(E)-1,4-Diphenyl-2-(phenylsulfonyl)-1-butene | 168007-41-8

• 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: (E)-1,4-Diphenyl-2-(phenylsulfonyl)-1-butene
• 英文别名: [(E)-3-(benzenesulfonyl)-4-phenylbut-3-enyl]benzene
• CAS: 168007-41-8
• 化学式: C₂₂H₂₀O₂S
• 分子量: 348.466
• InChiKey: IPNPBVDMYNTBHW-RELWKKBWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.4
• 重原子数：
  25
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.09
• 拓扑面积：
  42.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (E)-1,4-Diphenyl-2-(phenylsulfonyl)-1-butene 在 甲醇 、 N,N-二甲基丙烯基脲 、 samarium diiodide 作用下， 以 四氢呋喃 为溶剂， 反应 0.5h， 以85%的产率得到(E)-1,4-diphenylbut-1-ene
  参考文献：
  名称：

  Use of Samarium Diiodide as an Alternative to Sodium/Mercury Amalgam in the Julia-Lythgoe Olefination

  摘要：

  Studies into the use of samarium diiodide (SmI2) in the reductive elimination of 1,2-acetoxy sulfones and the reductive cleavage of vinyl sulfones are reported. Parallel investigations with sodium/mercury amalgam (Na/Hg) revealed over-reduction in several cases in which the desired products were heavily conjugated or conjugated to an aromatic moiety. A mechanistic study revealed some of the intricacies of the SmI2-promoted Julia-Lythgoe olefination. The classical Na/Hg reductive method was also examined, and an alternative mechanism is proposed. Observations described herein provide important insights into the mechanism and synthetic utility of these methods. The optimum protocol developed utilizes SmI2 reduction of vinyl sulfones in the presence of DMPU and MeOH and gives generally high yields with good to excellent E stereoselectivity.

  DOI：

  10.1021/jo00115a041
• 作为产物：
  描述：

  1-Acetoxy-1,4-diphenyl-2-(phenylsulfonyl)butane 在 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 四氢呋喃 为溶剂， 反应 18.0h， 生成 (Z)-1,4-Diphenyl-2-(phenylsulfonyl)-1-butene 、 (E)-1,4-Diphenyl-2-(phenylsulfonyl)-1-butene
  参考文献：
  名称：

  Use of Samarium Diiodide as an Alternative to Sodium/Mercury Amalgam in the Julia-Lythgoe Olefination

  摘要：

  Studies into the use of samarium diiodide (SmI2) in the reductive elimination of 1,2-acetoxy sulfones and the reductive cleavage of vinyl sulfones are reported. Parallel investigations with sodium/mercury amalgam (Na/Hg) revealed over-reduction in several cases in which the desired products were heavily conjugated or conjugated to an aromatic moiety. A mechanistic study revealed some of the intricacies of the SmI2-promoted Julia-Lythgoe olefination. The classical Na/Hg reductive method was also examined, and an alternative mechanism is proposed. Observations described herein provide important insights into the mechanism and synthetic utility of these methods. The optimum protocol developed utilizes SmI2 reduction of vinyl sulfones in the presence of DMPU and MeOH and gives generally high yields with good to excellent E stereoselectivity.

  DOI：

  10.1021/jo00115a041

文献信息

• Use of Samarium Diiodide as an Alternative to Sodium/Mercury Amalgam in the Julia-Lythgoe Olefination
  作者：Gary E. Keck、Kenneth A. Savin、Michael A. Weglarz

  DOI：10.1021/jo00115a041

  日期：1995.5

  Studies into the use of samarium diiodide (SmI2) in the reductive elimination of 1,2-acetoxy sulfones and the reductive cleavage of vinyl sulfones are reported. Parallel investigations with sodium/mercury amalgam (Na/Hg) revealed over-reduction in several cases in which the desired products were heavily conjugated or conjugated to an aromatic moiety. A mechanistic study revealed some of the intricacies of the SmI2-promoted Julia-Lythgoe olefination. The classical Na/Hg reductive method was also examined, and an alternative mechanism is proposed. Observations described herein provide important insights into the mechanism and synthetic utility of these methods. The optimum protocol developed utilizes SmI2 reduction of vinyl sulfones in the presence of DMPU and MeOH and gives generally high yields with good to excellent E stereoselectivity.