JPS58167581A - ビシクロラクトン化合物の製法 - Google Patents
ビシクロラクトン化合物の製法Info
- Publication number
- JPS58167581A JPS58167581A JP4882782A JP4882782A JPS58167581A JP S58167581 A JPS58167581 A JP S58167581A JP 4882782 A JP4882782 A JP 4882782A JP 4882782 A JP4882782 A JP 4882782A JP S58167581 A JPS58167581 A JP S58167581A
- Authority
- JP
- Japan
- Prior art keywords
- nickel carbonyl
- bicyclolactone
- formula
- cyclopropylmethanol
- derivative
- 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.)
- Granted
Links
- 238000004519 manufacturing process Methods 0.000 title claims description 4
- SQRDEVDPDGSBGC-UHFFFAOYSA-N 4,7,7-trimethyl-3-oxabicyclo[2.2.1]heptan-2-one Chemical compound C1CC2(C)OC(=O)C1C2(C)C SQRDEVDPDGSBGC-UHFFFAOYSA-N 0.000 title abstract 2
- 229910052759 nickel Inorganic materials 0.000 claims abstract description 16
- PXHVJJICTQNCMI-UHFFFAOYSA-N nickel Substances [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 claims abstract description 16
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 3
- 125000003118 aryl group Chemical group 0.000 claims abstract description 3
- 125000005843 halogen group Chemical group 0.000 claims abstract description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical class OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 7
- -1 bicyclolactone compound Chemical class 0.000 claims description 5
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 2
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims 1
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 abstract description 12
- 238000006243 chemical reaction Methods 0.000 abstract description 7
- GUDMZGLFZNLYEY-UHFFFAOYSA-N cyclopropylmethanol Chemical class OCC1CC1 GUDMZGLFZNLYEY-UHFFFAOYSA-N 0.000 abstract description 7
- 150000001875 compounds Chemical class 0.000 abstract description 5
- 239000002904 solvent Substances 0.000 abstract description 4
- 229940079593 drug Drugs 0.000 abstract description 3
- 239000003814 drug Substances 0.000 abstract description 3
- 239000000543 intermediate Substances 0.000 abstract description 2
- 239000002994 raw material Substances 0.000 abstract description 2
- QQZOPKMRPOGIEB-UHFFFAOYSA-N 2-Oxohexane Chemical compound CCCCC(C)=O QQZOPKMRPOGIEB-UHFFFAOYSA-N 0.000 abstract 2
- QQTVZURMTUWXIX-UHFFFAOYSA-N (2,2-dibromo-3,3-dimethylcyclopropyl)methanol Chemical compound CC1(C)C(CO)C1(Br)Br QQTVZURMTUWXIX-UHFFFAOYSA-N 0.000 abstract 1
- UGFAIRIUMAVXCW-UHFFFAOYSA-N Carbon monoxide Chemical compound [O+]#[C-] UGFAIRIUMAVXCW-UHFFFAOYSA-N 0.000 abstract 1
- ACIAHEMYLLBZOI-ZZXKWVIFSA-N Unsaturated alcohol Chemical compound CC\C(CO)=C/C ACIAHEMYLLBZOI-ZZXKWVIFSA-N 0.000 abstract 1
- 229910002091 carbon monoxide Inorganic materials 0.000 abstract 1
- 229910052736 halogen Inorganic materials 0.000 abstract 1
- MWUXSHHQAYIFBG-UHFFFAOYSA-N nitrogen oxide Inorganic materials O=[N] MWUXSHHQAYIFBG-UHFFFAOYSA-N 0.000 abstract 1
- 239000000126 substance Substances 0.000 abstract 1
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 21
- 238000005481 NMR spectroscopy Methods 0.000 description 5
- 229910052757 nitrogen Inorganic materials 0.000 description 5
- 238000010521 absorption reaction Methods 0.000 description 4
- 238000000862 absorption spectrum Methods 0.000 description 4
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- 238000001819 mass spectrum Methods 0.000 description 3
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- 238000003786 synthesis reaction Methods 0.000 description 3
- YEJRWHAVMIAJKC-UHFFFAOYSA-N 4-Butyrolactone Chemical compound O=C1CCCO1 YEJRWHAVMIAJKC-UHFFFAOYSA-N 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 230000007062 hydrolysis Effects 0.000 description 2
- 238000006460 hydrolysis reaction Methods 0.000 description 2
