GB1499094A - Asymmetric synthesis of alkyl chrysanthemate - Google Patents
Asymmetric synthesis of alkyl chrysanthemateInfo
- Publication number
- GB1499094A GB1499094A GB31985/76A GB3198576A GB1499094A GB 1499094 A GB1499094 A GB 1499094A GB 31985/76 A GB31985/76 A GB 31985/76A GB 3198576 A GB3198576 A GB 3198576A GB 1499094 A GB1499094 A GB 1499094A
- Authority
- GB
- United Kingdom
- Prior art keywords
- asymmetric synthesis
- formula
- alkyl
- catalyst
- isomers
- 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.)
- Expired
Links
- 125000000217 alkyl group Chemical group 0.000 title abstract 2
- 238000011914 asymmetric synthesis Methods 0.000 title 1
- 239000003054 catalyst Substances 0.000 abstract 2
- DZPCYXCBXGQBRN-UHFFFAOYSA-N 2,5-Dimethyl-2,4-hexadiene Chemical compound CC(C)=CC=C(C)C DZPCYXCBXGQBRN-UHFFFAOYSA-N 0.000 abstract 1
- 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 1
- 239000002262 Schiff base Substances 0.000 abstract 1
- 150000004753 Schiff bases Chemical class 0.000 abstract 1
- 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
- XLOPRKKSAJMMEW-UHFFFAOYSA-N chrysanthemic acid Chemical class CC(C)=CC1C(C(O)=O)C1(C)C XLOPRKKSAJMMEW-UHFFFAOYSA-N 0.000 abstract 1
- 150000004699 copper complex Chemical class 0.000 abstract 1
- -1 diazo acetate Chemical compound 0.000 abstract 1
- 230000003287 optical effect Effects 0.000 abstract 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)
Abstract
2,5-Dimethyl-2,4-hexadiene is reacted with a diazo acetate of the formula N2CHCOOR (V> in the presence of a catalyst. The catalyst used is a copper complex of a chiral Schiff base of the formula: <IMAGE> In the formulae, R, R<1>, R<2>, X<1>, X<2> and C<*> have the meanings given in Patent Claim 1. The optically active alkyl chrysanthemates thus prepared can be hydrolysed to give the corresponding optical isomers of chrysanthemic acid. These isomers can be used for the preparation of synthetic, insecticidally active pyrethroids.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP50094349A JPS5910336B2 (en) | 1975-08-01 | 1975-08-01 | Asymmetric synthesis method of primary chrysanthemum acid ester |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1499094A true GB1499094A (en) | 1978-01-25 |
Family
ID=14107796
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB31985/76A Expired GB1499094A (en) | 1975-08-01 | 1976-07-30 | Asymmetric synthesis of alkyl chrysanthemate |
Country Status (12)
| Country | Link |
|---|---|
| JP (1) | JPS5910336B2 (en) |
| BE (1) | BE844631A (en) |
| CA (1) | CA1121813A (en) |
| CH (1) | CH621767A5 (en) |
| DE (1) | DE2634663C3 (en) |
| DK (1) | DK142765B (en) |
| FR (1) | FR2319623A1 (en) |
| GB (1) | GB1499094A (en) |
| IL (1) | IL50100A (en) |
| IT (1) | IT1070323B (en) |
| NL (1) | NL7608508A (en) |
| SU (1) | SU719491A3 (en) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4350811A (en) | 1979-07-13 | 1982-09-21 | Imperial Chemical Industries Limited | Chiral sugar complexes |
| US4383112A (en) | 1979-07-13 | 1983-05-10 | Imperial Chemical Industries Limited | Chiral amino-alcohol complexes |
Families Citing this family (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2919820A1 (en) | 1979-05-16 | 1980-11-20 | Bayer Ag | FLUOR-SUBSTITUTED OXYALKENYL-CYCLOPROPANCARBONIC ACID ESTERS, METHODS FOR THE PRODUCTION THEREOF AND THEIR USE AS INSECTICIDES AND ACARICIDES |
