JPH0588210B2 - - Google Patents
Info
- Publication number
- JPH0588210B2 JPH0588210B2 JP5339285A JP5339285A JPH0588210B2 JP H0588210 B2 JPH0588210 B2 JP H0588210B2 JP 5339285 A JP5339285 A JP 5339285A JP 5339285 A JP5339285 A JP 5339285A JP H0588210 B2 JPH0588210 B2 JP H0588210B2
- Authority
- JP
- Japan
- Prior art keywords
- acid
- ester
- truxic
- truxic acid
- nitrophenyl
- 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
- 239000002253 acid Substances 0.000 claims description 74
- -1 cinnamic acid ester Chemical class 0.000 claims description 41
- WBYWAXJHAXSJNI-VOTSOKGWSA-M .beta-Phenylacrylic acid Natural products [O-]C(=O)\C=C\C1=CC=CC=C1 WBYWAXJHAXSJNI-VOTSOKGWSA-M 0.000 claims description 17
- 239000006185 dispersion Substances 0.000 claims description 17
- 229930016911 cinnamic acid Natural products 0.000 claims description 14
- 235000013985 cinnamic acid Nutrition 0.000 claims description 14
- WBYWAXJHAXSJNI-UHFFFAOYSA-N methyl p-hydroxycinnamate Natural products OC(=O)C=CC1=CC=CC=C1 WBYWAXJHAXSJNI-UHFFFAOYSA-N 0.000 claims description 14
- 150000005690 diesters Chemical class 0.000 claims description 11
- 239000002612 dispersion medium Substances 0.000 claims description 9
- 125000000636 p-nitrophenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)[N+]([O-])=O 0.000 claims description 9
- 230000002194 synthesizing effect Effects 0.000 claims description 7
- 238000000034 method Methods 0.000 claims description 5
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 4
- 230000001678 irradiating effect Effects 0.000 claims description 3
- 230000001235 sensitizing effect Effects 0.000 claims description 3
- 239000000126 substance Substances 0.000 claims description 3
- 238000001308 synthesis method Methods 0.000 claims description 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 2
- 150000002148 esters Chemical class 0.000 description 33
- 238000006243 chemical reaction Methods 0.000 description 19
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 17
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 15
- 239000002994 raw material Substances 0.000 description 14
- 238000004519 manufacturing process Methods 0.000 description 13
- 239000000047 product Substances 0.000 description 12
- 239000000539 dimer Substances 0.000 description 11
- 229940114081 cinnamate Drugs 0.000 description 9
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 9
- WBYWAXJHAXSJNI-SREVYHEPSA-N Cinnamic acid Chemical compound OC(=O)\C=C/C1=CC=CC=C1 WBYWAXJHAXSJNI-SREVYHEPSA-N 0.000 description 8
- 239000000463 material Substances 0.000 description 8
- 230000015572 biosynthetic process Effects 0.000 description 7
- 150000001875 compounds Chemical class 0.000 description 7
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 7
- 150000001408 amides Chemical class 0.000 description 6
- 238000007086 side reaction Methods 0.000 description 6
- 238000003786 synthesis reaction Methods 0.000 description 6
- JSJMWPBHPPNMQK-UHFFFAOYSA-N (4-nitrophenyl) 3-phenylprop-2-enoate Chemical compound C1=CC([N+](=O)[O-])=CC=C1OC(=O)C=CC1=CC=CC=C1 JSJMWPBHPPNMQK-UHFFFAOYSA-N 0.000 description 5
- 239000013078 crystal Substances 0.000 description 5
- 239000007790 solid phase Substances 0.000 description 5
- VHVXERQNJXFWLR-UHFFFAOYSA-N (4-nitronaphthalen-1-yl) 3-phenylprop-2-enoate Chemical compound C12=CC=CC=C2C([N+](=O)[O-])=CC=C1OC(=O)C=CC1=CC=CC=C1 VHVXERQNJXFWLR-UHFFFAOYSA-N 0.000 description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
- 239000012043 crude product Substances 0.000 description 4
- 230000007423 decrease Effects 0.000 description 4
