5,8-dioxo-4-thia-8-<(4S)-4-(1-methylethyl)-2-oxazolidinyl>octanethiol

• 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: 5,8-dioxo-4-thia-8-<(4S)-4-(1-methylethyl)-2-oxazolidinyl>octanethiol
• 英文别名: 5,8-dioxo-4-thia-8-[(4S)-4-(1-methylethyl)-2-oxazolidinyl]octanethiol；S-(3-sulfanylpropyl) 4-oxo-4-[(4S)-2-oxo-4-propan-2-yl-1,3-oxazolidin-3-yl]butanethioate
• 化学式: C₁₃H₂₁NO₄S₂
• 分子量: 319.446
• InChiKey: ALAZWTWMURMPSZ-SNVBAGLBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  20
• 可旋转键数：
  8
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.77
• 拓扑面积：
  90
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  (S)-4-异丙基-2-唑烷酮 在 正丁基锂 、 对甲苯磺酸 作用下， 以 二氯甲烷 为溶剂， 反应 3.67h， 生成 5,8-dioxo-4-thia-8-<(4S)-4-(1-methylethyl)-2-oxazolidinyl>octanethiol
  参考文献：
  名称：

  Enantioselective preparation of .beta.-alkyl-.gamma.-butyrolactones from functionalized ketene dithioacetals

  摘要：

  An efficient and general enantioselective synthesis of beta-alkyl-gamma-butyrolactones has been developed. The key step of this procedure is an oxazolidinone-directed alkylation of a lithiated ketene dithioacetal that proceeds with excellent regiochemical control and high diastereofacial selectivity. Reductive removal of the chiral auxiliary followed by acid-induced cyclization of the resultant hydroxy ketene dithioacetal gives the enantiomerically pure beta-alkyl-gamma-butyrolactone.

  DOI：

  10.1021/jo00062a013

文献信息

• Koch Stacie S. Canan, Chamberlin A. Richard, J. Org. Chem., 58 (1993) N 10, S 2725-2737
  作者：Koch Stacie S. Canan, Chamberlin A. Richard

  DOI：——

  日期：——
• Enantioselective preparation of .beta.-alkyl-.gamma.-butyrolactones from functionalized ketene dithioacetals
  作者：Stacie S. Canan Koch、A. Richard Chamberlin

  DOI：10.1021/jo00062a013

  日期：1993.5

  An efficient and general enantioselective synthesis of beta-alkyl-gamma-butyrolactones has been developed. The key step of this procedure is an oxazolidinone-directed alkylation of a lithiated ketene dithioacetal that proceeds with excellent regiochemical control and high diastereofacial selectivity. Reductive removal of the chiral auxiliary followed by acid-induced cyclization of the resultant hydroxy ketene dithioacetal gives the enantiomerically pure beta-alkyl-gamma-butyrolactone.