2-methyl-5-methylidenehept-2-en-4-ol | 1304511-68-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-methyl-5-methylidenehept-2-en-4-ol
• CAS: 1304511-68-9
• 化学式: C₉H₁₆O
• 分子量: 140.225
• InChiKey: HQKBFXWVAHTOCO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.28
• 重原子数：
  10.0
• 可旋转键数：
  3.0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  20.23
• 氢给体数：
  1.0
• 氢受体数：
  1.0

反应信息

• 作为反应物：
  描述：

  2-methyl-5-methylidenehept-2-en-4-ol 、 N-苄烯丁胺 在 titanium(IV) isopropylate 、 Cyclopentylmagnesium chloride 、 正丁基锂 、 碳酸氢钠 作用下， 以 乙醚 、 四氢呋喃 、 Petroleum ether 、 水 为溶剂， 反应 16.5h， 生成 (Z)-N-benzyl-3-ethyl-6-methyl-1-phenylhepta-3,5-dien-1-amine 、 (E)-N-benzyl-3-ethyl-6-methyl-1-phenylhepta-3,5-dien-1-amine
  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.