ES2721446T3 - Método para producir un compuesto de éster del ácido ciclopropano carboxílico ópticamente activo, un complejo de cobre asimétrico y un compuesto de salicilidenoaminoalcohol ópticamente activo - Google Patents
Método para producir un compuesto de éster del ácido ciclopropano carboxílico ópticamente activo, un complejo de cobre asimétrico y un compuesto de salicilidenoaminoalcohol ópticamente activo Download PDFInfo
- Publication number
- ES2721446T3 ES2721446T3 ES09813163T ES09813163T ES2721446T3 ES 2721446 T3 ES2721446 T3 ES 2721446T3 ES 09813163 T ES09813163 T ES 09813163T ES 09813163 T ES09813163 T ES 09813163T ES 2721446 T3 ES2721446 T3 ES 2721446T3
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- Spain
- Prior art keywords
- carbon atoms
- optically active
- group
- compound
- formula
- 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.)
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- 150000001875 compounds Chemical class 0.000 title abstract 3
- -1 carboxylic acid cyclopropane ester compound Chemical class 0.000 title abstract 2
- 150000004699 copper complex Chemical class 0.000 title abstract 2
- 238000004519 manufacturing process Methods 0.000 title 1
- 125000004432 carbon atom Chemical group C* 0.000 abstract 11
- 125000000217 alkyl group Chemical group 0.000 abstract 5
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract 4
- 125000003118 aryl group Chemical group 0.000 abstract 3
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 abstract 3
- 125000003710 aryl alkyl group Chemical group 0.000 abstract 2
- 239000005749 Copper compound Substances 0.000 abstract 1
- BXEFQPCKQSTMKA-UHFFFAOYSA-N OC(=O)C=[N+]=[N-] Chemical compound OC(=O)C=[N+]=[N-] BXEFQPCKQSTMKA-UHFFFAOYSA-N 0.000 abstract 1
- 125000003545 alkoxy group Chemical group 0.000 abstract 1
- 150000001880 copper compounds Chemical class 0.000 abstract 1
- 150000002148 esters Chemical class 0.000 abstract 1
- 125000005843 halogen group Chemical group 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
- C07B53/00—Asymmetric syntheses
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C215/00—Compounds containing amino and hydroxy groups bound to the same carbon skeleton
- C07C215/02—Compounds containing amino and hydroxy groups bound to the same carbon skeleton having hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton
- C07C215/04—Compounds containing amino and hydroxy groups bound to the same carbon skeleton having hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being saturated
- C07C215/06—Compounds containing amino and hydroxy groups bound to the same carbon skeleton having hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being saturated and acyclic
- C07C215/08—Compounds containing amino and hydroxy groups bound to the same carbon skeleton having hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being saturated and acyclic with only one hydroxy group and one amino group bound to the carbon skeleton
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C251/00—Compounds containing nitrogen atoms doubly-bound to a carbon skeleton
- C07C251/02—Compounds containing nitrogen atoms doubly-bound to a carbon skeleton containing imino groups
- C07C251/24—Compounds containing nitrogen atoms doubly-bound to a carbon skeleton containing imino groups having carbon atoms of imino groups bound to carbon atoms of six-membered aromatic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C67/00—Preparation of carboxylic acid esters
- C07C67/30—Preparation of carboxylic acid esters by modifying the acid moiety of the ester, such modification not being an introduction of an ester group
- C07C67/333—Preparation of carboxylic acid esters by modifying the acid moiety of the ester, such modification not being an introduction of an ester group by isomerisation; by change of size of the carbon skeleton
