(4S)-3-<1-oxo-3-(1,3-dithian-2-ylidene)propyl>-4-(1-methylethyl)-2-oxazolidinone | 147725-18-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑烷类
• 英文名称: (4S)-3-<1-oxo-3-(1,3-dithian-2-ylidene)propyl>-4-(1-methylethyl)-2-oxazolidinone
• 英文别名: (4S)-3-[3-(1,3-dithian-2-ylidene)propanoyl]-4-propan-2-yl-1,3-oxazolidin-2-one
• CAS: 147725-18-6
• 化学式: C₁₃H₁₉NO₃S₂
• 分子量: 301.431
• InChiKey: IFAGKBWQCFMGMR-SNVBAGLBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  19
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.69
• 拓扑面积：
  97.2
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (4S)-3-<1-oxo-3-(1,3-dithian-2-ylidene)propyl>-4-(1-methylethyl)-2-oxazolidinone 在 对甲苯磺酸 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 生成 (βS,γR)-γ-(3-bromopropyl)-β-<<(4S)-4-(1-methylethyl)-2-oxo-3-oxazolidinyl>carbonyl>-γ-butyrolactone
  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
• 作为产物：
  描述：

  (+)-(4S)-3-bromoacetyl-4-(1-methylethyl)-2-oxazolidinone 在 正丁基锂 作用下， 反应 2.0h， 生成 (4S)-3-<1-oxo-3-(1,3-dithian-2-ylidene)propyl>-4-(1-methylethyl)-2-oxazolidinone
  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：——