2-(2-formyl-4-oxo-4H-quinazolin-3-yl)-benzoic acid | 882039-02-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氮杂萘
• 英文名称: 2-(2-formyl-4-oxo-4H-quinazolin-3-yl)-benzoic acid
• 英文别名: 2-(2-Formyl-4-oxoquinazolin-3-yl)benzoic acid；2-(2-formyl-4-oxoquinazolin-3-yl)benzoic acid
• CAS: 882039-02-3
• 化学式: C₁₆H₁₀N₂O₄
• 分子量: 294.266
• InChiKey: MYDICTLXHAOIOJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  22
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  87
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2-(2-formyl-4-oxo-4H-quinazolin-3-yl)-benzoic acid 、 D-苯甘氨醇 在 2-fluoro-1-ethylpyridinium tetrafluoroborate 、 N,N-二异丙基乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 8.25h， 以70%的产率得到(2S,5R)-5-phenyl-3-oxa-6,14,22-triazapentacyclo[12.8.0.02,6.08,13.016,21]docosa-1(22),8,10,12,16,18,20-heptaene-7,15-dione
  参考文献：
  名称：

  New development of Meyers’ methodology: stereoselective preparation of an axially chiral 5,7-fused bicyclic lactam related to circumdatins/benzomalvins and asperlicins

  摘要：

  The stereoselective preparation of a new Meyers' bicyclic lactam-bridged biaryl 1, highly structurally related to circumdatins, benzornalvins and asperlicins, is reported. Using the popular Meyers' diastereo selective lactamization, under dehydrating conditions (CH2Cl2/reflux/MgSO4), trans-(aS,R,S)-1 was obtained in a rather modest yield of 25% and an excellent diastereoselectivity > 95%. An alternative procedure making use of the activating agents of carboxylic acid (Mukaiyama reagent and FEP) allowed the lactamization process to take place under milder conditions (CH2Cl2/20 degrees C) affording trans-(aS,R,S)-1 in fairly good yields (50%-85%) and in up to 65% de. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2005.12.019
• 作为产物：
  描述：

  邻乙酰胺苯甲酸內酯 在 selenium(IV) oxide 、 溶剂黄146 作用下， 以 1,4-二氧六环 为溶剂， 反应 171.0h， 生成 2-(2-formyl-4-oxo-4H-quinazolin-3-yl)-benzoic acid
  参考文献：
  名称：

  New development of Meyers’ methodology: stereoselective preparation of an axially chiral 5,7-fused bicyclic lactam related to circumdatins/benzomalvins and asperlicins

  摘要：

  The stereoselective preparation of a new Meyers' bicyclic lactam-bridged biaryl 1, highly structurally related to circumdatins, benzornalvins and asperlicins, is reported. Using the popular Meyers' diastereo selective lactamization, under dehydrating conditions (CH2Cl2/reflux/MgSO4), trans-(aS,R,S)-1 was obtained in a rather modest yield of 25% and an excellent diastereoselectivity > 95%. An alternative procedure making use of the activating agents of carboxylic acid (Mukaiyama reagent and FEP) allowed the lactamization process to take place under milder conditions (CH2Cl2/20 degrees C) affording trans-(aS,R,S)-1 in fairly good yields (50%-85%) and in up to 65% de. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2005.12.019

文献信息

• New development of Meyers’ methodology: stereoselective preparation of an axially chiral 5,7-fused bicyclic lactam related to circumdatins/benzomalvins and asperlicins
  作者：Maël Penhoat、Pierre Bohn、Georges Dupas、Cyril Papamicaël、Francis Marsais、Vincent Levacher

  DOI：10.1016/j.tetasy.2005.12.019

  日期：2006.1

  The stereoselective preparation of a new Meyers' bicyclic lactam-bridged biaryl 1, highly structurally related to circumdatins, benzornalvins and asperlicins, is reported. Using the popular Meyers' diastereo selective lactamization, under dehydrating conditions (CH2Cl2/reflux/MgSO4), trans-(aS,R,S)-1 was obtained in a rather modest yield of 25% and an excellent diastereoselectivity > 95%. An alternative procedure making use of the activating agents of carboxylic acid (Mukaiyama reagent and FEP) allowed the lactamization process to take place under milder conditions (CH2Cl2/20 degrees C) affording trans-(aS,R,S)-1 in fairly good yields (50%-85%) and in up to 65% de. (c) 2006 Elsevier Ltd. All rights reserved.