Ethyl 1-(phenylsulfanyl)ethyl carbonate | 185145-48-6

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 英文名称: Ethyl 1-(phenylsulfanyl)ethyl carbonate
• 英文别名: ethyl 1-phenylsulfanylethyl carbonate
• CAS: 185145-48-6
• 化学式: C₁₁H₁₄O₃S
• 分子量: 226.296
• InChiKey: LPANRNNCUITIFZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  15
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  60.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  Ethyl 1-(phenylsulfanyl)ethyl carbonate 在 溴 作用下， 以 四氯化碳 为溶剂， 反应 1.0h， 以55%的产率得到1-溴乙基乙基碳酸酯
  参考文献：
  名称：

  Cleavage of Carbon--Sulfur Bonds in the Synthesis of alpha-Haloalkyl Carbonates.

  摘要：

  alpha-Chloroalkyl and alpha-bromoalkyl carbonates have been prepared by cleavage of alpha-arylthioalkyl carbonates with sulfuryl chloride or bromine, respectively. The alpha-arylthioalkyl carbonates are prepared by reaction of the hemithioacetal 1 with chloroformates or by a destannylative tin-Pummerer rearrangement of alpha-stannyl sulfoxides.

  DOI：

  10.3891/acta.chem.scand.50-1041
• 作为产物：
  描述：

  氯甲酸乙酯 、 [1-(Benzenesulfinyl)ethyl](tributyl)stannane 以 二氯甲烷 为溶剂， 反应 22.0h， 以19%的产率得到Ethyl 1-(phenylsulfanyl)ethyl carbonate
  参考文献：
  名称：

  Tin-Pummerer Rearrangement in the Synthesis of O,S-Acetal Derivatives.

  摘要：

  alpha-Thioalkyl esters and carbonates have been prepared by a tin-Pummerer rearrangement in reactions of alpha-stannylated sulfoxides with acid chlorides or chloroformates, respectively. Acid chlorides have a higher reactivity than chloroformates in this reaction.

  DOI：

  10.3891/acta.chem.scand.51-1092

文献信息

• Cleavage of Carbon--Sulfur Bonds in the Synthesis of alpha-Haloalkyl Carbonates.
  作者：Jostein Hatlelid、Tore Benneche、Kjell Undheim、Neucírio Ricardo de Azevedo、Pedro Henrique Ferri、Kristian Rønning Pedersen、Muhammed Nour Homsi、Frank K. H. Kuske、Monika Haugg、Nathalie Trabesinger-Rüf、Elmar G. Weinhold

  DOI：10.3891/acta.chem.scand.50-1041

  日期：——

  alpha-Chloroalkyl and alpha-bromoalkyl carbonates have been prepared by cleavage of alpha-arylthioalkyl carbonates with sulfuryl chloride or bromine, respectively. The alpha-arylthioalkyl carbonates are prepared by reaction of the hemithioacetal 1 with chloroformates or by a destannylative tin-Pummerer rearrangement of alpha-stannyl sulfoxides.
• Tin-Pummerer Rearrangement in the Synthesis of O,S-Acetal Derivatives.
  作者：Jostein Hatlelid、Tore Benneche、Kjell Undheim、Frode Rise、Michael P. Hartshorn、Manuela Merchán、Ward T. Robinson、Björn O. Roos、Claire Vallance、Bryan R. Wood

  DOI：10.3891/acta.chem.scand.51-1092

  日期：——

  alpha-Thioalkyl esters and carbonates have been prepared by a tin-Pummerer rearrangement in reactions of alpha-stannylated sulfoxides with acid chlorides or chloroformates, respectively. Acid chlorides have a higher reactivity than chloroformates in this reaction.