2-{2-hydroxy-3-[methyl(phenyl)amino]propyl}-1H-isoindole-1,3(2H)-dione | 142910-03-0

• 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-{2-hydroxy-3-[methyl(phenyl)amino]propyl}-1H-isoindole-1,3(2H)-dione
• 英文别名: 2-[2-hydroxy-3-(N-methylanilino)propyl]isoindole-1,3-dione
• CAS: 142910-03-0
• 化学式: C₁₈H₁₈N₂O₃
• 分子量: 310.353
• InChiKey: PFVAFXBBPJMETA-UHFFFAOYSA-N

物化性质

• 沸点：
  506.9±45.0 °C(Predicted)
• 密度：
  1.309±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  23
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  60.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-{2-hydroxy-3-[methyl(phenyl)amino]propyl}-1H-isoindole-1,3(2H)-dione 在 戴斯-马丁氧化剂 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 以86%的产率得到2-{3-[methyl(phenyl)amino]-2-oxopropyl}-1H-isoindole-1,3(2H)-dione
  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 、 N-甲基苯胺 在 zinc perchlorate 作用下， 以 氯仿 为溶剂， 反应 4.0h， 以88%的产率得到2-{2-hydroxy-3-[methyl(phenyl)amino]propyl}-1H-isoindole-1,3(2H)-dione
  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

文献信息

• A straightforward and general access to α-phthalimido-α′-substituted propan-2-ones
  作者：Vittorio Pace、Wolfgang Holzer

  DOI：10.1016/j.tetlet.2012.07.045

  日期：2012.9

  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.