4-chloro-1-formyl-2-(4-methyl)phenyl-2H-quinoline | 347335-63-1

• 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: 4-chloro-1-formyl-2-(4-methyl)phenyl-2H-quinoline
• 英文别名: 4-Chloro-2-(p-tolyl)quinoline-1(2H)-carbaldehyde；4-chloro-2-(4-methylphenyl)-2H-quinoline-1-carbaldehyde
• CAS: 347335-63-1
• 化学式: C₁₇H₁₄ClNO
• 分子量: 283.757
• InChiKey: MBDSIYAVWAFKCF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  20
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  20.3
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  4-chloro-1-formyl-2-(4-methyl)phenyl-2H-quinoline 在 iron(III) chloride hexahydrate 作用下， 以 甲醇 为溶剂， 生成 4-chloro-2-(4-methyl)phenyl quinoline
  参考文献：
  名称：

  2,4-二芳基喹啉的合成：4-氯-2-芳基喹啉与芳基卤化镁在2-甲基四氢呋喃中的无镍催化配体交叉偶联

  摘要：

  描述了用于合成 2,4-二芳基喹啉的无配体和室温协议。在催化量的氯化镍 (II) 存在下，在 2-甲基四氢呋喃 (2-MeTHF) 中没有配体的情况下，用芳基卤化镁处理 4-氯-2-芳基喹啉，以良好的产率得到相应的交叉偶联产物。

  DOI：

  10.3184/174751911x13026226423986
• 作为产物：
  描述：

  邻氨基苯乙酮 在 三氯氧磷 作用下， 反应 3.0h， 生成 4-chloro-1-formyl-2-(4-methyl)phenyl-2H-quinoline
  参考文献：
  名称：

  The Vilsmeier cyclization of 2′-azido and 2′-aminochalcones—a mild one pot synthesis of 2-aryl-4-chloroquinoline and its N -formyl-1,2-dihydro derivatives

  摘要：

  The Vilsmeier cyclization of 2'-aminochalcones provides a mild one pot synthesis of 2-aryl-4-chloro-N-formyl-1,2-dihydroquinolines. The scope of the reaction has been extended for the synthesis of quinolines themselves, by replacing 2'-aminochalcones with 2'-azidochalcones as the starting material. The yields are reasonably good and a plausible mechanism for the formation of the products in each case has been discussed. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(01)00220-4

文献信息

• A novel one‐pot oxidative deformylation of <i>N</i> ‐formyldihydroquinolines employing ferric chloride hexahydrate. Synthesis of 4‐chloro‐2‐phenylquinolines and 4‐chloro‐2‐(1,3‐diphenyl‐1 <i>H</i> ‐pyrazol‐4‐yl)quinolines
  作者：Kalvi. Hemanth Kumar、Paramasivan. T. Perumal

  DOI：10.1002/jhet.5570450248

  日期：2008.3

  Abstractmagnified imageA novel versatile one‐pot oxidative deformylation approach has been developed to synthesize 4‐chloro‐2‐phenylquinolines and 4‐chloro‐2‐(1,3‐diphenyl‐1H‐pyrazol‐4‐yl)quinolines from the corresponding N‐formyldihydroquinolines.
• The Vilsmeier cyclization of 2′-azido and 2′-aminochalcones—a mild one pot synthesis of 2-aryl-4-chloroquinoline and its N -formyl-1,2-dihydro derivatives
  作者：Shanmugam Akila、Srinivasan Selvi、Krishna Balasubramanian

  DOI：10.1016/s0040-4020(01)00220-4

  日期：2001.4

  The Vilsmeier cyclization of 2'-aminochalcones provides a mild one pot synthesis of 2-aryl-4-chloro-N-formyl-1,2-dihydroquinolines. The scope of the reaction has been extended for the synthesis of quinolines themselves, by replacing 2'-aminochalcones with 2'-azidochalcones as the starting material. The yields are reasonably good and a plausible mechanism for the formation of the products in each case has been discussed. (C) 2001 Elsevier Science Ltd. All rights reserved.
• Synthesis of 2,4-Diarylquinolines: Nickel-Catalysed Ligand-Free Cross-Couplings of 4-Chloro-2-Arylquinolines with Arylmagnesium Halides in 2-Methyltetrahydrofuran
  作者：Zhenhua Li、Lingmin Xu、Weike Su

  DOI：10.3184/174751911x13026226423986

  日期：2011.4

  A ligand-free and room temperature protocol for the synthesis of 2,4-diarylquinolines is described. Treatment of 4-chloro-2-arylquinolines with arylmagnesium halides in the presence of a catalytic amount of nickel(II) chloride without ligands in 2-methyltetrahydrofuran (2-MeTHF) afforded the corresponding cross-coupling products in good yields.

  描述了用于合成 2,4-二芳基喹啉的无配体和室温协议。在催化量的氯化镍 (II) 存在下，在 2-甲基四氢呋喃 (2-MeTHF) 中没有配体的情况下，用芳基卤化镁处理 4-氯-2-芳基喹啉，以良好的产率得到相应的交叉偶联产物。