| DE3064018D1 (en) * | 1979-07-13 | 1983-08-11 | Ici Plc | Process for the preparation of cyclopropane carboxylic acid esters |
| EP0023075A1 (en) * | 1979-07-13 | 1981-01-28 | Imperial Chemical Industries 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 (en) * | 1983-02-28 | 1984-09-07 | Seikei Giken:Kk | Vacuum transfer apparatus |
| JPS59158261A (en) * | 1983-07-19 | 1984-09-07 | Seikei Giken:Kk | Transfer apparatus |
| JPH01232619A (en) * | 1988-03-11 | 1989-09-18 | Toska Co Ltd | Printing method for key top |
| JPH0671852A (en) * | 1992-08-31 | 1994-03-15 | Shizuoka Giken Sanki Kk | Method and device for subjecting curved surface to heat transfer by vacuum press |
| JP4576642B2 (en) * | 1998-01-29 | 2010-11-10 | 住友化学株式会社 | Process for producing optically active chrysanthemic acid |
| ITMI20041211A1 (en) * | 2004-06-16 | 2004-09-16 | Endura Spa | METAL COMPLEX-BASED CATALYSTS FOR THE SYNTHESIS OF OPTICALLY ACTIVE CHRYSANTHEMIC ACID |
| CN103789789B (en) * | 2014-02-11 | 2016-06-29 | 华东师范大学 | Electrochemical synthesis has the method for optically active Styrene carbonate |
| CN103789791B (en) * | 2014-02-12 | 2016-08-17 | 华东师范大学 | A kind of electrochemical synthesis has optically active 2-benzenpropanoic acid method |
Family Cites Families (1)
| 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/en not_active Expired
-
1976
- 1976-07-22 IL IL50100A patent/IL50100A/en unknown
- 1976-07-28 BE BE6045627A patent/BE844631A/en not_active IP Right Cessation
- 1976-07-30 SU SU762387252A patent/SU719491A3/en active
- 1976-07-30 CA CA000258220A patent/CA1121813A/en not_active Expired
- 1976-07-30 CH CH977576A patent/CH621767A5/en not_active IP Right Cessation
- 1976-07-30 FR FR7623388A patent/FR2319623A1/en active Granted
- 1976-07-30 IT IT68927/76A patent/IT1070323B/en active
- 1976-07-30 NL NL7608508A patent/NL7608508A/en not_active Application Discontinuation
- 1976-07-30 DK DK345276AA patent/DK142765B/en not_active IP Right Cessation
- 1976-07-30 GB GB31985/76A patent/GB1499094A/en not_active Expired
- 1976-08-02 DE DE2634663A patent/DE2634663C3/en not_active Expired
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4350811A (en) | 1979-07-13 | 1982-09-21 | Imperial Chemical Industries Limited | Chiral sugar complexes |
| US4383112A (en) | 1979-07-13 | 1983-05-10 | Imperial Chemical Industries Limited | Chiral amino-alcohol complexes |
Also Published As
| Publication number | Publication date |
|---|---|
| DE2634663A1 (en) | 1977-03-17 |
| DK142765B (en) | 1981-01-19 |
| JPS5910336B2 (en) | 1984-03-08 |
| IL50100A0 (en) | 1976-09-30 |
| IL50100A (en) | 1982-02-28 |
| FR2319623A1 (en) | 1977-02-25 |
| IT1070323B (en) | 1985-03-29 |
| DK345276A (en) | 1977-02-02 |
| DE2634663C3 (en) | 1980-01-17 |
| CA1121813A (en) | 1982-04-13 |
| JPS5217448A (en) | 1977-02-09 |
| DK142765C (en) | 1981-08-17 |
| SU719491A3 (en) | 1980-02-29 |
| NL7608508A (en) | 1977-02-03 |
| FR2319623B1 (en) | 1979-09-28 |
| CH621767A5 (en) | 1981-02-27 |
| BE844631A (en) | 1976-11-16 |
| DE2634663B2 (en) | 1979-05-31 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PS | Patent sealed [section 19, patents act 1949] | ||
| PCNP | Patent ceased through non-payment of renewal fee |