acetic acid 5-oxo-2,5-dihydro-1H-pyrrol-2-yl ester | 171292-10-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯啉
• 英文名称: acetic acid 5-oxo-2,5-dihydro-1H-pyrrol-2-yl ester
• 英文别名: 5-acetoxy-1,5-dihydro-2H-pyrrol-2-one；5-oxo-2,5-dihydro-1H-pyrrol-2-yl acetate；(5-oxo-1,2-dihydropyrrol-2-yl) acetate
• CAS: 171292-10-7
• 化学式: C₆H₇NO₃
• 分子量: 141.126
• InChiKey: TWMZVXALUSOBCB-UHFFFAOYSA-N

物化性质

• 沸点：
  325.9±42.0 °C(Predicted)
• 密度：
  1.26±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.3
• 重原子数：
  10
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  55.4
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  acetic acid 5-oxo-2,5-dihydro-1H-pyrrol-2-yl ester 350.0 ℃ 、0.0 Pa 条件下， 生成 cyclopyrrolone
  参考文献：
  名称：

  Generation, Direct Observation under Matrix Isolation Conditions, and ab Initio Calculations for 2-Azacyclopenta-2,4-dien-1-one

  摘要：

  Flash vacuum pyrolysis of a mixture of-argon and 5-acetoxy-1,5-dihydro-2H-pyrrol-2-one at 350 degrees C and condensation of the pyrolysate onto a cold plate at 12 K produces acetic acid and 2-azacyclopenta-2,4-dien-1-one (2H-pyrrol-2-one, 2), identified by IR spectroscopy. Ab initio calculations for 2 and cyclopentadienone at the MP2/6-31G** level successfully reproduce the observed IR spectra. Photochemically 2 is converted to acetylene, HCN, and CO. Attempts to chemically trap 2 have so far been unsuccessful.

  DOI：

  10.1021/j100043a027
• 作为产物：
  描述：

  乙酸酐 、 5(RS)-hydroxy-3-pyrrolin-2-one 在 三乙胺 作用下， 以 乙醚 为溶剂， 生成 acetic acid 5-oxo-2,5-dihydro-1H-pyrrol-2-yl ester
  参考文献：
  名称：

  Generation, Direct Observation under Matrix Isolation Conditions, and ab Initio Calculations for 2-Azacyclopenta-2,4-dien-1-one

  摘要：

  Flash vacuum pyrolysis of a mixture of-argon and 5-acetoxy-1,5-dihydro-2H-pyrrol-2-one at 350 degrees C and condensation of the pyrolysate onto a cold plate at 12 K produces acetic acid and 2-azacyclopenta-2,4-dien-1-one (2H-pyrrol-2-one, 2), identified by IR spectroscopy. Ab initio calculations for 2 and cyclopentadienone at the MP2/6-31G** level successfully reproduce the observed IR spectra. Photochemically 2 is converted to acetylene, HCN, and CO. Attempts to chemically trap 2 have so far been unsuccessful.

  DOI：

  10.1021/j100043a027

文献信息

• 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.
• Generation, Direct Observation under Matrix Isolation Conditions, and ab Initio Calculations for 2-Azacyclopenta-2,4-dien-1-one
  作者：Dana Lyn S. Yokotsuji、William P. Dailey、Andrew S. Kende、Liviu Birzan、Kun Liu

  DOI：10.1021/j100043a027

  日期：1995.10

  Flash vacuum pyrolysis of a mixture of-argon and 5-acetoxy-1,5-dihydro-2H-pyrrol-2-one at 350 degrees C and condensation of the pyrolysate onto a cold plate at 12 K produces acetic acid and 2-azacyclopenta-2,4-dien-1-one (2H-pyrrol-2-one, 2), identified by IR spectroscopy. Ab initio calculations for 2 and cyclopentadienone at the MP2/6-31G** level successfully reproduce the observed IR spectra. Photochemically 2 is converted to acetylene, HCN, and CO. Attempts to chemically trap 2 have so far been unsuccessful.