N-(2-chlorophenyl)pyridin-4-amine | 86776-00-3

• 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-(2-chlorophenyl)pyridin-4-amine
• 英文别名: 4-[(2-chlorophenyl)amino]pyridine
• CAS: 86776-00-3
• 化学式: C₁₁H₉ClN₂
• 分子量: 204.659
• InChiKey: QTRGXFMDWIQBBO-UHFFFAOYSA-N

物化性质

• 熔点：
  123 °C
• 沸点：
  327.2±22.0 °C(Predicted)
• 密度：
  1.273±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 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-(2-chlorophenyl)pyridin-4-amine 在 tris-(dibenzylideneacetone)dipalladium(0) 、 三叔丁基膦 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 1,4-二氧六环 、 甲苯 为溶剂， 以99%的产率得到5H-吡啶并[4,3-b]吲哚
  参考文献：
  名称：

  Structure–activity relationship of antiparasitic and cytotoxic indoloquinoline alkaloids, and their tricyclic and bicyclic analogues

  摘要：

  Based on the indoloquinoline alkaloids cryptolepine (1), neocryptolepine (2), isocryptolepine (3) and isoneocryptolepine (4), used as lead compounds for new antimalarial agents, a series of tricyclic and bicyclic analogues, including carbolines, azaindoles, pyrroloquinolines and pyrroloisoquinolines was synthesized and biologically evaluated. None of the bicyclic compounds was significantly active against the chloroquine-resistant strain Plasmodium falciparum K1, in contrast to the tricyclic derivatives. The tricyclic compound 2-methyl-2H-pyrido[3,4-b] indole (9), or 2-methyl-beta-carboline, showed the best in vitro activity, with an IC50 value of 0.45 mu M against P. falciparum K1, without apparent cytotoxicity against L6 cells (SI > 1000). However, this compound was not active in the Plasmodium berghei mouse model. Structure-activity relationships are discussed and compared with related naturally occurring compounds. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2009.08.057
• 作为产物：
  描述：

  4-氯吡啶盐酸盐 生成 N-(2-chlorophenyl)pyridin-4-amine
  参考文献：
  名称：

  KESTER, JEFFREY A.;MOOS, WALTER H.;THOMAS, ANTHONY J.

  摘要：

  DOI：

文献信息

• Lewis Acid Activation of Pyridines for Nucleophilic Aromatic Substitution and Conjugate Addition
  作者：Sarah Abou-Shehada、Matthew C. Teasdale、Steven D. Bull、Charles E. Wade、Jonathan M. J. Williams

  DOI：10.1002/cssc.201403154

  日期：2015.3

  clean, mild and sustainable method for the functionalization of pyridines and their analogues is reported. A zinc‐based Lewis acid is used to activate pyridine and its analogues towards nucleophilic aromatic substitution, conjugate addition, and cyclization reactions by binding to the nitrogen on the pyridine ring and activating the pyridine ring core towards further functionalization.

  据报道，有一种清洁，温和且可持续的方法使吡啶及其类似物官能化。锌基路易斯酸通过与吡啶环上的氮结合并激活吡啶环核以进一步官能化，用于活化吡啶及其类似物，以实现亲核芳香族取代，共轭加成和环化反应。
• C–H chlorination of (hetero)anilines <i>via</i> photo/organo co-catalysis
  作者：Wuchen Xie、Meng Wang、Siyu Yang、Yadong Chen、Jie Feng、Yatian Huang

  DOI：10.1039/d2ob00834c

  日期：——

  Chlorinated (hetero)anilines are a class of important structural motifs that are widely present in synthetic building blocks and pharmaceuticals. Despite recent advancements, direct aniline chlorination still suffers from ortho/para and mono/poly chlorination selectivity problems. Herein, we disclose a photo-redox and organo co-catalyzed chlorination method for anilines. This method has great substrate

  氯化（杂）苯胺是一类重要的结构基序，广泛存在于合成结构单元和药物中。尽管最近取得了进展，但直接苯胺氯化仍然存在邻/对和单/多氯化选择性问题。在此，我们公开了一种用于苯胺的光氧化还原和有机共催化氯化方法。该方法具有很好的底物通用性和优异的单氯化选择性。这种方法的另一个优点是药物分子的后期修饰，这将在药物化学中有用。
• Sammes, Michael P.; Ho, King-Wah; Tam, Ming-Lim, Journal of the Chemical Society. Perkin transactions I, 1983, # 5, p. 973 - 978
  作者：Sammes, Michael P.、Ho, King-Wah、Tam, Ming-Lim、Katritzky, Alan R.

  DOI：——

  日期：——
• US4855308A
  申请人：——

  公开号：US4855308A

  公开（公告）日：1989-08-08