α-(Z)-(1'-Bromo-6'-methylheptylidene)-β-(hydroxymethyl)-γ-butyrolactone | 161094-06-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 内酯类
• 英文名称: α-(Z)-(1'-Bromo-6'-methylheptylidene)-β-(hydroxymethyl)-γ-butyrolactone
• 英文别名: (3Z)-3-(1-bromo-6-methylheptylidene)-4-(hydroxymethyl)oxolan-2-one
• CAS: 161094-06-0
• 化学式: C₁₃H₂₁BrO₃
• 分子量: 305.212
• InChiKey: BHUPYMPBYSXCKT-QXMHVHEDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  17
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.77
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  α-(Z)-(1'-Bromo-6'-methylheptylidene)-β-(hydroxymethyl)-γ-butyrolactone 在 盐酸 、 二乙胺 作用下， 生成 (+/-)-A-factor
  参考文献：
  名称：

  Palladium-Templated Regio- and Stereoselective Cyclization of 2'-Alkenyl 2-Alkynoates and Its Synthetic Applications

  摘要：

  2'-Alkenyl 2-alkynoates undergo facile stereoselective cyclization to alpha-(haloalkylidene)-gamma-butyrolactones upon treatment with a catalytic amount of palladium complex in the presence of CuX(2) and LiX. When an alkyl group is introduced to the 1'-position of the alkenyl group, unsubstituted 2-propynoates mainly give trans-beta, gamma-disubstituted gamma-lactones, and substituted 2-propynoates afford cis-beta,gamma-disubstituted gamma-lactones. Further elaborations of the halogen atoms and the synthesis of A-factor using this method are exemplified.

  DOI：

  10.1021/jo00110a018
• 作为产物：
  描述：

  8-Methyl-2-nonynoic acid 在 tris(dibenzylideneacetone)dipalladium(0) chloroform complex lithium hydroxide 、 sodium carbonate 、 lithium bromide 、 copper(ll) bromide 作用下， 以 1,4-二氧六环 、 六甲基磷酰三胺 、 溶剂黄146 为溶剂， 反应 18.0h， 生成 α-(Z)-(1'-Bromo-6'-methylheptylidene)-β-(hydroxymethyl)-γ-butyrolactone
  参考文献：
  名称：

  Palladium-Templated Regio- and Stereoselective Cyclization of 2'-Alkenyl 2-Alkynoates and Its Synthetic Applications

  摘要：

  2'-Alkenyl 2-alkynoates undergo facile stereoselective cyclization to alpha-(haloalkylidene)-gamma-butyrolactones upon treatment with a catalytic amount of palladium complex in the presence of CuX(2) and LiX. When an alkyl group is introduced to the 1'-position of the alkenyl group, unsubstituted 2-propynoates mainly give trans-beta, gamma-disubstituted gamma-lactones, and substituted 2-propynoates afford cis-beta,gamma-disubstituted gamma-lactones. Further elaborations of the halogen atoms and the synthesis of A-factor using this method are exemplified.

  DOI：

  10.1021/jo00110a018

文献信息

• Palladium-Templated Regio- and Stereoselective Cyclization of 2'-Alkenyl 2-Alkynoates and Its Synthetic Applications
  作者：Jianguo Ji、Chunming Zhang、Xiyan Lu

  DOI：10.1021/jo00110a018

  日期：1995.3

  2'-Alkenyl 2-alkynoates undergo facile stereoselective cyclization to alpha-(haloalkylidene)-gamma-butyrolactones upon treatment with a catalytic amount of palladium complex in the presence of CuX(2) and LiX. When an alkyl group is introduced to the 1'-position of the alkenyl group, unsubstituted 2-propynoates mainly give trans-beta, gamma-disubstituted gamma-lactones, and substituted 2-propynoates afford cis-beta,gamma-disubstituted gamma-lactones. Further elaborations of the halogen atoms and the synthesis of A-factor using this method are exemplified.