2-phenyl-5,8-dimethoxyquinoline | 67188-08-3

• 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: 2-phenyl-5,8-dimethoxyquinoline
• 英文别名: 5,8-dimethoxy-2-phenyl-quinoline；2-Phenyl-5,8-dimethoxychinolin；5,8-Dimethoxy-2-phenylquinoline
• CAS: 67188-08-3
• 化学式: C₁₇H₁₅NO₂
• 分子量: 265.312
• InChiKey: RDLPJMNVXUZVRQ-UHFFFAOYSA-N

物化性质

• 沸点：
  439.9±40.0 °C(Predicted)
• 密度：
  1.153±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  20
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  31.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-phenyl-5,8-dimethoxyquinoline 在 吡啶-2,6-二羧酸 n-氧化物 、 ammonium cerium(IV) nitrate 作用下， 以 水 、 乙腈 为溶剂， 以85%的产率得到2-苯基喹啉-5,8-二酮
  参考文献：
  名称：

  Incorporation of the quinoline-5,8-quinone moiety into polyaza cavities

  摘要：

  Silica gel supported nitric acid treatment of 2,5-dimethoxybenzaldehyde followed by reduction with iron powder provides 3,6-dimethoxy-2-aminobenzaldehyde. Friedlander condensation of this species with a variety of ketones and diketones leads to 5,8-dimethoxyquinoline derivatives which may be oxidized by ceric ammonium nitrate (CAN) and pyridine-2,6-dicarboxylic acid N-oxide (PDANO) to the corresponding quinones. The quinone functionality can be incorporated into larger cavities by a selective stepwise Friedlander approach and the CAN/PDANO oxidation appears to work preferentially for 5,8-dimethoxyquinoline.

  DOI：

  10.1021/jo00059a012
• 作为产物：
  描述：

  (Z)-β-bromocinnamaldehyde 在 tris(dibenzylideneacetone)dipalladium (0) 、 potassium carbonate 、 (R)-2,2'-bis(diphenylphosphanyl)-1,1'-binaphthyl 、 三氟乙酸 作用下， 以 甲苯 为溶剂， 反应 16.0h， 生成 2-phenyl-5,8-dimethoxyquinoline
  参考文献：
  名称：

  Chemoselective arylamination of β-bromovinylaldehydes followed by acid catalyzed cyclization: a general method for polycyclic quinolines

  摘要：

  A synthesis of polycyclic quinolines is described via palladium-catalyzed chemoselective arylamination of beta-bromovinylaldehydes with aromatic amines followed by acid catalyzed cyclization. (C) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2007.05.111

文献信息

• Synthesis of quinolines through copper-catalyzed intermolecular cyclization reaction from anilines and terminal acetylene esters
  作者：Zhilei Zheng、Guobo Deng、Yun Liang

  DOI：10.1039/c6ra23858k

  日期：——

  A simple and convenient copper-catalyzed intermolecular cyclization reaction for the synthesis of quinolines from anilines and terminal acetylene esters has been developed. This methodology constructs the C–N and C–C bonds successively via a cascade process, and provides the desired products in moderate to good yields.

  开发了一种简单方便的铜催化分子间环化反应，用于由苯胺和末端乙炔酯合成喹啉。该方法通过级联过程依次构建C–N和C–C键，并以中等至良好的产率提供所需的产物。
• POLYMERIZABLE LIQUID CRYSTAL COMPOUND, COMPOSITION, LIQUID CRYSTAL POLYMERIZATION FILM-KIND THEREOF AND USE THEREOF
  申请人：JNC CORPORATION

  公开号：US20170174992A1

  公开（公告）日：2017-06-22

  An object is to provide a polymerizable liquid crystal compound, a polymerizable liquid crystal composition containing the compound and liquid crystal polymerization film-kind capable of controlling chromatic dispersion characteristics and having low positive chromatic dispersion characteristics. An aspect can be exemplified in which the polymerizable liquid crystal compound is represented by formula (1): in which, in formula (1), G is a group composed of a quinoline skeleton, an isoquinoline skeleton, a quinoxaline skeleton or a quinazoline skeleton, A 1 is 1,4-phenylene or 1,4-cyclohexylene, Z 1 is a connecting group, m is an integer from 0 to 3, and R 1 is a group containing a polymerizable group.