- C07C67/343—Preparation of carboxylic acid esters by modifying the acid moiety of the ester, such modification not being an introduction of an ester group by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms
- C07C67/347—Preparation of carboxylic acid esters by modifying the acid moiety of the ester, such modification not being an introduction of an ester group by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms by addition to unsaturated carbon-to-carbon bonds
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
- C07C69/74—Esters of carboxylic acids having an esterified carboxyl group bound to a carbon atom of a ring other than a six-membered aromatic ring
- C07C69/757—Esters of carboxylic acids having an esterified carboxyl group bound to a carbon atom of a ring other than a six-membered aromatic ring having any of the groups OH, O—metal, —CHO, keto, ether, acyloxy, groups, groups, or in the acid moiety
-
- 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
- C07F1/08—Copper compounds
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
- C07B2200/00—Indexing scheme relating to specific properties of organic compounds
- C07B2200/07—Optical isomers
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2601/00—Systems containing only non-condensed rings
- C07C2601/02—Systems containing only non-condensed rings with a three-membered ring
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Catalysts (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Abstract
Un proceso para producir un compuesto de ester del acido ciclopropanocarboxilico opticamente activo representado por la formula (4): **(Ver fórmula)** (en la que R5, R6 y * representan cada uno el mismo significado que se define mas adelante), que comprende hacer reaccionar un ester del acido diazoacetico representado por la formula (2): N2CHCO2R5 (2) (en la que R5 representa un grupo alquilo que tiene de 1 a 15 atomos de carbono o un grupo arilo que tiene de 6 a 10 atomos de carbono) con un compuesto representado por la formula (3): **(Ver fórmula)** (en la que R6 representa un grupo alquilo que tiene de 1 a 15 atomos de carbono, un grupo arilo que tiene de 6 a 10 atomos de carbono o un grupo aralquilo que tiene de 7 a 20 atomos de carbono), en presencia de un complejo de cobre asimetrico obtenible haciendo reaccionar un compuesto de cobre y un compuesto de salicilidenoaminoalcohol opticamente activo representado por la formula (1): **(Ver fórmula)** (en la que (a) R1 representa un grupo alquilo que tiene de 2 a 4 atomos de carbono, un grupo arilo que tiene de 6 a 10 atomos de carbono o un grupo aralquilo que tiene de 7 a 20 atomos de carbono, R2 representa un atomo de hidrogeno, un grupo alquilo que tiene de 1 a 4 atomos de carbono o un grupo alcoxi que tiene de 1 a 10 atomos de carbono, R3 representa un atomo de hidrogeno o un grupo nitro o halogeno y R4 representa un grupo nitro o (b) R1 representa un grupo alquilo que tiene de 2 a 4 atomos de carbono, R2 representa un atomo de hidrogeno, R3 representa un grupo nitro y R4 representa un atomo de hidrogeno y * representa un centro asimetrico).
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP2008231921 | 2008-09-10 | ||
PCT/JP2009/065973 WO2010030017A1 (ja) | 2008-09-10 | 2009-09-07 | 光学活性シクロプロパンカルボン酸エステル化合物の製造方法、不斉銅錯体および光学活性サリチリデンアミノアルコール化合物 |
Publications (1)
Publication Number | Publication Date |
---|---|
ES2721446T3 true ES2721446T3 (es) | 2019-07-31 |
Family
ID=42005267
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
ES09813163T Active ES2721446T3 (es) | 2008-09-10 | 2009-09-07 | Método para producir un compuesto de éster del ácido ciclopropano carboxílico ópticamente activo, un complejo de cobre asimétrico y un compuesto de salicilidenoaminoalcohol ópticamente activo |
