JPS6187677A - ブチロラクトン誘導体の製造方法 - Google Patents
ブチロラクトン誘導体の製造方法Info
- Publication number
- JPS6187677A JPS6187677A JP20989484A JP20989484A JPS6187677A JP S6187677 A JPS6187677 A JP S6187677A JP 20989484 A JP20989484 A JP 20989484A JP 20989484 A JP20989484 A JP 20989484A JP S6187677 A JPS6187677 A JP S6187677A
- Authority
- JP
- Japan
- Prior art keywords
- solvent
- trifluoroethanol
- hydrogen peroxide
- formula
- main component
- 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 6
- NSXYYYUKWBLFQH-MHECFPHRSA-N methyl (2r)-4-hydroxy-2-[[(3s)-3-hydroxy-2,2-dimethyl-3,4-dihydrochromen-6-yl]methyl]-3-(4-hydroxyphenyl)-5-oxofuran-2-carboxylate Chemical compound O([C@@]1(CC=2C=C3C[C@H](O)C(C)(C)OC3=CC=2)C(=O)OC)C(=O)C(O)=C1C1=CC=C(O)C=C1 NSXYYYUKWBLFQH-MHECFPHRSA-N 0.000 title description 2
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 claims abstract description 23
- 239000002904 solvent Substances 0.000 claims abstract description 12
- RHQDFWAXVIIEBN-UHFFFAOYSA-N Trifluoroethanol Chemical compound OCC(F)(F)F RHQDFWAXVIIEBN-UHFFFAOYSA-N 0.000 claims abstract description 9
- SHQSVMDWKBRBGB-UHFFFAOYSA-N cyclobutanone Chemical class O=C1CCC1 SHQSVMDWKBRBGB-UHFFFAOYSA-N 0.000 claims abstract description 7
- 125000003342 alkenyl group Chemical group 0.000 claims abstract description 3
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 3
- 125000003118 aryl group Chemical group 0.000 claims abstract description 3
- 229910052799 carbon Inorganic materials 0.000 claims abstract description 3
- 230000001590 oxidative effect Effects 0.000 claims abstract description 3
- 239000000126 substance Substances 0.000 claims abstract 3
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims abstract 2
- YEJRWHAVMIAJKC-UHFFFAOYSA-N 4-Butyrolactone Chemical class O=C1CCCO1 YEJRWHAVMIAJKC-UHFFFAOYSA-N 0.000 claims description 6
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 2
- 238000006243 chemical reaction Methods 0.000 abstract description 8
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 abstract description 6
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 abstract description 4
- 150000001875 compounds Chemical class 0.000 abstract description 3
- 150000003180 prostaglandins Chemical class 0.000 abstract description 2
- 239000002994 raw material Substances 0.000 abstract description 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 abstract description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 abstract 2
- 230000002194 synthesizing effect Effects 0.000 abstract 1
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 9
- 239000000047 product Substances 0.000 description 5
- STICKWIUXCNKRE-UHFFFAOYSA-N oct-6-en-3-one Chemical compound CCC(=O)CCC=CC STICKWIUXCNKRE-UHFFFAOYSA-N 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- -1 bicyclic butyrolactones Chemical class 0.000 description 3
- 229930188620 butyrolactone Natural products 0.000 description 3
- 239000004020 conductor Substances 0.000 description 3
- XYRFGFRTVXZAIU-UHFFFAOYSA-N 1,3a,4,6a-tetrahydrocyclopenta[c]furan-3-one Chemical compound C1=CCC2C(=O)OCC21 XYRFGFRTVXZAIU-UHFFFAOYSA-N 0.000 description 2
- RYBPGUMSFWGGLP-UHFFFAOYSA-N 3,3a,6,6a-tetrahydrocyclopenta[b]furan-2-one Chemical compound C1=CCC2OC(=O)CC21 RYBPGUMSFWGGLP-UHFFFAOYSA-N 0.000 description 2
- MTNPITXJKLMSKU-UHFFFAOYSA-N 3a,6,7,7a-tetrahydro-3h-1-benzofuran-2-one Chemical compound C1=CCCC2OC(=O)CC21 MTNPITXJKLMSKU-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 2
- 238000007796 conventional method Methods 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- 230000003595 spectral effect Effects 0.000 description 2
- 235000021419 vinegar Nutrition 0.000 description 2
- 239000000052 vinegar Substances 0.000 description 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- TVWWMKZMZALOFP-UHFFFAOYSA-N 2,2-dichloroethenone Chemical compound ClC(Cl)=C=O TVWWMKZMZALOFP-UHFFFAOYSA-N 0.000 description 1
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 1
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 1
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 230000004913 activation Effects 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 150000001336 alkenes Chemical class 0.000 description 1
- 230000000844 anti-bacterial effect Effects 0.000 description 1
- 230000001093 anti-cancer Effects 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- LNLLHUHPGPKRBM-UHFFFAOYSA-N bicyclo[3.2.0]hept-3-en-7-one Chemical compound C1=CCC2C(=O)CC21 LNLLHUHPGPKRBM-UHFFFAOYSA-N 0.000 description 1
- JKLZCTYQZFXPSW-UHFFFAOYSA-N bicyclo[4.2.0]oct-4-en-8-one Chemical compound C1=CCCC2C(=O)CC21 JKLZCTYQZFXPSW-UHFFFAOYSA-N 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 150000001721 carbon Chemical class 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 238000004440 column chromatography Methods 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- ZKQFHRVKCYFVCN-UHFFFAOYSA-N ethoxyethane;hexane Chemical compound CCOCC.CCCCCC ZKQFHRVKCYFVCN-UHFFFAOYSA-N 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 210000004709 eyebrow Anatomy 0.000 description 1
- 239000003205 fragrance Substances 0.000 description 1
- 150000008282 halocarbons Chemical class 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000005457 ice water Substances 0.000 description 1
- 239000000411 inducer Substances 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 238000011835 investigation Methods 0.000 description 1
- 210000003734 kidney Anatomy 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- 238000000034 method Methods 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 1
- 229940094443 oxytocics prostaglandins Drugs 0.000 description 1
- 150000002978 peroxides Chemical class 0.000 description 1
- 150000004965 peroxy acids Chemical class 0.000 description 1
- 230000001766 physiological effect Effects 0.000 description 1
- 230000001376 precipitating effect Effects 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 239000008399 tap water Substances 0.000 description 1
- 235000020679 tap water Nutrition 0.000 description 1
- 230000002747 voluntary effect Effects 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
Landscapes
- Furan Compounds (AREA)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP20989484A JPS6187677A (ja) | 1984-10-08 | 1984-10-08 | ブチロラクトン誘導体の製造方法 |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP20989484A JPS6187677A (ja) | 1984-10-08 | 1984-10-08 | ブチロラクトン誘導体の製造方法 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS6187677A true JPS6187677A (ja) | 1986-05-06 |
| JPH0417192B2 JPH0417192B2 (enrdf_load_stackoverflow) | 1992-03-25 |
Family
ID=16580406
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP20989484A Granted JPS6187677A (ja) | 1984-10-08 | 1984-10-08 | ブチロラクトン誘導体の製造方法 |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS6187677A (enrdf_load_stackoverflow) |
-
1984
- 1984-10-08 JP JP20989484A patent/JPS6187677A/ja active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| JPH0417192B2 (enrdf_load_stackoverflow) | 1992-03-25 |
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