(Z)-methyl 4-dodecylthio-2-methyl-3-propyl-2-hexenoate | 1194360-40-1

• 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: (Z)-methyl 4-dodecylthio-2-methyl-3-propyl-2-hexenoate
• CAS: 1194360-40-1
• 化学式: C₂₃H₄₄O₂S
• 分子量: 384.667
• InChiKey: WLSKSFWFHCWELY-MRCUWXFGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.71
• 重原子数：
  26.0
• 可旋转键数：
  17.0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.87
• 拓扑面积：
  26.3
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为产物：
  描述：

  ethyl 2,2-dibromopropanoate 、 3-(dodecylthio)heptan-4-one 、 碘甲烷 在 叔丁基锂 作用下， 以 四氢呋喃 、 正戊烷 、 六甲基磷酰三胺 为溶剂， 反应 18.5h， 以76%的产率得到(Z)-methyl 4-dodecylthio-2-methyl-3-propyl-2-hexenoate
  参考文献：
  名称：

  The effects of C–S and C–Se bonds on torquoselectivity: stereoselective olefination of α-thio and α-selenoketones with ynolates

  摘要：

  Highly Z-selective olefination of acyclic alpha-thio and alpha-selenoketones with ynolates has been achieved, and the theoretical calculations of the transition states in the ring-opening of the intermediates, the beta-lactone enolates, revealed that the torquoselectivity was controlled by the secondary orbital interactions between the sigma orbital of the C-S bond or a lone pair orbital on the S and sigma* orbitals of the breaking C-O bond, and the sigma orbital of the breaking C-O bond or a lone pair orbital on the O on the ring and the sigma* orbitals of the C-S bond. The synthetic applications of the resulting olefins are also shown. (c) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2009.08.060