ethyl phenylsulfonyl(trans-2-phenylvinyl)acetate

• 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: ethyl phenylsulfonyl(trans-2-phenylvinyl)acetate
• 英文别名: ethyl (E)-2-(benzenesulfonyl)-4-phenylbut-3-enoate
• 化学式: C₁₈H₁₈O₄S
• 分子量: 330.405
• InChiKey: AYIOCVIRAIKMKN-BUHFOSPRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  23
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  68.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  [(Z)-2-溴乙烯基]苯 、 苯砜乙酸乙酯 在 tris(dibenzylideneacetone)dipalladium(0) chloroform complex sodium hydride 、 三苯基膦 作用下， 以 乙二醇二甲醚 为溶剂， 反应 6.0h， 以40%的产率得到ethyl phenylsulfonyl(trans-2-phenylvinyl)acetate
  参考文献：
  名称：

  Palladium-Catalyzed Arylation of Sulfones

  摘要：

  A procedure was developed for monoarylation of sulfones with aryl halides in the presence of palladium complexes. Optimal reaction conditions were found, and the scope of application of the proposed procedure was determined. The arylation occurs only with those sulfones which are relatively strong CH acids, the corresponding monoarylated sulfones are formed in moderate to high yields. The arylation of carbanions derived from the sulfones and some other CH acids requires the presence of an additional equivalent of base. The presence of the latter is also necessary in stoichiometric reactions of carbanions with the palladium complex CF3C6H4Pd(PPh3)(2)Br; no reaction occurs in the absence of a base. A new mechanism of arylation was proposed, where the key stage is deprotonation of palladium intermediate ArPdL2CHXY which activates the reductive elimination stage.

  DOI：

  10.1023/b:rujo.0000044542.70121.04

文献信息

• Palladium-catalyzed arylation of sulfonyl CH-acids
  作者：Alexander N Kashin、Anton V Mitin、Irina P Beletskaya、Richard Wife

  DOI：10.1016/s0040-4039(02)00321-0

  日期：2002.4

  A method for the palladium-catalyzed monoarylation of a series of functionalized sulfones by aryl halides is described. The reaction proceeds in the presence of 2 mol%, of Pd(2)dba(3)(.)CHCl(3) (dba=dibenzylideneacetone), PPh3 and NaH as a base, only with relatively strong CH-acids and gives monoarylated products in moderate to high yields. (C) 2002 Elsevier Science Ltd. All rights reserved.
• Palladium-Catalyzed Arylation of Sulfones
  作者：A. V. Mitin、A. N. Kashin、I. P. Beletskaya

  DOI：10.1023/b:rujo.0000044542.70121.04

  日期：2004.6

  A procedure was developed for monoarylation of sulfones with aryl halides in the presence of palladium complexes. Optimal reaction conditions were found, and the scope of application of the proposed procedure was determined. The arylation occurs only with those sulfones which are relatively strong CH acids, the corresponding monoarylated sulfones are formed in moderate to high yields. The arylation of carbanions derived from the sulfones and some other CH acids requires the presence of an additional equivalent of base. The presence of the latter is also necessary in stoichiometric reactions of carbanions with the palladium complex CF3C6H4Pd(PPh3)(2)Br; no reaction occurs in the absence of a base. A new mechanism of arylation was proposed, where the key stage is deprotonation of palladium intermediate ArPdL2CHXY which activates the reductive elimination stage.