JPS6313425B2 - - Google Patents

Info

Publication number

JPS6313425B2

JPS6313425B2 JP7636782A JP7636782A JPS6313425B2 JP S6313425 B2 JPS6313425 B2 JP S6313425B2 JP 7636782 A JP7636782 A JP 7636782A JP 7636782 A JP7636782 A JP 7636782A JP S6313425 B2 JPS6313425 B2 JP S6313425B2

Authority

JP

Japan

Prior art keywords

cyclodextrin

nitrovinylphenol

reaction

derivatives

derivative

Prior art date

1982-05-07

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

Links

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• 229920000858 Cyclodextrin Polymers 0.000 claims description 13
• HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 12
• PMDYAIGGZBRBFX-UHFFFAOYSA-N 2-(2-nitroethenyl)phenol Chemical compound OC1=CC=CC=C1C=C[N+]([O-])=O PMDYAIGGZBRBFX-UHFFFAOYSA-N 0.000 claims description 11
• 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 claims description 10
• KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 claims description 9
• 238000000034 method Methods 0.000 claims description 6
• LYGJENNIWJXYER-UHFFFAOYSA-N nitromethane Chemical compound C[N+]([O-])=O LYGJENNIWJXYER-UHFFFAOYSA-N 0.000 claims description 6
• ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims description 5
• OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 4
• 229910052799 carbon Inorganic materials 0.000 claims description 4
• 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 3
• 125000003118 aryl group Chemical group 0.000 claims description 2
• 239000003054 catalyst Substances 0.000 claims 1
• 238000006243 chemical reaction Methods 0.000 description 14
• 239000000047 product Substances 0.000 description 9
• 239000000243 solution Substances 0.000 description 5
• RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
• 239000001116 FEMA 4028 Substances 0.000 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 description 3
• 235000011175 beta-cyclodextrine Nutrition 0.000 description 3
• 229960004853 betadex Drugs 0.000 description 3
• 239000003153 chemical reaction reagent Substances 0.000 description 3
• RGHHSNMVTDWUBI-UHFFFAOYSA-N 4-hydroxybenzaldehyde Chemical compound OC1=CC=C(C=O)C=C1 RGHHSNMVTDWUBI-UHFFFAOYSA-N 0.000 description 2
• HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
• VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
• 230000002378 acidificating effect Effects 0.000 description 2
• 239000003513 alkali Substances 0.000 description 2
• 239000007864 aqueous solution Substances 0.000 description 2
• WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 2
• 230000015572 biosynthetic process Effects 0.000 description 2
• 230000000052 comparative effect Effects 0.000 description 2
• 238000000425 proton nuclear magnetic resonance spectrum Methods 0.000 description 2
• 238000003786 synthesis reaction Methods 0.000 description 2
• 230000002194 synthesizing effect Effects 0.000 description 2
• VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
• 229920001450 Alpha-Cyclodextrin Polymers 0.000 description 1
• 239000005711 Benzoic acid Substances 0.000 description 1
• RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
• 238000010521 absorption reaction Methods 0.000 description 1
• 239000003905 agrochemical Substances 0.000 description 1
• 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 description 1
• 229940043377 alpha-cyclodextrin Drugs 0.000 description 1
• 239000003242 anti bacterial agent Substances 0.000 description 1
• 235000010233 benzoic acid Nutrition 0.000 description 1
• 239000006227 byproduct Substances 0.000 description 1
• 239000007806 chemical reaction intermediate Substances 0.000 description 1
• 238000001816 cooling Methods 0.000 description 1
• 230000003247 decreasing effect Effects 0.000 description 1
• 239000003814 drug Substances 0.000 description 1
• 239000000543 intermediate Substances 0.000 description 1
• 238000004519 manufacturing process Methods 0.000 description 1
• 239000000203 mixture Substances 0.000 description 1
• XNGIFLGASWRNHJ-UHFFFAOYSA-N phthalic acid Chemical compound OC(=O)C1=CC=CC=C1C(O)=O XNGIFLGASWRNHJ-UHFFFAOYSA-N 0.000 description 1
• 239000002244 precipitate Substances 0.000 description 1
• 239000002994 raw material Substances 0.000 description 1
• 238000000926 separation method Methods 0.000 description 1
• 238000001228 spectrum Methods 0.000 description 1
• 239000000126 substance Substances 0.000 description 1
• 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1