10,10-Diisopropylanthrone | 141377-22-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 蒽
• 英文名称: 10,10-Diisopropylanthrone
• 英文别名: 10,10-Di(propan-2-yl)anthracen-9-one
• CAS: 141377-22-2
• 化学式: C₂₀H₂₂O
• 分子量: 278.394
• InChiKey: RFNPUVPJNIUJRL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.8
• 重原子数：
  21
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  9,9-Diisopropyl-10-(trimethylsilyl)-9,10-dihydroanthracene 在 sodium dichromate 、 溶剂黄146 作用下， 反应 12.0h， 以91%的产率得到10,10-Diisopropylanthrone
  参考文献：
  名称：

  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

文献信息

• US8173274B2
  申请人：——

  公开号：US8173274B2

  公开（公告）日：2012-05-08
• A convenient synthesis of 9,9-dialkyl-9,10-dihydroanthracenes and 10,10-dialkylanthrones: silicon-mediated regioselective dialkylation of 9,10-dihydroanthracene
  作者：Raj K. Dhar、D. K. Clawson、Frank R. Fronczek、Peter W. Rabideau

  DOI：10.1021/jo00036a029

  日期：1992.5

  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.