실릴이며, X′ 및 X″는 각각 독립적으로, 이탈 그룹임)와 반응시킴으로써 얻을 수 있는 금속탄소 (metallocarbon)이나, 또는 (ii)하기 식(Ⅲ)의 화합물을 적당한 유기금속 시약 또는 무기 시약과 반응시킴으로써 얻을 수 있는 금속탄소와, 하기 식(Ⅱ) 화합물 및 식 SR6R7의 설파이드(식중, R6및 R7은 각각 독립적으로, 알킬, 아릴 또는 헤테로 방향족이거나, R6및 R7이 서로 결합하여 임의로 추가의 헤테로원자를 포함하는 싸이크로알킬 링을 형성함)혼합물을 반응시킴으로써 하기 식(I)의 옥시란, 아지리딘 또는 싸이클로프로판을 제조하는 방법에 관한다.
식중, X는 산소, NR4또는 CHR5이고; R1은 수소, 알킬, 아릴, 헤테로방향족, 복소환식 또는 사이클로알킬; R2는 수소,알킬, 아릴, 헤테로방향족, CO2R8, CHR14NHR13, 복소환식 또는 싸이클로알킬이거나; 또는 R1및 R2는 함께 결합하여 싸이클로알킬 링을 형성하며; R은 수소, 알킬, 및, 헤테로방향족, CO2R8, R8 3Sn, CONR8R9또는 트리메틸실릴; R4및 R5은 각각 독립적으로, 알킬, 싸이클로알킬, 아릴, 헤테로 방향족, SO2R8,SO3R8, COR8,CONR8R9또는 CN이거나, 또는 R4는 또한 P(O)(아릴)2일 수 있으며; R8및 R9는 각각 독립적으로 알킬, 아릴 또는 아릴알킬; R13및 R14는 각각 독립적으로, 수소, 알킬 또는 아릴임.
[식중, R1,R2및 X는 상기에서 정의한 바와 같은.
[식중, R3은 수소가 아님.
Description
본 내용은 요부공개 건이므로 전문내용을 수록하지 않았음
Claims (9)
- (i)알킬금속을 식 CHR3X′X″의 메탄 유도체(식중 R3은 수소, 알킬, 아릴, 헤테로방향족, CO2R8, R8 3Sn, CONR8R9또는 트리메틸실릴이며, X′ 및 X″는 각각 독립적으로, 이탈 그룹임)와 반응시킴으로써 얻을 수 있는 금속탄소 (metallocarbon)이나, 또는 (ii)하기 식(Ⅲ)의 화합물을 적당한 유기금속 시약 또는 무기 시약과 반응시킴으로써 얻을 수 있는 금속탄소와, 하기 식(Ⅱ) 화합물 및 식 SR6R7의 설파이드(식중, R6및 R7은 각각 독립적으로, 알킬, 아릴 또는 헤테로방향족이거나, R6및 R7이 서로 결합하여 임의로 추가의 헤테로원자를 포함하는 싸이크로알킬 링을 형성함)혼합물을 반응시킴으로써 하기 식(I)의 옥시란, 아지리딘 또는 싸이클로프로판을 제조하는 방법.식중, X는 산소, NR4또는 CHR5이고; R1은 수소, 알킬, 아릴, 헤테로방향족, 복소환식 또는 사이클로알킬; R2는 수소,알킬, 아릴, 헤테로방향족, CO2R8, CHR14NHR13, 복소환식 또는 싸이클로알킬이거나; 또는 R1및 R2는 함께 결합하여 싸이클로알킬 링을 형성하며; R은 수소, 알킬, 아릴, 헤테로방향족, CO2R8, R8 3Sn, CONR8R9또는 트리메틸실릴; R4및 R5은 각각 독립적으로, 알킬, 싸이클로알킬, 아릴, 헤테로 방향족, SO2R8,SO3R8, COR8,CONR8R9또는 CN이거나, 또는 R4는 또한 P(O)(아릴)2일 수 있으며; R8및 R9는 각각 독립적으로 알킬, 아릴 또는 아릴알킬; R13및 R14는 각각 독립적으로, 수소, 알킬 또는 아릴임.[식중, R1,R2및 X는 상기에서 정의한 바와 같은.[식중, R3은 수소가 아님.
- 제1항에 있어서, R1이 수소인 방법.
- 제1항 또는 제2항에 있어서, a)금속탄소 (식 CHR3X′X″의 메탄 유도체와 알킬금속을 반응시켜 얻을 수 있는)를 식 SR6R7의 설파이드와 반응시키는 단계; 및 b) 상기 단계 a)의 생성물을 식(Ⅱ)의 화합물과 반응시키는 단계로 구성되는 방법.
- 제1항, 제2항 또는 제3항에 있어서, a)식 CHR3X′X″의 메탄 유도체와 알킬금속을 반응시키는 단계; b)상기 단계 a)의 생성물을 식 SR6R7의 설파이드와 반응시키는 단계; 및 c)상기 단계 b)의 생성물을 식(Ⅱ)의 화합물과 반응시키는 단계로 구성되는 방법.
- 제1항 또는 제2항에 있어서, a)금속탄소[식(Ⅲ)의 화합물 (식중, R3은 수소가 아님)을 적당한 유기금속 시약 또는 무기 시약과 반응시킴으로써 얻을 수 있는]를 식 SR6R7의 설파이드와 반응시키는 단계; 및 b) 상기 단계 a)의 생성물을 식(Ⅱ)의 화합물과 반응시키는 단계로 구성되는 방법.
