CAS: 5447-86-9; 10,10-Dimethyl-9,10-Dihydroanthracen-9-One

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9,9-Dimethyl-10-(Trimethylsilyl)-9,10-Dihydroanthracene置于sodium Dichromate,溶剂黄146体系中,化学反应 12.0H,以90%的收率获得产物10,10-二甲基蒽酮
参考文献:A Convenient Synthesis Of 9,9-Dialkyl-9,10-Dihydroanthracenes And 10,10-Dialkylanthrones: Silicon-Mediated Regioselective Dialkylation Of 9,10-Dihydroanthracene
标题:A Convenient Synthesis Of 9,9-Dialkyl-9,10-Dihydroanthracenes And 10,10-Dialkylanthrones: Silicon-Mediated Regioselective Dialkylation Of 9,10-Dihydroanthracene
摘要:Described Is A Short And Convenient Approach To The Synthesis Of 9,9-Dialkyl-9,10-Dihydroanthracenes,9,9,10-Trialkyl-9,10-Dihydroanthracenes,And 10,10-Dialkylanthrones,Some Of Which Are Otherwise Unknown Or Inaccessible By Conventional Methods. Deprotonation Of 9-(Trimethylsilyl)-9,10-Dihydroanthracene (2; 9-(Trimethylsilyl)-9,10-Dha) Followed By Reaction With Alkyl Halides (Rx) Produces 9-Alkyl-9-(Trimethylsilyl)-9,10-Dhas 3-7 In 80-90% Yields. Treatment Of 3-7 With N-Buli Produces The 10-Lithio Derivatives That Rearrange To 9-Alkyl-9-Lithio-10-(Trimethylsilyl) Intermediates; Subsequent Alkylation With Rx Generates 9,9-Dialkyl-10-(Trimethylsilyl)-9,10-Dhas 8-19. Formation Of Single Stereoisomers 13-19 Was Suggested By NMR And Confirmed In Two Cases,15 And 16,By X-Ray Structure Determination. The Trimethylsilyl Group Is Removed By Tetra-Butlyammonium Fluoride (Tbaf) To Provide 9,9-Dialkyl-9,10-Dhas 20-29 With Impressive Yields. Oxidation Of Either The 9,9-Dialkyl-9,10-Dhas Or 9,9-Dialkyl-10-(Trimethylsilyl)-9,10-Dhas With Cr(Vi) Oxidant Furnished 10,10-Dialkylanthrones 36-41 In 80-90% Yields.
DOI:10.1021/jo00036A029

专利信息

专利号:CN-115417753-B
优先权日:2022-09-23
标 题:A kind of synthesis method of melitracen and its intermediates

专利号:CN-120058770-A
优先权日:2025-02-17
标题:A kind of aryl silicon modified spiro ring organic photoelectric functional material and its synthesis method