2-(2-formyl-4-oxo-4H-quinazolin-3-yl)-benzoic acid ethyl ester

• 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 ethyl ester
• 英文别名: Ethyl 2-(2-formyl-4-oxoquinazolin-3-yl)benzoate；ethyl 2-(2-formyl-4-oxoquinazolin-3-yl)benzoate
• 化学式: C₁₈H₁₄N₂O₄
• 分子量: 322.32
• InChiKey: OUNZWPUSLRUUIC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  24
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  76
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  2-氨基苯甲酸乙酯 在 selenium(IV) oxide 作用下， 以 1,4-二氧六环 为溶剂， 反应 161.0h， 生成 2-(2-formyl-4-oxo-4H-quinazolin-3-yl)-benzoic acid ethyl ester
  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.