(E)-1,4-bis-(1-hydroxycyclopentyl)but-2-ene

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (E)-1,4-bis-(1-hydroxycyclopentyl)but-2-ene
• 英文别名: 1-[(E)-4-(1-hydroxycyclopentyl)but-2-enyl]cyclopentan-1-ol
• 化学式: C₁₄H₂₄O₂
• 分子量: 224.343
• InChiKey: NQQDSPLNJHCUKW-AATRIKPKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  16
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.86
• 拓扑面积：
  40.5
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  反式-1,4-二氯-2-丁烯 、 环戊酮 在 4,4'-二叔丁基苯并 、 lithium 作用下， 以 四氢呋喃 为溶剂， 反应 0.75h， 以13%的产率得到3,4-bis-(1-hydroxycyclopentyl)but-1-ene
  参考文献：
  名称：

  Arene-catalysed lithiation of 1,4-dichlorobut-2-enes and 3,4-dichlorobut-1-ene and reaction with electrophiles: A common reaction pathway

  摘要：

  The reaction of (Z) or (E)-1,4-dichlorobut-2-ene (1,2) or 3,4-dichlorobut-1-ene (3) with an excess of lithium powder and a catalytic amount of 4,4'-di-tert-butylbiphenyl (5 mol %) in the presence of an electrophile [(CH2)(4)CO,Bu(t)CHO,Me(3)SiCl] in THF at 0 degrees C yields, after hydrolysis, the corresponding 1,4- and 1,2-disubstituted compounds (Z/E)-4 and 5, the ratio of them being independent on the starting material. In the case of compounds 4 the Z-diastereomer is largely the major one. When dichlorodiethylsilane was used as electrophile the corresponding substituted silacyclopentene 6 was the only reaction product isolated. A possible mechanism involving dilithiated species is proposed.

  DOI：

  10.1016/s0040-4020(01)85269-8

文献信息

• Arene-catalysed lithiation of 1,4-dichlorobut-2-enes and 3,4-dichlorobut-1-ene and reaction with electrophiles: A common reaction pathway
  作者：Albert Guijarro、Miguel Yus

  DOI：10.1016/s0040-4020(01)85269-8

  日期：1994.1

  The reaction of (Z) or (E)-1,4-dichlorobut-2-ene (1,2) or 3,4-dichlorobut-1-ene (3) with an excess of lithium powder and a catalytic amount of 4,4'-di-tert-butylbiphenyl (5 mol %) in the presence of an electrophile [(CH2)(4)CO,Bu(t)CHO,Me(3)SiCl] in THF at 0 degrees C yields, after hydrolysis, the corresponding 1,4- and 1,2-disubstituted compounds (Z/E)-4 and 5, the ratio of them being independent on the starting material. In the case of compounds 4 the Z-diastereomer is largely the major one. When dichlorodiethylsilane was used as electrophile the corresponding substituted silacyclopentene 6 was the only reaction product isolated. A possible mechanism involving dilithiated species is proposed.