2-allyl-N-(2-chlorobenzyl)aniline | 1215403-60-3

• 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: 2-allyl-N-(2-chlorobenzyl)aniline
• CAS: 1215403-60-3
• 化学式: C₁₆H₁₆ClN
• 分子量: 257.763
• InChiKey: WGAYMHRGDCIHSQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.68
• 重原子数：
  18.0
• 可旋转键数：
  5.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  12.03
• 氢给体数：
  1.0
• 氢受体数：
  1.0

反应信息

• 作为反应物：
  描述：

  2-allyl-N-(2-chlorobenzyl)aniline 在 sodium tungstate (VI) dihydrate 、 双氧水 作用下， 以 甲醇 、 水 为溶剂， 以63%的产率得到1,4-epoxy-2-exo-(2-chlorophenyl)-2,3,4,5-tetrahydro-1(1H)-benzazepine
  参考文献：
  名称：

  Four differently substituted 2-aryl-2,3,4,5-tetrahydro-1H-1,4-epoxy-1-benzazepines: hydrogen-bonded structures in one, two and three dimensions

  摘要：

  In (2RS, 4SR)-7-chloro-2-exo-(2-chloro-6-fluorophenyl)-2,3,4,5-tetrahydro-1H-1,4-epoxy-1-benzazepine, C16H12Cl2FNO, (I), molecules are linked into chains by a single C-H center dot center dot center dot pi(arene) hydrogen bond. (2RS, 4SR)-2-exo-(2-Chloro-6-fluorophenyl)2,3,4,5- tetrahydro-1H-1,4-epoxy-1-benzazepine, C16H13ClFNO, (II), is isomorphous with compound (I) but not strictly isostructural with it, as the hydrogen-bonded chains in (II) are linked into sheets by an aromatic pi-pi stacking interaction. The molecules of (2RS, 4SR)-7-methyl-2-exo-(4-methylphenyl)-2,3,4,5- tetrahydro-1H-1,4-epoxy-1-benzazepine, C18H19NO, (III), are linked into sheets by a combination of C-H center dot center dot center dot N and C-H center dot center dot center dot(arene) hydrogen bonds. (2S, 4R)-2-exo-(2-Chlorophenyl)- 2,3,4,5-tetrahydro-1H-1,4-epoxy-1-benzazepine, C16H14ClNO, (IV), crystallizes as a single enantiomer and the molecules are linked into a three-dimensional framework structure by a combination of one C-H center dot center dot center dot O hydrogen bond and three C-H center dot center dot center dot pi(arene) hydrogen bonds.

  DOI：

  10.1107/s0108270109030339
• 作为产物：
  描述：

  2-allyl-phenylamine 、 邻氯氯苄 在 sodium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以79%的产率得到2-allyl-N-(2-chlorobenzyl)aniline
  参考文献：
  名称：

  Synthesis, structural elucidation and in vitro antiparasitic activity against Trypanosoma cruzi and Leishmania chagasi parasites of novel tetrahydro-1-benzazepine derivatives

  摘要：

  Forty six new 1,4-epoxy-2-exo-aryl-and cis-2-aryl-4-hydroxytetrahydro-1-benzazepine derivatives were synthesized and fully characterized. All compounds were tested in vitro against both Trypanosoma cruzi and Leishmania chagasi parasites and also for cytotoxicity using Vero and THP-1 mammalian cell lines. Many of the evaluated compounds showed remarkable activity against the epimastigote and intracellular amastigote forms of T. cruzi, with IC50 values comparable with that of control drug nifurtimox, a nitrofuran derivative currently used in the treatment of Chagas' disease. Other derivatives were found to have good activity against L. chagasi promastigotes, with low toxicity against the mammalian cells, but neither of them was active on intracellular amastigotes of L. chagasi infecting THP-1 macrophages. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2010.05.018