3-methyl-4,4-bis(phenylthio)-1-butene | 133817-99-9

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 英文名称: 3-methyl-4,4-bis(phenylthio)-1-butene
• 英文别名: (2-methyl-1-phenylsulfanylbut-3-enyl)sulfanylbenzene
• CAS: 133817-99-9
• 化学式: C₁₇H₁₈S₂
• 分子量: 286.462
• InChiKey: GJXXIAGOCINMCL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.72
• 重原子数：
  19.0
• 可旋转键数：
  6.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  0.0
• 氢给体数：
  0.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  3-methyl-4,4-bis(phenylthio)-1-butene 在 间氯过氧苯甲酸 作用下， 以 氯仿 为溶剂， 以77%的产率得到<1-methyl-2,2-bis(phenylsulfonyl)ethyl>oxirane
  参考文献：
  名称：

  Methyl effects in the cyclization of .gamma.-epoxy bis-sulfones

  摘要：

  A quantitative study on the effects of methyl and gem-dimethyl groups in the intramolecular ring opening of epoxides by bis-sulfonyl carbanions is reported for the formation of cyclopropanes. Reaction rates are increased by methyl groups on the chain connecting the nucleophile with the oxirane and depressed by methyl substitution in the epoxide ring. When gem-dimethyl groups are present on the epoxide, ring opening is apparently inhibited. It will be shown that in this case the reaction is reversible and the apparent stabilization of the gem-dimethyl-substituted oxirane is actually due to a combination of effects on both the forward and the reverse reactions. On the basis of current theories on intramolecular reactions, it is suggested that release of ground-state strain and van der Waals repulsions in the transition state can account for the observed reactivity.

  DOI：

  10.1021/jo00011a017
• 作为产物：
  描述：

  3-氯-1-丁烯 、 双(苯硫基)甲烷 在 正丁基锂 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 以94%的产率得到3-methyl-4,4-bis(phenylthio)-1-butene
  参考文献：
  名称：

  Methyl effects in the cyclization of .gamma.-epoxy bis-sulfones

  摘要：

  A quantitative study on the effects of methyl and gem-dimethyl groups in the intramolecular ring opening of epoxides by bis-sulfonyl carbanions is reported for the formation of cyclopropanes. Reaction rates are increased by methyl groups on the chain connecting the nucleophile with the oxirane and depressed by methyl substitution in the epoxide ring. When gem-dimethyl groups are present on the epoxide, ring opening is apparently inhibited. It will be shown that in this case the reaction is reversible and the apparent stabilization of the gem-dimethyl-substituted oxirane is actually due to a combination of effects on both the forward and the reverse reactions. On the basis of current theories on intramolecular reactions, it is suggested that release of ground-state strain and van der Waals repulsions in the transition state can account for the observed reactivity.

  DOI：

  10.1021/jo00011a017

文献信息

• Lewis acid-catalyzed coupling reactions of allylsilanes with tris(phenylchalcogeno)methane. Synthesis of homoallylchalcogenoacetals
  作者：Claudio C Silveira、Gustavo L Fiorin、Antonio L Braga

  DOI：10.1016/0040-4039(96)01298-1

  日期：1996.8

  Reaction of allylsilanes with tris(phenylseleno)methane or tris(phenylthio)methane in the presence of a Lewis acid furnishes the corresponding homoallylchalcogenoacetals in moderate to good yields.

  在路易斯酸存在下，烯丙基硅烷与三（苯基硒代）甲烷或三（苯硫基）甲烷的反应以中等至良好的产率提供了相应的均烯丙基卤代缩醛。
• BENEDETTI, FABIO;BERTI, FEDERICO;FABRISSIN, SILVIO;GIANFERRARA, TERESA;RI+, J. ORG. CHEM., 56,(1991) N1, C. 3530-3537
  作者：BENEDETTI, FABIO、BERTI, FEDERICO、FABRISSIN, SILVIO、GIANFERRARA, TERESA、RI+

  DOI：——

  日期：——
• Methyl effects in the cyclization of .gamma.-epoxy bis-sulfones
  作者：Fabio Benedetti、Federico Berti、Silvio Fabrissin、Teresa Gianferrara、Amerigo Risaliti

  DOI：10.1021/jo00011a017

  日期：1991.5

  A quantitative study on the effects of methyl and gem-dimethyl groups in the intramolecular ring opening of epoxides by bis-sulfonyl carbanions is reported for the formation of cyclopropanes. Reaction rates are increased by methyl groups on the chain connecting the nucleophile with the oxirane and depressed by methyl substitution in the epoxide ring. When gem-dimethyl groups are present on the epoxide, ring opening is apparently inhibited. It will be shown that in this case the reaction is reversible and the apparent stabilization of the gem-dimethyl-substituted oxirane is actually due to a combination of effects on both the forward and the reverse reactions. On the basis of current theories on intramolecular reactions, it is suggested that release of ground-state strain and van der Waals repulsions in the transition state can account for the observed reactivity.