JPH0376295B2 - - Google Patents
Info
- Publication number
- JPH0376295B2 JPH0376295B2 JP61049248A JP4924886A JPH0376295B2 JP H0376295 B2 JPH0376295 B2 JP H0376295B2 JP 61049248 A JP61049248 A JP 61049248A JP 4924886 A JP4924886 A JP 4924886A JP H0376295 B2 JPH0376295 B2 JP H0376295B2
- Authority
- JP
- Japan
- Prior art keywords
- methyl
- methylazulene
- furan
- carboxylate
- 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
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 22
- 238000004519 manufacturing process Methods 0.000 claims description 9
- 125000000217 alkyl group Chemical group 0.000 claims description 6
- 239000002253 acid Substances 0.000 claims description 4
- WSQIUQGZWDQMEL-UHFFFAOYSA-N 1-methylazulene Chemical class C1=CC=CC=C2C(C)=CC=C21 WSQIUQGZWDQMEL-UHFFFAOYSA-N 0.000 claims description 2
- RHDGNLCLDBVESU-UHFFFAOYSA-N but-3-en-4-olide Chemical class O=C1CC=CO1 RHDGNLCLDBVESU-UHFFFAOYSA-N 0.000 claims description 2
- 229910052500 inorganic mineral Inorganic materials 0.000 claims description 2
- 239000011707 mineral Substances 0.000 claims description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 1
- 125000000467 secondary amino group Chemical class [H]N([*:1])[*:2] 0.000 claims 1
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 27
- 238000000034 method Methods 0.000 description 12
- 238000006243 chemical reaction Methods 0.000 description 11
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 10
- HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 description 9
- ZRCFBHGCJAIXIH-UHFFFAOYSA-N 2-methylazulene Chemical compound C1=CC=CC2=CC(C)=CC2=C1 ZRCFBHGCJAIXIH-UHFFFAOYSA-N 0.000 description 7
- 150000001545 azulenes Chemical class 0.000 description 7
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 6
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 5
- CUFNKYGDVFVPHO-UHFFFAOYSA-N azulene Chemical compound C1=CC=CC2=CC=CC2=C1 CUFNKYGDVFVPHO-UHFFFAOYSA-N 0.000 description 5
- 238000010992 reflux Methods 0.000 description 5
- 239000002904 solvent Substances 0.000 description 5
- 230000002194 synthesizing effect Effects 0.000 description 5
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 4
- -1 alkyl azulene Chemical compound 0.000 description 4
- 239000003921 oil Substances 0.000 description 4
- 150000003335 secondary amines Chemical class 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- AWUMFQREGHLKJB-UHFFFAOYSA-N (7-oxocyclohepta-1,3,5-trien-1-yl) 4-methylbenzenesulfonate Chemical compound C1=CC(C)=CC=C1S(=O)(=O)OC1=CC=CC=CC1=O AWUMFQREGHLKJB-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 3
- 150000001875 compounds Chemical class 0.000 description 3
- 239000013078 crystal Substances 0.000 description 3
- UAOMVDZJSHZZME-UHFFFAOYSA-N diisopropylamine Chemical compound CC(C)NC(C)C UAOMVDZJSHZZME-UHFFFAOYSA-N 0.000 description 3
- 238000010438 heat treatment Methods 0.000 description 3
- 238000002844 melting Methods 0.000 description 3
- 230000008018 melting Effects 0.000 description 3
- XUKZGJCCXHLQBP-UHFFFAOYSA-N methyl 2-methylazulene-1-carboxylate Chemical compound C1=CC=CC=C2C(C(=O)OC)=C(C)C=C21 XUKZGJCCXHLQBP-UHFFFAOYSA-N 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- 239000002994 raw material Substances 0.000 description 3
- 238000001953 recrystallisation Methods 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- 239000000341 volatile oil Substances 0.000 description 3
- NCYASJPJXZZJDE-UHFFFAOYSA-N 2-methyl-5-propan-2-ylazulene Chemical compound CC(C)C1=CC=CC2=CC(C)=CC2=C1 NCYASJPJXZZJDE-UHFFFAOYSA-N 0.000 description 2
- JVRMLEOLKRMHCU-UHFFFAOYSA-N 2-methyl-6-propan-2-ylazulene Chemical compound C1=CC(C(C)C)=CC=C2C=C(C)C=C21 JVRMLEOLKRMHCU-UHFFFAOYSA-N 0.000 description 2
- ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- FWKQNCXZGNBPFD-UHFFFAOYSA-N Guaiazulene Chemical compound CC(C)C1=CC=C(C)C2=CC=C(C)C2=C1 FWKQNCXZGNBPFD-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 2
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 2
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 2
- 125000004453 alkoxycarbonyl group Chemical group 0.000 description 2
- 125000005907 alkyl ester group Chemical group 0.000 description 2
- 239000002537 cosmetic Substances 0.000 description 2
- 239000012043 crude product Substances 0.000 description 2
- 150000002081 enamines Chemical class 0.000 description 2
- CNURRDGUSKKATA-UHFFFAOYSA-N methyl 2-methyl-7-propan-2-ylazulene-1-carboxylate Chemical compound C1=CC=C(C(C)C)C=C2C(C(=O)OC)=C(C)C=C21 CNURRDGUSKKATA-UHFFFAOYSA-N 0.000 description 2
- HZDXGIMPRKMFDE-UHFFFAOYSA-N methyl azulene-1-carboxylate Chemical compound C1=CC=CC=C2C(C(=O)OC)=CC=C21 HZDXGIMPRKMFDE-UHFFFAOYSA-N 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- IQYJSKNHDZZDGA-UHFFFAOYSA-N 2-methoxycyclohepta-2,4,6-trien-1-one Chemical compound COC1=CC=CC=CC1=O IQYJSKNHDZZDGA-UHFFFAOYSA-N 0.000 description 1
