2-[bis[(4-methylphenyl)methyl]amino]-N,N-diethylbenzamide | 1222534-45-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 2-[bis[(4-methylphenyl)methyl]amino]-N,N-diethylbenzamide
• CAS: 1222534-45-3
• 化学式: C₂₇H₃₂N₂O
• 分子量: 400.564
• InChiKey: NLWGZQOUAKWYBA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6
• 重原子数：
  30
• 可旋转键数：
  8
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  23.6
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-[bis[(4-methylphenyl)methyl]amino]-N,N-diethylbenzamide 在 正丁基锂 、 溶剂黄146 作用下， 以 乙醚 、 甲醇 为溶剂， 反应 17.0h， 以33%的产率得到
  参考文献：
  名称：

  Synthesis of 2-hydroxy-3-indolinones and 3-hydroxy-2-indolinones by anionic cyclization, in situ oxidation and rearrangement

  摘要：

  Lithiation with butyllithium of 2-(benzylamino)benzamides (N-benzyl anthranilamides) occurs at the benzylic position to give an alpha-amino-organolithium that cyclizes to the 3-indolinone (indoxyl) ring (similar to a Parham cyclization). Autoxidation in air gives 2-hydroxy-3-indolinones. In the absence of a proton source, rearrangement of the aryl group from C-2 to C-3 occurs to give the 3-hydroxy-2-indolinone (oxindole) ring. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2010.02.159
• 作为产物：
  描述：

  2-氨基-N,N-二乙基苯甲酰胺 、 4-甲基苄溴 在 potassium carbonate 作用下， 以 乙腈 为溶剂， 以79%的产率得到2-[bis[(4-methylphenyl)methyl]amino]-N,N-diethylbenzamide
  参考文献：
  名称：

  Synthesis of 2-hydroxy-3-indolinones and 3-hydroxy-2-indolinones by anionic cyclization, in situ oxidation and rearrangement

  摘要：

  Lithiation with butyllithium of 2-(benzylamino)benzamides (N-benzyl anthranilamides) occurs at the benzylic position to give an alpha-amino-organolithium that cyclizes to the 3-indolinone (indoxyl) ring (similar to a Parham cyclization). Autoxidation in air gives 2-hydroxy-3-indolinones. In the absence of a proton source, rearrangement of the aryl group from C-2 to C-3 occurs to give the 3-hydroxy-2-indolinone (oxindole) ring. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2010.02.159

文献信息

• Synthesis of 2-hydroxy-3-indolinones and 3-hydroxy-2-indolinones by anionic cyclization, in situ oxidation and rearrangement
  作者：Iain Coldham、Harry Adams、Neil J. Ashweek、Thomas A. Barker、Andrew T. Reeder、Melanie C. Skilbeck

  DOI：10.1016/j.tetlet.2010.02.159

  日期：2010.5

  Lithiation with butyllithium of 2-(benzylamino)benzamides (N-benzyl anthranilamides) occurs at the benzylic position to give an alpha-amino-organolithium that cyclizes to the 3-indolinone (indoxyl) ring (similar to a Parham cyclization). Autoxidation in air gives 2-hydroxy-3-indolinones. In the absence of a proton source, rearrangement of the aryl group from C-2 to C-3 occurs to give the 3-hydroxy-2-indolinone (oxindole) ring. (C) 2010 Elsevier Ltd. All rights reserved.