benzoylmethyl 3-(1-phenylethyl)benzothien-2-yl sulfide

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: benzoylmethyl 3-(1-phenylethyl)benzothien-2-yl sulfide
• 英文别名: 1-Phenyl-2-[[3-(1-phenylethyl)-1-benzothiophen-2-yl]sulfanyl]ethanone
• 化学式: C₂₄H₂₀OS₂
• 分子量: 388.554
• InChiKey: VQFJIEVBHUVKDT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.4
• 重原子数：
  27
• 可旋转键数：
  6
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  70.6
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  苯乙烯 、 1-苯并噻吩-2-硫醇 以 苯 为溶剂， 反应 2.0h， 以5%的产率得到3-(1-phenylethyl)benzothien-2-yl 2-hydroxy-2-phenylethyl sulfide
  参考文献：
  名称：

  Addition of heteroaromatic thiols to electron-rich alkenes: a reversed hetero ene reaction

  摘要：

  Benzothiophenethiol la reacted with styrene to give thiol 2a, which resulted from a ''reversed hetero ene reaction''. When the reaction was carried out in the presence of radical precursors, products deriving from radical addition to the styrene double bond of both thiols la and 2a were formed. The reaction of 1a with butyl vinyl ether (EVE) gave the alpha,beta-unsaturated dithioester 23a, deriving from the ''ene reaction product'' 22a through elimination of butanol. Similar behavior was exhibited by benzofuranthiol Ib, which reacted with styrene to give thiol 2b and with EVE to give the thionoester 23b. Both dithio- and thionoesters 23a,b were trapped as Diels-Alder adducts. In contrast, thiophenethiol Ic did not react with styrene and reacted with EVE to give an electrophilic 1:1 adduct. Ene reaction of thiols la,b occurred only with electron-rich olefins. In agreement, la did not react with hex-l-ene and methyl acrylate and reacted with dimethyl maleate to give a nucleophilic adduct.

  DOI：

  10.1021/jo00125a036

文献信息

• Addition of heteroaromatic thiols to electron-rich alkenes: a reversed hetero ene reaction
  作者：Pier Carlo Montevecchi、Maria Luisa Navacchia

  DOI：10.1021/jo00125a036

  日期：1995.10

  Benzothiophenethiol la reacted with styrene to give thiol 2a, which resulted from a ''reversed hetero ene reaction''. When the reaction was carried out in the presence of radical precursors, products deriving from radical addition to the styrene double bond of both thiols la and 2a were formed. The reaction of 1a with butyl vinyl ether (EVE) gave the alpha,beta-unsaturated dithioester 23a, deriving from the ''ene reaction product'' 22a through elimination of butanol. Similar behavior was exhibited by benzofuranthiol Ib, which reacted with styrene to give thiol 2b and with EVE to give the thionoester 23b. Both dithio- and thionoesters 23a,b were trapped as Diels-Alder adducts. In contrast, thiophenethiol Ic did not react with styrene and reacted with EVE to give an electrophilic 1:1 adduct. Ene reaction of thiols la,b occurred only with electron-rich olefins. In agreement, la did not react with hex-l-ene and methyl acrylate and reacted with dimethyl maleate to give a nucleophilic adduct.