2-benzyl-2,3,4,5-tetrahydro-1H-benzo[c]azepine | 54311-89-6

• 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: 2-benzyl-2,3,4,5-tetrahydro-1H-benzo[c]azepine
• 英文别名: 1H-2-Benzazepine, 2,3,4,5-tetrahydro-2-(phenylmethyl)-；2-benzyl-1,3,4,5-tetrahydro-2-benzazepine
• CAS: 54311-89-6
• 化学式: C₁₇H₁₉N
• 分子量: 237.345
• InChiKey: NTKSCRDSGUPFJG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  3.2
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  methyl (E)-2-(3-methoxy-3-oxoprop-1-en-1-yl)benzoate 在 lithium aluminium tetrahydride 、 5%-palladium/activated carbon 、 氢气 、 甲基磺酰氯 、 三乙胺 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 为溶剂， 20.0 ℃ 、206.85 kPa 条件下， 反应 14.0h， 生成 2-benzyl-2,3,4,5-tetrahydro-1H-benzo[c]azepine
  参考文献：
  名称：

  Facile and Simple Synthesis of N-Alkyl and N-Aryl 2-Benzazepines by Nucleophilic Heteroannulation

  摘要：

  DOI：

  10.1080/00397911.2014.928327

文献信息

• An Improved Stereocontrolled Access Route to Piperidine or Azepane β‐Amino Esters and Azabicyclic β‐ and γ‐Lactams; Synthesis of Novel Functionalized Azaheterocyles
  作者：Lamiaa Ouchakour、Melinda Nonn、Attila M. Remete、Loránd Kiss

  DOI：10.1002/ejoc.202100540

  日期：2021.7.26

  An efficient synthesis of some functionalized saturated azaheterocycles has been accomplished by controlled functionalization through ozonolysis and cyclization with reductive amination of various readily available cycloalkenes.

  一些官能化的饱和氮杂杂环的有效合成是通过臭氧分解和环化以及各种容易获得的环烯烃的还原胺化的受控官能化来实现的。
• A de novo synthetic method to the access of N-substituted benzazepines
  作者：Lamiaa Ouchakour、Melinda Nonn、Matthias D’hooghe、Loránd Kiss

  DOI：10.1016/j.jfluchem.2020.109466

  日期：2020.4

  benzazepines. The synthetic protocol starting from readily available dihydronaphthalene regioisomers is based on oxidative ring olefin bond cleavage followed by ring closure of the diformyl intermediates in the presence of some fluorine-containing primary amines across double reductive amination. The applicability of the developed synthetic method was demonstrated by the synthesis of 13 benzazepine compounds

  已经描述了一种新颖，方便的方法用于构建含氟苯并ze庚因。从容易获得的二氢萘区域异构体开始的合成方案是基于氧化环烯烃键的裂解，然后在一些含氟伯胺的存在下通过双还原胺化对二甲酰基中间体进行闭环。合成的13种苯并ze庚因化合物的合成以22–35％的总收率证明了开发的合成方法的适用性。
• ‘Counter-intuitive’ regioselectivity, subtle steric and solvation effects in lithiation of cyclic tertiary aralkylamines
  作者：Satinder V. Kessar、Paramjit Singh、Kamal Nain Singh、P. Venugopalan、Amarjit Kaur、Manu Mahendru、Rajiv Kapoor

  DOI：10.1016/j.tetlet.2005.07.110

  日期：2005.9

  Lithiation of a series of cyclic aralkyl tertiary amines with sec-BuLi in various solvents has been studied. There is a subtle sensitivity to steric factors and lithium coordinating solvents/additives have an adverse effect. ortho-Lithiation is observed only in the case of an eight-membered cyclic amine and the ease of benzylic lithiation with respect to nitrogen is in the surprising order gamma > beta >> alpha, delta. These observations are discussed in the context of nitrogen coordination promoted lithiation. (c) 2005 Elsevier Ltd. All rights reserved.
• GOMEZ PARRA V.; MADRONERO R., AN. QUIM. REAL SOC. ESP. FIS. Y QUIM., 1974, 70, NO 7-8, 614-616
  作者：GOMEZ PARRA V.、 MADRONERO R.

  DOI：——

  日期：——
• Facile and Simple Synthesis of <i>N</i>-Alkyl and <i>N</i>-Aryl 2-Benzazepines by Nucleophilic Heteroannulation
  作者：A. K. Srinivasan、K. Rajashekar、B. Shyamapada、U. K. Syam Kumar

  DOI：10.1080/00397911.2014.928327

  日期：2014.11.2