N-(quinolin-8-yl)-2-N-(N-dibenzylamino)-3-naphthalenecarboxamide | 1531629-20-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: N-(quinolin-8-yl)-2-N-(N-dibenzylamino)-3-naphthalenecarboxamide
• 英文别名: 3-(dibenzylamino)-N-quinolin-8-ylnaphthalene-2-carboxamide
• CAS: 1531629-20-5
• 化学式: C₃₄H₂₇N₃O
• 分子量: 493.608
• InChiKey: HIYVLFZZIIPCBE-UHFFFAOYSA-N

物化性质

• 沸点：
  671.7±55.0 °C(Predicted)
• 密度：
  1.268±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  7.4
• 重原子数：
  38
• 可旋转键数：
  7
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  45.2
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  N-benzyl-N-chloro-1-phenylmethanamine 、 N-(quinolin-8-yl)-2-naphthamide 在 iron(III)-acetylacetonate 、 1,2-bis[di-(4-fluorophenyl)-phosphino]benzene 、 苯基溴化镁 作用下， 以 四氢呋喃 为溶剂， 反应 0.01h， 以96%的产率得到N-(quinolin-8-yl)-2-N-(N-dibenzylamino)-3-naphthalenecarboxamide
  参考文献：
  名称：

  Synthesis of Anthranilic Acid Derivatives through Iron-Catalyzed Ortho Amination of Aromatic Carboxamides with N-Chloroamines

  摘要：

  Arenes possessing an 8-quinolinylamide group as a directing group are ortho aminated with N-chloroamines and N-benzoyloxyamines in the presence of an iron/diphosphine catalyst and an organometallic base to produce anthranilic acid derivatives in high yield. The reaction proceeds via iron-catalyzed C H activation, followed by the reaction of the resulting iron intermediate with N-chloroamine. The choice of the directing group and diphosphine ligand is crucial for obtaining the anthranilic acid derivative with high yield and product selectivity.

  DOI：

  10.1021/ja412521k

文献信息

• Synthesis of Anthranilic Acid Derivatives through Iron-Catalyzed Ortho Amination of Aromatic Carboxamides with <i>N</i>-Chloroamines
  作者：Tatsuaki Matsubara、Sobi Asako、Laurean Ilies、Eiichi Nakamura

  DOI：10.1021/ja412521k

  日期：2014.1.15

  Arenes possessing an 8-quinolinylamide group as a directing group are ortho aminated with N-chloroamines and N-benzoyloxyamines in the presence of an iron/diphosphine catalyst and an organometallic base to produce anthranilic acid derivatives in high yield. The reaction proceeds via iron-catalyzed C H activation, followed by the reaction of the resulting iron intermediate with N-chloroamine. The choice of the directing group and diphosphine ligand is crucial for obtaining the anthranilic acid derivative with high yield and product selectivity.