2-[1-isobutyl-3-(2-chloroethyl)but-3-enyloxy]tetrahydro-2H-pyran | 929689-33-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 氧烷类
• 英文名称: 2-[1-isobutyl-3-(2-chloroethyl)but-3-enyloxy]tetrahydro-2H-pyran
• 英文别名: 2-(8-Chloro-2-methyl-6-methylideneoctan-4-yl)oxyoxane
• CAS: 929689-33-8
• 化学式: C₁₅H₂₇ClO₂
• 分子量: 274.831
• InChiKey: UJCWRAWJMYMWJN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.9
• 重原子数：
  18
• 可旋转键数：
  8
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.87
• 拓扑面积：
  18.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-[1-isobutyl-3-(2-chloroethyl)but-3-enyloxy]tetrahydro-2H-pyran 在 氢氧化钾 、 4-甲基苯磺酸吡啶 作用下， 以 乙醇 为溶剂， 反应 11.0h， 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：

  2-bromomethyl-4-chloro-1-butene 在 4-甲基苯磺酸吡啶 、 锌 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 3.33h， 生成 2-[1-isobutyl-3-(2-chloroethyl)but-3-enyloxy]tetrahydro-2H-pyran
  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.