2-(4-Chlorophenyl)-5-methylhex-4-en-2-ol | 1268248-86-7

• 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-(4-Chlorophenyl)-5-methylhex-4-en-2-ol
• CAS: 1268248-86-7
• 化学式: C₁₃H₁₇ClO
• 分子量: 224.73
• InChiKey: USAYXZZDXMTMIR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  15
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.38
• 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：

  1-溴-3-甲基-2-丁烯 在 正丁基锂 、 锌 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 1.0h， 生成 2-(4-Chlorophenyl)-5-methylhex-4-en-2-ol 、 2-(2-Chlorophenyl)-5-methylhex-4-en-2-ol
  参考文献：
  名称：

  General and Highly α-Regioselective Zinc-Mediated Prenylation of Aldehydes and Ketones

  摘要：

  A simple, efficient, and general alpha-prenylation approach for the synthesis of a variety of alpha-prenylated alcohols has been successfully developed. A wide range of alpha-prenylated alcohol derivatives could be obtained in good yields by highly alpha-regioselective zinc-mediated prenylation of various aldehydes and ketones with prenyl bromide at 120 degrees C in HMPA. By simply altering the reaciton solvent and temperature, the method allows the achievement of a highly notable opposite regiocontrol, providing the expected regiochemical product. The method provides a convenient route for the direct alpha-prenylation of carbonyl compounds in a highly alpha-regioselective manner using a cheap and convenient mediator. Two possible pathways are proposed to account for the formation of these synthetically difficult-to-obtain molecules.

  DOI：

  10.1021/jo102516a

文献信息

• General and Highly α-Regioselective Zinc-Mediated Prenylation of Aldehydes and Ketones
  作者：Li-Ming Zhao、Hai-Shan Jin、Li-Jing Wan、Li-Ming Zhang

  DOI：10.1021/jo102516a

  日期：2011.3.18

  A simple, efficient, and general alpha-prenylation approach for the synthesis of a variety of alpha-prenylated alcohols has been successfully developed. A wide range of alpha-prenylated alcohol derivatives could be obtained in good yields by highly alpha-regioselective zinc-mediated prenylation of various aldehydes and ketones with prenyl bromide at 120 degrees C in HMPA. By simply altering the reaciton solvent and temperature, the method allows the achievement of a highly notable opposite regiocontrol, providing the expected regiochemical product. The method provides a convenient route for the direct alpha-prenylation of carbonyl compounds in a highly alpha-regioselective manner using a cheap and convenient mediator. Two possible pathways are proposed to account for the formation of these synthetically difficult-to-obtain molecules.