N-benzyl-3-phenylisoquinolin-1-amine | 751479-61-5

• 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-benzyl-3-phenylisoquinolin-1-amine
• CAS: 751479-61-5
• 化学式: C₂₂H₁₈N₂
• 分子量: 310.398
• InChiKey: JMMBVJRJUDVPON-UHFFFAOYSA-N

物化性质

• 沸点：
  501.5±38.0 °C(Predicted)
• 密度：
  1.183±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.6
• 重原子数：
  24
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.05
• 拓扑面积：
  24.9
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  N-benzyl-3-phenylisoquinolin-1-amine 在 palladium on activated charcoal 氢气 作用下， 以 溶剂黄146 为溶剂， 66.0 ℃ 、620.52 kPa 条件下， 以62%的产率得到3-苯基-1-氨基异喹啉
  参考文献：
  名称：

  Molecular modeling of 3-arylisoquinoline antitumor agents active against A-549. A comparative molecular field analysis study

  摘要：

  A series of 58 3-arylisoquinoline antitumor agents were investigated for defining the pharmacophore model using comparative molecular field analysis (CoMFA) program. The studied compounds related to bioisostere of benzophenanthridine alkaloid were synthesized and evaluated for antitumor cytotoxicity against human lung tumor cell (A 549). In order to perform the systematic molecular modeling study of these compounds, the conformational search was carried out based on the single X-ray crystallographic structure of 7,8-dimethoxy-3-phenylisoquinolin-(2H)-one (2). Interestingly, two types of structures having different dihedral angles between the isoquinoline ring and 3-aryl ring were found in the crystals. Therefore, CoMFA was performed two different, overlapping ways. The alignments of the structures were based on the common isoquinoline ring and 3-aryl ring. The 3-D-quantitative structure-activity relationship study resulted in significant cross-validated, conventional r(2) values equal to 0.715 and 0.927, respectively. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(02)00137-2
• 作为产物：
  描述：

  N-甲基邻甲苯酰胺 在 正丁基锂 、 potassium carbonate 、 三氯氧磷 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 生成 N-benzyl-3-phenylisoquinolin-1-amine
  参考文献：
  名称：

  Synthesis of new 3-Arylisoquinolinamines: effect on topoisomerase I inhibition and cytotoxicity

  摘要：

  To investigate the structure-activity relationships of 3-arylisoquinolines, diverse substituted 3-aryisoquinolinamines were synthesized and tested in vitro antitumor activity against four tumor cell lines. Some of the compounds showed potent topoisomerase I inhibitory activity. Docking study of 7d with topoisomerase I-DNA complex was also performed. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2003.09.001

文献信息

• Rh-Catalyzed Reaction of Vinyl Azides with Isonitriles and Alkynes/Benzynes
  作者：Zongyang Li、Tongyu Huo、Li Li、Shuo Feng、Qian Wang、Zhen Zhang、Sen Pang、Zhiyuan Zhang、Peng Wang、Zhenhua Zhang

  DOI：10.1021/acs.orglett.8b03115

  日期：2018.12.21

  In contrast to well-known transformations of vinyl azides via azirine intermediates or initiating at the alkene moiety, herein we report a Rh(I)-catalyzed coupling reaction of vinyl azides with isonitriles at the azide moiety to form active vinyl carbodiimide intermediates and following tandem cyclization with unsaturated compounds, such as alkynes and benzynes, to give different classes of azaheterocycles

  与通过叠氮基中间体或起始于烯烃部分的乙烯基叠氮化物的众所周知的转化相反，本文中我们报道了Rh（I）催化的叠氮化物部分上的乙烯基叠氮化物与异腈形成活性乙烯基碳二亚胺中间体并随后串联与不饱和化合物（例如炔烃和苯炔烃）环合，得到不同种类的氮杂杂环。从机理上讲，受控实验和DFT计算表明，Rh-nitrene是第一步偶联过程中的重要物质，Rh（I）催化剂也可以在炔烃的环化步骤中发挥重要作用。
• Metal-free construction of aminated isoquinoline frameworks from 2-(2-oxo-2-arylethyl) benzonitrile in an aqueous medium
  作者：Himanshi Sharma、Manoj Kumar、Aaftaab Sethi、Poonam、Brijesh Rathi

  DOI：10.1039/d2gc04044a

  日期：——

  for the activation of nitrile towards nucleophilic addition and subsequent annulation under an aqueous medium for the first time. The protocol divulges an efficient and atom economical route for the construction of diverse aminated isoquinolines. Differently substituted primary as well as secondary amines underwent the reaction in a highly regioselective manner. The reaction is operationally simple

  在此，我们报告了一种无金属/添加剂的方案，用于首次在水性介质下激活腈进行亲核加成和随后的环化。该协议揭示了一种高效且原子经济的路线，用于构建各种胺化异喹啉。不同取代的伯胺和仲胺以高度区域选择性的方式进行反应。该反应操作简单，具有较高的官能团耐受性，更易于对知名药物进行修饰，可成功扩展至克级合成。
• Molecular modeling of 3-arylisoquinoline antitumor agents active against A-549. A comparative molecular field analysis study
  作者：Won-Jea Cho、Eui-Ki Kim、Il Yeong Park、Eun Young Jeong、Tae Sung Kim、Thanh Nguyen Le、Dae-Duk Kim、Eung-Seok Lee

  DOI：10.1016/s0968-0896(02)00137-2

  日期：2002.9

  A series of 58 3-arylisoquinoline antitumor agents were investigated for defining the pharmacophore model using comparative molecular field analysis (CoMFA) program. The studied compounds related to bioisostere of benzophenanthridine alkaloid were synthesized and evaluated for antitumor cytotoxicity against human lung tumor cell (A 549). In order to perform the systematic molecular modeling study of these compounds, the conformational search was carried out based on the single X-ray crystallographic structure of 7,8-dimethoxy-3-phenylisoquinolin-(2H)-one (2). Interestingly, two types of structures having different dihedral angles between the isoquinoline ring and 3-aryl ring were found in the crystals. Therefore, CoMFA was performed two different, overlapping ways. The alignments of the structures were based on the common isoquinoline ring and 3-aryl ring. The 3-D-quantitative structure-activity relationship study resulted in significant cross-validated, conventional r(2) values equal to 0.715 and 0.927, respectively. (C) 2002 Elsevier Science Ltd. All rights reserved.
• Synthesis of new 3-Arylisoquinolinamines: effect on topoisomerase I inhibition and cytotoxicity
  作者：Won-Jea Cho、Sun Young Min、Thanh Nguyen Le、Tae Sung Kim

  DOI：10.1016/j.bmcl.2003.09.001

  日期：2003.12

  To investigate the structure-activity relationships of 3-arylisoquinolines, diverse substituted 3-aryisoquinolinamines were synthesized and tested in vitro antitumor activity against four tumor cell lines. Some of the compounds showed potent topoisomerase I inhibitory activity. Docking study of 7d with topoisomerase I-DNA complex was also performed. (C) 2003 Elsevier Ltd. All rights reserved.