(Z)-methyl 4-dodecylthio-2-methyl-3-phenyl-2-pentenoate | 1194360-36-5

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂酸及其衍生物
• 英文名称: (Z)-methyl 4-dodecylthio-2-methyl-3-phenyl-2-pentenoate
• 英文别名: methyl (Z)-4-dodecylsulfanyl-2-methyl-3-phenylpent-2-enoate
• CAS: 1194360-36-5
• 化学式: C₂₅H₄₀O₂S
• 分子量: 404.657
• InChiKey: RACBJDMICTXGKT-DARPEHSRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9.3
• 重原子数：
  28
• 可旋转键数：
  16
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.64
• 拓扑面积：
  51.6
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  ethyl 2,2-dibromopropanoate 、 2-(dodecylthio)-1-phenylpropan-1-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77%的产率得到(Z)-methyl 4-dodecylthio-2-methyl-3-phenyl-2-pentenoate
  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

文献信息

• The effects of C–S and C–Se bonds on torquoselectivity: stereoselective olefination of α-thio and α-selenoketones with ynolates
  作者：Takashi Yoshikawa、Seiji Mori、Mitsuru Shindo

  DOI：10.1016/j.tet.2009.08.060

  日期：2009.10

  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.