JPS5772934A - Preparation of cyclopenetenone derviative - Google Patents
Preparation of cyclopenetenone derviativeInfo
- Publication number
- JPS5772934A JPS5772934A JP14853080A JP14853080A JPS5772934A JP S5772934 A JPS5772934 A JP S5772934A JP 14853080 A JP14853080 A JP 14853080A JP 14853080 A JP14853080 A JP 14853080A JP S5772934 A JPS5772934 A JP S5772934A
- Authority
- JP
- Japan
- Prior art keywords
- formula
- alkenyl
- alkyl
- give
- hydroxyl group
- 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
- 150000001875 compounds Chemical class 0.000 abstract 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 abstract 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 abstract 2
- 125000003342 alkenyl group Chemical group 0.000 abstract 2
- 125000000217 alkyl group Chemical group 0.000 abstract 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 abstract 2
- 239000002304 perfume Substances 0.000 abstract 2
- 239000002904 solvent Substances 0.000 abstract 2
- OCTFKHXFMOKGCD-UHFFFAOYSA-N 1-hydroxypent-3-en-2-one Chemical class CC=CC(=O)CO OCTFKHXFMOKGCD-UHFFFAOYSA-N 0.000 abstract 1
- WOPKYMRPOKFYNI-UHFFFAOYSA-N 2-hydroxycyclopent-2-en-1-one Chemical class OC1=CCCC1=O WOPKYMRPOKFYNI-UHFFFAOYSA-N 0.000 abstract 1
- XMLSXPIVAXONDL-PLNGDYQASA-N Jasmone Chemical compound CC\C=C/CC1=C(C)CCC1=O XMLSXPIVAXONDL-PLNGDYQASA-N 0.000 abstract 1
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 abstract 1
- 229960000583 acetic acid Drugs 0.000 abstract 1
- 239000002253 acid Substances 0.000 abstract 1
- 125000000304 alkynyl group Chemical group 0.000 abstract 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 abstract 1
- 125000003710 aryl alkyl group Chemical group 0.000 abstract 1
- 125000003118 aryl group Chemical group 0.000 abstract 1
- 239000007853 buffer solution Substances 0.000 abstract 1
- 239000003054 catalyst Substances 0.000 abstract 1
- 125000000753 cycloalkyl group Chemical group 0.000 abstract 1
- ZPWVASYFFYYZEW-UHFFFAOYSA-L dipotassium hydrogen phosphate Chemical compound [K+].[K+].OP([O-])([O-])=O ZPWVASYFFYYZEW-UHFFFAOYSA-L 0.000 abstract 1
- 229910000396 dipotassium phosphate Inorganic materials 0.000 abstract 1
- 235000019797 dipotassium phosphate Nutrition 0.000 abstract 1
- GTUVXOOHBUUGBH-UHFFFAOYSA-N furan;methanol Chemical compound OC.C=1C=COC=1 GTUVXOOHBUUGBH-UHFFFAOYSA-N 0.000 abstract 1
- 239000012362 glacial acetic acid Substances 0.000 abstract 1
- 229910052751 metal Inorganic materials 0.000 abstract 1
- 239000002184 metal Substances 0.000 abstract 1
- 238000000034 method Methods 0.000 abstract 1
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 abstract 1
- 238000010979 pH adjustment Methods 0.000 abstract 1
- 125000001544 thienyl group Chemical group 0.000 abstract 1
- XMLSXPIVAXONDL-UHFFFAOYSA-N trans-jasmone Natural products CCC=CCC1=C(C)CCC1=O XMLSXPIVAXONDL-UHFFFAOYSA-N 0.000 abstract 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 abstract 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
PURPOSE: To obtain the titled compound useful as high-quality perfume, a jasmone component of natural perfume, inexpensively, industrially practically in high yield, by removing reductively a hydroxyl group of a specific hydroxycyclopentenone derivative.
CONSTITUTION: A furancarbinol shown by the formulaI(R1 is H, alkyl, or alkenyl; R2 is alkyl, alkenyl, alkynyl, aryl, aralkyl, thienyl, cycloalkyl; with the proviso that the case where R1 is CH3 and R2 is n-pentyl is omitted) is rearrnged a in the presence or absence of catalyst at 20W160°C in a solvent consisting of water as a main solvent, being adjusted to a pH of 3W7 by adding a buffer solution for pH adjustment, e.g, potassium hydrogenphosphate and phosphoric acid, etc., to give a hydroxypentenone derivative shown by the formula II. This compound shown by the formula II is reductively reacted with a metal and an acid, e.g., zinc powder and glacial acetic acid, etc. at 20W160°C by reduction method, so that the hydroxyl group of the compound is removed, to give the desired compound shown by the formula III.
COPYRIGHT: (C)1982,JPO&Japio
Priority Applications (8)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP14853080A JPS5772934A (en) | 1980-10-22 | 1980-10-22 | Preparation of cyclopenetenone derviative |
| HU111681A HU188043B (en) | 1980-04-30 | 1981-04-29 | Process for producing cyclopentenolene derivatives |
| DK190981A DK151796C (en) | 1980-04-30 | 1981-04-29 | PROCEDURE FOR THE PREPARATION OF CYCLOPENTENOLONS |
| EP19810103288 EP0039089B1 (en) | 1980-04-30 | 1981-04-30 | Process for preparing cyclopentenolones |
| DE8181103288T DE3161108D1 (en) | 1980-04-30 | 1981-04-30 | Process for preparing cyclopentenolones |
| CH380581A CH647747A5 (en) | 1980-08-19 | 1981-06-10 | METHOD FOR PRODUCING CYCLOPENTENONES. |
| DE19813123177 DE3123177A1 (en) | 1980-08-19 | 1981-06-11 | Process for the preparation of cyclopentenones |
| FR8111542A FR2488885A1 (en) | 1980-08-19 | 1981-06-11 | PROCESS FOR PREPARING CYCLOPENTENONE DERIVATIVES BY TRANSPOSITION OF A FURANECARBINOL |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP14853080A JPS5772934A (en) | 1980-10-22 | 1980-10-22 | Preparation of cyclopenetenone derviative |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS5772934A true JPS5772934A (en) | 1982-05-07 |
| JPS6254411B2 JPS6254411B2 (en) | 1987-11-14 |
Family
ID=15454839
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP14853080A Granted JPS5772934A (en) | 1980-04-30 | 1980-10-22 | Preparation of cyclopenetenone derviative |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS5772934A (en) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2008005967A (en) * | 2006-06-28 | 2008-01-17 | Univ Nihon | toothbrush |
| JP2008544785A (en) * | 2005-07-01 | 2008-12-11 | グラクソスミスクライン・コンシューマー・ヘルスケア・ゲゼルシャフト・ミット・ベシュレンクテル・ハフツング・ウント・コムパニー・コマンディットゲゼルシャフト | toothbrush |
-
1980
- 1980-10-22 JP JP14853080A patent/JPS5772934A/en active Granted
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2008544785A (en) * | 2005-07-01 | 2008-12-11 | グラクソスミスクライン・コンシューマー・ヘルスケア・ゲゼルシャフト・ミット・ベシュレンクテル・ハフツング・ウント・コムパニー・コマンディットゲゼルシャフト | toothbrush |
| JP2008005967A (en) * | 2006-06-28 | 2008-01-17 | Univ Nihon | toothbrush |
Also Published As
| Publication number | Publication date |
|---|---|
| JPS6254411B2 (en) | 1987-11-14 |
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