4,4,6,6-tetramethyl-4H,6H-pyrrolo[1,2-a][4,1]benzoxazepine-1,10-dicarboxylic acid

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯
• 英文名称: 4,4,6,6-tetramethyl-4H,6H-pyrrolo[1,2-a][4,1]benzoxazepine-1,10-dicarboxylic acid
• 英文别名: 4,4,6,6-Tetramethylpyrrolo[1,2-a][4,1]benzoxazepine-1,10-dicarboxylic acid；4,4,6,6-tetramethylpyrrolo[1,2-a][4,1]benzoxazepine-1,10-dicarboxylic acid
• 化学式: C₁₈H₁₉NO₅
• 分子量: 329.353
• InChiKey: GPUOCVABFCAGJG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  24
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  88.8
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  1-苯基吡咯 在 正丁基锂 、 四甲基乙二胺 、 (S)-(-)- α-甲基苄胺 、 potassium tert-butylate 作用下， 以 乙醚 、 乙醇 、 正己烷 为溶剂， 反应 1.5h， 生成 4,4,6,6-tetramethyl-4H,6H-pyrrolo[1,2-a][4,1]benzoxazepine-1,10-dicarboxylic acid
  参考文献：
  名称：

  Synthesis and resolution of 4,4,6,6-tetramethyl-4H,6H-pyrrolo[1,2-a][4,1]benzoxazepine-1,10-dicarboxylic acid

  摘要：

  Optimized consecutive regioselective dimetallation and carboxylation of 4,4,6,6-tetramethyl-4H,6H-pyrrolo[1,2-a][4,1]benzoxazepine provided the corresponding dicarboxylic acid as a new, structurally rigid member of the atropisomeric 1-arylpyrrole family. Resolution of the new racemate was accomplished with several chiral bases and the absolute configurations of the pure enantiomers were determined by the combined application of ECD spectroscopy and quantum chemical calculations. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2010.12.005

文献信息

• Synthesis and resolution of 4,4,6,6-tetramethyl-4H,6H-pyrrolo[1,2-a][4,1]benzoxazepine-1,10-dicarboxylic acid
  作者：Ferenc Faigl、Béla Mátravölgyi、Zsuzsanna Erdélyi、Krisztina Pál、Dóra Hessz、Miklós Kubinyi

  DOI：10.1016/j.tetasy.2010.12.005

  日期：2010.12

  Optimized consecutive regioselective dimetallation and carboxylation of 4,4,6,6-tetramethyl-4H,6H-pyrrolo[1,2-a][4,1]benzoxazepine provided the corresponding dicarboxylic acid as a new, structurally rigid member of the atropisomeric 1-arylpyrrole family. Resolution of the new racemate was accomplished with several chiral bases and the absolute configurations of the pure enantiomers were determined by the combined application of ECD spectroscopy and quantum chemical calculations. (C) 2010 Elsevier Ltd. All rights reserved.