JPS5838414B2 - シクロペンテノロン ノ ブンカツホウ - Google Patents
シクロペンテノロン ノ ブンカツホウInfo
- Publication number
- JPS5838414B2 JPS5838414B2 JP47129476A JP12947672A JPS5838414B2 JP S5838414 B2 JPS5838414 B2 JP S5838414B2 JP 47129476 A JP47129476 A JP 47129476A JP 12947672 A JP12947672 A JP 12947672A JP S5838414 B2 JPS5838414 B2 JP S5838414B2
- Authority
- JP
- Japan
- Prior art keywords
- ester
- arethrolone
- allethrone
- acid
- ephedrin
- 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
- 150000002148 esters Chemical class 0.000 claims description 43
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 33
- 239000002253 acid Substances 0.000 claims description 29
- 238000000034 method Methods 0.000 claims description 20
- KDYFGRWQOYBRFD-UHFFFAOYSA-N succinic acid Chemical compound OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 claims description 10
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 9
- KWGRBVOPPLSCSI-WPRPVWTQSA-N (-)-ephedrine Chemical class CN[C@@H](C)[C@H](O)C1=CC=CC=C1 KWGRBVOPPLSCSI-WPRPVWTQSA-N 0.000 claims description 7
- 229960002179 ephedrine Drugs 0.000 claims description 7
- 150000003839 salts Chemical class 0.000 claims description 5
- 239000001384 succinic acid Substances 0.000 claims description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 15
- 241000723353 Chrysanthemum Species 0.000 description 7
- 235000007516 Chrysanthemum Nutrition 0.000 description 7
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 6
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 5
- 241000238631 Hexapoda Species 0.000 description 5
- 238000003756 stirring Methods 0.000 description 5
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
- 238000004458 analytical method Methods 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- 150000007659 semicarbazones Chemical class 0.000 description 4
- 229940126062 Compound A Drugs 0.000 description 3
- NLDMNSXOCDLTTB-UHFFFAOYSA-N Heterophylliin A Natural products O1C2COC(=O)C3=CC(O)=C(O)C(O)=C3C3=C(O)C(O)=C(O)C=C3C(=O)OC2C(OC(=O)C=2C=C(O)C(O)=C(O)C=2)C(O)C1OC(=O)C1=CC(O)=C(O)C(O)=C1 NLDMNSXOCDLTTB-UHFFFAOYSA-N 0.000 description 3
- 150000008064 anhydrides Chemical class 0.000 description 3
- 238000004364 calculation method Methods 0.000 description 3
- 150000001875 compounds Chemical class 0.000 description 3
- 238000002425 crystallisation Methods 0.000 description 3
- 230000008025 crystallization Effects 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 238000005259 measurement Methods 0.000 description 3
- 239000012071 phase Substances 0.000 description 3
- 238000000926 separation method Methods 0.000 description 3
- FALRKNHUBBKYCC-UHFFFAOYSA-N 2-(chloromethyl)pyridine-3-carbonitrile Chemical compound ClCC1=NC=CC=C1C#N FALRKNHUBBKYCC-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- LOUPRKONTZGTKE-WZBLMQSHSA-N Quinine Chemical compound C([C@H]([C@H](C1)C=C)C2)C[N@@]1[C@@H]2[C@H](O)C1=CC=NC2=CC=C(OC)C=C21 LOUPRKONTZGTKE-WZBLMQSHSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 230000007062 hydrolysis Effects 0.000 description 2
- 238000006460 hydrolysis reaction Methods 0.000 description 2
- 230000003301 hydrolyzing effect Effects 0.000 description 2
- 230000000749 insecticidal effect Effects 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 229940014800 succinic anhydride Drugs 0.000 description 2
