cis-4-hydroxy-2-phenyl-2,3,4,5-tetrahydro-1(1H)-benzazepine

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯氮卓类
• 英文名称: cis-4-hydroxy-2-phenyl-2,3,4,5-tetrahydro-1(1H)-benzazepine
• 英文别名: (2S,4R)-2-phenyl-2,3,4,5-tetrahydro-1H-1-benzazepin-4-ol
• 化学式: C₁₆H₁₇NO
• 分子量: 239.317
• InChiKey: MXAMSUMHFVNGPE-ZBFHGGJFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  18
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  32.3
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  苯甲基苯胺 在 三氟化硼乙醚 sodium tungstate 、 双氧水 、 potassium carbonate 、 锌 作用下， 以 水 、 溶剂黄146 、 丙酮 为溶剂， 生成 cis-4-hydroxy-2-phenyl-2,3,4,5-tetrahydro-1(1H)-benzazepine
  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

文献信息

• 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.
• 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。