(Z)-3-chloro-4-cyclohexyl-2-buten-1-ol

• 分子结构分类: 有机化合物 - 有机卤素化合物 - 乙烯基卤化物
• 英文名称: (Z)-3-chloro-4-cyclohexyl-2-buten-1-ol
• 英文别名: (Z)-3-chloro-4-cyclohexylbut-2-en-1-ol
• 化学式: C₁₀H₁₇ClO
• 分子量: 188.697
• InChiKey: XRLUJNHPLCHHNT-POHAHGRESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  12
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  20.2
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  2-氯-3,4-环氧-1-丁烯 、 环己基溴化镁 在 二甲基硫 、 copper(I) bromide 作用下， 以 四氢呋喃 为溶剂， 反应 1.0h， 生成 (E)-3-chloro-4-cyclohexyl-2-buten-1-ol 、 (Z)-3-chloro-4-cyclohexyl-2-buten-1-ol
  参考文献：
  名称：

  Preparation and Reactions of 2-Chloro-3,4-epoxy-1-butene:  A Convenient Route to (Z)-3-Chloroallylic Alcohols

  摘要：

  Epoxide 2 was prepared from 3,4-dichloro-1-butene (1) by epoxidation with m-CPBA and subsequent dehydrohalogenation of the intermediate dichloroepoxide, with molten KOH, affording 2 in 64% overall yield (2 steps). Catalytic CuBr/SMe2-mediated S(N)2'addition of Sp(2)- or sp(3)-hybridized Grignard reagents to 2-chloro-3,4-epoxy-1-butene (2) afforded (Z)-3-chloroallylic alcohols such as 3 in good yields and with high regio- and stereoselectivity.

  DOI：

  10.1021/jo020079l

文献信息

• Preparation and Reactions of 2-Chloro-3,4-epoxy-1-butene:  A Convenient Route to (<i>Z</i>)-3-Chloroallylic Alcohols
  作者：Douglass F. Taber、Jeffrey V. Mitten

  DOI：10.1021/jo020079l

  日期：2002.5.1

  Epoxide 2 was prepared from 3,4-dichloro-1-butene (1) by epoxidation with m-CPBA and subsequent dehydrohalogenation of the intermediate dichloroepoxide, with molten KOH, affording 2 in 64% overall yield (2 steps). Catalytic CuBr/SMe2-mediated S(N)2'addition of Sp(2)- or sp(3)-hybridized Grignard reagents to 2-chloro-3,4-epoxy-1-butene (2) afforded (Z)-3-chloroallylic alcohols such as 3 in good yields and with high regio- and stereoselectivity.