2-benzyl-4-oxo-3-phenylselanyloct-2(E)-enoic acid ethyl ester

• 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: 2-benzyl-4-oxo-3-phenylselanyloct-2(E)-enoic acid ethyl ester
• 英文别名: ethyl (E)-2-benzyl-4-oxo-3-phenylselanyloct-2-enoate
• 化学式: C₂₃H₂₆O₃Se
• 分子量: 429.418
• InChiKey: LYEGPSBWMPWQEG-LSDHQDQOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.84
• 重原子数：
  27
• 可旋转键数：
  11
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  43.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  ethyl 2-benzyl-2,3-octadienoate 、 苯基氯化硒 在 lithium carbonate 作用下， 以 乙腈 为溶剂， 反应 48.0h， 以67%的产率得到2-benzyl-4-oxo-3-phenylselanyloct-2(E)-enoic acid ethyl ester
  参考文献：
  名称：

  Electrophilic Interaction of 2,3-Allenoates with PhSeCl. An Unexpected Highly Stereoselective Synthesis of 3-Phenylseleno-4-oxo-2(E)-alkenoates

  摘要：

  We have previously reported an efficient synthesis of beta-phenylselenium-substituted butenolides via electrophilic cyclization of 2,3-allenoates with PhSeCl in aqueous MeCN. However, when 2,3-allenoates were treated with PhSeCl in MeCN, 3-phenylseleno-4-oxo-2(E)-alkenoates were formed unexpectedly. The addition of Li2CO3 improved the yield and the selectivity of the reaction. A possible mechanism involving a decomposition of selenate esters was proposed.

  DOI：

  10.1021/jo061680c