1-phenyl-1-deutero-2-phenylthioethene | 84783-07-3

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 英文名称: 1-phenyl-1-deutero-2-phenylthioethene
• CAS: 84783-07-3
• 化学式: C₁₄H₁₂S
• 分子量: 213.307
• InChiKey: NCSYOCXYJXZCGQ-WORMITQPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.45
• 重原子数：
  15.0
• 可旋转键数：
  3.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  0.0
• 氢给体数：
  0.0
• 氢受体数：
  1.0

反应信息

• 作为反应物：
  描述：

  1-phenyl-1-deutero-2-phenylthioethene 在 间氯过氧苯甲酸 作用下， 以 氯仿 为溶剂， 反应 48.0h， 生成 Z-2-deutero-2-phenyl-1-(phenylsulfonyl)ethene 、 E-2-deutero-2-phenyl-1-(phenylsulfonyl)ethene
  参考文献：
  名称：

  Benati, Luisa; Capella, Laura; Montevecchi, Pier Carlo, Journal of the Chemical Society. Perkin transactions I, 1995, # 8, p. 1035 - 1038

  摘要：

  DOI：
• 作为产物：
  描述：

  1-phenyl-1-deutero-2-phenylthioethanol 以 六甲基磷酰三胺 为溶剂， 反应 1.0h， 生成 1-phenyl-1-deutero-2-phenylthioethene
  参考文献：
  名称：

  Rearrangements and fragmentations of phenyl styryl sulfides: 2—labelling studies

  摘要：

  AbstractMetastable molecular ions of phenyl styryl sulfides may decompose by loss of CH3˙, SH˙, CHS˙, C6H5˙, C6H6 or C7H7˙. Labelling with carbon‐13 and deuterium gave information about the mechanisms of these reactions. It appears that extensive rearrangements occur prior to most of these fragmentations. In the case of phenyl β‐styryl sulfide both phenyl groups and both vinyl carbon atoms are found in the C7H7 fragment in comparable amounts. For phenyl α‐styryl sulfide this fragmentation leads more specifically to the loss of the S‐phenyl group and the β‐vinyl carbon atom. It was concluded that rearrangements occur, partly via symmetric diphenyl ethene sulfide structures, to benzyl phenyl thione ions, from which the fragmentation occurs. For the loss of CHS˙ an earlier proposed mechanism was confirmed. From both compounds the S‐phenyl ring can be lost as C6H5˙ or C6H6 as well as the C‐phenyl ring. Fragmentation occurs from one of the initial structures as well as from benzyl phenyl thione. Loss of CH3˙ is thought to occur after ring closure with formation of dihydrobenzo[b]thiophenes followed by ring opening by rupture of a CS bond. While phenyl β‐styryl sulfide shows a strong tendency towards isomerization to a symmetric structure like 1,2‐diphenylethene sulfide, phenyl α‐styryl sulfide easily rearranges in an electrocyclic reaction with formation of benzyl phenyl thione.

  DOI：

  10.1002/oms.1210170907