- 150000002596 lactones Chemical group 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- HCRFKZNNRFJHKW-UHFFFAOYSA-N (2,2-dimethylcyclopropyl)methanol Chemical compound CC1(C)CC1CO HCRFKZNNRFJHKW-UHFFFAOYSA-N 0.000 description 1
- GZVJRUASQZSDKH-UHFFFAOYSA-N 3-(hydroxymethyl)-2,2-dimethylcyclopropane-1-carboxylic acid Chemical compound CC1(C)C(CO)C1C(O)=O GZVJRUASQZSDKH-UHFFFAOYSA-N 0.000 description 1
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 1
- 235000007516 Chrysanthemum Nutrition 0.000 description 1
- 244000189548 Chrysanthemum x morifolium Species 0.000 description 1
- VQXSOUPNOZTNAI-UHFFFAOYSA-N Pyrethrin I Natural products CC(=CC1CC1C(=O)OC2CC(=O)C(=C2C)CC=C/C=C)C VQXSOUPNOZTNAI-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 239000003905 agrochemical Substances 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 229930188620 butyrolactone Natural products 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 229910002090 carbon oxide Inorganic materials 0.000 description 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
- JYFJNCCRKBBRKZ-UHFFFAOYSA-N chembl194764 Chemical compound C=1C=CC=C(F)C=1CCN1C(=O)C(CC)=C(C)N=C1C1=CC=CC=C1O JYFJNCCRKBBRKZ-UHFFFAOYSA-N 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 238000004440 column chromatography Methods 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- KQUICRUYRJSYKC-UHFFFAOYSA-N diphenyl(propan-2-ylidene)-$l^{4}-sulfane Chemical compound C=1C=CC=CC=1S(=C(C)C)C1=CC=CC=C1 KQUICRUYRJSYKC-UHFFFAOYSA-N 0.000 description 1
- 125000000623 heterocyclic group Chemical group 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 238000000034 method Methods 0.000 description 1
- 125000002524 organometallic group Chemical group 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 239000002243 precursor Substances 0.000 description 1
- HYJYGLGUBUDSLJ-UHFFFAOYSA-N pyrethrin Natural products CCC(=O)OC1CC(=C)C2CC3OC3(C)C2C2OC(=O)C(=C)C12 HYJYGLGUBUDSLJ-UHFFFAOYSA-N 0.000 description 1
- VJFUPGQZSXIULQ-XIGJTORUSA-N pyrethrin II Chemical compound CC1(C)[C@H](/C=C(\C)C(=O)OC)[C@H]1C(=O)O[C@@H]1C(C)=C(C\C=C/C=C)C(=O)C1 VJFUPGQZSXIULQ-XIGJTORUSA-N 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
Landscapes
- Furan Compounds (AREA)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP4882782A JPS58167581A (ja) | 1982-03-29 | 1982-03-29 | ビシクロラクトン化合物の製法 |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP4882782A JPS58167581A (ja) | 1982-03-29 | 1982-03-29 | ビシクロラクトン化合物の製法 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS58167581A true JPS58167581A (ja) | 1983-10-03 |
| JPH0316354B2 JPH0316354B2 (enrdf_load_stackoverflow) | 1991-03-05 |
Family
ID=12814057
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP4882782A Granted JPS58167581A (ja) | 1982-03-29 | 1982-03-29 | ビシクロラクトン化合物の製法 |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS58167581A (enrdf_load_stackoverflow) |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN114105859A (zh) * | 2022-01-27 | 2022-03-01 | 南京桦冠生物技术有限公司 | 一种6,6-二甲基-3-氮杂双环[3.1.0]己烷的合成方法 |
| CN114702431A (zh) * | 2022-05-10 | 2022-07-05 | 浙江江北药业有限公司 | 一种6,6-二甲基-3-氮杂双环[3.1.0]己烷的制备方法 |
| CN116396255A (zh) * | 2023-04-10 | 2023-07-07 | 西安交通大学 | 一种1,5,6-多取代-2-氧代-3-氧杂双环[3.1.0]己烷及其制备方法 |
-
1982
- 1982-03-29 JP JP4882782A patent/JPS58167581A/ja active Granted
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN114105859A (zh) * | 2022-01-27 | 2022-03-01 | 南京桦冠生物技术有限公司 | 一种6,6-二甲基-3-氮杂双环[3.1.0]己烷的合成方法 |
| CN114702431A (zh) * | 2022-05-10 | 2022-07-05 | 浙江江北药业有限公司 | 一种6,6-二甲基-3-氮杂双环[3.1.0]己烷的制备方法 |
| CN116396255A (zh) * | 2023-04-10 | 2023-07-07 | 西安交通大学 | 一种1,5,6-多取代-2-氧代-3-氧杂双环[3.1.0]己烷及其制备方法 |
Also Published As
| Publication number | Publication date |
|---|---|
| JPH0316354B2 (enrdf_load_stackoverflow) | 1991-03-05 |
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