(2-chlorobenzyl)(naphthalen-1-yl)amine | 113250-80-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: (2-chlorobenzyl)(naphthalen-1-yl)amine
• 英文别名: N-(2-chlorobenzyl)naphthalen-1-amine；N-(o-chlorobenzyl)-1-naphthylamine；N-(2-Chlorobenzyl)-1-naphthalenamine；N-[(2-chlorophenyl)methyl]naphthalen-1-amine
• CAS: 113250-80-9
• 化学式: C₁₇H₁₄ClN
• 分子量: 267.758
• InChiKey: NIYKCTBMCZDZSM-UHFFFAOYSA-N

物化性质

• 熔点：
  109-110.2 °C(Solv: ligroine (8032-32-4); dichloromethane (75-09-2))
• 沸点：
  423.3±25.0 °C(Predicted)
• 密度：
  1.241±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.3
• 重原子数：
  19
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  12
• 氢给体数：
  1
• 氢受体数：
  1

安全信息

• 危险等级：
  IRRITANT
• 海关编码：
  2921499090

反应信息

• 作为反应物：
  描述：

  (2-chlorobenzyl)(naphthalen-1-yl)amine 在 氨 、 potassium amide 作用下， 以 乙醚 为溶剂， 反应 3.0h， 以64%的产率得到benzo[c]phenanthridine
  参考文献：
  名称：

  Benzyne cyclization route to benzo[c]phenanthridine alkaloids. Synthesis of chelerythrine, decarine, and nitidine

  摘要：

  DOI：

  10.1021/jo00243a020
• 作为产物：
  描述：

  2-氯苯甲醛 在 sodium tetrahydroborate 作用下， 以 乙醇 为溶剂， 生成 (2-chlorobenzyl)(naphthalen-1-yl)amine
  参考文献：
  名称：

  Use of Quantitative Structure–Activity Relationship (QSAR) and ADMET prediction studies as screening methods for design of benzyl urea derivatives for anti-cancer activity

  摘要：

  2D and 3D quantitative structure--activity relationship studies have been carried out for establishing a correlation between the structural properties of benzyl urea derivatives and their anti-tumour activities. From this correlation, the new chemical entities were designed, and their activity and absorption, distribution, metabolism, excretion, and toxicity properties were also predicted. Finally, the most promising compounds from these screening were synthesized and biologically evaluated for their anti-cancer properties. Compound 1-(2, 4-dimethylphenyl)-3, 3-dimethyl-1-(2-nitrobenzyl) urea (7d) showed significant anti-proliferative activity (at 100 mu A mu g/mL) in human cancer cell lines-T-cell leukemia (Jurkat J6), myelogenous leukemia (K562), and breast cancer (MCF-7) compared to reference standard 5-flurouracil.

  DOI：

  10.3109/14756366.2010.506437

文献信息

• Syntheses of phenanthridines and benzophenanthridines by intramolecular ortho-arylation of aryl amide ions with aryl halides via SRN1 reactions
  作者：Maria E. Budén、Roberto A. Rossi

  DOI：10.1016/j.tetlet.2007.10.009

  日期：2007.12

  The photostimulated reaction of N-(2-halo-benzyl)aryl amines with t-BuOK in liquid ammonia affords fused azaheterocycles by the SRN1 mechanism. The starting materials are easily obtained by the reaction of 2-halo-benzyl chloride and aromatic amines to prepare the secondary amines. Through this approach, phenanthridine (90%), 4-phenylphenanthridine (87%), benzo[a]phenanthridine (98%), and benzo[c]phenanthridine

  的光刺激反应ñ - （2-卤代-苄基）芳基胺与吨-BuOK在由S稠合氮杂杂环液氨得到RN 1机构。通过使2-卤代苄基氯与芳族胺反应以制备仲胺，可以容易地获得起始原料。通过这种方法，合成了菲啶（90％），4-苯基菲啶（87％），苯并[ a ]菲啶（98％）和苯并[ c ]菲啶（84％）。
• Electron-Transfer-Mediated Synthesis of Phenanthridines by Intramolecular Arylation of Anions from <i>N</i>-(<i>ortho</i>-Halobenzyl)arylamines: Regiochemical and Mechanistic Analysis
  作者：María E. Budén、Viviana B. Dorn、Martina Gamba、Adriana B. Pierini、Roberto A. Rossi

  DOI：10.1021/jo9025918

  日期：2010.4.2

  The synthesis of a series of substituted phenanthridines by photostimulated C-C cyclization of anions from N-(ortho-halobenzyl)arylamines has been found to proceed in very good to excellent yields (79-95%) in liquid ammonia and in DMSO. The N-(ortho-halobenzyl)arylamines are obtained in good to very good isolated yields (44-85%) by nucleophilic substitution of ortho-halobenzylchlorides with different arylamines. The reaction of the anions of a diverse set of N-(ortho-halobenzyl)arylamines was studied, and the methodology was extended to the synthesis of tri-spheridine, a natural product, in very good yield. In order to explain the regiochemical outcome or these reactions, a theoretical analysis was performed with DFT methods and the B3LYP functional.
• Synthesis and in vitro activity of new tetrahydronaphtho[1,2-b]azepine derivatives against Trypanosoma cruzi and Leishmania chagasi parasites
  作者：Alirio Palma、Andrés Felipe Yépes、Sandra Milena Leal、Carlos Andrés Coronado、Patricia Escobar

  DOI：10.1016/j.bmcl.2008.05.013

  日期：2009.4

  Series of 2-exo-aryl-1,4-epoxy-2,3,4,5-tetrahydronaphtho[1,2-b]azepines 3a-k and cis-2-aryl-4-hydroxy2,3,4,5-tetrahydronaphtho[1,2-b] azepines 4a-j were synthesized and evaluated against free and intracellular live forms of Trypanosoma cruzi and Leishmania chagasi parasites using in vitro assays. Cell toxicity was also analyzed on Vero and THP-1 mammalian cell lines. The compounds 3c, 3f, and 4d were the most active against both live forms of T. cruzi parasites with low mammalian cell toxicity. Some compounds were active on free live forms of L. chagasi parasites but none was active on intracellular amastigotes of L. chagasi infecting THP-1 macrophages. (C) 2008 Elsevier Ltd. All rights reserved.
• KESSAR, SATINDER V.;GUPTA, YASH P.;BALAKRISHNAN, PRASANNA;SAWAL, KEWAL K.+, J. ORG. CHEM., 53,(1988) N 8, 1708-1713
  作者：KESSAR, SATINDER V.、GUPTA, YASH P.、BALAKRISHNAN, PRASANNA、SAWAL, KEWAL K.+

  DOI：——

  日期：——
• ORGANOMETALLIC COMPLEX, ORGANIC LIGHT-EMITTING ELEMENT USING SAME, AND DISPLAY DEVICE
  申请人：Kamatani Jun

  公开号：US20090134785A1

  公开（公告）日：2009-05-28

  An organometallic complex is represented by Formula (1) below. ML m L′ n (1) In Formula (1) M stands for Ir, Rh, Pt, or Pd, m is an integer of 1 to 3, and n is an integer of 0 to 2, where m+n=3. ML m denotes a partial structure represented by Formula (2) below. ML′ n denotes a partial structure represented by at least one of Formulas (3) to (5) below.