4-Methyl-2-(phenylsulfonyl)-1-phenyl-1,3-pentadiene | 56631-62-0

• 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-Methyl-2-(phenylsulfonyl)-1-phenyl-1,3-pentadiene
• 英文别名: [(1E)-2-(benzenesulfonyl)-4-methylpenta-1,3-dienyl]benzene
• CAS: 56631-62-0
• 化学式: C₁₈H₁₈O₂S
• 分子量: 298.406
• InChiKey: BIEBWDXWACJDRP-NBVRZTHBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  21
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.11
• 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：

  4-Methyl-2-(phenylsulfonyl)-1-phenyl-1,3-pentadiene 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95%的产率得到(E)-(4-methylpenta-1,3-dien-1-yl)benzene
  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：

  3-methyl-1-(phenylsulfonyl)but-2-ene 在 四丁基溴化铵 sodium hydroxide 、 六氯乙烷 作用下， 以 二氯甲烷 为溶剂， 反应 5.0h， 生成 4-Methyl-2-(phenylsulfonyl)-1-phenyl-1,3-pentadiene
  参考文献：
  名称：

  α-氯烯丙基砜的一些碳负离子反应

  摘要：

  在碱性介质中用六氯乙烷或 1,1-二氯-3-甲基-2-丁烯基苯砜氯化 3-甲基-2-丁烯基苯砜生成 1-氯-3-甲基-2-丁烯基苯砜其反过来与亲电子化合物原位反应，以良好的产率得到各种产物。

  DOI：

  10.1246/cl.1983.1557

文献信息

• JONCZYK, A.;RADWAN-PYTLEWSKI, T., CHEM. LETT., 1983, N 10, 1557-1560
  作者：JONCZYK, A.、RADWAN-PYTLEWSKI, T.

  DOI：——

  日期：——
• CARDILLO G.; SAVOIA D.; UMANI-RONCHI A., SYNTHESIS <SYNT-BF>, 1975, NO 7, 453-455
  作者：CARDILLO G.、 SAVOIA D.、 UMANI-RONCHI A.

  DOI：——

  日期：——
• 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.
• SOME CARBANIONIC REACTIONS OF α-CHLOROALLYL SULFONES
  作者：Andrzej Jonczyk、Tadeusz Radwan-Pytlewski

  DOI：10.1246/cl.1983.1557

  日期：1983.10.5

  The chlorination of 3-methyl-2-butenyl phenyl sulfone with either hexachloroethane or 1,1-dichloro-3-methyl-2-butenyl phenyl sulfone in basic medium gives rise to 1-chloro-3-methyl-2-butenyl phenyl sulfone which in turn reacts in situ with electrophilic compounds to give a variety of products in good yields.

  在碱性介质中用六氯乙烷或 1,1-二氯-3-甲基-2-丁烯基苯砜氯化 3-甲基-2-丁烯基苯砜生成 1-氯-3-甲基-2-丁烯基苯砜其反过来与亲电子化合物原位反应，以良好的产率得到各种产物。