2-(2-chloroethyl)-6-methylhepta-1,5-dien-4-ol | 929689-32-7

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: 2-(2-chloroethyl)-6-methylhepta-1,5-dien-4-ol
• 英文别名: 8-chloro-2-methyl-6-methylideneoct-2-en-4-ol；8-Chloro-2-methyl-6-methylideneoct-2-en-4-ol
• CAS: 929689-32-7
• 化学式: C₁₀H₁₇ClO
• 分子量: 188.697
• InChiKey: XIIVCWSBCYYADV-UHFFFAOYSA-N

物化性质

• 沸点：
  91-97 °C(Press: 2-3 Torr)
• 密度：
  0.986±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  12
• 可旋转键数：
  5
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.6
• 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-methylhepta-1,5-dien-4-ol 在 硫酸 、 potassium tert-butylate 、 水 、 三乙胺 、 叔丁醇 作用下， 以 丙酮 、 苯 为溶剂， 反应 13.75h， 生成 (R)-(-)-2-Methyl-6-methylene-2,7-octadien-4-ol
  参考文献：
  名称：

  Stereoselective synthesis of (R)- and (S)-Ipsdienols, pheromone components of bark beetles of the Ips family

  摘要：

  (R)- and (S)-Ipsdienols, components of pheromones of bark beetles of the Ips family, were synthesized with high enantiomeric purity (> 98%) from 8-chloro-2-methyl-6-methylideneoct-2-en-4-ol prepared from ethyl 3-chloropropionate via cyclopropanation according to Kulinkovich. 8-Chloro-2-methyl-6-methylideneoct-2-en-4-ol was converted into the corresponding hydrogen phthalate whose stereoisomeric salts with (R)- and (S)-1-phenylethanamines were separated by crystallization, and subsequent hydrolysis of the latter and dehydrohalogenation with potassium tert-butoxide gave targeted (R)- and (S)-ipsdienols.

  DOI：

  10.1134/s1070428012090035
• 作为产物：
  描述：

  3-甲基-2-丁烯醛 、 2-bromomethyl-4-chloro-1-butene 在 锌 作用下， 以 四氢呋喃 为溶剂， 反应 0.33h， 以76%的产率得到2-(2-chloroethyl)-6-methylhepta-1,5-dien-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.
• Stereoselective synthesis of (R)- and (S)-Ipsdienols, pheromone components of bark beetles of the Ips family
  作者：V. N. Kovalenko、E. A. Matyushenkov

  DOI：10.1134/s1070428012090035

  日期：2012.9

  (R)- and (S)-Ipsdienols, components of pheromones of bark beetles of the Ips family, were synthesized with high enantiomeric purity (> 98%) from 8-chloro-2-methyl-6-methylideneoct-2-en-4-ol prepared from ethyl 3-chloropropionate via cyclopropanation according to Kulinkovich. 8-Chloro-2-methyl-6-methylideneoct-2-en-4-ol was converted into the corresponding hydrogen phthalate whose stereoisomeric salts with (R)- and (S)-1-phenylethanamines were separated by crystallization, and subsequent hydrolysis of the latter and dehydrohalogenation with potassium tert-butoxide gave targeted (R)- and (S)-ipsdienols.