(4S)-3-<1-oxo-3-(1,3-dithian-2-ylidene)-2-benzylpropyl>-4-(1-methylethyl)-2-oxazolidinone | 147725-25-5

• 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)-2-benzylpropyl>-4-(1-methylethyl)-2-oxazolidinone
• 英文别名: (4S)-3-[(2S)-2-benzyl-3-(1,3-dithian-2-ylidene)propanoyl]-4-propan-2-yl-1,3-oxazolidin-2-one
• CAS: 147725-25-5
• 化学式: C₂₀H₂₅NO₃S₂
• 分子量: 391.555
• InChiKey: JLNPJQYMLJLYIV-DLBZAZTESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  26
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.5
• 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)-2-benzylpropyl>-4-(1-methylethyl)-2-oxazolidinone 在 lithium aluminium tetrahydride 、 对甲苯磺酸 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 1.5h， 生成 (S)-(-)-β-benzyl-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 、 lithium diisopropyl amide 作用下， 反应 6.5h， 生成 (4S)-3-<1-oxo-3-(1,3-dithian-2-ylidene)-2-benzylpropyl>-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