(Z)-2-(phenylthio)-1-(trimethylsilyl)-1,3-butadiene | 173546-17-3

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 英文名称: (Z)-2-(phenylthio)-1-(trimethylsilyl)-1,3-butadiene
• 英文别名: trimethyl-[(1Z)-2-phenylsulfanylbuta-1,3-dienyl]silane
• CAS: 173546-17-3
• 化学式: C₁₃H₁₈SSi
• 分子量: 234.437
• InChiKey: IVTOEVHNZRIEDK-QXMHVHEDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.73
• 重原子数：
  15
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  25.3
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  (Z)-2-(phenylthio)-1-(trimethylsilyl)-1,3-butadiene 在 间氯过氧苯甲酸 作用下， 以 二氯甲烷 为溶剂， 反应 3.0h， 以78%的产率得到(Z)-2-phenylsulfonyl-1-trimethylsilyl-1,3-butadiene
  参考文献：
  名称：

  Synthesis and Applications of 3-Phenylthio-2-Sulfolenes

  摘要：

  AbstractTreatment of 3‐phenylthio‐2‐sulfolene (1) with an equimolar proportion of butyllithium at −78 °C in THF followed by addition of an electrophile gave the 2‐substituted 3‐phenylthio‐2‐sulfolenes (2). The deprotonation was found to proceed only at the vinylic C‐2 position. Some of the 2‐sulfolenes 2 underwent desulfonylation upon heating with base. Of particular interest was the conversion of 3‐phenylthio‐2‐trimethylsilyl‐2‐sulfolene (2h) to its 3‐sulfolene isomer 6 by sequential addition of butyllithium and salicylic acid at low temperatures. The 3‐sulfolene 6 was desulfonylated by Kugelrohr distillation at 150° C under vacuum to give (Z)‐2‐phenylthio‐l‐trimethylsilyl‐1,3‐butadiene (8). The regiochemistry of the Diels Alder reaction of this highly reactive diene 8 was found to be controlled by the phenylthio group, and the stereochemistry is endo addition. Diene 8 was oxidized to its sulfone derivative 12 which also underwent a stereospecific Diels‐Alder reaction.

  DOI：

  10.1002/jccs.199600009
• 作为产物：
  描述：

  3-(phenylthio)-2-sulfolene 在 正丁基锂 、 水杨酸 作用下， -78.0~150.0 ℃ 、13.33 Pa 条件下， 生成 (Z)-2-(phenylthio)-1-(trimethylsilyl)-1,3-butadiene
  参考文献：
  名称：

  （Z）-2-（苯硫基）-1-（三甲基甲硅烷基）-1,3-丁二烯的区域和立体控制合成及Diels-Alder反应

  摘要：

  由其3-亚砜前体3合成标题化合物4，并研究了4的狄尔斯-阿尔德反应。

  DOI：

  10.1016/0040-4039(95)01884-k

文献信息

• Regio- and stereocontrolled synthesis and Diels-Alder reactions of (Z)-2-(phenylthio)-1-(trimethylsilyl)-1,3-butadiene
  作者：Shang-Shing P. Chou、Mao-Hsun Chao

  DOI：10.1016/0040-4039(95)01884-k

  日期：1995.11

  The title compound 4 was synthesized from its 3-sulfolene precursor 3, and the Diels-Alder reactions of 4 were studied.

  由其3-亚砜前体3合成标题化合物4，并研究了4的狄尔斯-阿尔德反应。
• Synthesis and Applications of 3-Phenylthio-2-Sulfolenes
  作者：Shang-Shing P. Chou、Mao-Hsun Chao

  DOI：10.1002/jccs.199600009

  日期：1996.2

  AbstractTreatment of 3‐phenylthio‐2‐sulfolene (1) with an equimolar proportion of butyllithium at −78 °C in THF followed by addition of an electrophile gave the 2‐substituted 3‐phenylthio‐2‐sulfolenes (2). The deprotonation was found to proceed only at the vinylic C‐2 position. Some of the 2‐sulfolenes 2 underwent desulfonylation upon heating with base. Of particular interest was the conversion of 3‐phenylthio‐2‐trimethylsilyl‐2‐sulfolene (2h) to its 3‐sulfolene isomer 6 by sequential addition of butyllithium and salicylic acid at low temperatures. The 3‐sulfolene 6 was desulfonylated by Kugelrohr distillation at 150° C under vacuum to give (Z)‐2‐phenylthio‐l‐trimethylsilyl‐1,3‐butadiene (8). The regiochemistry of the Diels Alder reaction of this highly reactive diene 8 was found to be controlled by the phenylthio group, and the stereochemistry is endo addition. Diene 8 was oxidized to its sulfone derivative 12 which also underwent a stereospecific Diels‐Alder reaction.