2-Methylene-3-phenyl-4-penten-1-ol | 57217-07-9

• 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: 2-Methylene-3-phenyl-4-penten-1-ol
• 英文别名: 2-Methyliden-3-phenyl-pent-4-en-1-ol；2-Methylidene-3-phenylpent-4-en-1-ol
• CAS: 57217-07-9
• 化学式: C₁₂H₁₄O
• 分子量: 174.243
• InChiKey: WYJGJFJQPXCDHL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  13
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.17
• 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-丙炔-1-醇 、 Cinnamyl bromide 在 indium 作用下， 生成 2-Methylene-3-phenyl-4-penten-1-ol 、 (E)-4-Phenyl-2,5-hexadien-1-ol
  参考文献：
  名称：

  炔醇的羰基化。轻松合成代木醇

  摘要：

  在100 – 140°C下，通过顺式加成，在DMF中进行烯丙基倍半卤化物对炔诺醇的碳合成；用这种方法在一个锅中制备代木醇。

  DOI：

  10.1016/s0040-4039(00)92248-2

文献信息

• Carboindation of alkynols. A facile synthesis of yomogi alcohol
  作者：Shuki Araki、Akira Imai、Ken Shimizu、Yasuo Butsugan

  DOI：10.1016/s0040-4039(00)92248-2

  日期：1992.4

  Carboindation of alkynols by allylic indium sesquihalides proceeded in DMF at 100 – 140 °C via a syn-addition; yomogi alcohol was prepared in onepot by this method.

  在100 – 140°C下，通过顺式加成，在DMF中进行烯丙基倍半卤化物对炔诺醇的碳合成；用这种方法在一个锅中制备代木醇。
• Carboindation of Alkynes. Regio- and Stereoselective Allylation of Carbon-Carbon Triple Bonds of Alkynols by Allylic Indium Reagents
  作者：Shuki Araki、Akira Imai、Ken Shimizu、Masafumi Yamada、Akihiro Mori、Yasuo Butsugan

  DOI：10.1021/jo00111a049

  日期：1995.3

  Allylindium sesquihalides undergo smooth allylindation with terminal alkynes bearing a neighboring hydroxyl group at 100-140 degrees C to give allylalkenols. The coupling occurred regioselectively at the gamma-carbon of the allylindium reagents via syn-addition, whereas the regioselectivity concerning the alkynol depends upon the structures of both allylindium and alkynol. The allylation of nonfunctionalized alkynes is less efficient, requiring higher reaction temperature (150-180 degrees C) and giving lower yields. Mechanistic considerations suggest a hydroxyl-assisted concerted process for the allylindation of alkynols, whereas a radical pathway is more likely for nonfunctionalized alkynes. Three monoterpene alcohols, i.e., yomogi alcohol, achillenol, and isomyrcenol, were conveniently prepared via allylindation of appropriate alkynols.