4'-(Allyloxy)-2'(Z)-butenyl 2-butynoate | 161093-65-8

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: 4'-(Allyloxy)-2'(Z)-butenyl 2-butynoate
• 英文别名: [(Z)-4-prop-2-enoxybut-2-enyl] but-2-ynoate
• CAS: 161093-65-8
• 化学式: C₁₁H₁₄O₃
• 分子量: 194.23
• InChiKey: AAVRJAYDEUMHKF-WAYWQWQTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.31
• 重原子数：
  14.0
• 可旋转键数：
  6.0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  35.53
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  4'-(Allyloxy)-2'(Z)-butenyl 2-butynoate 在 tris(dibenzylideneacetone)dipalladium(0) chloroform complex lithium bromide 、 copper(ll) bromide 作用下， 以 溶剂黄146 为溶剂， 以23%的产率得到4-[1-Bromo-2-(2,3-dibromo-propoxy)-ethyl]-3-[1-bromo-eth-(Z)-ylidene]-dihydro-furan-2-one
  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：

  2-丁炔酸 、 4-(Allyloxy)-2-buten-1-ol 在 4-二甲氨基吡啶 、 N,N'-二环己基碳二亚胺 作用下， 以 乙醚 为溶剂， 反应 20.0h， 以82%的产率得到4'-(Allyloxy)-2'(Z)-butenyl 2-butynoate
  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