(S)-2-hydroxymethyl-N-benzoylformyl pyrrolidine | 219598-58-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 恶嗪烷类
• 英文名称: (S)-2-hydroxymethyl-N-benzoylformyl pyrrolidine
• 英文别名: (8aS)-3-hydroxy-3-phenyl-6,7,8,8a-tetrahydro-1H-pyrrolo[2,1-c][1,4]oxazin-4-one
• CAS: 219598-58-0
• 化学式: C₁₃H₁₅NO₃
• 分子量: 233.267
• InChiKey: UXIBPNIWAHXEGZ-AMGKYWFPSA-N

物化性质

• 沸点：
  451.8±45.0 °C(Predicted)
• 密度：
  1.32±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  17
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  49.8
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (S)-2-hydroxymethyl-N-benzoylformyl pyrrolidine 在 钾硼氢 、 硫酸 作用下， 以 甲醇 、 水 为溶剂， 反应 10.5h， 生成 D-扁桃酸
  参考文献：
  名称：

  Asymmetric reactions of α-ketoacid-derived hemiacetals: Stereoselective synthesis of α-hydroxy acids

  摘要：

  N-Acylation of prolinol with alpha-ketoacid chlorides results in concomitant hemiacetalization of the alpha-keto amide by the prolinol hydroxyl group, (R) or (S) alpha-hydroxy acids are obtained with good enantiomeric excess by stereodivergent reduction of these hemiacetals. Reaction with Grignard reagents at ambient temperature furnishes (R) alpha-alkyl mandelic acids with good stereoselectivity. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(98)00914-4
• 作为产物：
  描述：

  (S)-2-hydroxymethyl-N,O-bisbenzoylformyl pyrrolidine 在 sodium hydroxide 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 2.0h， 以85%的产率得到(S)-2-hydroxymethyl-N-benzoylformyl pyrrolidine
  参考文献：
  名称：

  Asymmetric reactions of α-ketoacid-derived hemiacetals: Stereoselective synthesis of α-hydroxy acids

  摘要：

  N-Acylation of prolinol with alpha-ketoacid chlorides results in concomitant hemiacetalization of the alpha-keto amide by the prolinol hydroxyl group, (R) or (S) alpha-hydroxy acids are obtained with good enantiomeric excess by stereodivergent reduction of these hemiacetals. Reaction with Grignard reagents at ambient temperature furnishes (R) alpha-alkyl mandelic acids with good stereoselectivity. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(98)00914-4

文献信息

• Asymmetric reactions of α-ketoacid-derived hemiacetals: Stereoselective synthesis of α-hydroxy acids
  作者：Sunil V. Pansare、R.Gnana Ravi

  DOI：10.1016/s0040-4020(98)00914-4

  日期：1998.11

  N-Acylation of prolinol with alpha-ketoacid chlorides results in concomitant hemiacetalization of the alpha-keto amide by the prolinol hydroxyl group, (R) or (S) alpha-hydroxy acids are obtained with good enantiomeric excess by stereodivergent reduction of these hemiacetals. Reaction with Grignard reagents at ambient temperature furnishes (R) alpha-alkyl mandelic acids with good stereoselectivity. (C) 1998 Elsevier Science Ltd. All rights reserved.