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

• 分子结构分类: 有机化合物 - 木脂素、新木脂素和相关化合物
• 英文名称: 2-benzyl-4-oxo-4-phenyl-3-phenylselanylbut-2(E)-enoic acid ethyl ester
• 英文别名: ethyl (E)-2-benzyl-4-oxo-4-phenyl-3-phenylselanylbut-2-enoate
• 化学式: C₂₅H₂₂O₃Se
• 分子量: 449.408
• InChiKey: AEMFMCARCZHLGT-ZNTNEXAZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.96
• 重原子数：
  29
• 可旋转键数：
  9
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.12
• 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：

  苯基氯化硒 、 ethyl 2-benzyl-4-phenylbuta-2,3-dienoate 在 lithium carbonate 作用下， 以 乙腈 为溶剂， 反应 1.0h， 以77%的产率得到2-benzyl-4-oxo-4-phenyl-3-phenylselanylbut-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

文献信息

• Electrophilic Interaction of 2,3-Allenoates with PhSeCl. An Unexpected Highly Stereoselective Synthesis of 3-Phenylseleno-4-oxo-2(<i>E</i>)-alkenoates
  作者：Guofei Chen、Chunling Fu、Shengming Ma

  DOI：10.1021/jo061680c

  日期：2006.12.1

  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.