(E)-4,4-Dimethyl-2,5-hexadien-1-ol | 141993-24-0

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: (E)-4,4-Dimethyl-2,5-hexadien-1-ol
• 英文别名: 4,4-dimethyl-2,5-hexadien-1-ol；(2E)-4,4-dimethylhexa-2,5-dien-1-ol
• CAS: 141993-24-0
• 化学式: C₈H₁₄O
• 分子量: 126.199
• InChiKey: BKIKIFZEVPEXMS-AATRIKPKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  9
• 可旋转键数：
  3
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.5
• 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 、 1-溴-3-甲基-2-丁烯 在 indium 作用下， 生成 2-methylene-3,3-dimethyl-4-penten-1-ol 、 (E)-4,4-Dimethyl-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.