(Z)-2-methyl-3-phenyl-4-phenylselanylpent-2-enoic acid | 1194360-66-1

• 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)-2-methyl-3-phenyl-4-phenylselanylpent-2-enoic acid
• CAS: 1194360-66-1
• 化学式: C₁₈H₁₈O₂Se
• 分子量: 345.3
• InChiKey: ZHNCVBQDWJZTSA-GHRIWEEISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.38
• 重原子数：
  21
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  37.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  甲醇 、 (Z)-2-methyl-3-phenyl-4-phenylselanylpent-2-enoic acid 在 4-二甲氨基吡啶 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 作用下， 以 二氯甲烷 为溶剂， 反应 4.0h， 以117.5 mg的产率得到methyl (Z)-2-methyl-3-phenyl-4-(phenylseleno)pent-2-enoate
  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
• 作为产物：
  描述：

  ethyl 2,2-dibromopropanoate 、 1-phenyl-2-(phenylselanyl)propanone 在 叔丁基锂 、 盐酸 作用下， 以 四氢呋喃 、 正戊烷 、 水 为溶剂， 反应 1.0h， 生成 (Z)-2-methyl-3-phenyl-4-phenylselanylpent-2-enoic acid
  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.