1,3-di-(2'-quinolinyl)benzene | 189694-27-7

• 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: 1,3-di-(2'-quinolinyl)benzene
• 英文别名: 1,3-di(quinolin-2-yl)benzene；1,3-di(2'quinolinyl)benzene；2-[3-(2-Quinolinyl)phenyl]quinoline；2-(3-quinolin-2-ylphenyl)quinoline
• CAS: 189694-27-7
• 化学式: C₂₄H₁₆N₂
• 分子量: 332.404
• InChiKey: HZJTZSDOEHNNGP-UHFFFAOYSA-N

物化性质

• 熔点：
  138-139 °C(Solv: ethyl ether (60-29-7); dichloromethane (75-09-2))
• 沸点：
  546.6±40.0 °C(Predicted)
• 密度：
  1.210±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.8
• 重原子数：
  26
• 可旋转键数：
  2
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  25.8
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1,3-di-(2'-quinolinyl)benzene 、 ammonium hexafluorophosphate 、 Ru(tpy)(Cl)₃ 在 Et₃N 作用下， 以 乙醇 、 水 为溶剂， 以31%的产率得到2,6-dipyridin-2-ylpyridine;2-(3-quinolin-2-ylbenzene-2-id-1-yl)quinoline;ruthenium(2+);hexafluorophosphate
  参考文献：
  名称：

  Cyclometalated Complexes of Ru(II) with 2-Aryl Derivatives of Quinoline and 1,10-Phenanthroline

  摘要：

  Difficulty in cyclometalating 1-(2'-quinolinyl)pyrene and 1,3-di-(2'-quinolinyl)pyrene with Ru(H) led to a more detailed study of the cyclometalation process. A series of 2-aryl-1,10-phenanthrolines, where aryl = phenyl, 2-naphthyl, 1-anthracenyl, and 1-pyrenyl, were treated with [Ru(tPY)Cl-3] to provide either the N5Cl complex [Ru(tpy)(L)Cl](+) or this same material as a mixture with the N5C cyclometalated species [Ru(tpy)L](+). Steric effects appear to govern the ability of the ligand to attain the near planar conformation required for cyclometalation. The bridged ligand 3,1'-dimethylene-2-(2'-pyrenyl)-1,10-phenanthroline was prepared along with a quinoline analogue. The former species was found to cyclometalate at the Cl of pyrene and afford the N5Cl complex. Both the N5C (P2(1)/n (monoclinic), a = 28.1102(11), b = 8.4638(3),- c = 31.2908(12) Angstrom, Z = 8) and N5Cl (P-1 (triclinic), a = 11.7235 (10), b = 14.5306(12), c = 14.5725(12) Angstrom, Z = 2) complexes were analyzed by X-ray crystallography, and the N5Cl species evidenced a congested environment for pyrene, which is apparently stabilized by pi stacking with tpy. Similar reactions with a series of three 3,2'-bridged derivatives of 2-phenyl-1,10-phenanthroline provide both N5Cl and cyclometalated products in proportions which support the importance of,7 stacking. The electronic absorption spectra and redox potentials for these complexes evidence strong sigma donation by the cyclometalated ligand and an apparant insensitivity to the orthogonal 2-aryl group.

  DOI：

  10.1021/ic0102844
• 作为产物：
  描述：

  1,3-二乙炔苯 、 苯甲醯亞胺酸 在 6,6'-二甲基-2,2'-联吡啶 、 nickel(II) tetrafluoroborate hexahydrate 、 甲基二乙氧基硅烷 作用下， 以 N,N-二甲基乙酰胺 为溶剂， 反应 12.0h， 以80%的产率得到1,3-di-(2'-quinolinyl)benzene
  参考文献：
  名称：

