(4S)-4-(chloromethyl)oxolan-2-one | 1333379-20-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 内酯类
• 英文名称: (4S)-4-(chloromethyl)oxolan-2-one
• CAS: 1333379-20-6
• 化学式: C₅H₇ClO₂
• 分子量: 134.562
• InChiKey: HXKZBKOHNQPAJE-SCSAIBSYSA-N

物化性质

• 沸点：
  274.3±13.0 °C(Predicted)
• 密度：
  1.237±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.79
• 重原子数：
  8.0
• 可旋转键数：
  1.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  26.3
• 氢给体数：
  0.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  (4S)-4-(chloromethyl)oxolan-2-one 在 sodium iodide 作用下， 以 丙酮 为溶剂， 以90%的产率得到(S)-4-(Iodomethyl)dihydrofuran-2(3H)-one
  参考文献：
  名称：

  Development of a Scalable Synthesis of (S)-3-Fluoromethyl-γ-butyrolactone, Building Block for Carmegliptin’s Lactam Moiety

  摘要：

  Several new routes are reported for the synthesis of (S)-3-fluoromethyl-gamma-butyrolactone. An asymmetric hydrogenation-based synthesis was chosen as the enabling route to produce the lactone on a 10-kg scale. A superior stereoselective route starting from (S)-tert-butyl glycidyl ether which afforded the desired lactone in three steps with similar to 50% overall yield was finally selected for further development and production.

  DOI：

  10.1021/op200019k
• 作为产物：
  描述：

  methyl (1R,5S)-2-oxo-3-oxabicyclo[3.1.0]hexane-1-carboxylate 在 盐酸 、 aluminum (III) chloride 、 对甲苯磺酸 作用下， 以 乙二醇二甲醚 、 二甲基亚砜 为溶剂， 反应 3.0h， 生成 (4S)-4-(chloromethyl)oxolan-2-one
  参考文献：
  名称：

  Development of a Scalable Synthesis of (S)-3-Fluoromethyl-γ-butyrolactone, Building Block for Carmegliptin’s Lactam Moiety

  摘要：

  Several new routes are reported for the synthesis of (S)-3-fluoromethyl-gamma-butyrolactone. An asymmetric hydrogenation-based synthesis was chosen as the enabling route to produce the lactone on a 10-kg scale. A superior stereoselective route starting from (S)-tert-butyl glycidyl ether which afforded the desired lactone in three steps with similar to 50% overall yield was finally selected for further development and production.

  DOI：

  10.1021/op200019k