Country Status (11)
Country | Link |
---|---|
US (1) | US8680328B2 (es) |
EP (1) | EP2341042B1 (es) |
JP (1) | JP2010090115A (es) |
KR (1) | KR20110058874A (es) |
CN (1) | CN102216251B (es) |
AU (1) | AU2009292470B2 (es) |
ES (1) | ES2721446T3 (es) |
IL (1) | IL211613A (es) |
PT (1) | PT2341042T (es) |
SG (1) | SG193207A1 (es) |
WO (1) | WO2010030017A1 (es) |
Families Citing this family (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2008050661A1 (fr) * | 2006-10-26 | 2008-05-02 | Sumitomo Chemical Company, Limited | Procédé servant à produire un cristal de complexe asymétrique du cuivre |
FR3079237A1 (fr) * | 2018-03-20 | 2019-09-27 | Commissariat A L'energie Atomique Et Aux Energies Alternatives | Particules inorganiques greffees par des composes organiques specifiques presentant des proprietes de protection contre les rayons uv |
WO2020118307A1 (en) * | 2018-12-07 | 2020-06-11 | The Regents Of The Univefisity Of California | Fluorous metal chelates compositions |
Family Cites Families (11)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPS59225194A (ja) * | 1983-06-03 | 1984-12-18 | Sumitomo Chem Co Ltd | 新規不斉銅錯体ならびに同錯体を触媒とするシクロプロパンカルボン酸エステルの不斉合成法 |
JP2003012675A (ja) | 2001-04-27 | 2003-01-15 | Sumitomo Chem Co Ltd | 不斉銅錯体、その製造方法および不斉銅錯体を用いる光学活性シクロプロパン化合物の製造方法 |
ATE489356T1 (de) | 2001-04-27 | 2010-12-15 | Sumitomo Chemical Co | Asymmetrischer kupferkomplex und dessen verwendung in cyclopropanierungsreaktion |
JP4093550B2 (ja) | 2002-07-17 | 2008-06-04 | 住友化学株式会社 | 光学活性シクロプロパンカルボン酸エステル類の製造方法 |
BRPI0408971A (pt) | 2003-03-31 | 2006-04-04 | Sumitomo Chemical Co | composição de catalisador de cobre opticamente ativo |
US7612227B2 (en) | 2004-03-25 | 2009-11-03 | Sumitomo Chemical Company, Limited | Processes for producing 3-methyl-2-butenyl acetate |
ZA200700028B (en) * | 2004-07-01 | 2008-05-28 | Sumitomo Chemical Co | Method for producing optically active cyclopropaneca boxylate compound |
JP5002916B2 (ja) * | 2004-07-01 | 2012-08-15 | 住友化学株式会社 | 不斉銅錯体およびそれを用いた光学活性なシクロプロパンカルボン酸エステル化合物の製造方法 |
JP2006045190A (ja) | 2004-07-02 | 2006-02-16 | Sumitomo Chemical Co Ltd | 酢酸3−メチル−2−ブテニルの製造方法 |
US7928253B2 (en) | 2005-11-01 | 2011-04-19 | Sumitomo Chemical Company, Limited | Method of producing 6,6-dimethyl-3-oxabicyclo[3.1.0]hexan-2-one |
JP5082382B2 (ja) | 2005-11-01 | 2012-11-28 | 住友化学株式会社 | 6,6−ジメチル−3−オキサビシクロ[3.1.0]ヘキサン−2−オンの製造法 |
-
2009
- 2009-09-07 EP EP09813163.4A patent/EP2341042B1/en active Active
- 2009-09-07 WO PCT/JP2009/065973 patent/WO2010030017A1/ja active Application Filing
- 2009-09-07 US US13/062,288 patent/US8680328B2/en not_active Expired - Fee Related
- 2009-09-07 KR KR1020117008033A patent/KR20110058874A/ko not_active Application Discontinuation
- 2009-09-07 PT PT09813163T patent/PT2341042T/pt unknown
- 2009-09-07 SG SG2013061718A patent/SG193207A1/en unknown
- 2009-09-07 AU AU2009292470A patent/AU2009292470B2/en not_active Ceased
- 2009-09-07 ES ES09813163T patent/ES2721446T3/es active Active
- 2009-09-07 CN CN200980143493.1A patent/CN102216251B/zh active Active
- 2009-09-08 JP JP2009206770A patent/JP2010090115A/ja active Pending
-
2011
- 2011-03-07 IL IL211613A patent/IL211613A/en active IP Right Grant
Also Published As
Publication number | Publication date |
---|---|
IL211613A0 (en) | 2011-05-31 |
KR20110058874A (ko) | 2011-06-01 |
EP2341042B1 (en) | 2019-03-20 |
JP2010090115A (ja) | 2010-04-22 |
CN102216251B (zh) | 2014-08-27 |
IL211613A (en) | 2014-09-30 |
US20110166372A1 (en) | 2011-07-07 |
AU2009292470A1 (en) | 2010-03-18 |
US8680328B2 (en) | 2014-03-25 |
WO2010030017A1 (ja) | 2010-03-18 |
AU2009292470B2 (en) | 2014-01-16 |
EP2341042A1 (en) | 2011-07-06 |
SG193207A1 (en) | 2013-09-30 |
EP2341042A4 (en) | 2013-05-22 |
PT2341042T (pt) | 2019-05-21 |
CN102216251A (zh) | 2011-10-12 |
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