2-(4-氯-苯基)-8-甲基-喹啉 | 107027-56-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 中文名称: 2-(4-氯-苯基)-8-甲基-喹啉
• 英文名称: 8-methyl-2-(4-chlorophenyl)quinoline
• 英文别名: 2-(4-chlorophenyl)-8-methylquinoline；2-(4-Chlor-phenyl)-8-methyl-chinolin；2-(4-Chlorophenyl)-8-methylquinoline
• CAS: 107027-56-5
• 化学式: C₁₆H₁₂ClN
• 分子量: 253.731
• InChiKey: BVKWZOGFEHUGSK-UHFFFAOYSA-N

物化性质

• 熔点：
  79-80 °C
• 沸点：
  404.2±35.0 °C(Predicted)
• 密度：
  1.206±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  18
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  12.9
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  2-(4-氯-苯基)-8-甲基-喹啉 在 chromium(VI) oxide 、 盐酸 、 硫酸 、 N,N'-羰基二咪唑 作用下， 以 水 为溶剂， 反应 0.58h， 生成 2-(4-Chloro-phenyl)-quinoline-8-carboxylic acid (2-dimethylamino-ethyl)-amide; hydrochloride
  参考文献：
  名称：

  Potential antitumor agents. 57. 2-Phenylquinoline-8-carboxamides as minimal DNA-intercalating antitumor agents with in vivo solid tumor activity

  摘要：

  A series of phenyl-substituted derivatives of the "minimal" DNA-intercalating agent N-[2-(dimethylamino)-ethyl]-2-phenylquinoline-8-carboxamide (1) have been synthesized and evaluated for in vivo antitumor activity, in a continuing search for active compounds of this class with the lowest possible DNA association constants. Substitution on the 2'-position of the phenyl ring gave compounds of lower DNA binding ability that did not intercalate DNA, indicating that it is necessary for the phenyl ring to be essentially coplanar with the quinoline for intercalative binding. An extensive series of 4'-substituted derivatives was evaluated, but there was no overall relationship between biological activity and substituent lipophilic or electronic properties. However, several compounds showed good solid tumor activity, with the 4'-aza derivative 18 being clearly superior to the parent compound, effecting about 50% cures in both leukemia and solid tumor models.

  DOI：

  10.1021/jm00122a018
• 作为产物：
  描述：

  7-甲基靛红 在 氢氧化钾 、 铜 作用下， 以 乙醇 为溶剂， 生成 2-(4-氯-苯基)-8-甲基-喹啉
  参考文献：
  名称：

  Potential antitumor agents. 57. 2-Phenylquinoline-8-carboxamides as minimal DNA-intercalating antitumor agents with in vivo solid tumor activity

  摘要：

  A series of phenyl-substituted derivatives of the "minimal" DNA-intercalating agent N-[2-(dimethylamino)-ethyl]-2-phenylquinoline-8-carboxamide (1) have been synthesized and evaluated for in vivo antitumor activity, in a continuing search for active compounds of this class with the lowest possible DNA association constants. Substitution on the 2'-position of the phenyl ring gave compounds of lower DNA binding ability that did not intercalate DNA, indicating that it is necessary for the phenyl ring to be essentially coplanar with the quinoline for intercalative binding. An extensive series of 4'-substituted derivatives was evaluated, but there was no overall relationship between biological activity and substituent lipophilic or electronic properties. However, several compounds showed good solid tumor activity, with the 4'-aza derivative 18 being clearly superior to the parent compound, effecting about 50% cures in both leukemia and solid tumor models.

  DOI：

  10.1021/jm00122a018

文献信息

• Copper‐Catalyzed Acceptorless Dehydrogenative Coupling of 2‐Aminoaryl Methanols with Nitriles for Accessing Quinazolines and Quinolines
  作者：Swadhin Chetia、Samprity Sarmah、Apurba Dutta、Diganta Sarma

  DOI：10.1002/ejoc.202300390

  日期：2023.7.8

  Cu(OAc)2 ⋅ H2O catalyzed ligand free approach for the synthesis of quinazoline via acceptorless dehydrogenative coupling of 2-aminoaryl methanols and nitriles. The same catalytic approach is also highly effective for the construction of quinolines.

  Cu(OAc) 2  ⋅ H 2 O 催化的无配体方法，通过 2-氨基芳基甲醇和腈的无受体脱氢偶联合成喹唑啉。同样的催化方法对于喹啉的构建也非常有效。
• I2 and aqueous TBHP induced aerial oxidative coupling of 2-aminobenzyl alcohols and nitriles: A novel metal-free route towards quinazolines synthesis
  作者：Swadhin Chetia、Dipankar Nath、Siddhartha K. Purkayastha、Ankur K. Guha、Diganta Sarma

  DOI：10.1016/j.tetlet.2024.155084

  日期：2024.6

  I/-butyl hydroperoxide via oxidative coupling of 2-aminobenzyl alcohols and nitriles. Metal free approach, shorter reaction time, high atom efficiency and scale up synthesis are the salient features of the protocol. Experimental evidence followed by DFT calculations indicate that the reaction pathway of quinazoline formation proceed through radical intermediate.

  以异丁基过氧化氢为原料，通过2-氨基苯甲醇和腈的氧化偶联合成了一系列2-苯基喹唑啉。无金属方法、更短的反应时间、高原子效率和放大合成是该方案的显着特征。 DFT 计算的实验证据表明，喹唑啉形成的反应途径是通过自由基中间体进行的。
• Some Quinolines Patterned as “Open Models” of a Modified Atebrin
  作者：Henry Gilman、Robert V. Christian、Sydney M. Spatz

  DOI：10.1021/ja01210a021

  日期：1946.6