2-(2-chloroethyl)-6-methylhept-1-en-4-ol | 929689-31-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-(2-chloroethyl)-6-methylhept-1-en-4-ol
• 英文别名: 8-Chloro-2-methyl-6-methylideneoctan-4-ol
• CAS: 929689-31-6
• 化学式: C₁₀H₁₉ClO
• 分子量: 190.713
• InChiKey: DTIWSCMIXKSYEH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  12
• 可旋转键数：
  6
• 环数：
  0.0
• 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

• 作为反应物：
  描述：

  2-(2-chloroethyl)-6-methylhept-1-en-4-ol 在 氢氧化钾 、 4-甲基苯磺酸吡啶 作用下， 以 乙醇 、 二氯甲烷 为溶剂， 反应 14.0h， 生成 (+/-)-ipsenol
  参考文献：
  名称：

  Transformation of carboxylic acid esters into 2-substituted allyl halides through tertiary cyclopropyl sulfonates. Application in the synthesis of (±)-ipsenol and (±)-ipsdienol, components of Ips typographus spark beetle pheromone

  摘要：

  Cyclopropanation of the ester group in ethyl 3-chloropropanoate and subsequent cleavage of the three-membered carbocycle in intermediate 1-(2-chloroethyl)cyclopropyl methanesulfonate gave 2-bromomethyl-4-chlorobut-1-ene, and the latter was used as key intermediate in the synthesis of racemic ipsenol and ipsdienol which are components of Ips typographus L. European spruce spark beetle pheromone.

  DOI：

  10.1134/s1070428006040038
• 作为产物：
  描述：

  异戊醛 、 2-bromomethyl-4-chloro-1-butene 在 锌 作用下， 以 四氢呋喃 为溶剂， 反应 0.33h， 以73%的产率得到2-(2-chloroethyl)-6-methylhept-1-en-4-ol
  参考文献：
  名称：

  Transformation of carboxylic acid esters into 2-substituted allyl halides through tertiary cyclopropyl sulfonates. Application in the synthesis of (±)-ipsenol and (±)-ipsdienol, components of Ips typographus spark beetle pheromone

  摘要：

  Cyclopropanation of the ester group in ethyl 3-chloropropanoate and subsequent cleavage of the three-membered carbocycle in intermediate 1-(2-chloroethyl)cyclopropyl methanesulfonate gave 2-bromomethyl-4-chlorobut-1-ene, and the latter was used as key intermediate in the synthesis of racemic ipsenol and ipsdienol which are components of Ips typographus L. European spruce spark beetle pheromone.

  DOI：

  10.1134/s1070428006040038

文献信息

• Transformation of carboxylic acid esters into 2-substituted allyl halides through tertiary cyclopropyl sulfonates. Application in the synthesis of (±)-ipsenol and (±)-ipsdienol, components of Ips typographus spark beetle pheromone
  作者：E. A. Matyushenkov、O. G. Kulinkovich

  DOI：10.1134/s1070428006040038

  日期：2006.4

  Cyclopropanation of the ester group in ethyl 3-chloropropanoate and subsequent cleavage of the three-membered carbocycle in intermediate 1-(2-chloroethyl)cyclopropyl methanesulfonate gave 2-bromomethyl-4-chlorobut-1-ene, and the latter was used as key intermediate in the synthesis of racemic ipsenol and ipsdienol which are components of Ips typographus L. European spruce spark beetle pheromone.