- 239000002270 dispersing agent Substances 0.000 description 4
- 230000000694 effects Effects 0.000 description 4
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 4
- 230000007062 hydrolysis Effects 0.000 description 4
- 238000006460 hydrolysis reaction Methods 0.000 description 4
- 239000000203 mixture Substances 0.000 description 4
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- BTJIUGUIPKRLHP-UHFFFAOYSA-N 4-nitrophenol Chemical compound OC1=CC=C([N+]([O-])=O)C=C1 BTJIUGUIPKRLHP-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 238000002844 melting Methods 0.000 description 3
- 230000008018 melting Effects 0.000 description 3
- 230000003287 optical effect Effects 0.000 description 3
- 239000002861 polymer material Substances 0.000 description 3
- 238000001953 recrystallisation Methods 0.000 description 3
- WDEFWOPTRFWZLM-LEQGEALCSA-N (2,5-dioxopyrrolidin-1-yl) (2r)-2,5,7,8-tetramethyl-6-(oxan-2-yloxy)-3,4-dihydrochromene-2-carboxylate Chemical compound C([C@@](C)(OC=1C(C)=C2C)C(=O)ON3C(CCC3=O)=O)CC=1C(C)=C2OC1CCCCO1 WDEFWOPTRFWZLM-LEQGEALCSA-N 0.000 description 2
- MTWHRQTUBOTQTE-UHFFFAOYSA-N 4-nitro-n-(4-nitrophenyl)aniline Chemical compound C1=CC([N+](=O)[O-])=CC=C1NC1=CC=C([N+]([O-])=O)C=C1 MTWHRQTUBOTQTE-UHFFFAOYSA-N 0.000 description 2
- 239000005264 High molar mass liquid crystal Substances 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- 239000003513 alkali Substances 0.000 description 2
- 239000006227 byproduct Substances 0.000 description 2
- 239000007795 chemical reaction product Substances 0.000 description 2
- 238000007697 cis-trans-isomerization reaction Methods 0.000 description 2
- 238000007796 conventional method Methods 0.000 description 2
- 238000006471 dimerization reaction Methods 0.000 description 2
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 2
- 229910052753 mercury Inorganic materials 0.000 description 2
- AYXKBTUZYMUPEC-UHFFFAOYSA-N n-(4-nitrophenyl)-3-phenylprop-2-enamide Chemical compound C1=CC([N+](=O)[O-])=CC=C1NC(=O)C=CC1=CC=CC=C1 AYXKBTUZYMUPEC-UHFFFAOYSA-N 0.000 description 2
- 125000006501 nitrophenyl group Chemical group 0.000 description 2
- 239000012071 phase Substances 0.000 description 2
- 238000006552 photochemical reaction Methods 0.000 description 2
- 238000011907 photodimerization Methods 0.000 description 2
- 229920000642 polymer Polymers 0.000 description 2
- 230000035484 reaction time Effects 0.000 description 2
- 238000011084 recovery Methods 0.000 description 2
- 230000002441 reversible effect Effects 0.000 description 2
- 238000000926 separation method Methods 0.000 description 2
- 229910052708 sodium Inorganic materials 0.000 description 2
- 239000011734 sodium Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
- ZVLWSRIFUAPFFA-ZHACJKMWSA-N (2-nitrophenyl) (e)-3-phenylprop-2-enoate Chemical compound [O-][N+](=O)C1=CC=CC=C1OC(=O)\C=C\C1=CC=CC=C1 ZVLWSRIFUAPFFA-ZHACJKMWSA-N 0.000 description 1
- JSJMWPBHPPNMQK-IZZDOVSWSA-N (4-nitrophenyl) (e)-3-phenylprop-2-enoate Chemical compound C1=CC([N+](=O)[O-])=CC=C1OC(=O)\C=C\C1=CC=CC=C1 JSJMWPBHPPNMQK-IZZDOVSWSA-N 0.000 description 1
- WOGITNXCNOTRLK-VOTSOKGWSA-N (e)-3-phenylprop-2-enoyl chloride Chemical compound ClC(=O)\C=C\C1=CC=CC=C1 WOGITNXCNOTRLK-VOTSOKGWSA-N 0.000 description 1
- IQUPABOKLQSFBK-UHFFFAOYSA-N 2-nitrophenol Chemical compound OC1=CC=CC=C1[N+]([O-])=O IQUPABOKLQSFBK-UHFFFAOYSA-N 0.000 description 1
- OVWSNDOUOHKMOM-UHFFFAOYSA-N 3-phenylprop-2-enoic acid;hydrochloride Chemical compound Cl.OC(=O)C=CC1=CC=CC=C1 OVWSNDOUOHKMOM-UHFFFAOYSA-N 0.000 description 1
