(3-nitrophenyl)(quinolin-3-yl)methanone | 1187167-64-1

• 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
• 英文名称: (3-nitrophenyl)(quinolin-3-yl)methanone
• 英文别名: (3-nitrophenyl)-quinolin-3-ylmethanone
• CAS: 1187167-64-1
• 化学式: C₁₆H₁₀N₂O₃
• 分子量: 278.267
• InChiKey: BJEGACKRKNTXPW-UHFFFAOYSA-N

物化性质

• 沸点：
  478.0±25.0 °C(Predicted)
• 密度：
  1.346±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  21
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  75.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  3-硝基苯丙酮 、 苯甲醯亞胺酸 在 2,2,6,6-四甲基哌啶氧化物 、 copper diacetate 作用下， 以 邻二氯苯 为溶剂， 反应 12.0h， 以95%的产率得到(3-nitrophenyl)(quinolin-3-yl)methanone
  参考文献：
  名称：

  一锅中通过铜催化的顺序脱氢/氮杂-迈克尔加成/环化级联反应使饱和酮与α，β-官能化

  摘要：

  已经研究了从容易获得的饱和酮和蒽基中获得官能化喹啉的有效方法。这种一锅法级联反应涉及通过铜催化饱和酮的脱氢反应，然后通过氮杂-迈克尔加成蒽基并随后进行环合反应，原位生成α，β-不饱和酮。

  DOI：

  10.1039/c7cc01195d

文献信息

• Transition-Metal-Free Quinoline Synthesis from Acetophenones and Anthranils via Sequential One-Carbon Homologation/Conjugate Addition/Annulation Cascade
  作者：Sandip Balasaheb Wakade、Dipak Kumar Tiwari、Pothapragada S. K. Prabhakar Ganesh、Mandalaparthi Phanindrudu、Pravin R. Likhar、Dharmendra Kumar Tiwari

  DOI：10.1021/acs.orglett.7b02429

  日期：2017.9.15

  the construction of functionalized quinolines from readily available acetophenones and anthranils is reported. This one-pot reaction cascade involves in situ generation of α,β-unsaturated ketones from the acetophenone via one-carbon homologation by DMSO followed by the aza-Michael addition of anthranils and subsequent annulation. DMSO acted in this reaction not only as solvent but also as one carbon source

  据报道，无过渡金属的方法可从容易获得的苯乙酮和蒽基构建官能化喹啉。该一锅法反应级联涉及通过DMSO的一碳同系物从苯乙酮中原位生成α，β-不饱和酮，然后通过aza-Michael加入蒽并随后进行环化反应。DMSO在该反应中不仅充当溶剂，而且充当一种碳源，因此为合成3-取代的喹啉提供了一种极富原子经济性和环境友好性的方法。
• Copper-catalyzed one-pot domino reactions <i>via</i> C–H bond activation: synthesis of 3-aroylquinolines from 2-aminobenzylalcohols and propiophenones under metal–organic framework catalysis
  作者：Ha V. Dang、Hoang T. B. Le、Loan T. B. Tran、Hiep Q. Ha、Ha V. Le、Nam T. S. Phan

  DOI：10.1039/c8ra05459b

  日期：——

  A Cu2(OBA)2(BPY) metal–organic framework was utilized as a productive heterogeneous catalyst for the synthesis of 3-aroylquinolines via one-pot domino reactions of 2-aminobenzylalcohols with propiophenones. This Cu-MOF was considerably more active towards the one-pot domino reaction than a series of transition metal salts, as well as nano oxide and MOF-based catalysts. The MOF-based catalyst was reusable

  Cu 2 (OBA) 2 (BPY) 金属有机骨架被用作生产多相催化剂，通过 2-氨基苄醇与苯丙酮的一锅多米诺反应合成 3-芳酰基喹啉。与一系列过渡金属盐以及纳米氧化物和 MOF 基催化剂相比，这种 Cu-MOF 对一锅多米诺反应的活性要高得多。基于 MOF 的催化剂可重复使用，催化效率不会显着下降。据我们所知, 2-氨基苯甲醇向 3-芳基喹啉的转化以前没有在文献中报道过, 该协议将与以前合成这些有价值的杂环的策略相辅相成。
• One-Pot Phosphine-Catalyzed Syntheses of Quinolines
  作者：San Khong、Ohyun Kwon

  DOI：10.1021/jo3015825

  日期：2012.9.21

  In this study we developed an efficient one-pot procedure for the preparation of 3-substituted and 3,4-disubstituted quinolines from stable starting materials (activated acetylenes reacting with o-tosylamidobenzaldehydes and o-tosylamidophenones, respectively) under mild conditions. The reaction appears to operate under a general base catalysis mechanism, instigated by the beta-phosphonium enoate alpha-vinyl anion generated in situ through nucleophilic addition of PPh3 to the activated alkyne. Michael addition of the deprotonated tosylamides to the activated alkynes and subsequent rapid aldol cyclization led to the formation of labile N-tosyldihydroquinoline intermediates. Driven by aromatization, detosylation of the dihydroquinoline intermediates occurred readily in the presence of dilute aqueous HCl to give the final quinoline products.