4-chloro-1-formyl-2-(4-methoxy)phenyl-2H-quinoline | 347335-64-2

• 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-methoxy)phenyl-2H-quinoline
• 英文别名: 4-chloro-2-(4-methoxyphenyl)-2H-quinoline-1-carbaldehyde
• CAS: 347335-64-2
• 化学式: C₁₇H₁₄ClNO₂
• 分子量: 299.757
• InChiKey: IAHLTIGXESNXRX-UHFFFAOYSA-N

物化性质

• 熔点：
  69-71 °C
• 沸点：
  493.0±45.0 °C(Predicted)
• 密度：
  1.31±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  21
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  29.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  4-chloro-1-formyl-2-(4-methoxy)phenyl-2H-quinoline 在 sodium azide 作用下， 以 二甲基亚砜 为溶剂， 反应 3.5h， 以84%的产率得到2-(4-甲氧基苯基)-喹啉
  参考文献：
  名称：

  Unexpected and Divergent Reactions of N-Formyl-1,2-dihydroquinolines with Sodium Azide: Highly Chemoselective Formation of 2-Substituted Quinolines and Isoxazolo[4,3-c]quinolines

  摘要：

  在叠氮化钠的帮助下，以 N-甲酰基-1,2-二氢喹啉为原料，实现了 2-取代喹啉和异噁唑并[4,3-c]喹啉的高效和发散合成。合成过程与取代基有关。因此，在 3 位含有一个氢原子的 N-甲酰基-1,2-二氢喹啉能以良好到极好的收率得到 2-取代的喹啉，而含有 3-甲酰基的 N-甲酰基-1,2-二氢喹啉则意外地以高收率得到异恶唑并[4,3-c]喹啉。

  DOI：

  10.1055/s-0029-1219800
• 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-methoxy)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

• 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。
• 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.
• Intramolecular Cyclization of 2′-Aminochalcones by Halomethyleniminium Salts Derived from BTC/DMF
  作者：Zhen-Hua Li、Cun Zheng、Ren-Er Chen、Weike Su

  DOI：10.1080/00304940902802156

  日期：2009.5.12
• 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.
• Unexpected and Divergent Reactions of N-Formyl-1,2-dihydroquinolines with Sodium Azide: Highly Chemoselective Formation of 2-Substituted Quinolines and Isoxazolo[4,3-c]quinolines
  作者：Weike Su、Jingbo Yu、Zhenhua Li、Bei Zheng

  DOI：10.1055/s-0029-1219800

  日期：2010.5

  Efficient and divergent synthesis of 2-substituted quinolines and isoxazolo[4,3-c]quinolines was achieved from N-formyl-1,2-dihydroquinolines with the aid of sodium azide. The synthesis is substituent-dependent. Thus N-formyl-1,2-dihydroquinolines with a hydrogen atom at the 3-position afforded 2-substituted quinolines in good to excellent yields, while with a 3-formyl group, N-formyl-1,2-dihydroquinolines unexpectedly gave isoxazolo[4,3-c]quinolines in high yields.

  在叠氮化钠的帮助下，以 N-甲酰基-1,2-二氢喹啉为原料，实现了 2-取代喹啉和异噁唑并[4,3-c]喹啉的高效和发散合成。合成过程与取代基有关。因此，在 3 位含有一个氢原子的 N-甲酰基-1,2-二氢喹啉能以良好到极好的收率得到 2-取代的喹啉，而含有 3-甲酰基的 N-甲酰基-1,2-二氢喹啉则意外地以高收率得到异恶唑并[4,3-c]喹啉。