trans-(-)-(S)-Methylethylen Sulfit | 51260-41-4

• 分子结构分类: 有机化合物 - 有机氧化合物 - 有机含氧阴离子化合物
• 英文名称: trans-(-)-(S)-Methylethylen Sulfit
• 英文别名: (4S)-4-methyl-[1,3,2]dioxathiolane trans-2-oxide；(2S,4S)-4-methyl-1,3,2-dioxathiolane 2-oxide
• CAS: 51260-41-4
• 化学式: C₃H₆O₃S
• 分子量: 122.145
• InChiKey: SJHAYVFVKRXMKG-NOWQDGDBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.4
• 重原子数：
  7
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  54.7
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  (S)-(+)-1,2-丙二醇 在 氯化亚砜 作用下， 生成 trans-(-)-(S)-Methylethylen Sulfit
  参考文献：
  名称：

  Chiroptical properties of cyclic esters and ketals derived from (S)-1,2-propylene glycol and (S,S)- and (R,R)-2,3-butylene glycol

  摘要：

  DOI：

  10.1021/jo00928a022

文献信息

• A general route to enantiomerically pure sulfoxides from a chiral sulfite
  作者：F. Rebiere、O. Samuel、L. Ricard、H. B. Kagan

  DOI：10.1021/jo00021a008

  日期：1991.10

  Enantiomerically pure cyclic chiral sulfite (S)-7 (trans stereochemistry) has been easily obtained in two steps from (S)-ethyl lactate. This compound was found to react cleanly with many organometallics to give crystalline sulfinates with high regioselectivity (> 90:10). Addition of a second organometallic transforms the purified sulfinate in excellent yield into a chiral sulfoxide (100% ee) of predictable absolute configuration. The mechanism and scope of this approach are discussed. This method completes the various other methods of preparation of chiral sulfoxides and is especially convenient for the preparation of tert-butyl sulfoxides. Examples for the synthesis of many chiral tert-butyl sulfoxides are given. The case of chiral sulfites derived from a C2 diol or of a chiral monoalcohol is also proposed as a route to chiral sulfinates, and some promising preliminary results have been obtained. The general main routes to obtain chiral sulfoxides from sulfites are also discussed.
• Chiroptical properties of cyclic esters and ketals derived from (S)-1,2-propylene glycol and (S,S)- and (R,R)-2,3-butylene glycol
  作者：Varda Usieli、A. Pilersdorf、Sharona Shor、J. Katzhendler、S. Sarel

  DOI：10.1021/jo00928a022

  日期：1974.7