4-(4'-bromophenyl)-4-oxo-3-phenylselanyl-2-propylbut-2(E)-enoic acid ethyl ester

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 4-(4'-bromophenyl)-4-oxo-3-phenylselanyl-2-propylbut-2(E)-enoic acid ethyl ester
• 英文别名: ethyl (2E)-2-[2-(4-bromophenyl)-2-oxo-1-phenylselanylethylidene]pentanoate
• 化学式: C₂₁H₂₁BrO₃Se
• 分子量: 480.26
• InChiKey: LIKFCBFGZXQMEM-CZIZESTLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.28
• 重原子数：
  26
• 可旋转键数：
  9
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.24
• 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-propyl-4-(p-bromophenyl)buta-2,3-dienoate 、 苯基氯化硒 在 lithium carbonate 作用下， 以 乙腈 为溶剂， 反应 1.0h， 以85%的产率得到4-(4'-bromophenyl)-4-oxo-3-phenylselanyl-2-propylbut-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.