N-allyl-N-benzyl-4-chloroaniline | 839731-84-9

• 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: N-allyl-N-benzyl-4-chloroaniline
• 英文别名: N-benzyl-4-chloro-N-prop-2-enylaniline
• CAS: 839731-84-9
• 化学式: C₁₆H₁₆ClN
• 分子量: 257.763
• InChiKey: WRSDBEKLYGBIFJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  18
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  3.2
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  N-allyl-N-benzyl-4-chloroaniline 在 三氟化硼乙醚 作用下， 生成 2-allyl-N-benzyl-4-chloroaniline
  参考文献：
  名称：

  顺式-4-羟基-2-芳基-2,3,4,5-四氢-1(1H)-苯并氮杂的立体选择性合成的连续氨基-克莱森重排/分子内1,3-偶极环加成/还原裂解方法

  摘要：

  描述了一种新的立体选择性合成 cis-2-aryl-4-hydroxy-2,3,4,5-tetrahydro-1-benzazepines 从 N-allylanilines 利用芳香氨基-克莱森重排和分子内 1,3-偶极环加成方法。该序列涉及相应 N-苄基苯胺的 N-烯丙基化，然后是氨基-克莱森重排，随后用原位 1,3-偶极环加成氧化得到异恶唑烷，最后还原裂解异恶唑烷 NO 键。

  DOI：

  10.1055/s-2006-949654
• 作为产物：
  描述：

  N-(4-氯-苯基)-苯甲酰胺 、 3-溴丙烯 以 N,N-二甲基甲酰胺 为溶剂， 生成 N-allyl-N-benzyl-4-chloroaniline
  参考文献：
  名称：

  6,11-二氢-11-乙基-5H-二苯并[b,e]氮杂环衍生物的新型高效合成，以N-苄基苯胺为原料，通过氨基-克莱森和弗里德尔-克拉夫茨方法

  摘要：

  6,11-二氢-11-乙基-5H-二苯并[b,e]氮杂衍生物的新型高效合成，使用BF 3 .OEt 2 -催化芳香氨基-克莱森重排和分子内烯烃Friedel-Crafts烷基化的关键步骤, 报道。

  DOI：

  10.1055/s-2004-836026

文献信息

• New and Efficient Synthesis of 6,11-Dihydro-11-ethyl-5<i>H</i>-dibenz[<i>b</i>,<i>e</i>]azepine Derivatives Starting from <i>N</i>-Benzylanilines via Amino-Claisen and Friedel-Crafts Methodologies
  作者：Vladimir Kouznetsov、Alirio Palma、Jacqueline Barajas、Elena Stashenko、Ali Bahsas、Juan Amaro-Luis

  DOI：10.1055/s-2004-836026

  日期：——

  New and efficient synthesis of 6,11-dihydro-11-ethyl-5H-dibenz[b,e]azepine derivatives, using the key steps of BF 3 .OEt 2 -catalyzed aromatic amino-Claisen rearrangement and the intramolecular alkene Friedel-Craftsalkylation, is reported.

  6,11-二氢-11-乙基-5H-二苯并[b,e]氮杂衍生物的新型高效合成，使用BF 3 .OEt 2 -催化芳香氨基-克莱森重排和分子内烯烃Friedel-Crafts烷基化的关键步骤, 报道。
• A Simple and Practical Approach to the Dibenzo[c,f]thiazolo[3,2-a]azepines: A Novel Fused Tetracyclic Azepine System
  作者：Alirio Palma、Nelson Galeano、Ali Bahsas

  DOI：10.1055/s-0029-1218674

  日期：2010.4

  A novel set of functionalized dibenzo[c,f]thiazolo[3,2-a]azepines, which is a new ring system, were successfully synthesized in a four-step protocol starting from readily available substituted N-allyl-N-benzylanilines. The synthesis of the title compounds was accomplished through cyclocondensation of morphanthridines with mercaptoacetic acid. Morphanthridines were prepared by selective oxidation of

  从容易获得的取代的N-烯丙基-N-苄基苯胺开始，采用四步方案成功合成了一组新的功能化的二苯并[ c，f ]噻唑并[3,2- a ]氮杂s。标题化合物的合成是通过吗啡啶与巯基乙酸的环缩合完成的。通过在二氯甲烷中用氯铬酸吡啶鎓选择性氧化二氢吗啡啶来制备吗啡啶。通过酸催化取代的2-烯丙基-N-苄基苯胺的分子内Friedel-Crafts烷基化反应获得二氢吗啡啶，后者又由N-烯丙基-制备N-苄基苯胺通过芳香氨基-克莱森重排。还报告了通过高分辨率NMR对所有合成化合物的结构解析。 氨基克莱森重排-分子内Friedel-Crafts烷基化-2-烯丙基-N-苄基苯胺-二氢吗啡啶-二苯并[ c，f ]噻唑并[3,2- a ]氮杂
• Sequential Amino-Claisen Rearrangement/Intramolecular 1,3-Dipolar ­Cycloaddition/Reductive Cleavage Approach to the Stereoselective Synthesis of <i>cis</i>-4-Hydroxy-2-aryl-2,3,4,5-tetrahydro-1(1<i>H</i>)-benzazepines
  作者：Alirio Palma、Sandra Gómez Ayala、Elena Stashenko、Alí Bahsas、Juan Amaro-Luis

  DOI：10.1055/s-2006-949654

  日期：2006.9

  cis-2-aryl-4-hydroxy-2,3,4,5-tetrahydro-1-benzazepines from N-allylanilines utilizing aromatic amino-Claisen rearrangement and intramolecular 1,3-dipolar cycloaddition methodologies is described. This sequence involves N-allylation of corresponding N-benzylanilines followed by amino-Claisen rearrangement, subsequent oxidation with in situ 1,3-dipolar cycloaddition affording isoxazolidines, and finally

  描述了一种新的立体选择性合成 cis-2-aryl-4-hydroxy-2,3,4,5-tetrahydro-1-benzazepines 从 N-allylanilines 利用芳香氨基-克莱森重排和分子内 1,3-偶极环加成方法。该序列涉及相应 N-苄基苯胺的 N-烯丙基化，然后是氨基-克莱森重排，随后用原位 1,3-偶极环加成氧化得到异恶唑烷，最后还原裂解异恶唑烷 NO 键。
• Synthesis, structural elucidation and in vitro antiparasitic activity against Trypanosoma cruzi and Leishmania chagasi parasites of novel tetrahydro-1-benzazepine derivatives
  作者：Sandra Gómez-Ayala、Julián A. Castrillón、Alirio Palma、Sandra M. Leal、Patricia Escobar、Alí Bahsas

  DOI：10.1016/j.bmc.2010.05.018

  日期：2010.7

  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.