JPS5829736A - ４−アリル−２，５−シクロヘキサジエノン誘導体の合成法 - Google Patents
４−アリル−２，５−シクロヘキサジエノン誘導体の合成法Info
- Publication number
- JPS5829736A JPS5829736A JP56127077A JP12707781A JPS5829736A JP S5829736 A JPS5829736 A JP S5829736A JP 56127077 A JP56127077 A JP 56127077A JP 12707781 A JP12707781 A JP 12707781A JP S5829736 A JPS5829736 A JP S5829736A
- Authority
- JP
- Japan
- Prior art keywords
- allyl
- cyclodextrin
- para
- derivative
- substituted
- 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
- 238000003786 synthesis reaction Methods 0.000 title abstract description 3
- 230000015572 biosynthetic process Effects 0.000 title description 2
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims abstract description 15
- 239000003054 catalyst Substances 0.000 claims abstract description 4
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 claims 1
- 229920000858 Cyclodextrin Polymers 0.000 abstract description 13
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 abstract description 12
- HFHDHCJBZVLPGP-UHFFFAOYSA-N schardinger α-dextrin Chemical compound O1C(C(C2O)O)C(CO)OC2OC(C(C2O)O)C(CO)OC2OC(C(C2O)O)C(CO)OC2OC(C(O)C2O)C(CO)OC2OC(C(C2O)O)C(CO)OC2OC2C(O)C(O)C1OC2CO HFHDHCJBZVLPGP-UHFFFAOYSA-N 0.000 abstract description 10
- 238000006243 chemical reaction Methods 0.000 abstract description 9
- -1 allyl halide Chemical class 0.000 abstract description 6
- 239000000126 substance Substances 0.000 abstract description 6
- 150000002989 phenols Chemical class 0.000 abstract description 5
- 239000000243 solution Substances 0.000 abstract description 5
- 229920001450 Alpha-Cyclodextrin Polymers 0.000 abstract description 4
- HFHDHCJBZVLPGP-RWMJIURBSA-N alpha-cyclodextrin Chemical compound OC[C@H]([C@H]([C@@H]([C@H]1O)O)O[C@H]2O[C@@H]([C@@H](O[C@H]3O[C@H](CO)[C@H]([C@@H]([C@H]3O)O)O[C@H]3O[C@H](CO)[C@H]([C@@H]([C@H]3O)O)O[C@H]3O[C@H](CO)[C@H]([C@@H]([C@H]3O)O)O3)[C@H](O)[C@H]2O)CO)O[C@@H]1O[C@H]1[C@H](O)[C@@H](O)[C@@H]3O[C@@H]1CO HFHDHCJBZVLPGP-RWMJIURBSA-N 0.000 abstract description 4
- 229940043377 alpha-cyclodextrin Drugs 0.000 abstract description 4
- 239000007864 aqueous solution Chemical class 0.000 abstract description 4
- 239000001116 FEMA 4028 Substances 0.000 abstract description 3
- 125000003545 alkoxy group Chemical group 0.000 abstract description 3
- 125000000217 alkyl group Chemical group 0.000 abstract description 3
- 125000003118 aryl group Chemical group 0.000 abstract description 3
- WHGYBXFWUBPSRW-FOUAGVGXSA-N beta-cyclodextrin Chemical compound OC[C@H]([C@H]([C@@H]([C@H]1O)O)O[C@H]2O[C@@H]([C@@H](O[C@H]3O[C@H](CO)[C@H]([C@@H]([C@H]3O)O)O[C@H]3O[C@H](CO)[C@H]([C@@H]([C@H]3O)O)O[C@H]3O[C@H](CO)[C@H]([C@@H]([C@H]3O)O)O[C@H]3O[C@H](CO)[C@H]([C@@H]([C@H]3O)O)O3)[C@H](O)[C@H]2O)CO)O[C@@H]1O[C@H]1[C@H](O)[C@@H](O)[C@@H]3O[C@@H]1CO WHGYBXFWUBPSRW-FOUAGVGXSA-N 0.000 abstract description 3
- 235000011175 beta-cyclodextrine Nutrition 0.000 abstract description 3
- 229960004853 betadex Drugs 0.000 abstract description 3
- 150000001875 compounds Chemical class 0.000 abstract description 3
- 239000013543 active substance Substances 0.000 abstract description 2
- 239000002994 raw material Substances 0.000 abstract description 2
- OSDWBNJEKMUWAV-UHFFFAOYSA-N Allyl chloride Chemical compound ClCC=C OSDWBNJEKMUWAV-UHFFFAOYSA-N 0.000 abstract 1
- 230000002194 synthesizing effect Effects 0.000 abstract 1
- 239000000047 product Substances 0.000 description 11
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 10
- 239000003153 chemical reaction reagent Substances 0.000 description 6
- WGHKKEJHRMUKDK-UHFFFAOYSA-N cyclohexa-2,5-dien-1-one Chemical class O=C1C=CCC=C1 WGHKKEJHRMUKDK-UHFFFAOYSA-N 0.000 description 4
- 238000005160 1H NMR spectroscopy Methods 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical class [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- 238000005259 measurement Methods 0.000 description 3
