N-(tert-butyl)-2-(2-phenylethyl)-4H-3,1-benzoxazine-4-carboxamide | 1193490-75-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并恶嗪类
• 英文名称: N-(tert-butyl)-2-(2-phenylethyl)-4H-3,1-benzoxazine-4-carboxamide
• 英文别名: N-tert-butyl-2-(2-phenylethyl)-4H-3,1-benzoxazine-4-carboxamide
• CAS: 1193490-75-3
• 化学式: C₂₁H₂₄N₂O₂
• 分子量: 336.434
• InChiKey: JWSTXUUUZMGSHM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  25
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  50.7
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  1-(2-azidophenyl)-2-(tert-butylamino)-2-oxoethyl 3-phenylpropanoate 在 三苯基膦 作用下， 以 甲苯 为溶剂， 反应 10.0h， 以90%的产率得到N-(tert-butyl)-2-(2-phenylethyl)-4H-3,1-benzoxazine-4-carboxamide
  参考文献：
  名称：

  New efficient synthesis of 4-aminocarbonyl substituted 4H-3,1-benzoxazines by a Passerini 3CC/Staudinger/aza-Wittig sequence

  摘要：

  alpha-Acyloxy-carboxamide azides 1, obtained from Passerini reaction of easily accessible o-azidobenzaldehyde with isocyanides and carboxylic acids, reacted with triphenylphosphine to give various 4-aminocarbonyl substituted 4H-1,3-benzoxazines 3 in moderate to high yields via sequential Staudinger and intramolecular aza-Wittig reaction. However, alpha-hydroxy carboxamide azides 5 were obtained in moderate yields when pyruvic acid was used in the Passerini reaction. Further sequential reaction of azides 5 with triphenylphosphine and isocyanates produced 2-amino-4-aminocarbonyl substituted 4H-1,3-benzoxazines 8 via a tandem Staudinger/aza-Wittig/heterocumulene-mediated annulation. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2009.08.022

文献信息

• New efficient synthesis of 4-aminocarbonyl substituted 4H-3,1-benzoxazines by a Passerini 3CC/Staudinger/aza-Wittig sequence
  作者：Ping He、Jing Wu、Yi-Bo Nie、Ming-Wu Ding

  DOI：10.1016/j.tet.2009.08.022

  日期：2009.10

  alpha-Acyloxy-carboxamide azides 1, obtained from Passerini reaction of easily accessible o-azidobenzaldehyde with isocyanides and carboxylic acids, reacted with triphenylphosphine to give various 4-aminocarbonyl substituted 4H-1,3-benzoxazines 3 in moderate to high yields via sequential Staudinger and intramolecular aza-Wittig reaction. However, alpha-hydroxy carboxamide azides 5 were obtained in moderate yields when pyruvic acid was used in the Passerini reaction. Further sequential reaction of azides 5 with triphenylphosphine and isocyanates produced 2-amino-4-aminocarbonyl substituted 4H-1,3-benzoxazines 8 via a tandem Staudinger/aza-Wittig/heterocumulene-mediated annulation. (C) 2009 Elsevier Ltd. All rights reserved.