but-2-enoic acid 1-acetyl-5-oxo-2,5-dihydro-1H-pyrrol-2-yl ester | 256458-30-7

• 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: but-2-enoic acid 1-acetyl-5-oxo-2,5-dihydro-1H-pyrrol-2-yl ester
• CAS: 256458-30-7
• 化学式: C₁₀H₁₁NO₄
• 分子量: 209.202
• InChiKey: YIPCQOKCRWMRAF-SECBINFHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.38
• 重原子数：
  15.0
• 可旋转键数：
  2.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  63.68
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  异丙醇 、 but-2-enoic acid 1-acetyl-5-oxo-2,5-dihydro-1H-pyrrol-2-yl ester 在 双(乙腈)氯化钯(II) 作用下， 生成 (R)-1-acetyl-5-isopropoxy-3-pyrrolin-2-one
  参考文献：
  名称：

  Kinetic Resolutions and Enantioselective Transformations of 5-(Acyloxy)pyrrolinones Using Candida antarctica Lipase B:  Synthetic and Structural Aspects

  摘要：

  Various 5-(acyloxy)pyrrolinones have been prepared in enantiomerically pure form by means of an enzymatic resolution or an asymmetric transformation. Either enantiomer is obtained using the same enzyme, Candida antarctica lipase B, by modification of the procedure from transesterification to esterification. N-Acyl-5-(acyloxy)pyrrolinones 1 (R-2 = acyl) are synthesized by applying this method with 100% yield and >99% ee. To rationalize the observed enantioselectivity and the substituent effects of these reactions both empirical models and molecular modeling studies have been used, and a qualitative agreement was found between the results from these studies and the experimental results.

  DOI：

  10.1021/jo991062e
• 作为产物：
  描述：

  1-乙酰基-5-氧代-2,5-二氢-1H-吡咯-2-基乙酸酯 在 lipase B of Candida antarctica 作用下， 以 正己烷 、 二氯甲烷 、 叔丁醇 为溶剂， 反应 86.0h， 生成 but-2-enoic acid 1-acetyl-5-oxo-2,5-dihydro-1H-pyrrol-2-yl ester
  参考文献：
  名称：

  Kinetic Resolutions and Enantioselective Transformations of 5-(Acyloxy)pyrrolinones Using Candida antarctica Lipase B:  Synthetic and Structural Aspects

  摘要：

  Various 5-(acyloxy)pyrrolinones have been prepared in enantiomerically pure form by means of an enzymatic resolution or an asymmetric transformation. Either enantiomer is obtained using the same enzyme, Candida antarctica lipase B, by modification of the procedure from transesterification to esterification. N-Acyl-5-(acyloxy)pyrrolinones 1 (R-2 = acyl) are synthesized by applying this method with 100% yield and >99% ee. To rationalize the observed enantioselectivity and the substituent effects of these reactions both empirical models and molecular modeling studies have been used, and a qualitative agreement was found between the results from these studies and the experimental results.

  DOI：

  10.1021/jo991062e