- ULGZDMOVFRHVEP-RWJQBGPGSA-N Erythromycin Chemical compound O([C@@H]1[C@@H](C)C(=O)O[C@@H]([C@@]([C@H](O)[C@@H](C)C(=O)[C@H](C)C[C@@](C)(O)[C@H](O[C@H]2[C@@H]([C@H](C[C@@H](C)O2)N(C)C)O)[C@H]1C)(C)O)CC)[C@H]1C[C@@](C)(OC)[C@@H](O)[C@H](C)O1 ULGZDMOVFRHVEP-RWJQBGPGSA-N 0.000 description 2
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical group [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 2
- BHELZAPQIKSEDF-UHFFFAOYSA-N allyl bromide Chemical compound BrCC=C BHELZAPQIKSEDF-UHFFFAOYSA-N 0.000 description 2
- 230000000052 comparative effect Effects 0.000 description 2
- 229910052739 hydrogen Inorganic materials 0.000 description 2
- 239000001257 hydrogen Substances 0.000 description 2
- 125000004435 hydrogen atom Chemical class [H]* 0.000 description 2
- 238000000034 method Methods 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 230000002378 acidificating effect Effects 0.000 description 1
- 239000003849 aromatic solvent Substances 0.000 description 1
- 230000003115 biocidal effect Effects 0.000 description 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- 229960003276 erythromycin Drugs 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- FUKUFMFMCZIRNT-UHFFFAOYSA-N hydron;methanol;chloride Chemical compound Cl.OC FUKUFMFMCZIRNT-UHFFFAOYSA-N 0.000 description 1
- 229920001542 oligosaccharide Polymers 0.000 description 1
- 238000005580 one pot reaction Methods 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 238000007363 ring formation reaction Methods 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 238000007039 two-step reaction Methods 0.000 description 1
Classifications
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/52—Improvements relating to the production of bulk chemicals using catalysts, e.g. selective catalysts
Landscapes
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Priority Applications (7)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP56127077A JPS5829736A (ja) | 1981-08-13 | 1981-08-13 | ４−アリル−２，５−シクロヘキサジエノン誘導体の合成法 |
| DE8282900665T DE3274104D1 (en) | 1981-03-09 | 1982-03-09 | Process for selectively producing para-substituted derivatives of phenols |
| DE8484112783T DE3276858D1 (en) | 1981-03-09 | 1982-03-09 | A process for producing a para-substituted phenol derivative |
| PCT/JP1982/000066 WO1982003073A1 (fr) | 1981-03-09 | 1982-03-09 | Procede permettant d'introduire un substituant dans une position p d'un phenol |
| EP19840112783 EP0158709B1 (en) | 1981-03-09 | 1982-03-09 | A process for producing a para-substituted phenol derivative |
| EP82900665A EP0073837B1 (en) | 1981-03-09 | 1982-03-09 | Process for selectively producing para-substituted derivatives of phenols |
| US06/530,158 US4523031A (en) | 1981-08-11 | 1983-09-07 | Process for producing a para-substituted phenol derivative |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP56127077A JPS5829736A (ja) | 1981-08-13 | 1981-08-13 | ４−アリル−２，５−シクロヘキサジエノン誘導体の合成法 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS5829736A true JPS5829736A (ja) | 1983-02-22 |
| JPH0134212B2 JPH0134212B2 (enrdf_load_stackoverflow) | 1989-07-18 |
Family
ID=14951000
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP56127077A Granted JPS5829736A (ja) | 1981-03-09 | 1981-08-13 | ４−アリル−２，５−シクロヘキサジエノン誘導体の合成法 |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS5829736A (enrdf_load_stackoverflow) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2007055225A (ja) * | 2005-07-29 | 2007-03-08 | Asami Seisakusho:Kk | コンクリートの養生方法及びコンクリート用型枠並びにコンクリート製品の養生装置 |
-
1981
- 1981-08-13 JP JP56127077A patent/JPS5829736A/ja active Granted
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2007055225A (ja) * | 2005-07-29 | 2007-03-08 | Asami Seisakusho:Kk | コンクリートの養生方法及びコンクリート用型枠並びにコンクリート製品の養生装置 |
Also Published As
| Publication number | Publication date |
|---|---|
| JPH0134212B2 (enrdf_load_stackoverflow) | 1989-07-18 |
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