  NiH 催化的加氢胺化/环化级联：快速获得喹啉

  摘要：

  尽管金属-H 催化的加氢胺化方法取得了重大成功，但炔烃的选择性加氢胺化仍然存在相当大的局限性，特别是对于末端炔烃。在此，我们开发了一种高效的 NiH 催化系统，可激活容易获得的炔烃，用于与邻氨基苯甲酸的级联加氢胺化/环化反应。这种温和、操作简单的方案适用于各种炔烃，包括末端和内部、芳基和烷基、缺电子和富电子的炔烃，提供结构多样的喹啉，产率非常高（>80 个例子，高达 93%屈服）。该程序的效用体现在几种天然产物的后期功能化以及抗肿瘤分子墓地宁和三链 DNA 嵌入剂的简明合成中。

  DOI：

  10.1021/acscatal.1c02055

文献信息

• Superbase-Mediated Indirect Friedländer Reaction: A Transition Metal-Free Oxidative Annulation toward Functionalized Quinolines
  作者：Rahul P.、Nitha P. R.、Vishnu K. Omanakuttan、Sheba Ann Babu、P. Sasikumar、Vakayil K. Praveen、Henning Hopf、Jubi John

  DOI：10.1002/ejoc.202000365

  日期：2020.5.29

  A transition metal‐free superbase mediated indirect Friedländer reaction was developed for accessing functionalized quinolines using o‐aminobenzyl alcohol and ketones with an active methylene moiety. The reaction was employed in the functionalization of natural products and the applicability of the reaction for gram‐scale synthesis of quinolines was also demonstrated.

  开发了一种不含过渡金属的超碱介导的间接Friedländer反应，可使用邻氨基苯甲醇和具有活性亚甲基的酮来获得官能化的喹啉。该反应被用于天然产物的功能化，并且也证明了该反应在克规模合成喹啉中的适用性。
• Synthesis of Quinolines Through Acceptorless Dehydrogenative Coupling Catalyzed by Rhenium PN(H)P Complexes
  作者：Duo Wei、Vincent Dorcet、Christophe Darcel、Jean‐Baptiste Sortais

  DOI：10.1002/cssc.201802636

  日期：2019.7.5

  A practical and sustainable synthesis of substituted quinolines was achieved through the annulation of 2‐aminobenzyl alcohol with various secondary alcohols, ketones, aldehydes, or nitriles, under hydrogen‐borrowing conditions. Under the catalysis of well‐defined rhenium complexes bearing tridentate diphosphinoamino ligands, the reaction proceeded efficiently (31 examples were isolated with yields

  在氢借入条件下，通过2-氨基苄醇与各种仲醇，酮，醛或腈的环化反应，实现了取代喹啉的实用，可持续的合成。在带有三齿二膦氨基配体的明确定义的rh络合物的催化下，反应有效进行（分离出31个实例，收率高达96％），提供了多种喹啉衍生物。
• Molybdenum Catalyzed Acceptorless Dehydrogenation of Alcohols for the Synthesis of Quinolines
  作者：Beatriz Garcia、Beatriz Royo

  DOI：10.1002/cctc.202400024

  日期：2024.8.12

  Molybdenum triazolylidene complexes displayed excellent catalytic activity in the synthesis of a wide variety of quinolines through acceptorless dehydrogenative coupling reactions.

  三唑基钼配合物在通过无受体脱氢偶联反应合成多种喹啉时表现出优异的催化活性。
• Palladium-catalyzed Sonogashira coupling reaction followed by isomerization and cyclization
  作者：Chan Sik Cho

  DOI：10.1016/j.jorganchem.2005.06.002

  日期：2005.9

  2-Iodoaniline reacts with terminal acetylenic carbinols in THF at 80 degrees C in the presence of a catalytic amount of PdCl2(PPh3)(2) and CuI along with aqueous tetrabutylammonium hydroxide to afford the corresponding 2-arylquinolines in good yields. The catalytic pathway seems to be proceeded via a sequence involving initial Sonogashira coupling between 2-iodoaniline and terminal acetylenic carbinols to form coupled acetylenic carbinols, isomerization of coupled acetylenic carbinols to alpha,beta-unsaturated ketones, and cyclodehydration. (c) 2005 Published by Elsevier B.V.