2-allyl-N-(2-chlorobenzyl)-4-chloroaniline | 1240273-49-7

• 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: 2-allyl-N-(2-chlorobenzyl)-4-chloroaniline
• CAS: 1240273-49-7
• 化学式: C₁₆H₁₅Cl₂N
• 分子量: 292.208
• InChiKey: SNNSQADSJAGVOH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.33
• 重原子数：
  19.0
• 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)-4-chloroaniline 在 sodium tungstate (VI) dihydrate 、 双氧水 作用下， 以 甲醇 、 水 为溶剂， 反应 72.0h， 生成
  参考文献：
  名称：

  Three aryl-substituted tetrahydro-1,4-epoxy-1-benzazepines: hydrogen-bonded structures in two or three dimensions

  摘要：

  In (2SR,4RS)-7-chloro-2-exo-(4-chlorophenyl)-2,3,4,5-tetrahydro-1H-1,4-epoxy-1-benzazepine, C16H13Cl2NO, (I), the molecules are linked by a combination of C-H center dot center dot center dot O and C-H center dot center dot center dot N hydrogen bonds into a chain of edge-fused R-3(3)(12) rings. The isomeric compound (2S,4R)-7-chloro-2-exo(2-chlorophenyl)-2,3,4,5-tetrahydro-1H-1,4-epoxy-1-benzazepine, (II), crystallizes as a single 2S, 4R enantiomer and the molecules are linked into a three-dimensional framework structure by two C-H center dot center dot center dot O hydrogen bonds and one C-H center dot center dot center dot( arene) hydrogen bond. The molecules of (2S,4R)-7chloro-2-exo-(1-naphthyl)-2,3,4,5-tetrahydro-1H-1,4-epoxy-1benzazepine, C20H16ClNO, (III), are also linked into a three-dimensional framework structure, here by one C-H center dot center dot center dot O hydrogen bond and two C-H center dot center dot center dot pi(arene) hydrogen bonds. The significance of this study lies in its observation of the variations in molecular configuration and conformation, and in the variation in the patterns of supramolecular aggregation, consequent upon modest changes in the peripheral substituents.

  DOI：

  10.1107/s0108270108025961
• 作为产物：
  描述：

  邻氯氯苄 、 4-chloro-2-(prop-2-en-1-yl)aniline 在 sodium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以80%的产率得到2-allyl-N-(2-chlorobenzyl)-4-chloroaniline
  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