N-[benzotriazol-1-yl-(4-fluorophenyl)methyl]benzamide | 562099-76-7

• 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: N-[benzotriazol-1-yl-(4-fluorophenyl)methyl]benzamide
• CAS: 562099-76-7
• 化学式: C₂₀H₁₅FN₄O
• 分子量: 346.364
• InChiKey: GIUDNQHRGSBDHG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  26
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.05
• 拓扑面积：
  59.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  N-[benzotriazol-1-yl-(4-fluorophenyl)methyl]benzamide 在 sodium methylate 、 四氯化锡 作用下， 以 二氯甲烷 、 甲苯 为溶剂， 反应 0.5h， 生成 (4R,6R)-6-[(2R)-3,3-dimethyl-γ-butyrolacton-2-yl]oxy-4-(4-fluorophenyl)-2-phenyl-5,6-dihydro-4H-1,3-oxazine
  参考文献：
  名称：

  Novel Use of N-Benzoyl-N,O-acetals as N-Acylimine Equivalents in Asymmetric Heterocycloaddition:  An Extended Enantioselective Pathway to β-Benzamido Aldehydes

  摘要：

  For the first time, easily available N-(alpha-methoxyalkyl)amides were successfully used as synthetic equivalents of N-acylimines in an asymmetric heterocycloaddition process. The facial-controlled formation of 6-alkoxydihydrooxazines was thus achieved by SnCl4-promoted heterocycloaddition of (R)-O-vinyl pantolactone. By simple acidic hydrolysis of the crude heteroadducts, new beta-aryl- and beta-alkyl-substituted benzamido aldehydes were thus obtained in good overall yields with high enantioselectivities.

  DOI：

  10.1021/jo0203138
• 作为产物：
  描述：

  T406石油添加剂 、 对氟苯甲醛 、 苯甲酰胺 以 甲苯 为溶剂， 以60.5%的产率得到N-[benzotriazol-1-yl-(4-fluorophenyl)methyl]benzamide
  参考文献：
  名称：

  Novel Use of N-Benzoyl-N,O-acetals as N-Acylimine Equivalents in Asymmetric Heterocycloaddition:  An Extended Enantioselective Pathway to β-Benzamido Aldehydes

  摘要：

  For the first time, easily available N-(alpha-methoxyalkyl)amides were successfully used as synthetic equivalents of N-acylimines in an asymmetric heterocycloaddition process. The facial-controlled formation of 6-alkoxydihydrooxazines was thus achieved by SnCl4-promoted heterocycloaddition of (R)-O-vinyl pantolactone. By simple acidic hydrolysis of the crude heteroadducts, new beta-aryl- and beta-alkyl-substituted benzamido aldehydes were thus obtained in good overall yields with high enantioselectivities.

  DOI：

  10.1021/jo0203138

文献信息

• Novel Use of <i>N</i>-Benzoyl-<i>N,O</i>-acetals as <i>N</i>-Acylimine Equivalents in Asymmetric Heterocycloaddition:  An Extended Enantioselective Pathway to β-Benzamido Aldehydes
  作者：Patricia Gizecki、Robert Dhal、Céline Poulard、Pascal Gosselin、Gilles Dujardin

  DOI：10.1021/jo0203138

  日期：2003.5.1

  For the first time, easily available N-(alpha-methoxyalkyl)amides were successfully used as synthetic equivalents of N-acylimines in an asymmetric heterocycloaddition process. The facial-controlled formation of 6-alkoxydihydrooxazines was thus achieved by SnCl4-promoted heterocycloaddition of (R)-O-vinyl pantolactone. By simple acidic hydrolysis of the crude heteroadducts, new beta-aryl- and beta-alkyl-substituted benzamido aldehydes were thus obtained in good overall yields with high enantioselectivities.