- 238000003776 cleavage reaction Methods 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- 238000010586 diagram Methods 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 238000000921 elemental analysis Methods 0.000 description 1
- 125000004494 ethyl ester group Chemical group 0.000 description 1
- 229920001002 functional polymer Polymers 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 230000003301 hydrolyzing effect Effects 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 238000004811 liquid chromatography Methods 0.000 description 1
- 229910001507 metal halide Inorganic materials 0.000 description 1
- 150000005309 metal halides Chemical class 0.000 description 1
- 150000004702 methyl esters Chemical class 0.000 description 1
- 239000012046 mixed solvent Substances 0.000 description 1
- 210000005155 neural progenitor cell Anatomy 0.000 description 1
- 238000006386 neutralization reaction Methods 0.000 description 1
- NBFNGRDFKUJVIN-VAWYXSNFSA-N phenyl (e)-3-phenylprop-2-enoate Chemical compound C=1C=CC=CC=1/C=C/C(=O)OC1=CC=CC=C1 NBFNGRDFKUJVIN-VAWYXSNFSA-N 0.000 description 1
- 230000002165 photosensitisation Effects 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 230000007017 scission Effects 0.000 description 1
- 238000003746 solid phase reaction Methods 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000000967 suction filtration Methods 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 230000007704 transition Effects 0.000 description 1
- 238000002211 ultraviolet spectrum Methods 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 229910052724 xenon Inorganic materials 0.000 description 1
- FHNFHKCVQCLJFQ-UHFFFAOYSA-N xenon atom Chemical compound [Xe] FHNFHKCVQCLJFQ-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J19/00—Chemical, physical or physico-chemical processes in general; Their relevant apparatus
- B01J19/08—Processes employing the direct application of electric or wave energy, or particle radiation; Apparatus therefor
- B01J19/12—Processes employing the direct application of electric or wave energy, or particle radiation; Apparatus therefor employing electromagnetic waves
- B01J19/122—Incoherent waves
Landscapes
- Chemical & Material Sciences (AREA)
- Physics & Mathematics (AREA)
- Electromagnetism (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Toxicology (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Physical Or Chemical Processes And Apparatus (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP5339285A JPS61212532A (ja) | 1985-03-19 | 1985-03-19 | シクロブタン環化合物の合成法 |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP5339285A JPS61212532A (ja) | 1985-03-19 | 1985-03-19 | シクロブタン環化合物の合成法 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS61212532A JPS61212532A (ja) | 1986-09-20 |
| JPH0588210B2 true JPH0588210B2 (enExample) | 1993-12-21 |
Family
ID=12941550
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP5339285A Granted JPS61212532A (ja) | 1985-03-19 | 1985-03-19 | シクロブタン環化合物の合成法 |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS61212532A (enExample) |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2001199884A (ja) * | 2000-01-21 | 2001-07-24 | Seiwa Yakuhin Kk | 鎮痛作用剤 |
| JP4074155B2 (ja) | 2001-09-17 | 2008-04-09 | 富士フイルム株式会社 | 四員環化合物、それを用いた複屈折媒体および光学部材 |
| CN102898322B (zh) * | 2012-10-29 | 2014-05-07 | 林励 | 一种化合物及其制法和用途 |
| JP6483481B2 (ja) * | 2015-03-10 | 2019-03-13 | 国立大学法人北陸先端科学技術大学院大学 | トルキシン酸系ポリマーおよびその製造中間体 |
-
1985
- 1985-03-19 JP JP5339285A patent/JPS61212532A/ja active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| JPS61212532A (ja) | 1986-09-20 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
| EXPY | Cancellation because of completion of term |