(Z)-1-Iodo-3-phenylprop-1-en-3-ol | 154055-72-8

• 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: (Z)-1-Iodo-3-phenylprop-1-en-3-ol
• 英文别名: [(Z)-3-iodo-1-(methoxymethoxy)prop-2-enyl]benzene
• CAS: 154055-72-8
• 化学式: C₁₁H₁₃IO₂
• 分子量: 304.128
• InChiKey: TXPTZNYBZACSEG-FPLPWBNLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  14
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  18.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (Z)-1-Iodo-3-phenylprop-1-en-3-ol 、 烯丙基溴化镁 在 zinc dibromide 作用下， 以 乙醚 为溶剂， 以53%的产率得到((1R,2S)-1-Methoxymethoxy-2-methyl-pent-4-enyl)-benzene
  参考文献：
  名称：

  Diastereoselective allylzincation of γ-oxygenated vinyllithiums bearing functionalized side-chains

  摘要：

  Allylzincation of gamma-oxygenated vinyllithiums bearing functionalized side-chains proved to be more difficult than that reported in the case of gamma-oxygenated vinyllithiums with unfunctionalized side-chains. However, when allylzincation occurs it gives the corresponding linear compounds with high diastereoselection as a consequence of the zinc being coordinated by the two oxygen atoms of the methoxymethyl ether moiety. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2004.04.020
• 作为产物：
  描述：

  溴甲基甲基醚 、 (Z)-1-Iodo-3-phenylprop-1-en-3-ol 在 乙基溴化镁 作用下， 生成 (Z)-1-Iodo-3-phenylprop-1-en-3-ol
  参考文献：
  名称：

  Stereodefined Substituted Cyclopropyl Zinc Reagents from Gem-Bismetallics

  摘要：

  1,1- or n,n-Bismetallic reagents bearing a methoxymethyl ether in the gamma position undergo cyclization at room temperature to give monometalated, diastereoselectively substituted cyclopropanes, The nature of the substituents is crucial for this diastereoselection, a pi-chelation between one metal and a properly located unsaturation, as well as 1,2-strain, are proposed to explain the steric outcome of these reactions.

  DOI：

  10.1021/jo00113a032

文献信息

• Cyclic stereocontrol via organobismetallic reagents. Part VI. stereodefined substituted cyclopropyl zinc reagents
  作者：Dov Beruben、Ilane Marek、Jean-F. Normant、Nicole Platzer

  DOI：10.1016/s0040-4039(00)60404-5

  日期：1993.11

  The Metalla Claisen reaction followed by a 1,3-elimination generates a diastereoselectively substituted metallated cyclopropane.