- 238000005292 vacuum distillation Methods 0.000 description 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- 241000424000 Berberomeloe majalis Species 0.000 description 1
- 235000001258 Cinchona calisaya Nutrition 0.000 description 1
- BZKFMUIJRXWWQK-UHFFFAOYSA-N Cyclopentenone Chemical compound O=C1CCC=C1 BZKFMUIJRXWWQK-UHFFFAOYSA-N 0.000 description 1
- 241000257226 Muscidae Species 0.000 description 1
- 238000005904 alkaline hydrolysis reaction Methods 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- RRKTZKIUPZVBMF-IBTVXLQLSA-N brucine Chemical compound O([C@@H]1[C@H]([C@H]2C3)[C@@H]4N(C(C1)=O)C=1C=C(C(=CC=11)OC)OC)CC=C2CN2[C@@H]3[C@]41CC2 RRKTZKIUPZVBMF-IBTVXLQLSA-N 0.000 description 1
- RRKTZKIUPZVBMF-UHFFFAOYSA-N brucine Natural products C1=2C=C(OC)C(OC)=CC=2N(C(C2)=O)C3C(C4C5)C2OCC=C4CN2C5C31CC2 RRKTZKIUPZVBMF-UHFFFAOYSA-N 0.000 description 1
- KDYFGRWQOYBRFD-NUQCWPJISA-N butanedioic acid Chemical class O[14C](=O)CC[14C](O)=O KDYFGRWQOYBRFD-NUQCWPJISA-N 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 210000000038 chest Anatomy 0.000 description 1
- LOUPRKONTZGTKE-UHFFFAOYSA-N cinchonine Natural products C1C(C(C2)C=C)CCN2C1C(O)C1=CC=NC2=CC=C(OC)C=C21 LOUPRKONTZGTKE-UHFFFAOYSA-N 0.000 description 1
- 238000002983 circular dichroism Methods 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 239000012141 concentrate Substances 0.000 description 1
- KWGRBVOPPLSCSI-UHFFFAOYSA-N d-ephedrine Natural products CNC(C)C(O)C1=CC=CC=C1 KWGRBVOPPLSCSI-UHFFFAOYSA-N 0.000 description 1
- 238000010908 decantation Methods 0.000 description 1
- 239000000539 dimer Substances 0.000 description 1
- 235000013305 food Nutrition 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 239000002917 insecticide Substances 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- 239000003350 kerosene Substances 0.000 description 1
- 230000001665 lethal effect Effects 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 229960000948 quinine Drugs 0.000 description 1
- 238000007127 saponification reaction Methods 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 230000000699 topical effect Effects 0.000 description 1
- 238000002211 ultraviolet spectrum Methods 0.000 description 1
Classifications
-
- 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
-
- 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
- C07C49/707—Unsaturated compounds containing a keto groups being part of a ring containing hydroxy groups a keto group being part of a three- to five-membered ring
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR7146981A FR2166503A5 (de) | 1971-12-28 | 1971-12-28 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS4875545A JPS4875545A (de) | 1973-10-11 |
| JPS5838414B2 true JPS5838414B2 (ja) | 1983-08-23 |
Family
ID=9088218
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP47129476A Expired JPS5838414B2 (ja) | 1971-12-28 | 1972-12-25 | シクロペンテノロン ノ ブンカツホウ |
Country Status (19)
| Country | Link |
|---|---|
| JP (1) | JPS5838414B2 (de) |
| AU (1) | AU463657B2 (de) |
| BE (1) | BE793190A (de) |
| BR (1) | BR7209164D0 (de) |
| CA (1) | CA998402A (de) |
| CH (1) | CH560662A5 (de) |
| DD (1) | DD102139A5 (de) |
| DE (1) | DE2263880C3 (de) |
