S-(2-cyclohexyl-3-phenylallyl) S-methyl carbonodithioate | 140226-86-4

• 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: S-(2-cyclohexyl-3-phenylallyl) S-methyl carbonodithioate
• CAS: 140226-86-4；140226-93-3
• 化学式: C₁₇H₂₂OS₂
• 分子量: 306.493
• InChiKey: NYLXRBGJYJAGOP-UHFFFAOYSA-N

物化性质

• 沸点：
  427.1±34.0 °C(Predicted)
• 密度：
  1.146±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.87
• 重原子数：
  20.0
• 可旋转键数：
  4.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  17.07
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  S-(2-cyclohexyl-3-phenylallyl) S-methyl carbonodithioate 在 偶氮二异丁腈 、 三正丁基氢锡 作用下， 以 苯 为溶剂， 反应 10.0h， 生成 (2-cyclohexylallyl)benzene 、 [(Z)-2-cyclohexylprop-1-enyl]benzene 、 (E)-(2-cyclohexylprop-1-en-1-yl)benzene
  参考文献：
  名称：

  A convergent method for the stereoselective synthesis of trisubstituted alkenes

  摘要：

  A method for the stereoselective, convergent synthesis of trisubstituted alkenes has been developed. The procedure features the synthesis of allylic alcohols 9 by coupling an aldehyde with a vinyl organometallic reagent. Treatment of 9 with carbon disulfide and methyl iodide gave the intermediate allylic xanthates 10 that underwent facile [3,3]-sigmatropic rearrangement to give the dithiocarbonates 11 and 12, radical reduction of which gave the (E)-alkenes 13 as the major products.

  DOI：

  10.1021/jo00035a004
• 作为产物：
  描述：

  2-Cyclohexyl-1-phenylprop-2-en-1-ol 在 sodium hydride 作用下， 以 苯 为溶剂， 反应 15.0h， 生成 S-(2-cyclohexyl-3-phenylallyl) S-methyl carbonodithioate
  参考文献：
  名称：

  A convergent method for the stereoselective synthesis of trisubstituted alkenes

  摘要：

  A method for the stereoselective, convergent synthesis of trisubstituted alkenes has been developed. The procedure features the synthesis of allylic alcohols 9 by coupling an aldehyde with a vinyl organometallic reagent. Treatment of 9 with carbon disulfide and methyl iodide gave the intermediate allylic xanthates 10 that underwent facile [3,3]-sigmatropic rearrangement to give the dithiocarbonates 11 and 12, radical reduction of which gave the (E)-alkenes 13 as the major products.

  DOI：

  10.1021/jo00035a004

文献信息

• A convergent method for the stereoselective synthesis of trisubstituted alkenes
  作者：Stephen F. Martin、Dilon Daniel、Robert J. Cherney、Spiros Liras

  DOI：10.1021/jo00035a004

  日期：1992.4

  A method for the stereoselective, convergent synthesis of trisubstituted alkenes has been developed. The procedure features the synthesis of allylic alcohols 9 by coupling an aldehyde with a vinyl organometallic reagent. Treatment of 9 with carbon disulfide and methyl iodide gave the intermediate allylic xanthates 10 that underwent facile [3,3]-sigmatropic rearrangement to give the dithiocarbonates 11 and 12, radical reduction of which gave the (E)-alkenes 13 as the major products.