5-hydroxy-1-methyl-1,5-dihydropyrrol-2-one | 55260-27-0

• 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: 5-hydroxy-1-methyl-1,5-dihydropyrrol-2-one
• 英文别名: 5-hydroxy-1-methyl-1,5-dihydro-pyrrol-2-one；N-Methyl-5-hydroxy-Δ³-pyrrolin-2-on；2-hydroxy-1-methyl-2H-pyrrol-5-one
• CAS: 55260-27-0
• 化学式: C₅H₇NO₂
• 分子量: 113.116
• InChiKey: CJHRHMDZSPXOTB-UHFFFAOYSA-N

物化性质

• 沸点：
  337.8±41.0 °C(Predicted)
• 密度：
  1.306±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.7
• 重原子数：
  8
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  40.5
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  5-hydroxy-1-methyl-1,5-dihydropyrrol-2-one 、 乙酸酐 在 吡啶 、 Candida antarctica lipase 作用下， 生成 acetic acid 1-methyl-5-oxo-2,5-dihydro-1H-pyrrol-2-yl ester
  参考文献：
  名称：

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

  摘要：

  DOI：

  10.1021/jo982151e
• 作为产物：
  描述：

  N-甲基马来酰亚胺 在 sodium tetrahydroborate 、 cerium(III) chloride 作用下， 以 甲醇 为溶剂， 反应 1.5h， 以90%的产率得到5-hydroxy-1-methyl-1,5-dihydropyrrol-2-one
  参考文献：
  名称：

  Regioselective reduction of maleimide and citraconimide derivatives: general preparation of 5-hydroxy-1,5-dihydropyrrol-2-one

  摘要：

  NaBH4对顺丁烯酰胺衍生物的还原选择性地生成了5-羟基-4-甲基-1,5-二氢吡咯-2-酮，而NaBH4–CeCl3或DIBAL-H还原则生成了5-羟基-3-甲基-1,5-二氢吡咯-2-酮。

  DOI：

  10.1039/b200729k

文献信息

• Regioselective reduction of maleimide and citraconimide derivatives: general preparation of 5-hydroxy-1,5-dihydropyrrol-2-one
  作者：Nobuyuki Mase、Toshiki Nishi、Masaomi Hiyoshi、Kazuhiro Ichihara、Junichiro Bessho、Hidemi Yoda、Kunihiko Takabe

  DOI：10.1039/b200729k

  日期：2002.3.8

  NaBH4 reduction of citraconimide derivatives regioselectively afforded 5-hydroxy-4-methyl-1,5-dihydropyrrol-2-ones, whereas NaBH4–CeCl3 or DIBAL-H reduction gave 5-hydroxy-3-methyl-1,5-dihydropyrrol-2-ones.

  NaBH4对顺丁烯酰胺衍生物的还原选择性地生成了5-羟基-4-甲基-1,5-二氢吡咯-2-酮，而NaBH4–CeCl3或DIBAL-H还原则生成了5-羟基-3-甲基-1,5-二氢吡咯-2-酮。
• Visible light dye-photosensitised oxidation of pyrroles using a simple LED photoreactor
  作者：James K. Howard、Kieran J. Rihak、Christopher J. T. Hyland、Alex C. Bissember、Jason A. Smith

  DOI：10.1039/c6ob01719c

  日期：——

  The photooxidation of pyrrole is typically low yielding due to the absorbance of ultraviolet light, which leads to uncontrolled polymerisation and decomposition. Presented herein is the development of a simple and cost-effective photoreactor utilising Light Emitting Diodes (LEDs) as the light source, and its application to the dye-sensitised oxidation of a range of pyrroles to give corresponding 3-pyrrolin-2-ones

  吡咯的光氧化通常由于紫外线的吸收而产率低，这导致不受控制的聚合和分解。本文提出了利用发光二极管（LED）作为光源的简单且成本有效的光反应器的开发，并将其应用于一系列吡咯的染料敏化氧化以产生相应的3-吡咯啉-2-酮。还探讨了该方法在1 O 2生成中的广泛应用。
• 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.
• A concise synthesis of 3-(1-alkenyl)isoindolin-1-ones and 5-(1-alkenyl)pyrrol-2-ones by the intermolecular coupling reactions of <i>N</i>-acyliminium ions with unactivated olefins
  作者：Nianhong Lu、Lihong Wang、Zhanshan Li、Wei Zhang

  DOI：10.3762/bjoc.8.21

  日期：——

  A concise synthesis of 3-(1-alkenyl)isoindolin-1-ones and 5-(1-alkenyl)pyrrol-2-ones has been achieved by the coupling reactions of N-acyliminium ions produced from 3-hydroxyisoindol-1-ones or 5-hydroxy-1-pyrrol-2-ones with unactivated olefins in the presence of BF₃·OEt₂ at room temperature. For most of the olefins, the reactions afforded the C_sp3–C_sp2 cross-coupling products, but for the α-methylstyrene and 1-hexene, the C_sp3–C_sp3 cross-coupling products were obtained.

  通过在室温下在BF₃·OEt_{2>存在下，将从3-羟基异吲哚酮或5-羟基-1-吡咯-2-酮产生的N-酰基亚胺离子与未活化烯烃进行偶联反应，成功合成了3-(1-烯基)异吲哚酮和5-(1-烯基)吡咯-2-酮。对于大多数烯烃，反应产生了Csp3–Csp2交叉偶联产物，但对于α-甲基苯乙烯和1-己烯，得到了Csp3–Csp3交叉偶联产物。}
• 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