| DK (1) | DK139384B (de) |
| ES (1) | ES410060A1 (de) |
| FR (1) | FR2166503A5 (de) |
| GB (1) | GB1401350A (de) |
| HU (1) | HU167951B (de) |
| IL (1) | IL41030A (de) |
| IT (1) | IT974312B (de) |
| NL (1) | NL179812C (de) |
| SE (1) | SE396376B (de) |
| SU (1) | SU577966A3 (de) |
| ZA (1) | ZA728905B (de) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS62175907U (de) * | 1986-04-28 | 1987-11-09 |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3931291A (en) * | 1973-03-28 | 1976-01-06 | Sumitomo Chemical Company, Limited | Preparation of optically active allethrorone via allethronyl acid phthalate |
| FR2458531A1 (fr) * | 1979-06-12 | 1981-01-02 | Roussel Uclaf | Procede de preparation d'allethrolone optiquement active par scission d'un ester d'acide chiral d'allethrolone optiquement active a l'aide d'un halogenure de bore |
| EP0122779B1 (de) * | 1983-04-19 | 1986-07-23 | Sumitomo Chemical Company, Limited | Herstellung von optisch aktiven Cyclopentenolonen |
-
0
- BE BE793190D patent/BE793190A/xx not_active IP Right Cessation
-
1971
- 1971-12-28 FR FR7146981A patent/FR2166503A5/fr not_active Expired
-
1972
- 1972-12-07 IL IL41030A patent/IL41030A/xx unknown
- 1972-12-15 CH CH1836172A patent/CH560662A5/xx not_active IP Right Cessation
- 1972-12-18 ZA ZA728905A patent/ZA728905B/xx unknown
- 1972-12-25 JP JP47129476A patent/JPS5838414B2/ja not_active Expired
- 1972-12-27 SE SE7217008A patent/SE396376B/xx unknown
- 1972-12-27 SU SU7201862815A patent/SU577966A3/ru active
- 1972-12-27 HU HURO690A patent/HU167951B/hu not_active IP Right Cessation
- 1972-12-27 BR BR9164/72A patent/BR7209164D0/pt unknown
- 1972-12-27 CA CA159,984A patent/CA998402A/fr not_active Expired
- 1972-12-27 IT IT55020/72A patent/IT974312B/it active
- 1972-12-27 ES ES410060A patent/ES410060A1/es not_active Expired
- 1972-12-28 DD DD167952A patent/DD102139A5/xx unknown
- 1972-12-28 DK DK650172AA patent/DK139384B/da unknown
- 1972-12-28 AU AU50551/72A patent/AU463657B2/en not_active Expired
- 1972-12-28 GB GB5988272A patent/GB1401350A/en not_active Expired
- 1972-12-28 NL NLAANVRAGE7217763,A patent/NL179812C/xx not_active IP Right Cessation
- 1972-12-28 DE DE2263880A patent/DE2263880C3/de not_active Expired
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS62175907U (de) * | 1986-04-28 | 1987-11-09 |
Also Published As
| Publication number | Publication date |
|---|---|
| BR7209164D0 (pt) | 1973-09-13 |
| CH560662A5 (de) | 1975-04-15 |
| BE793190A (fr) | 1973-06-22 |
| NL179812C (nl) | 1986-11-17 |
| DE2263880C3 (de) | 1979-06-28 |
| HU167951B (de) | 1976-01-28 |
| JPS4875545A (de) | 1973-10-11 |
| NL7217763A (de) | 1973-07-02 |
| SE396376B (sv) | 1977-09-19 |
| AU5055172A (en) | 1974-07-04 |
| DE2263880A1 (de) | 1973-07-05 |
| DE2263880B2 (de) | 1978-11-02 |
| CA998402A (fr) | 1976-10-12 |
| AU463657B2 (en) | 1975-07-15 |
| NL179812B (nl) | 1986-06-16 |
| IT974312B (it) | 1974-06-20 |
| IL41030A (en) | 1975-06-25 |
| DD102139A5 (de) | 1973-12-05 |
| DK139384B (da) | 1979-02-12 |
| SU577966A3 (ru) | 1977-10-25 |
| ZA728905B (en) | 1974-02-27 |
| IL41030A0 (en) | 1973-02-28 |
| FR2166503A5 (de) | 1973-08-17 |
| GB1401350A (en) | 1975-07-16 |
| DK139384C (de) | 1979-07-23 |
| ES410060A1 (es) | 1976-01-01 |
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