9,9-Diisopropyl-9,10-dihydroanthracene | 136591-06-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 蒽
• 英文名称: 9,9-Diisopropyl-9,10-dihydroanthracene
• 英文别名: 10,10-di(propan-2-yl)-9H-anthracene
• CAS: 136591-06-5
• 化学式: C₂₀H₂₄
• 分子量: 264.411
• InChiKey: FZDPPKPJOXBWSU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.3
• 重原子数：
  20
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  0

反应信息

• 作为反应物：
  描述：

  9,9-Diisopropyl-9,10-dihydroanthracene 在 sodium dichromate 、 溶剂黄146 作用下， 反应 12.0h， 生成 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
• 作为产物：
  描述：

  9,9-Diisopropyl-10-(trimethylsilyl)-9,10-dihydroanthracene 在 四丁基氟化铵 作用下， 以 四氢呋喃 为溶剂， 以95%的产率得到9,9-Diisopropyl-9,10-dihydroanthracene
  参考文献：
  名称：

  9,10-二氢蒽系统中的硅介导的烷基化：9,9-二烷基-9,10-二氢蒽的便捷合成。

  摘要：

  三甲基甲硅烷基（TMS）取代基用于控制提供9,9-二烷基-10-TMS-9,10-DHA的9,10-二氢蒽（9,10-DHA）中烷基化的区域化学。随后除去TMS基团，从而以高产率至优异产率首次方便地合成各种9,9-二烷基-9,10-DHA。

  DOI：

  10.1016/0040-4039(91)80602-3

文献信息

• Silicon Mediated Alkylations in the 9,10-Dihydroanthracene System: a Convenient Synthesis of 9,9-Dialkyl-9,10- Dihydroanthracenes.
  作者：Peter W. Rabideau、R.K. Dhar、D.K. Clawson、Zhengyun Zhan

  DOI：10.1016/0040-4039(91)80602-3

  日期：1991.8

  A trimethylsilyl (TMS) substituent is used to control the regiochemistry of alkylation in 9,10-dihydroanthracene (9,10-DHA) furnishing 9,9-dialkyl-10-TMS-9,10-DHAs. The TMS group is subsequently removed resulting in the first convenient synthesis of a variety of 9,9-dialkyl-9,10-DHAs in good to excellent yields.

  三甲基甲硅烷基（TMS）取代基用于控制提供9,9-二烷基-10-TMS-9,10-DHA的9,10-二氢蒽（9,10-DHA）中烷基化的区域化学。随后除去TMS基团，从而以高产率至优异产率首次方便地合成各种9,9-二烷基-9,10-DHA。
• 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.