1-(3,5-bis(trifluoromethyl)phenyl)-2,2-dimethyl-4-(trimethylsilyl)butan-1-ol | 1304511-63-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 1-(3,5-bis(trifluoromethyl)phenyl)-2,2-dimethyl-4-(trimethylsilyl)butan-1-ol
• 英文别名: 1-[3,5-Bis(trifluoromethyl)phenyl]-2,2-dimethyl-4-trimethylsilylbutan-1-ol；1-[3,5-bis(trifluoromethyl)phenyl]-2,2-dimethyl-4-trimethylsilylbutan-1-ol
• CAS: 1304511-63-4
• 化学式: C₁₇H₂₄F₆OSi
• 分子量: 386.453
• InChiKey: XTCVIBIRXXYWDC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.51
• 重原子数：
  25
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.65
• 拓扑面积：
  20.2
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  1-[3,5-Bis(trifluoromethyl)phenyl]-2-methylprop-2-en-1-ol 、 乙烯基三甲基硅烷 在 正丁基锂 、 三异丙氧基氯化钛 、 Cyclopentylmagnesium chloride 、 盐酸 作用下， 以 四氢呋喃 、 Petroleum ether 、 乙醚 、 水 为溶剂， 反应 2.83h， 以48%的产率得到1-(3,5-bis(trifluoromethyl)phenyl)-2,2-dimethyl-4-(trimethylsilyl)butan-1-ol
  参考文献：
  名称：

  Generation of quaternary centers by reductive cross-coupling: shifting of regioselectivity in a subset of allylic alcohol-based coupling reactions

  摘要：

  Regioselective titanium alkoxide-mediated reductive cross-coupling reactions of allylic alcohols with vinylsilanes and imines have previously been demonstrated to proceed with allylic transposition by formal metallo-[3,3]-rearrangement [thought to proceed by a sequence of: (1) directed carbometalation, and (2) syn-elimination]. While many examples have been described that support this reaction path, a collection of substrates have recently been identified that react by way of an alternative pathway, delivering a concise convergent route to coupled products bearing a quaternary center. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2010.11.059

文献信息

• Generation of quaternary centers by reductive cross-coupling: shifting of regioselectivity in a subset of allylic alcohol-based coupling reactions
  作者：Dexi Yang、Justin K. Belardi、Glenn C. Micalizio

  DOI：10.1016/j.tetlet.2010.11.059

  日期：2011.4

  Regioselective titanium alkoxide-mediated reductive cross-coupling reactions of allylic alcohols with vinylsilanes and imines have previously been demonstrated to proceed with allylic transposition by formal metallo-[3,3]-rearrangement [thought to proceed by a sequence of: (1) directed carbometalation, and (2) syn-elimination]. While many examples have been described that support this reaction path, a collection of substrates have recently been identified that react by way of an alternative pathway, delivering a concise convergent route to coupled products bearing a quaternary center. (C) 2010 Elsevier Ltd. All rights reserved.