N-[3-(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)-2-hydroxypropyl]acetamide | 1396010-16-4

• 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: N-[3-(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)-2-hydroxypropyl]acetamide
• CAS: 1396010-16-4
• 化学式: C₁₃H₁₄N₂O₄
• 分子量: 262.265
• InChiKey: PXEKQBODAOFFBS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.22
• 重原子数：
  19.0
• 可旋转键数：
  4.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  86.71
• 氢给体数：
  2.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  N-[3-(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)-2-hydroxypropyl]acetamide 在 戴斯-马丁氧化剂 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 以87%的产率得到N-[3-(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)-2-oxopropyl]acetamide
  参考文献：
  名称：

  A straightforward and general access to α-phthalimido-α′-substituted propan-2-ones

  摘要：

  The regioselective ring opening of the commercially available N-(2,3-epoxypropyl)phthalimide with different nucleophiles, to obtain the corresponding phthalimidopropan-2-ols (including a challenging fluorohydrin) followed by the Dess-Martin periodinane oxidation, constitutes a general and widely applicable protocol for the preparation of differently functionalized alpha-phthalimido-alpha'-substituted propan-2-ones. The incorporation of the substituent in the alpha' position takes place in an early stage of the process, thus furnishing a divergent and valuable approach. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2012.07.045
• 作为产物：
  描述：

  N-(2,3-环氧丙基)邻苯二甲酰胺 在 2,6-二甲基吡啶 、 sodium azide 、 水 、 溶剂黄146 作用下， 以 氯仿 为溶剂， 反应 12.0h， 生成 N-[3-(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)-2-hydroxypropyl]acetamide
  参考文献：
  名称：

  A straightforward and general access to α-phthalimido-α′-substituted propan-2-ones

  摘要：

  The regioselective ring opening of the commercially available N-(2,3-epoxypropyl)phthalimide with different nucleophiles, to obtain the corresponding phthalimidopropan-2-ols (including a challenging fluorohydrin) followed by the Dess-Martin periodinane oxidation, constitutes a general and widely applicable protocol for the preparation of differently functionalized alpha-phthalimido-alpha'-substituted propan-2-ones. The incorporation of the substituent in the alpha' position takes place in an early stage of the process, thus furnishing a divergent and valuable approach. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2012.07.045