N-((2-hydroxynaphthalen-1-yl)(1H-indol-3-yl)methyl)benzamide | 1398122-97-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: N-((2-hydroxynaphthalen-1-yl)(1H-indol-3-yl)methyl)benzamide
• 英文别名: N-[(2-hydroxynaphthalen-1-yl)-(1H-indol-3-yl)methyl]benzamide
• CAS: 1398122-97-8
• 化学式: C₂₆H₂₀N₂O₂
• 分子量: 392.457
• InChiKey: AYHGOZKUDSKNTN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6
• 重原子数：
  30
• 可旋转键数：
  4
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.04
• 拓扑面积：
  65.1
• 氢给体数：
  3
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  N-((2-hydroxynaphthalen-1-yl)(1H-indol-3-yl)methyl)benzamide 以 乙醇 为溶剂， 反应 1.0h， 以51%的产率得到1-(1H-indol-3-yl)-3-phenyl-1H-naphtho[1,2-e][1,3]oxazin
  参考文献：
  名称：

  Synthesis of 1-amidoalkyl-2-naphthols and oxazine derivatives with study of their antibacterial and antiviral activities

  摘要：

  An efficient and direct protocol for the preparation of 1-amidoalkyl-2-naphthols 1a-f employing a multi-component, one-pot condensation reaction of 2-naphthol, heterocyclic aldehydes, and amides in the presence of anhydrous zinc chloride under solvent-free conditions is described. The thermal solvent-free offer advantages such as shorter reaction times, simple work-up and excellent yield. Ring closure of 1a-f gave the pyrazolyl- and indolyl oxazine derivatives 2a-f. On the other hand, the reaction of 2-naphthol, aldehydes, and ammonia solution gave the dipyrazolyl- and di-indolyl oxazine derivatives 3a,b. Some of the newly synthesized compounds showed promising antibacterial and anti-H5N1 activities.

  DOI：

  10.1007/s00044-012-0205-9
• 作为产物：
  描述：

  3-吲哚甲醛 、 苯甲酰胺 、 2-萘酚 在 zinc(II) chloride 作用下， 以 neat (no solvent) 为溶剂， 反应 1.0h， 以91%的产率得到N-((2-hydroxynaphthalen-1-yl)(1H-indol-3-yl)methyl)benzamide
  参考文献：
  名称：

  Synthesis of 1-amidoalkyl-2-naphthols and oxazine derivatives with study of their antibacterial and antiviral activities

  摘要：

  An efficient and direct protocol for the preparation of 1-amidoalkyl-2-naphthols 1a-f employing a multi-component, one-pot condensation reaction of 2-naphthol, heterocyclic aldehydes, and amides in the presence of anhydrous zinc chloride under solvent-free conditions is described. The thermal solvent-free offer advantages such as shorter reaction times, simple work-up and excellent yield. Ring closure of 1a-f gave the pyrazolyl- and indolyl oxazine derivatives 2a-f. On the other hand, the reaction of 2-naphthol, aldehydes, and ammonia solution gave the dipyrazolyl- and di-indolyl oxazine derivatives 3a,b. Some of the newly synthesized compounds showed promising antibacterial and anti-H5N1 activities.

  DOI：

  10.1007/s00044-012-0205-9

文献信息

• Synthesis of 1-amidoalkyl-2-naphthols and oxazine derivatives with study of their antibacterial and antiviral activities
  作者：Wael S. I. Abou-Elmagd、Ahmed I. Hashem

  DOI：10.1007/s00044-012-0205-9

  日期：2013.4

  An efficient and direct protocol for the preparation of 1-amidoalkyl-2-naphthols 1a-f employing a multi-component, one-pot condensation reaction of 2-naphthol, heterocyclic aldehydes, and amides in the presence of anhydrous zinc chloride under solvent-free conditions is described. The thermal solvent-free offer advantages such as shorter reaction times, simple work-up and excellent yield. Ring closure of 1a-f gave the pyrazolyl- and indolyl oxazine derivatives 2a-f. On the other hand, the reaction of 2-naphthol, aldehydes, and ammonia solution gave the dipyrazolyl- and di-indolyl oxazine derivatives 3a,b. Some of the newly synthesized compounds showed promising antibacterial and anti-H5N1 activities.