(2-(4-甲氧基苯基)-8-甲基喹啉) | 107027-60-1

• 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-甲氧基苯基)-8-甲基喹啉)
• 英文名称: (2-(4-methoxyphenyl)-8-methylquinoline)
• 英文别名: 2-(4-methoxyphenyl)-8-methylquinoline；2-(4-methoxy-phenyl)-8-methyl-quinoline；2-(4-Methoxy-phenyl)-8-methyl-chinolin；Quinoline,2-(4-methoxyphenyl)-8-methyl-
• CAS: 107027-60-1
• 化学式: C₁₇H₁₅NO
• 分子量: 249.312
• InChiKey: ROHVLUAIQKOCGV-UHFFFAOYSA-N

物化性质

• 熔点：
  83-84 °C(Solv: ethanol (64-17-5))
• 沸点：
  160-200 °C(Press: 3 Torr)
• 密度：
  1.121±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  19
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  22.1
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (2-(4-甲氧基苯基)-8-甲基喹啉) 在 chromium(VI) oxide 、 硫酸 作用下， 以 水 为溶剂， 生成 2-(4-甲氧基-苯基)-喹啉-8-羧酸
  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-甲氧基苯基)-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

• Unsymmetrical triazolyl-naphthyridinyl-pyridine bridged highly active copper complexes supported on reduced graphene oxide and their application in water
  作者：Wenkang Hu、Yilin Zhang、Haiyan Zhu、Dongdong Ye、Dawei Wang

  DOI：10.1039/c9gc02086a

  日期：——

  A novel unsymmetrical triazolyl-naphthyridinyl-pyridine ligand was designed and synthesized, and employed in the synthesis of a heterogeneous copper complex on reduced graphene oxide. The resulting copper composite was characterized by scanning electron microscopy (SEM), transmission electron microscopy (TEM), X-ray photoelectron spectroscopy (XPS) and energy dispersive X-ray spectroscopy (EDX). This

  设计并合成了一种新型的不对称三唑基-萘啶基-吡啶配体，并将其用于在氧化石墨烯上合成异质铜配合物。通过扫描电子显微镜（SEM），透射电子显微镜（TEM），X射线光电子能谱（XPS）和能量色散X射线能谱（EDX）来表征所得的铜复合材料。该包含不对称三唑基-萘啶基-吡啶（仅0.1mol％）的负载型铜催化剂在水中具有优异的催化活性，并具有良好的再循环性。通过绿色策略在水中成功地合成了各种功能化的喹啉衍生物。其他杂环化合物，例如吡啶，2-（吡啶-2-基）喹啉，1,8-萘啶，5,6-二氢萘[1,2- b在水中以超过80％的产率获得了] [1,8]萘啶和2-（吡啶-2-基）-1,8-萘啶衍生物。机理研究表明，这种转化是通过脱氢，缩合以及转移加氢和脱氢过程而发生的，氘标记实验支持了这一过程。
• Three-Component Povarov Reaction with Alcohols as Alkene Precursors: Efficient Access to 2-Arylquinolines
  作者：Xinjian Li、Qi Xing、Pan Li、Jingjing Zhao、Fuwei Li

  DOI：10.1002/ejoc.201601343

  日期：2017.1.18

  An atom-economic and efficient approach to the synthesis of 2-arylquinolines has been developed. The protocol involves an iron-catalysed cascade N-alkylation/aerobic oxidation/Povarov reaction, and the desired quinolines were prepared in moderate to excellent yields from readily accessible anilines, aldehydes, and EtOH/nPrOH, with water as the only side-product. The aniline substrates also act as a

  已开发出一种原子经济且有效的合成 2-芳基喹啉的方法。该协议涉及铁催化的级联 N-烷基化/有氧氧化/Povarov 反应，所需的喹啉是从易于获得的苯胺、醛和 EtOH/nPrOH 中以中等至极好的收率制备的，水作为唯一的副产品。苯胺底物还通过原位 N-烷基化/氧化过程充当 EtOH/nPrOH 的可回收转移介质。这使得 EtOH/nPrOH 成为一种经济且环保的烯烃前体和溶剂。
• 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。
• Direct C–H Arylation and Alkylation of Electron-Deficient Heteroaromatic Compounds with Organozinc Reagents
  作者：Zhihua Peng、Chuanman Yu、Yilei Wang、Dongyue Wei、Cuiyu Jiang

  DOI：10.1021/acs.organomet.1c00505

  日期：2021.11.8