JPH0513144B2 - - Google Patents
Info
- Publication number
- JPH0513144B2 JPH0513144B2 JP16401884A JP16401884A JPH0513144B2 JP H0513144 B2 JPH0513144 B2 JP H0513144B2 JP 16401884 A JP16401884 A JP 16401884A JP 16401884 A JP16401884 A JP 16401884A JP H0513144 B2 JPH0513144 B2 JP H0513144B2
- Authority
- JP
- Japan
- Prior art keywords
- cyclopentenone
- hydroxy
- nitric acid
- nitrate ester
- reaction
- 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 - Lifetime
Links
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 claims description 15
- BZKFMUIJRXWWQK-UHFFFAOYSA-N Cyclopentenone Chemical compound O=C1CCC=C1 BZKFMUIJRXWWQK-UHFFFAOYSA-N 0.000 claims description 14
- -1 Nitrate ester Chemical class 0.000 claims description 14
- 229910017604 nitric acid Inorganic materials 0.000 claims description 12
- DHNDDRBMUVFQIZ-UHFFFAOYSA-N 4-hydroxycyclopent-2-en-1-one Chemical compound OC1CC(=O)C=C1 DHNDDRBMUVFQIZ-UHFFFAOYSA-N 0.000 claims description 11
- 229910002651 NO3 Inorganic materials 0.000 claims description 7
- 238000004519 manufacturing process Methods 0.000 claims description 4
- 239000013543 active substance Substances 0.000 claims 1
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 12
- 238000006243 chemical reaction Methods 0.000 description 10
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- 230000003287 optical effect Effects 0.000 description 6
- 239000002904 solvent Substances 0.000 description 6
- 150000003180 prostaglandins Chemical class 0.000 description 5
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 239000012024 dehydrating agents Substances 0.000 description 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 238000009833 condensation Methods 0.000 description 2
- 230000005494 condensation Effects 0.000 description 2
- 230000018044 dehydration Effects 0.000 description 2
- 238000006297 dehydration reaction Methods 0.000 description 2
- 150000002148 esters Chemical class 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 239000012044 organic layer Substances 0.000 description 2
- 239000002994 raw material Substances 0.000 description 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- WOPKYMRPOKFYNI-UHFFFAOYSA-N 2-hydroxycyclopent-2-en-1-one Chemical compound OC1=CCCC1=O WOPKYMRPOKFYNI-UHFFFAOYSA-N 0.000 description 1
- 239000003905 agrochemical Substances 0.000 description 1
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- OAMZXMDZZWGPMH-UHFFFAOYSA-N ethyl acetate;toluene Chemical compound CCOC(C)=O.CC1=CC=CC=C1 OAMZXMDZZWGPMH-UHFFFAOYSA-N 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 150000008282 halocarbons Chemical class 0.000 description 1
- 230000003301 hydrolyzing effect Effects 0.000 description 1
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 1
- 235000019341 magnesium sulphate Nutrition 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 229930014626 natural product Natural products 0.000 description 1
- WYVAMUWZEOHJOQ-UHFFFAOYSA-N propionic anhydride Chemical compound CCC(=O)OC(=O)CC WYVAMUWZEOHJOQ-UHFFFAOYSA-N 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 238000010898 silica gel chromatography Methods 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Priority Applications (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP16401884A JPS6143145A (ja) | 1984-08-03 | 1984-08-03 | シクロペンテノンの硝酸エステルおよびその製造法 |
| US06/758,801 US4683323A (en) | 1984-07-31 | 1985-07-25 | Method for inversion of optically active 4-hydroxy-2-cyclopentenones |
| DE8585305343T DE3582201D1 (de) | 1984-07-31 | 1985-07-26 | Verfahren zur inversion von optisch aktiven 4-hydroxy-2-cyclopentenonen. |
| EP85305343A EP0170506B1 (de) | 1984-07-31 | 1985-07-26 | Verfahren zur Inversion von optisch aktiven 4-Hydroxy-2-cyclopentenonen |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP16401884A JPS6143145A (ja) | 1984-08-03 | 1984-08-03 | シクロペンテノンの硝酸エステルおよびその製造法 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS6143145A JPS6143145A (ja) | 1986-03-01 |
| JPH0513144B2 true JPH0513144B2 (de) | 1993-02-19 |
Family
ID=15785219
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP16401884A Granted JPS6143145A (ja) | 1984-07-31 | 1984-08-03 | シクロペンテノンの硝酸エステルおよびその製造法 |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS6143145A (de) |
-
1984
- 1984-08-03 JP JP16401884A patent/JPS6143145A/ja active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| JPS6143145A (ja) | 1986-03-01 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| US5247083A (en) | Direct esterification of mycophenolic acid | |
| FR1449628A (fr) | Procédé de préparation d'indoles polynucléaires désacylés, notamment d'esters de la série de la désacétyl-vincaleucoblastine et de la désacétyl-vincristine | |
| SU656526A3 (ru) | Способ получени производных изомеров цефалоспорановой кислоты | |
| JPH0513144B2 (de) | ||
| JPH0768163B2 (ja) | シクロペンテノン誘導体の製法 | |
| US3910958A (en) | Process for preparing arylacetic acids and esters thereof | |
| JPS62146B2 (de) | ||
| JPH01233255A (ja) | シクロペンテノン誘導体及びその製造法 | |
| JPH0523756B2 (de) | ||
| JPS58194853A (ja) | シクロヘキセン−アセチルオキシム誘導体 | |
| JP2668435B2 (ja) | シクロペンテノン誘導体及びその製造法 | |
| JP2718715B2 (ja) | ９，１０−セコ−シクロアルタン誘導体 | |
| JPS5823374B2 (ja) | ３−ヒドロキシ−５−オキソ−２−置換−シクロペンタンアルケン酸の製造法 | |
| CN1034808Y (zh) | 4，5-二氢-3-丁基苯酞的合成方法 | |
| JPH0528693B2 (de) | ||
| JPS6140669B2 (de) | ||
| JPS5852995B2 (ja) | フルフラ−ル誘導体の製造法 | |
| JPH03261744A (ja) | １，３―ペンタジエン誘導体及びその製造法 | |
| JP2880203B2 (ja) | フラノン誘導体の製法 | |
| JPS6317841A (ja) | カルボニル基の２位にアルキル基の置換基を有する６員環ケトン化合物からカルボニル基の３位にアルキル基の置換基を有する７員環ケトン化合物の合成方法 | |
| JPS6123193B2 (de) | ||
| JPS596310B2 (ja) | 新規なセスキテルペン誘導体及びその製造法 | |
| JPH0149277B2 (de) | ||
| JPH0477752B2 (de) | ||
| JPS5845415B2 (ja) | トリメチルシクロヘキセン誘導体 |