Dithiocarbonic acid S-((Z)-2-isopropyl-non-2-enyl) ester S-methyl ester | 140226-82-0

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: Dithiocarbonic acid S-((Z)-2-isopropyl-non-2-enyl) ester S-methyl ester
• CAS: 140226-82-0；140226-89-7
• 化学式: C₁₄H₂₆OS₂
• 分子量: 274.492
• InChiKey: GMKGYEQFCUFYNV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.76
• 重原子数：
  17.0
• 可旋转键数：
  8.0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.79
• 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：

  Dithiocarbonic acid S-((Z)-2-isopropyl-non-2-enyl) ester S-methyl ester 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-Methyl-3-methylidenedecane 、 (Z)-2,3-dimethyldec-3-ene 、 (E)-2,3-dimethyldec-3-ene
  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：

  4-癸醇,2-甲基-3-亚甲基- 在 sodium hydride 作用下， 以 苯 为溶剂， 反应 15.0h， 生成 Dithiocarbonic acid S-((Z)-2-isopropyl-non-2-enyl) ester S-methyl ester
  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