- JOWUSBDLSYTMKV-UHFFFAOYSA-N 2-methylazulene-1-carboxylic acid Chemical compound C1=CC=CC2=C(C(O)=O)C(C)=CC2=C1 JOWUSBDLSYTMKV-UHFFFAOYSA-N 0.000 description 1
- 208000010445 Chilblains Diseases 0.000 description 1
- 206010008528 Chillblains Diseases 0.000 description 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
- HPJYKMSFRBJOSW-JHSUYXJUSA-N Damsin Chemical compound C[C@H]1CC[C@H]2C(=C)C(=O)O[C@H]2[C@]2(C)C(=O)CC[C@@H]12 HPJYKMSFRBJOSW-JHSUYXJUSA-N 0.000 description 1
- 238000005481 NMR spectroscopy Methods 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 150000001299 aldehydes Chemical class 0.000 description 1
- 239000002260 anti-inflammatory agent Substances 0.000 description 1
- 229940121363 anti-inflammatory agent Drugs 0.000 description 1
- HGLFWLLFPGIKOT-UHFFFAOYSA-N azulene-1-carboxylic acid Chemical class C1=CC=CC=C2C(C(=O)O)=CC=C21 HGLFWLLFPGIKOT-UHFFFAOYSA-N 0.000 description 1
- 125000003828 azulenyl group Chemical group 0.000 description 1
- 150000007514 bases Chemical class 0.000 description 1
- 125000002619 bicyclic group Chemical group 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 150000003997 cyclic ketones Chemical class 0.000 description 1
- LBFAKLHYVDQHRO-UHFFFAOYSA-N cyclohepta[b]furan-2-one Chemical compound C1=CC=CC=C2OC(=O)C=C21 LBFAKLHYVDQHRO-UHFFFAOYSA-N 0.000 description 1
- 230000000911 decarboxylating effect Effects 0.000 description 1
- 229940043279 diisopropylamine Drugs 0.000 description 1
- 238000007865 diluting Methods 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 230000008030 elimination Effects 0.000 description 1
- 238000003379 elimination reaction Methods 0.000 description 1
- 239000003480 eluent Substances 0.000 description 1
- 238000010931 ester hydrolysis Methods 0.000 description 1
- 235000019441 ethanol Nutrition 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 239000003205 fragrance Substances 0.000 description 1
- 229960002350 guaiazulen Drugs 0.000 description 1
- 230000003301 hydrolyzing effect Effects 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- 239000006210 lotion Substances 0.000 description 1
- HGZZHABSWJXDNL-UHFFFAOYSA-N methyl 2-methyl-6-propan-2-ylazulene-1-carboxylate Chemical compound C1=CC(C(C)C)=CC=C2C(C(=O)OC)=C(C)C=C21 HGZZHABSWJXDNL-UHFFFAOYSA-N 0.000 description 1
- HOVPKDFNWCKKGB-UHFFFAOYSA-N methyl 2-oxo-5-propan-2-ylcyclohepta[b]furan-3-carboxylate Chemical compound C1=C(C(C)C)C=CC=C2OC(=O)C(C(=O)OC)=C21 HOVPKDFNWCKKGB-UHFFFAOYSA-N 0.000 description 1
- AIUSVDWWUJHIOV-UHFFFAOYSA-N methyl 2-oxo-6-propan-2-ylcyclohepta[b]furan-3-carboxylate Chemical compound C1=CC(C(C)C)=CC=C2OC(=O)C(C(=O)OC)=C21 AIUSVDWWUJHIOV-UHFFFAOYSA-N 0.000 description 1
- NWECYFMGBPWBAL-UHFFFAOYSA-N methyl 2-oxocyclohepta[b]furan-3-carboxylate Chemical compound C1=CC=CC=C2OC(=O)C(C(=O)OC)=C21 NWECYFMGBPWBAL-UHFFFAOYSA-N 0.000 description 1
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 1
- 239000002674 ointment Substances 0.000 description 1
- 239000007800 oxidant agent Substances 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 239000002884 skin cream Substances 0.000 description 1
- 239000000344 soap Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 238000010189 synthetic method Methods 0.000 description 1
- 239000000606 toothpaste Substances 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP4924886A JPS62207232A (ja) | 1986-03-06 | 1986-03-06 | ２−メチルアズレン類の製造方法 |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP4924886A JPS62207232A (ja) | 1986-03-06 | 1986-03-06 | ２−メチルアズレン類の製造方法 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS62207232A JPS62207232A (ja) | 1987-09-11 |
| JPH0376295B2 true JPH0376295B2 (fr) | 1991-12-05 |
Family
ID=12825547
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP4924886A Granted JPS62207232A (ja) | 1986-03-06 | 1986-03-06 | ２−メチルアズレン類の製造方法 |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS62207232A (fr) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN100453515C (zh) * | 2005-12-31 | 2009-01-21 | 渤海大学 | 2-甲基奥类衍生物的合成方法 |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS57126427A (en) * | 1981-01-27 | 1982-08-06 | Takasago Corp | Preparation of 1-substituted-azulene derivative |
-
1986
- 1986-03-06 JP JP4924886A patent/JPS62207232A/ja active Granted
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS57126427A (en) * | 1981-01-27 | 1982-08-06 | Takasago Corp | Preparation of 1-substituted-azulene derivative |
Also Published As
| Publication number | Publication date |
|---|---|
| JPS62207232A (ja) | 1987-09-11 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| LAPS | Cancellation because of no payment of annual fees |