2,4-二苯基苯并[h]喹啉 | 34987-58-1

• 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: 2,4-二苯基苯并[h]喹啉
• 英文名称: 2,4-diphenylbenzo[h]quinoline
• 英文别名: 2,4-diphenylbenzo[h]quinolone；2,4-diphenyl-benzo[h]quinoline
• CAS: 34987-58-1
• 化学式: C₂₅H₁₇N
• 分子量: 331.417
• InChiKey: DYEOZWGZLMAUJO-UHFFFAOYSA-N

物化性质

• 熔点：
  163.5-164.1 °C(Solv: benzene (71-43-2); ethanol (64-17-5))
• 沸点：
  529.4±29.0 °C(Predicted)
• 密度：
  1.177±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  6.7
• 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：
  12.9
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  2-(1,3-diphenyl-3-oxopropylidene)-1-tetralone 在 氢氟酸 、 三乙胺 作用下， 以 二氯甲烷 、 甲苯 为溶剂， 反应 23.0h， 生成 2,4-二苯基苯并[h]喹啉
  参考文献：
  名称：

  Reductive deamination of aryl- and heteroaryl-amines via pyridinium fluorides

  摘要：

  DOI：

  10.1016/s0040-4020(01)98888-x

文献信息

• Mn(III)‐Mediated Regioselective 6‐ <i>endo</i> ‐trig Radical Cyclization of <i>o</i> ‐Vinylaryl Isocyanides to Access 2‐Functionalized Quinolines
  作者：Yan Liu、Shi‐Jun Li、Xiao‐Lan Chen、Lu‐Lu Fan、Xiao‐Yun Li、Shan‐Shan Zhu、Ling‐Bo Qu、Bing Yu

  DOI：10.1002/adsc.201901300

  日期：2020.2.6

  A Mn(III)‐mediated radical cyclization reaction of o‐vinylaryl isocyanides and arylboronic acids or diphenylphosphine oxides to access various 2‐functionalized quinolines under mild conditions was developed. With the introduction of radical stabilizing substituents (e. g. aryl and methyl group) on vinyl group, this reaction provides a regiospecific 6‐endo‐trig radical cyclization of o‐vinylaryl isocyanides

  在温和的条件下，开发了由Mn（III）介导的邻乙烯基芳基异氰化物与芳基硼酸或二苯基膦氧化物进行自由基环化反应，以访问各种2-官能化喹啉的方法。通过引入对乙烯基自由基稳定化用取代（例如芳基和甲基），该反应提供了区域专一的6-内-trig的自由基环化ø -vinylaryl异氰化物，得到数结构独特的和生物学潜力2官能喹啉衍生物的。
• Indium(III) Triflate-Catalyzed Reactions of Aza-Michael Adducts of Chalcones with Aromatic Amines: Retro-Michael Addition versus Quinoline Formation
  作者：Thangavel Selvi、Sivan Velmathi

  DOI：10.1021/acs.joc.7b03151

  日期：2018.4.6

  The indium(III) triflate-catalyzed reaction of aza-Michael adducts of chalcones with aromatic amines has been investigated. The Michael adducts derived from substituted anilines and chalcones underwent retro-Michael addition to give the original starting materials, whereas the adducts derived from 1-naphthylamines and chalcones afforded quinolines. A six-membered cyclic transition state has been proposed

  研究了查尔酮的氮杂-迈克尔加合物与芳族胺的三氟甲磺酸铟（III）催化反应。衍生自取代苯胺和查耳酮的迈克尔加合物进行了逆迈克尔加成反应，得到了原始原料，而衍生自1-萘胺和查耳酮的迈克尔加合物得到了喹啉。有人提出了六元环过渡态来解释反迈克尔加成反应，而提出了一种Povarov机理来解释喹啉的形成。
• A Facile Synthesis of Benzo[<i>h</i> ]quinolines via Silica-TsOH-P₂ O₅ Promoted Condensation of 1-Naphthylamines with 1,3-Diketones under Solvent Free Conditions
  作者：Chuanlei Zhu、Ruiqiang Guo、Zhe Sheng、Yanzhe Li、Changhu Chu

  DOI：10.1002/cjoc.201700128

  日期：2017.10

  A facile synthesis of benzo[h]quinolines has been developed via improved Combes reaction. A combination of silica gel, p‐toluenesulfonic acid and phosphorus pentoxide was utilized to promote the condensation of 1‐naphthylamines with 1,3‐diketones under solvent free conditions. In this case, silica gel was used as reaction media, p‐toluenesulfonic acid and phosphorus pentoxide were acted as catalyst

  通过改进的Combes反应，已轻松合成了苯并[ h ]喹啉。在无溶剂的条件下，将硅胶，对甲苯磺酸和五氧化二磷结合使用可促进1-萘胺与1,3-二酮的缩合。在这种情况下，硅胶用作反应介质，对甲苯磺酸和五氧化二磷分别充当催化剂和脱水剂。
• Rare-Earth Metal Chlorides Catalyzed One-pot Syntheses of Quinolines under Solvent-free Microwave Irradiation Conditions
  作者：Lijun Zhang、Bing Wu、Yongqing Zhou、Jing Xia、Shuangliu Zhou、Shaowu Wang

  DOI：10.1002/cjoc.201300047

  日期：2013.4

  Under microwave irradiation and solvent‐free conditions, rare‐earth metal chlorides (RECl3) have been efficient catalysts for one‐pot synthesis of quinoline derivatives to give products in good to excellent yields through the multi‐component reactions of aldehydes, amines, and alkynes. The rare‐earth metal chlorides can be recycled for six times without notable loss of catalytic activities. This new

  在微波辐射和无溶剂条件下，稀土金属氯化物（RECl 3）已成为单罐合成喹啉衍生物的有效催化剂，通过醛类，胺类和胺类的多组分反应可提供高至优等收率的产品。炔烃。稀土金属氯化物可以循环使用六次，而不会明显降低催化活性。这种新的合成方法的突出特点是反应时间短，产物收率高，操作简便，底物范围广，环境友好性和可商购的催化剂。它扩展了稀土金属化合物作为有机合成催化剂的应用。
• Iron-catalyzed tandem reactions of aldehydes, terminal alkynes, and primary amines as a strategy for the synthesis of quinoline derivatives
  作者：Yicheng Zhang、Pinhua Li、Lei Wang

  DOI：10.1002/jhet.417

  日期：2011.1

  FeCl3‐catalyzed three‐component tandem condensation/addition/cyclization/oxidation reactions of aldehydes, terminal alkynes, and primary amines have been developed. The processes can provide a diverse range of quinoline derivatives in good yields from simple starting materials. A possible reaction mechanism was proposed. J. Heterocyclic Chem., (2010).

  已经开发了FeCl 3催化的醛，末端炔烃和伯胺的三组分串联缩合/加成/环化/氧化反应。该方法可以由简单的起始原料以高收率提供多种喹啉衍生物。提出了一种可能的反应机理。J.杂环化​​学。（2010）。