- 제1항,제2항 또는 제5항에 있어서, a)식(Ⅲ)의 화합물 (식중, R3은 수소가 아님)을 적당한 유기금속 시약 또는 무기 시약과 반응시키는 단계; b) 상기 단계 a)의 생성물을 식SR6R7의 설파이드와 반응시키는 단계; 및 c)상기 단계 b)의 생성물을 식(Ⅱ)의 화합물과 반응시키는 단계로 구성되는 방법.
- 제1항,제2항 또는 제5항 또는 제6항에 있어서, 식SR6R7의 설파이드, 식(Ⅱ)의 화합물 및 유기금속 시약 또는 무기 시약의 혼합물에 식(Ⅲ)의 화합물 (식중, R3은 상기에서 정의한 바와 같으나 수소는 아님)을 가하는 것으로 구성되는 방법.
- 제7항에 있어서, 가하는 것을 2-36시간에 걸쳐 가하는 방법.
- 제7항 또는 제8항에 있어서, 설파이드가 화학량론적 양보다 적게 존재하는 방법.※ 참고사항 : 최초출원 내용에 의하여 공개하는 것임.
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| Application Number | Priority Date | Filing Date | Title |
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| GB939321803A GB9321803D0 (en) | 1993-10-22 | 1993-10-22 | Chemical process |
| GB9321803.0 | 1994-06-22 | ||
| GB9412496.3 | 1994-06-22 | ||
| GB9412496A GB9412496D0 (en) | 1994-06-22 | 1994-06-22 | Chemical process |
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| KR960704841A true KR960704841A (ko) | 1996-10-09 |
| KR100346749B1 KR100346749B1 (ko) | 2003-01-08 |
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| KR1019960701990A KR100346749B1 (ko) | 1993-10-22 | 1994-10-19 | 옥시란,아지리딘또는싸이클로프로판제조방법 |
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| US (1) | US5703246A (ko) |
| EP (1) | EP0724569B1 (ko) |
| JP (1) | JP3759950B2 (ko) |
| KR (1) | KR100346749B1 (ko) |
| AU (1) | AU7942794A (ko) |
| DE (1) | DE69432259T2 (ko) |
| WO (1) | WO1995011230A1 (ko) |
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| GB9709528D0 (en) * | 1997-05-09 | 1997-07-02 | Zeneca Ltd | Chemical process |
| JP4166056B2 (ja) * | 2002-08-16 | 2008-10-15 | 富士通株式会社 | データベース操作履歴管理装置、データベース操作履歴管理方法、およびデータベース操作履歴管理プログラム |
| US7662969B2 (en) | 2005-03-17 | 2010-02-16 | University Of Maryland, College Park | Efficient aziridination of olefins catalyzed by dirhodium catalysts |
| EP2906518A4 (en) | 2012-10-09 | 2016-07-27 | California Inst Of Techn | CYCLOPROPANATION OF OLEFIN IN VIVO AND IN VITRO CATALYZED BY ENZYMES HEMMES |
| US9399762B2 (en) | 2014-02-18 | 2016-07-26 | California Institute Of Technology | Methods and systems for sulfimidation or sulfoximidation of organic molecules |
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|---|---|---|---|---|
| EP0205400A3 (de) * | 1985-06-03 | 1987-10-14 | Ciba-Geigy Ag | Verfahren zur Herstellung von Alkyloxiranen |
| DE3901327A1 (de) * | 1989-01-18 | 1990-07-19 | Basf Ag | Verfahren zur herstellung von in 2-position z-substituierten 1-hydroxymethyl-oxiranen |
| JPH0383973A (ja) * | 1989-08-28 | 1991-04-09 | Sumitomo Pharmaceut Co Ltd | エポキシ体のスレオ選択的製造法 |
| GB9103260D0 (en) * | 1991-02-15 | 1991-04-03 | Ici Plc | Chemical process |
-
1994
- 1994-10-19 DE DE69432259T patent/DE69432259T2/de not_active Expired - Fee Related
- 1994-10-19 EP EP94930260A patent/EP0724569B1/en not_active Expired - Lifetime
- 1994-10-19 KR KR1019960701990A patent/KR100346749B1/ko not_active IP Right Cessation
- 1994-10-19 AU AU79427/94A patent/AU7942794A/en not_active Abandoned
- 1994-10-19 WO PCT/GB1994/002280 patent/WO1995011230A1/en active IP Right Grant
- 1994-10-19 JP JP51151195A patent/JP3759950B2/ja not_active Expired - Fee Related
- 1994-10-19 US US08/617,755 patent/US5703246A/en not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| KR100346749B1 (ko) | 2003-01-08 |
| DE69432259D1 (de) | 2003-04-17 |
| EP0724569B1 (en) | 2003-03-12 |
| DE69432259T2 (de) | 2003-11-06 |
| WO1995011230A1 (en) | 1995-04-27 |
| US5703246A (en) | 1997-12-30 |
| EP0724569A1 (en) | 1996-08-07 |
| AU7942794A (en) | 1995-05-08 |
| JPH09504019A (ja) | 1997-04-22 |
| JP3759950B2 (ja) | 2006-03-29 |
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