1-乙酰基-2-羟基-3-甲基-2H-吡咯-5-酮 | 917989-06-1

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 中文名称: 1-乙酰基-2-羟基-3-甲基-2H-吡咯-5-酮
• 英文名称: 1-acetyl-5-hydroxy-4-methyl-1H-pyrrol-2(5H)-one
• 英文别名: 1-Acetyl-5-hydroxy-4-methyl-1,5-dihydro-2H-pyrrol-2-one；1-acetyl-2-hydroxy-3-methyl-2H-pyrrol-5-one
• CAS: 917989-06-1
• 化学式: C₇H₉NO₃
• 分子量: 155.153
• InChiKey: BNMZVSCLYDXKMQ-UHFFFAOYSA-N

物化性质

• 沸点：
  344.6±42.0 °C(Predicted)
• 密度：
  1.339±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.5
• 重原子数：
  11
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  57.6
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 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 以 二氯甲烷 、 甲苯 为溶剂， 反应 67.0h， 生成 1-乙酰基-2-羟基-3-甲基-2H-吡咯-5-酮
  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

• Ceric Ammonium Nitrate Promoted Oxidation of Oxazoles
  作者：David A. Evans、Pavel Nagorny、Risheng Xu

  DOI：10.1021/ol0624530

  日期：2006.11.1

  The ceric ammonium nitrate promoted oxidations of 4,5-diphenyloxazoles and oxazoles with various substitution patterns have been investigated. This transformation results in the formation of the corresponding imide in good yield and tolerates a wide variety of functional groups and substituents on the oxazole moiety. [reaction: see text].

  硝酸铈铵促进了具有各种取代方式的4,5-二苯基恶唑和恶唑的氧化反应。该转化导致以良好的产率形成相应的酰亚胺，并容许恶唑部分上的多种官能团和取代基。[反应：请参见文字]。
• 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.