JPS58194835A - ４−アリル−２，５−シクロヘキサジエノン誘導体の合成方法 - Google Patents
４−アリル−２，５−シクロヘキサジエノン誘導体の合成方法Info
- Publication number
- JPS58194835A JPS58194835A JP57076368A JP7636882A JPS58194835A JP S58194835 A JPS58194835 A JP S58194835A JP 57076368 A JP57076368 A JP 57076368A JP 7636882 A JP7636882 A JP 7636882A JP S58194835 A JPS58194835 A JP S58194835A
- Authority
- JP
- Japan
- Prior art keywords
- cyclodextrin
- group
- derivative
- allyl
- reacting
- 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
- 230000015572 biosynthetic process Effects 0.000 title description 2
- 238000003786 synthesis reaction Methods 0.000 title description 2
- HFHDHCJBZVLPGP-UHFFFAOYSA-N schardinger α-dextrin Chemical class 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 claims abstract description 12
- 229920000858 Cyclodextrin Polymers 0.000 claims abstract description 6
- 239000003054 catalyst Substances 0.000 claims abstract description 6
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 6
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims description 10
- 150000002989 phenols Chemical class 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 claims 1
- WFDIJRYMOXRFFG-UHFFFAOYSA-N acetic acid anhydride Natural products CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 abstract description 6
- -1 allyl halide Chemical class 0.000 abstract description 6
- 150000001875 compounds Chemical class 0.000 abstract description 6
- 229920001353 Dextrin Polymers 0.000 abstract description 5
- 239000004375 Dextrin Substances 0.000 abstract description 5
- 235000019425 dextrin Nutrition 0.000 abstract description 5
- YYROPELSRYBVMQ-UHFFFAOYSA-N 4-toluenesulfonyl chloride Chemical compound CC1=CC=C(S(Cl)(=O)=O)C=C1 YYROPELSRYBVMQ-UHFFFAOYSA-N 0.000 abstract description 4
- 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
- 239000001116 FEMA 4028 Substances 0.000 abstract description 2
- ZMZINYUKVRMNTG-UHFFFAOYSA-N acetic acid;formic acid Chemical compound OC=O.CC(O)=O ZMZINYUKVRMNTG-UHFFFAOYSA-N 0.000 abstract description 2
- 239000013543 active substance Substances 0.000 abstract description 2
- 150000003973 alkyl amines Chemical class 0.000 abstract description 2
- 150000008064 anhydrides Chemical class 0.000 abstract description 2
- 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 2
- 235000011175 beta-cyclodextrine Nutrition 0.000 abstract description 2
- 229960004853 betadex Drugs 0.000 abstract description 2
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical class C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 abstract description 2
- 239000002994 raw material Substances 0.000 abstract description 2
- 230000002194 synthesizing effect Effects 0.000 abstract description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 14
- 239000000047 product Substances 0.000 description 12
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical class [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
- 238000006243 chemical reaction Methods 0.000 description 9
- 239000003153 chemical reaction reagent Substances 0.000 description 8
- 239000000243 solution Substances 0.000 description 6
- 238000000034 method Methods 0.000 description 5
- 239000000126 substance Substances 0.000 description 5
- 230000000052 comparative effect Effects 0.000 description 4
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical class [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- BHELZAPQIKSEDF-UHFFFAOYSA-N allyl bromide Chemical compound BrCC=C BHELZAPQIKSEDF-UHFFFAOYSA-N 0.000 description 3
- 238000005259 measurement Methods 0.000 description 3
- KXVQNYJQRWGSNW-UHFFFAOYSA-N 1,2,3-trimethyl-4-(2,3,4-trimethylphenoxy)benzene Chemical compound CC1=C(C)C(C)=CC=C1OC1=CC=C(C)C(C)=C1C KXVQNYJQRWGSNW-UHFFFAOYSA-N 0.000 description 2
- 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
- 125000000217 alkyl group Chemical group 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- 125000003118 aryl group Chemical group 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
- 238000005160 1H NMR spectroscopy Methods 0.000 description 1
- PMDCZENCAXMSOU-UHFFFAOYSA-N N-ethylacetamide Chemical group CCNC(C)=O PMDCZENCAXMSOU-UHFFFAOYSA-N 0.000 description 1
- 241001648319 Toronia toru Species 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 125000003545 alkoxy group Chemical group 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
- 239000000203 mixture Substances 0.000 description 1
- KERBAAIBDHEFDD-UHFFFAOYSA-N n-ethylformamide Chemical group CCNC=O KERBAAIBDHEFDD-UHFFFAOYSA-N 0.000 description 1
- OHLUUHNLEMFGTQ-AZXPZELESA-N n-methylacetamide Chemical group C[15NH]C(C)=O OHLUUHNLEMFGTQ-AZXPZELESA-N 0.000 description 1
- ATHHXGZTWNVVOU-VQEHIDDOSA-N n-methylformamide Chemical group CN[13CH]=O ATHHXGZTWNVVOU-VQEHIDDOSA-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
- 238000007363 ring formation reaction Methods 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 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
- Catalysts (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP57076368A JPS58194835A (ja) | 1982-05-07 | 1982-05-07 | ４−アリル−２，５−シクロヘキサジエノン誘導体の合成方法 |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP57076368A JPS58194835A (ja) | 1982-05-07 | 1982-05-07 | ４−アリル−２，５−シクロヘキサジエノン誘導体の合成方法 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS58194835A true JPS58194835A (ja) | 1983-11-12 |
| JPS647062B2 JPS647062B2 (enrdf_load_stackoverflow) | 1989-02-07 |
Family
ID=13603397
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP57076368A Granted JPS58194835A (ja) | 1982-05-07 | 1982-05-07 | ４−アリル−２，５−シクロヘキサジエノン誘導体の合成方法 |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS58194835A (enrdf_load_stackoverflow) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1985003701A1 (en) * | 1984-02-14 | 1985-08-29 | Hidefumi Hirai | Process for preparing p-substituted phenol derivatives |
| WO1996019502A1 (en) * | 1994-12-20 | 1996-06-27 | Kimberly-Clark Worldwide, Inc. | Improved mutable composition |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH04100762A (ja) * | 1990-08-17 | 1992-04-02 | Mk Seiko Co Ltd | 洗車機 |
-
1982
- 1982-05-07 JP JP57076368A patent/JPS58194835A/ja active Granted
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1985003701A1 (en) * | 1984-02-14 | 1985-08-29 | Hidefumi Hirai | Process for preparing p-substituted phenol derivatives |
| US4663478A (en) * | 1984-02-14 | 1987-05-05 | Hidefuni Hirai | Process for producing a para-substituted phenol derivative |
| EP0173748B1 (en) * | 1984-02-14 | 1990-01-03 | HIRAI, Hidefumi | Process for producing substituted unsaturated six-membered ring compounds from phenol derivatives |
| WO1996019502A1 (en) * | 1994-12-20 | 1996-06-27 | Kimberly-Clark Worldwide, Inc. | Improved mutable composition |
Also Published As
| Publication number | Publication date |
|---|---|
| JPS647062B2 (enrdf_load_stackoverflow) | 1989-02-07 |
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