decanoic acid 1-acetyl-5-oxo-2,5-dihydro-1H-pyrrol-2-yl ester | 205656-64-0

• 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: decanoic acid 1-acetyl-5-oxo-2,5-dihydro-1H-pyrrol-2-yl ester
• 英文别名: [(2R)-1-acetyl-5-oxo-2H-pyrrol-2-yl] decanoate
• CAS: 205656-64-0
• 化学式: C₁₆H₂₅NO₄
• 分子量: 295.379
• InChiKey: RXULAEAPJYIYPP-OAHLLOKOSA-N

物化性质

• 沸点：
  421.7±45.0 °C(Predicted)
• 密度：
  1.08±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  21
• 可旋转键数：
  10
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.69
• 拓扑面积：
  63.7
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  异丙醇 、 decanoic 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：

  乙烯基癸酸 、 1-acetyl-5-hydroxy-1,5-dihydropyrrol-2-one 在 lipase B of Candida antarctica 作用下， 以 正己烷 、 二氯甲烷 为溶剂， 反应 62.0h， 生成 decanoic acid 1-acetyl-5-oxo-2,5-dihydro-1H-pyrrol-2-yl ester 、 decanoic 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

文献信息

• Enantioselective palladium catalyzed allylic substitution of acyloxypyrrolinones by alcohols
  作者：Agnes D. Cuiper、Richard M. Kellogg

  DOI：10.1039/a800444g

  日期：——

  Chiral non-racemic acyloxypyrrolinones are converted into alkoxypyrrolinones with retention of configuration by a palladium catalyzed allylic substitution; this comprises a key step in a short chemo-enzymatic route to acyliminium ion precursors.

  通过钯催化的烯丙基取代作用，手性非气相酰氧基吡咯烷酮被转化为保留构型的烷氧基吡咯烷酮；这是酰亚胺离子前体的简短化学酶途径中的一个关键步骤。
• Kinetic Resolutions and Enantioselective Transformations of 5-(Acyloxy)pyrrolinones Using <i>Candida antarctica </i>Lipase B:  Synthetic and Structural Aspects
  作者：Agnes D. Cuiper、Milou L. C. E. Kouwijzer、Peter D. J. Grootenhuis、Richard M. Kellogg、Ben L. Feringa

  DOI：10.1021/jo991062e

  日期：1999.12.1

  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.