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

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: O-sec-butyl-S-4-(naphthalen-2-yl)-4-oxo-1-(trimethylsilyl)butyl carbonodithioate
• 化学式: C₂₂H₃₀O₂S₂Si
• 分子量: 418.697
• InChiKey: HMJBMHDXKSBGIR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.88
• 重原子数：
  27.0
• 可旋转键数：
  8.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  26.3
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  O-sec-butyl-S-4-(naphthalen-2-yl)-4-oxo-1-(trimethylsilyl)butyl carbonodithioate 在 间氯过氧苯甲酸 作用下， 以 二苯醚 、 二氯甲烷 为溶剂， 反应 2.0h， 生成 5-(naphthalen-2-yl)-2-(trimethylsilyl)-2,3-dihydrothiophene-1,1-dioxide
  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80%的产率得到O-sec-butyl-S-4-(naphthalen-2-yl)-4-oxo-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.