1-乙酰基-5-氧代-2,5-二氢-1H-吡咯-2-基乙酸酯 | 175796-29-9

• 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-5-氧代-2,5-二氢-1H-吡咯-2-基乙酸酯
• 英文名称: acetic acid 1-acetyl-5-oxo-2,5-dihydro-1H-pyrrol-2-yl ester
• 英文别名: 1-acetyl-5-acetoxy-3-pyrrolin-2-one；1-Acetyl-5-oxo-2,5-dihydro-1H-pyrrol-2-yl acetate；(1-acetyl-5-oxo-2H-pyrrol-2-yl) acetate
• CAS: 175796-29-9
• 化学式: C₈H₉NO₄
• 分子量: 183.164
• InChiKey: IOYQGMFWPBBRBZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.4
• 重原子数：
  13
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.38
• 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：

  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 acrylic 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
• 作为产物：
  描述：

  乙酸酐 、 5(RS)-hydroxy-3-pyrrolin-2-one 在 吡啶 、 4-二甲氨基吡啶 作用下， 生成 1-乙酰基-5-氧代-2,5-二氢-1H-吡咯-2-基乙酸酯
  参考文献：
  名称：

  Determination of the Absolute Configuration of 3-Pyrrolin-2-ones

  摘要：

  DOI：

  10.1021/jo982151e

文献信息

• Lipase-Catalyzed Second-Order Asymmetric Transformations as Resolution and Synthesis Strategies for Chiral 5-(Acyloxy)-2(5<i>H</i>)-furanone and Pyrrolinone Synthons
  作者：Hanneke van der Deen、Agnes D. Cuiper、Robert P. Hof、Arjan van Oeveren、Ben L. Feringa、Richard M. Kellogg

  DOI：10.1021/ja953812h

  日期：1996.4.24

  By use of lipase R (Amano, Penicillium roqueforti) immobilized on Hyflo Super Cell it is possible to convert at ambient temperature 5-hydroxy-5H-furan-2-one (5) to acetic acid 5-oxo-2,5-dihydrofuran-2-yl ester (1b) by acylation with vinyl acetate in 1:1 cyclohexane−butyl acetate. At 90% conversion the enantiomeric excess of 1b is 100%. This is an example of an enzyme-catalyzed second-order transformation

  通过使用固定在 Hyflo Super Cell 上的脂肪酶 R（Amano，Penicillium roqueforti），可以在环境温度下将 5-hydroxy-5H-furan-2-one (5) 转化为乙酸 5-oxo-2,5-dihydrofuran -2-基酯 (1b) 通过在 1:1 环己烷-乙酸丁酯中与乙酸乙烯酯酰化。在 90% 转化率时，1b 的对映体过量为 100%。这是酶催化二级转化的一个例子，其中 5 个非反应性对映体在反应过程中外消旋，转化率高达 100%，并获得高对映体过量。该方法对于 5-(酰氧基)-2(5H)-吡咯啉酮更为有效。外消旋乙酸 1-乙酰基-5-氧代-2,5-二氢-1H-吡咯-2-基酯 (2) 在环境温度下在 3:1 正己烷-丁醇中用来自南极念珠菌的脂肪酶处理50% 转化率可提供 (+)-2 in > 99% 对映体过量。这是非反应性的对映异构体。(-)-对映异构体转化为
• 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.
• Determination of the Absolute Configuration of 3-Pyrrolin-2-ones
  作者：Agnes D. Cuiper、Malgorzata Brzostowska、Jacek K. Gawronski、Wilberth J. J. Smeets、Anthony L. Spek、Henk Hiemstra、Richard M. Kellogg、Ben L. Feringa

  DOI：10.1021/jo982151e

  日期：1999.4.1