  提供一种可聚合的液晶化合物，包含该化合物的可聚合液晶组合物以及能够控制色散特性并具有低正色散特性的液晶聚合膜。一种例子是该可聚合液晶化合物由式(1)表示：其中，在式(1)中，G是由喹啉骨架、异喹啉骨架、喹啉骨架或喹嗪骨架组成的基团，A1为1,4-苯基或1,4-环己基，Z1为连接基，m为0至3的整数，R1为含有可聚合基团的基团。
• Polymerizable liquid crystal compound, composition, liquid crystal polymerization film-kind thereof and use thereof
  申请人：JNC CORPORATION

  公开号：US10581022B2

  公开（公告）日：2020-03-03

  An object is to provide a polymerizable liquid crystal compound, a polymerizable liquid crystal composition containing the compound and liquid crystal polymerization film-kind capable of controlling chromatic dispersion characteristics and having low positive chromatic dispersion characteristics. An aspect can be exemplified in which the polymerizable liquid crystal compound is represented by formula (1): in which, in formula (1), G is a group composed of a quinoline skeleton, an isoquinoline skeleton, a quinoxaline skeleton or a quinazoline skeleton, A1 is 1,4-phenylene or 1,4-cyclohexylene, Z1 is a connecting group, m is an integer from 0 to 3, and R1 is a group containing a polymerizable group.

  目的是提供一种可聚合液晶化合物、含有该化合物的可聚合液晶组合物以及能够控制色散特性并具有低正色散特性的液晶聚合膜。 可举例说明的一个方面是，可聚合液晶化合物由式（1）表示： 其中，在式 (1) 中，G 是由喹啉骨架、异喹啉骨架、喹喔啉骨架或喹唑啉骨架组成的基团，A1 是 1，4-亚苯基或 1，4-环己烯，Z1 是连接基团，m 是 0 至 3 的整数，R1 是含有可聚合基团的基团。
• Incorporation of the quinoline-5,8-quinone moiety into polyaza cavities
  作者：Randolph P. Thummel、Sara Chirayil、Christophe Hery、Jean Luc Lim、Tie Lin Wang

  DOI：10.1021/jo00059a012

  日期：1993.3

  Silica gel supported nitric acid treatment of 2,5-dimethoxybenzaldehyde followed by reduction with iron powder provides 3,6-dimethoxy-2-aminobenzaldehyde. Friedlander condensation of this species with a variety of ketones and diketones leads to 5,8-dimethoxyquinoline derivatives which may be oxidized by ceric ammonium nitrate (CAN) and pyridine-2,6-dicarboxylic acid N-oxide (PDANO) to the corresponding quinones. The quinone functionality can be incorporated into larger cavities by a selective stepwise Friedlander approach and the CAN/PDANO oxidation appears to work preferentially for 5,8-dimethoxyquinoline.
• Design of quinolinedione-Based geldanamycin analogues
  作者：Robert Hargreaves、Cynthia L. David、Luke Whitesell、Edward B. Skibo

  DOI：10.1016/s0960-894x(03)00650-4

  日期：2003.9

  Quinoline-5,8-dione-based compounds were designed from the structure of the geldanamycin-bound Hsp-90 active site. The active site model predicted that aromatic substituents should be present at the 2-position, to take advantage of a hydrophobic pocket, and amino substituents should be present at the 6- or 7-position. COMPARE analysis revealed that the LC50 profile of 2-phenyl-6-(2-chloroethylamino)quinoline-5,8-dione has the highest geldanamycin-like activity (0.74 correlation coefficient). (C) 2003 Elsevier Ltd. All rights reserved.