N-(o-Chlorbenzyliden)-1-naphthylamin | 113250-73-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: N-(o-Chlorbenzyliden)-1-naphthylamin
• 英文别名: (2-chloro-benzylidene)-[1]naphthyl-amine；2-Chlor-benzaldehyd-[1]naphthylimin；(2-Chlor-benzyliden)-[1]naphthyl-amin；1-Naphthalenamine, N-[(2-chlorophenyl)methylene]-；1-(2-chlorophenyl)-N-naphthalen-1-ylmethanimine
• CAS: 113250-73-0
• 化学式: C₁₇H₁₂ClN
• 分子量: 265.742
• InChiKey: PXXFNKDJMZPGMA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.1
• 重原子数：
  19
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  12.4
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  N-(o-Chlorbenzyliden)-1-naphthylamin 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
• 作为产物：
  描述：

  2-氯苯甲醛 、 1-萘胺 以 乙醇 为溶剂， 生成 N-(o-Chlorbenzyliden)-1-naphthylamin
  参考文献：
  名称：

  通过镍催化的 C-Cl 键活化和芳基化引入 (2-CF3) 苯基

  摘要：

  描述了通过 C-Cl 键活化的简单和温和的催化芳基化。通过氯芳烃与有机锌试剂双(2-(三氟甲基)苯基)锌、四(三甲基膦)镍(0)之间的C,C-偶联反应，将含有2-三氟甲基的苯基引入到芳族亚胺分子中络合物作为有效的催化剂。在催化条件下，氯化苯甲亚胺被定量转化为预期的具有三氟甲基的苯甲亚胺。

  DOI：

  10.1002/zaac.201400609

文献信息

• A simple and clean procedure for the synthesis of polyhydroacridine and quinoline derivatives: reaction of Schiff base with 1,3-dicarbonyl compounds in aqueous medium
  作者：Xiang-Shan Wang、Mei-Mei Zhang、Zhao-Sen Zeng、Da-Qing Shi、Shu-Jiang Tu、Xian-Yong Wei、Zhi-Min Zong

  DOI：10.1016/j.tetlet.2005.08.091

  日期：2005.10

  A clean and simple synthesis of benzo[c]acridine, benzo[a]acridine, pyrido[2,3-c]acridine and benzo[f]quinoline derivatives was accomplished in good to excellent yields via the reaction of Schiff base with 1,3-dicarbonyl compounds in aqueous medium catalyzed by TEBA. The structures were characterized by 1H NMR, IR and elemental analysis, and confirmed by X-ray diffraction study.

  通过席夫碱与1的反应，可以很好地收率很好地完成苯并[ c ] ac啶，苯并[ a ] ac啶，吡啶并[2,3- c ] ac啶和苯并[ f ]喹啉衍生物的清洁，简单合成。TEBA催化的水性介质中的3-二羰基化合物。通过1 H NMR，IR和元素分析对结构进行表征，并通过X射线衍射研究证实。
• Chemotherapeutic Dyes. I. 5-Aralkylamino-9-alkylaminobenzo [a]phenoxazines¹
  作者：Moses L. Crossley、Paul F. Dreisbach、Corris M. Hofmann、Robert P. Parker

  DOI：10.1021/ja01123a001

  日期：1952.2
• Introduction of (2-CF₃)Phenyl Group via Nickel-catalyzed C-Cl Bond Activation and Arylation
  作者：Zheng Peng、Hongjian Sun、Aiqin Du、Xiaoyan Li

  DOI：10.1002/zaac.201400609

  日期：2015.4

  A simple and mild catalytic arylation via C–Cl bond activation is described. The phenyl group containing a 2-trifluoromethyl group was introduced into the aromatic imine molecules through C,C-coupling reaction between chloroarenes and the organozinc reagent, bis(2-(trifluoromethyl)phenyl)zinc, with tetrakis(trimethylphosphine)nickel(0) complex as an effective catalyst. Under catalytic conditions chlorinated

  描述了通过 C-Cl 键活化的简单和温和的催化芳基化。通过氯芳烃与有机锌试剂双(2-(三氟甲基)苯基)锌、四(三甲基膦)镍(0)之间的C,C-偶联反应，将含有2-三氟甲基的苯基引入到芳族亚胺分子中络合物作为有效的催化剂。在催化条件下，氯化苯甲亚胺被定量转化为预期的具有三氟甲基的苯甲亚胺。
• Use of Quantitative Structure–Activity Relationship (QSAR) and ADMET prediction studies as screening methods for design of benzyl urea derivatives for anti-cancer activity
  作者：Deepak Lokwani、Shashikant Bhandari、Radha Pujari、Padma Shastri、Ganesh shelke、Vidya Pawar

  DOI：10.3109/14756366.2010.506437

  日期：2011.6.1

  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.