O-sec-butyl S-4-oxo-4-(thiophen-2-yl)-1-(trimethylsilyl)butyl carbonodithioate

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: O-sec-butyl S-4-oxo-4-(thiophen-2-yl)-1-(trimethylsilyl)butyl carbonodithioate
• 英文别名: O-butan-2-yl (4-oxo-4-thiophen-2-yl-1-trimethylsilylbutyl)sulfanylmethanethioate
• 化学式: C₁₆H₂₆O₂S₃Si
• 分子量: 374.665
• InChiKey: NAPPNZYESFYBHZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.79
• 重原子数：
  22
• 可旋转键数：
  10
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  112
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  O-sec-butyl S-4-oxo-4-(thiophen-2-yl)-1-(trimethylsilyl)butyl carbonodithioate 以 二苯醚 为溶剂， 反应 2.0h， 生成
  参考文献：
  名称：

  A Synthesis of (1E,3E)-TMS Dienes from Keto-Xanthates via Chugaev-Type Elimination

  摘要：

  An efficient route leading to exclusively (1E,3E)-TMS dienes is described. Radical xanthate addition of keto-xanthates to vinyltrimethylsilane followed by one-pot Chugaev elimination/cyclization and in situ oxidation with m-CPBA afforded the corresponding TMS 2-sulfolenes. Isomerization to 3-sulfolenes by the action of DBU with the extrusion of sulfur dioxide in refluxing toluene gave the titled (1E,3E)-TMS dienes.

  DOI：

  10.1021/jo402169v
• 作为产物：
  描述：

  、 乙烯基三甲基硅烷 在 过氧化双月桂酰 作用下， 以 乙酸乙酯 为溶剂， 以83%的产率得到O-sec-butyl S-4-oxo-4-(thiophen-2-yl)-1-(trimethylsilyl)butyl carbonodithioate
  参考文献：
  名称：

  A Synthesis of (1E,3E)-TMS Dienes from Keto-Xanthates via Chugaev-Type Elimination

  摘要：

  An efficient route leading to exclusively (1E,3E)-TMS dienes is described. Radical xanthate addition of keto-xanthates to vinyltrimethylsilane followed by one-pot Chugaev elimination/cyclization and in situ oxidation with m-CPBA afforded the corresponding TMS 2-sulfolenes. Isomerization to 3-sulfolenes by the action of DBU with the extrusion of sulfur dioxide in refluxing toluene gave the titled (1E,3E)-TMS dienes.

  DOI：

  10.1021/jo402169v

文献信息

• A Synthesis of (1<i>E</i>,3<i>E</i>)-TMS Dienes from Keto-Xanthates via Chugaev-Type Elimination
  作者：Kelvin Kau Kiat Goh、Sunggak Kim、Samir Z. Zard

  DOI：10.1021/jo402169v

  日期：2013.12.6

  An efficient route leading to exclusively (1E,3E)-TMS dienes is described. Radical xanthate addition of keto-xanthates to vinyltrimethylsilane followed by one-pot Chugaev elimination/cyclization and in situ oxidation with m-CPBA afforded the corresponding TMS 2-sulfolenes. Isomerization to 3-sulfolenes by the action of DBU with the extrusion of sulfur dioxide in refluxing toluene gave the titled (1E,3E)-TMS dienes.