2-(1,3-dioxoisoindolin-2-yl)-N-methoxy-N-methylacetamide | 1090469-33-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 异吲哚及其衍生物
• 英文名称: 2-(1,3-dioxoisoindolin-2-yl)-N-methoxy-N-methylacetamide
• 英文别名: 2-(1,3-dioxoisoindol-2-yl)-N-methoxy-N-methylacetamide
• CAS: 1090469-33-2
• 化学式: C₁₂H₁₂N₂O₄
• 分子量: 248.238
• InChiKey: RSHYOGMSILLXIN-UHFFFAOYSA-N

物化性质

• 熔点：
  147-148 °C
• 沸点：
  364.4±44.0 °C(Predicted)
• 密度：
  1.349±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.5
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  66.9
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  N-甲氧基-N-甲基-1H-咪唑-1-甲酰胺 、 邻苯二甲酰甘氨酸 以 乙腈 为溶剂， 反应 24.0h， 以92%的产率得到2-(1,3-dioxoisoindolin-2-yl)-N-methoxy-N-methylacetamide
  参考文献：
  名称：

  Chemoselective Esterification and Amidation of Carboxylic Acids with Imidazole Carbamates and Ureas

  摘要：

  Imidazole carbamates and ureas were found to be chemoselective esterification and amidation reagents. A wide variety of carboxylic acids were converted to their ester or amide analogues by a simple synthetic procedure in high yields

  DOI：

  10.1021/ol1018882

文献信息

• Highly efficient and environmentally benign preparation of Weinreb amides in the biphasic system 2-MeTHF/water
  作者：Vittorio Pace、Laura Castoldi、Andrés R. Alcántara、Wolfgang Holzer

  DOI：10.1039/c3ra41262h

  日期：——

  A straightforward chromatography-free preparation of Weinreb amides starting from acid halides has been achieved in the biphasic medium 2-MeTHF/water. Analytically pure compounds were isolated in excellent yields simply after removal of 2-MeTHF, which absolutely avoids the use of any contaminant organic solvent within the whole process due to its (practically) immiscibility with water.

  在 2-MeTHF/ 水的双相介质中，实现了从酸性卤化物开始的 Weinreb 酰胺的直接无色谱制备。由于 2-MeTHF 与水（实际上）不相溶，因此在整个制备过程中完全避免了使用任何污染性有机溶剂。
• Chemoselective Esterification and Amidation of Carboxylic Acids with Imidazole Carbamates and Ureas
  作者：Stephen T. Heller、Richmond Sarpong

  DOI：10.1021/ol1018882

  日期：2010.10.15

  Imidazole carbamates and ureas were found to be chemoselective esterification and amidation reagents. A wide variety of carboxylic acids were converted to their ester or amide analogues by a simple synthetic procedure in high yields
• On the reactivity of imidazole carbamates and ureas and their use as esterification and amidation reagents
  作者：Stephen T. Heller、Richmond Sarpong

  DOI：10.1016/j.tet.2011.09.057

  日期：2011.11

  The optimization, substrate scope, and mechanism of esterification and amidation of carboxylic acids mediated by imidazole-based reagents are discussed. The innate reactivity of carbonylimidazole reagents with a range of nucleophiles is also explored. New reagents developed for the synthesis of alpha,beta-unsaturated esters are described, as are reagents for the preparation of tertiary amides directly from carboxylic acids. (C) 2011 Elsevier Ltd. All rights reserved.