cis-1,1-Dichloro-2-(6-hydroxyhept-1-en-1-yl)cyclopropane

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: cis-1,1-Dichloro-2-(6-hydroxyhept-1-en-1-yl)cyclopropane
• 英文别名: (Z)-7-(2,2-dichlorocyclopropyl)hept-6-en-2-ol
• 化学式: C₁₀H₁₆Cl₂O
• 分子量: 223.142
• InChiKey: BJQCKQJAQFATOS-XQRVVYSFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  13
• 可旋转键数：
  5
• 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：

  2,2-dichlorocyclopropanecarbaldehyde 、 Lithium; 6-(triphenyl-λ⁵-phosphanylidene)-hexan-2-olate 在 正丁基锂 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 生成 cis-1,1-Dichloro-2-(6-hydroxyhept-1-en-1-yl)cyclopropane 、 trans-1,1-Dichloro-2-(6-hydroxyhept-1-en-1-yl)cyclopropane
  参考文献：
  名称：

  Macrocyclization through radical-mediated vinylcyclopropane/alkene condensation. Facile entry into the brefeldin ring system

  摘要：

  Bicyclic products featuring an 11-membered ring fused to a core vinylcyclopentane unit are produced upon treatment of functionalized vinylcyclopropanes bearing an omega-alkene unit with a catalytic amount of phenylthio radical. This intramolecular extension of a radical-mediated vinylcyclopropane/alkene cyclocondensation proceeds with only modest diastereoselectivity. The reaction products resemble members of the brefeldin family of naturally occurring antibiotics.

  DOI：

  10.1021/jo00076a056

文献信息

• Macrocyclization through radical-mediated vinylcyclopropane/alkene condensation. Facile entry into the brefeldin ring system
  作者：Ken S. Feldman、Heidi M. Berven、Anthony L. Romanelli、Masood Parvez

  DOI：10.1021/jo00076a056

  日期：1993.11

  Bicyclic products featuring an 11-membered ring fused to a core vinylcyclopentane unit are produced upon treatment of functionalized vinylcyclopropanes bearing an omega-alkene unit with a catalytic amount of phenylthio radical. This intramolecular extension of a radical-mediated vinylcyclopropane/alkene cyclocondensation proceeds with only modest diastereoselectivity. The reaction products resemble members of the brefeldin family of naturally occurring antibiotics.