4-methoxy-2-(4'-methylphenyl)quinoline | 219850-90-5

• 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
• 英文名称: 4-methoxy-2-(4'-methylphenyl)quinoline
• 英文别名: 4-methoxy-2-(p-methylphenyl)quinoline；4-methoxy-2-(p-tolyl)quinoline；4-Methoxy-2-(4-methylphenyl)quinoline
• CAS: 219850-90-5
• 化学式: C₁₇H₁₅NO
• 分子量: 249.312
• InChiKey: FDGDFWQUKJXKHK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 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

• 作为产物：
  描述：

  4(1H)-喹啉酮,2,3-二氢-2-(4-甲基苯基)- 在 高氯酸 、 溶剂黄146 作用下， 反应 2.25h， 生成 4-methoxy-2-(4'-methylphenyl)quinoline
  参考文献：
  名称：

  硝酸铊 (III) 介导的 2-Aryl-1,2,3,4-四氢-4-喹诺酮环收缩：2-Aryl-2,3-dihydroindol-3-carboxylates 的立体选择性合成

  摘要：

  摘要 N-乙酰基-2-芳基-1,2,3,4-四氢-4-喹诺酮1a-d 与硝酸铊（III）在原甲酸三甲酯中的缩环得到立体选择性反式甲基N-乙酰基-2-芳基-通过芳环 A 的氧化重排得到 2,3-二氢吲哚-3-羧酸盐 5a-d。

  DOI：

  10.1080/00397910500466462

文献信息

• Novel 2-aryl-4-aryloxyquinoline-based fungistatics for Mucor circinelloides. Biological evaluation of activity, QSAR and docking study
  作者：Pradip D. Nahide、Clara Alba-Betancourt、Rubén Chávez-Rivera、Pamela Romo-Rodríguez、Manuel Solís-Hernández、Luis A. Segura-Quezada、Karina R. Torres-Carbajal、Rocío Gámez-Montaño、Martha A. Deveze-Álvarez、Marco A. Ramírez-Morales、Angel J. Alonso-Castro、Juan R. Zapata-Morales、Alan J. Ruiz-Padilla、Claudia L. Mendoza-Macías、Victor Meza-Carmen、Carlos J. Cortés-García、Alma R. Corrales-Escobosa、Rosa E. Núñez-Anita、Rafael Ortíz-Alvarado、Luis Chacón-García、César R. Solorio-Alvarado

  DOI：10.1016/j.bmcl.2022.128649

  日期：2022.5

  environments which transform organic matter. Some zygomycetes of gender Mucor have attracted interest in health sector. Due to its ability as opportunistic microorganisms infecting immuno-compromised people and to the few available pharmacological treatments, the mucormycosis is receiving worldwide attention. Concerning to the pharmacological treatments, some triazole-based compounds such as fluconazole

  接合菌是自然环境中普遍存在的腐生菌，可转化有机物。一些性别毛霉的接合菌引起了卫生部门的兴趣。由于其作为机会性微生物感染免疫功能低下的人的能力以及少数可用的药物治疗，毛霉菌病正受到全世界的关注。关于药物治疗，一些基于三唑的化合物如氟康唑被广泛使用。尽管如此，我们还是专注于喹啉，因为它们被广泛用于设计和开发新型合成抗真菌剂的模型。在本研究中，M. circinelloides的抑菌活性发现了各种基于 2-芳基-4-芳氧基喹啉的化合物，在某些情况下，其结果优于参考化合物氟康唑。这些喹啉衍生物是通过使用二芳基碘鎓 (III) 盐化学形成C sp 2 -O 键来合成的。进行了一项 QSAR 研究，以定量地将测试化合物的化学结构与其生物活性相关联。此外，还进行了一项对接研究，以确定我们更活跃的喹啉的合理作用目标。结果突出了含氟和含硝基衍生物的活性增加。鉴于为数不多的毛霉菌病药物治疗，在此我们提出了一些
• Synthesis and evaluation of graveoline and graveolinine derivatives with potent anti-angiogenesis activities
  作者：Zeng-Yun An、Yi-Yong Yan、Dan Peng、Tian-Miao Ou、Jia-Heng Tan、Shi-Liang Huang、Lin-Kun An、Lian-Quan Gu、Zhi-Shu Huang

  DOI：10.1016/j.ejmech.2010.05.043

  日期：2010.9

  A series of graveoline and graveolinine derivatives were synthesized. The biological results showed that most of graveoline derivatives possessed higher cytotoxicity and better inhibitive effect against the adhesion and migration of human umbilical vein endothelial cell (HUVEC) than graveolinine derivatives. Among these compounds, 8d was the most potent agents that also showed significant anti-angiogenesis activities in chick embryo chorioallantoic membrane (CAM) assay. (C) 2010 Elsevier Masson SAS. All rights reserved.
• Sulfuric acid promoted condensation cyclization of 2-(2-(trimethylsilyl) ethynyl)anilines with arylaldehydes in alcoholic solvents: an efficient one-pot synthesis of 4-alkoxy-2-arylquinolines
  作者：Yong Wang、Changlan Peng、Lanying Liu、Jiaji Zhao、Li Su、Qiang Zhu

  DOI：10.1016/j.tetlet.2009.02.206

  日期：2009.5

  An efficient method for the synthesis of 4-alkoxy-2-arylquinolines has been developed. The reaction proceeds smoothly by heating a mixture of easily accessible 2-(2-(trimethylsilyl) ethynyl)anilines and arylaldehydes in alcoholic solvents in the presence of sulfuric acid. (C) 2009 Elsevier Ltd. All rights reserved.
• Hypervalent iodine oxidation of 2-aryl-1,2,3,4-tetrahydro-4-quinolones: An expedient route to naturally occurring 4-alkoxy-2-arylquinolines
  作者：Rajender S. Varma、Dalip Kumar

  DOI：10.1016/s0040-4039(98)02059-0

  日期：1998.12

  Easily accessible 2-aryl-1,2,3,4-tetrahydro-4-quinolones are readily oxidized to the corresponding 4-alkoxy-2-arylquinolines using a relatively safe hypervalent iodine reagent, [hydroxy (tosyloxy)iodo]benzene (HTIB), in high yields, thus providing a concise route to an important class of naturally occurring alkaloids. (C) 1998 Elsevier Science Ltd. All rights reserved.
• An efficient oxidation of 2-aryl-1,2,3,4-tetrahydro-4-quinolones employing ferric chloride hexahydrate–methanol: synthesis of naturally occurring 4-alkoxy-2-arylquinolines
  作者：K. Hemanth Kumar、D. Muralidharan、P.T. Perumal

  DOI：10.1016/j.tetlet.2004.08.144

  日期：2004.10

  A simple, inexpensive and efficient oxidation of 2-aryl-1,2,3,4-tetrahydro-4-quinolones has been carried out by employing FeCl3-6H(2)O-methanol under mild conditions. This method has been investigated for the synthesis of an endothelin receptor antagonist, benzofuro[3,2-b]pyridine core structure. (C) 2004 Elsevier Ltd. All rights reserved.