2-allyl-4-fluoro-N-((5-methylthiophen-2-yl)methyl)aniline | 1383957-01-4

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: 2-allyl-4-fluoro-N-((5-methylthiophen-2-yl)methyl)aniline
• CAS: 1383957-01-4
• 化学式: C₁₅H₁₆FNS
• 分子量: 261.363
• InChiKey: PRQUZRXRPZBJPZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.54
• 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：
  0.2
• 拓扑面积：
  12.03
• 氢给体数：
  1.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  2-allyl-4-fluoro-N-((5-methylthiophen-2-yl)methyl)aniline 在 sodium tungstate (VI) dihydrate 、 双氧水 作用下， 以 甲醇 、 水 、 甲苯 为溶剂， 以64%的产率得到(2SR,4RS)-7-fluoro-2-(5-methylthiophen-2-yl)-2,3,4,5-tetrahydro-1,4-epoxy-1-benzazepine
  参考文献：
  名称：

  Nine closely related tetrahydro-1,4-epoxy-1-benzazepines carrying pendant heterocyclic substituents: hydrogen-bonded supramolecular assembly in zero, one and two dimensions

  摘要：

  报告了九种密切相关的带有杂环取代基的四氢-1,4-环氧-1-苯并氮杂卓的结构，它们是2-exo-(5-nitrofuran-2-yl)-2,3,4,5-tetrahydro-1,4-epoxy-1H-1-benzazepine, C14H12N2O4, (I), 7-fluoro-2-exo-(1-methyl-1H-pyrrol-2-yl)-2,3,4,5-tetrahydro-1,4-epoxy-1H-1-benzazepine, C15H15FN2O, (II), 7-fluoro-2-exo-(5-methylfuran-2-yl)-2,3,4,5-tetrahydro-1,4-epoxy-1H-1-benzazepine, C15H14FNO2, (III), 7-fluoro-2-exo-(3-methylthiophen-2-yl)-2,3,4,5-tetrahydro-1,4-epoxy-1H-1-benzazepine, C15H14FNOS, (IV), 7-fluoro-2-exo-(5-methylthiophen-2-yl)-2,3,4,5-tetrahydro-1,4-epoxy-1H-1-benzazepine,C15H14FNOS, (V), 7-chloro-2-exo-(5-methylfuran-2-yl)-2,3,4,5-tetrahydro-1,4-epoxy-1H-1-benzazepine, C15H14ClNO2, (VI), 2-exo-(5-methylfuran-2-yl)-7-trifluoromethoxy-2,3,4,5-tetrahydro-1,4-epoxy-1H-1-benzazepine, C16H14F3NO3, (VII),2-exo-(3-methylthiophen-2-yl)-7-trifluoromethoxy-2,3,4,5-tetrahydro-1,4-epoxy-1H-1-benzazepine, C16H14F3NO2S, (VIII), and 2-exo-(5-nitrofuran-2-yl)-7-trifluoromethoxy-2,3,4,5-tetrahydro-1,4-epoxy-1H-1-benzazepine, C15H11F3N2O5, (IX).所有九种化合物都在中心对称空间群中结晶为外消旋混合物，构型为 (2RS,4SR)。(V)中的分子之间没有特定方向的相互作用。(III)、(IV)、(VI)和(VII)中的分子通过单个 C-H...O 氢键连接成简单的链，(IV)中的分子通过单个 C-H...π(arene)氢键连接成简单的链，而(VIII)中的分子则连接成环链。在（I）和（II）中，一个 C-H...O氢键和一个C-H...π（arene）氢键的组合将分子连接成片状，尽管这两种化合物的结构完全不同。在 (IX) 中，薄片结构是由四个独立的 C-H...O 氢键和一个 C-H...π（炔）氢键组合而成。与一些相关化合物进行了比较。

  DOI：

  10.1107/s010827011200707x
• 作为产物：
  描述：

  在 sodium tetrahydroborate 作用下， 以 甲醇 为溶剂， 反应 6.0h， 生成 2-allyl-4-fluoro-N-((5-methylthiophen-2-yl)methyl)aniline
  参考文献：
  名称：

  Synthesis of novel polysubstituted (2SR,4RS)-2-heteroaryltetrahydro-1,4-epoxy-1-benzazepines and cis-2-heteroaryl-4-hydroxytetrahydro-1H-1-benzazepines as antiparasitic agents

  摘要：

  New series of polysubstituted (2SR,4RS)-2-heteroaryltetrahydro-1,4-epoxy-1-benzazepines and cis-2-heteroaryl-4-hydroxytetrahydro-1H-1-benzazepines were designed and synthesized in moderate to high yields using a three-step procedure from ortho-allylanilines. Their antiparasitic activity was evaluated against the extracellular and intracellular forms of Trypanosoma cruzi and Leishmania (Leishmania) infantum parasites. Their cytotoxicity was also determined on Vero and THP-1 mammalian cells. Many of the tested compounds inhibited significantly the growth of extracellular forms of T. cruzi and L (L) infantum without showing cytotoxicity on Vero and HTP-1 cells. Only compounds 10h and 14f demonstrated good activity against amastigotes of T. cruzi, but none was able to inhibit the growth of L (L) infantum amastigotes. (C) 2014 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2014.08.055