1-(2-chloro-6-methylquinolin-3-yl)-N-phenylmethanimine | 329719-11-1

• 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: 1-(2-chloro-6-methylquinolin-3-yl)-N-phenylmethanimine
• CAS: 329719-11-1
• 化学式: C₁₇H₁₃ClN₂
• 分子量: 280.757
• InChiKey: DHFIBVLUPOGPLK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  20
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  25.2
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1-(2-chloro-6-methylquinolin-3-yl)-N-phenylmethanimine 在 sodium tetrahydroborate 、 caesium carbonate 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 15.0h， 生成
  参考文献：
  名称：

  分子内Heck反应：1,2,3,4-四氢苯并[ b ] [1,6]萘啶的简便连续一锅合成

  摘要：

  已经开发了一种简单，方便的顺序一锅法合成1,2,3,4-四氢苯并[ b ] [1,6]萘啶。在硼氢化钠存在下，用各种胺对2-氯-3-甲酰基喹啉进行还原性胺化反应可提供高产率的相应仲胺。此外，对仲胺进行了涉及N-烯丙基化和分子内Heck型6-exo-trig环化的顺序一锅反应，得到了所需的1,2,3,4-四氢苯并[ b ] [1,6]对-萘啶衍生物的产率高至高。

  DOI：

  10.1016/j.tetlet.2018.09.068
• 作为产物：
  描述：

  2-氯-6-甲基喹啉-3-甲醛 、 苯胺 生成 1-(2-chloro-6-methylquinolin-3-yl)-N-phenylmethanimine
  参考文献：
  名称：

  分子内Heck反应：1,2,3,4-四氢苯并[ b ] [1,6]萘啶的简便连续一锅合成

  摘要：

  已经开发了一种简单，方便的顺序一锅法合成1,2,3,4-四氢苯并[ b ] [1,6]萘啶。在硼氢化钠存在下，用各种胺对2-氯-3-甲酰基喹啉进行还原性胺化反应可提供高产率的相应仲胺。此外，对仲胺进行了涉及N-烯丙基化和分子内Heck型6-exo-trig环化的顺序一锅反应，得到了所需的1,2,3,4-四氢苯并[ b ] [1,6]对-萘啶衍生物的产率高至高。

  DOI：

  10.1016/j.tetlet.2018.09.068

文献信息

• An efficient synthesis of strained thio-bridged compounds via Pd(0) catalyzed intramolecular Csp2(aryl)-Csp3(alkyl) cross dehydrohalogenative coupling reaction
  作者：Mayur I. Morja、Janki J. Patel、Prakashsingh M. Chauhan、Kishor H. Chikhalia

  DOI：10.1016/j.tet.2020.131348

  日期：2020.8

  An operationally simple and efficient strategy employing palladium(0) catalyst to construct a wide range of thiobridged compounds through intramolecular Csp2(aryl)-Csp3(alkyl) cross-dehydrohalogenative coupling reaction has been reported. This methodology proceeds smoothly through six-membered palladacycles and serving as a keystone for the generation of C–C bond to furnish thiobridged derivative in

  已经报道了一种使用钯（0）催化剂通过分子内Csp 2（芳基）-Csp 3（烷基）交叉脱卤化氢偶合反应构建各种硫桥化合物的操作简单有效的策略。该方法通过六元的palladacycles顺利进行，并成为生成C–C键的基石，从而以良好或优异的产率提供硫桥化合物。
• An efficient carbodiimide-mediated synthesis and DNA-binding studies of novel 2-chloro/mercapto-quinoline-fused 1,3-thiazolidinones via one-pot three-component condensation
  作者：Devappa S. Lamani、K. R. Venugopala Reddy、H. S. Bhojya Naik、H. R. Prakash Naik、L. R. Naik

  DOI：10.1080/17415990903295678

  日期：2010.2

  A new and efficient method for the preparation of 2-(2-chloroquinolin-3-yl)-3-(4-methylphenyl)-1, 3-thiazolidin-4-one derivatives has been assembled by DCC:-mediated three-component one-pot reaction of amine, aldehyde, and mercaptoacetic acid. The final compounds were obtained in quantitative yields within 50min. The synthesized compounds were characterized by elemental analysis, FT-IR, 1H-NMR, and mass spectral data. The selected compounds were studied for interaction with calf thymus DNA by electronic spectra, viscosity measurements as well as thermal denaturation studies. On binding to DNA, the absorption spectrum underwent bathochromic and hypochromic shifts. The binding constant (Kb) had a value of 5.3x105M-1 for 2a and 5.8x105M-1 for 3a. The viscosity measurements indicated that the viscosity of sonicated rod-like DNA fragments increased.
• Intramolecular Heck reaction: A facile sequential one-pot synthesis of 1,2,3,4-tetrahydrobenzo[b][1,6]naphthyridines
  作者：Puchakayala Bharath Kumar Reddy、Kanakaraju Ravi、Kukkamudi Mahesh、Panaganti Leelavathi

  DOI：10.1016/j.tetlet.2018.09.068

  日期：2018.11

  A simple and convenient sequential one-pot synthesis of 1,2,3,4-tetrahydrobenzo[b][1,6] naphthyridines has been developed. The reductive amination of 2-chloro-3-formylquinolines with various amines in the presence of sodium borohydride provided the corresponding secondary amines in high yields. Further, a sequential one-pot reaction involving N-allylation and intramolecular Heck type 6-exo-trig cyclization

  已经开发了一种简单，方便的顺序一锅法合成1,2,3,4-四氢苯并[ b ] [1,6]萘啶。在硼氢化钠存在下，用各种胺对2-氯-3-甲酰基喹啉进行还原性胺化反应可提供高产率的相应仲胺。此外，对仲胺进行了涉及N-烯丙基化和分子内Heck型6-exo-trig环化的顺序一锅反应，得到了所需的1,2,3,4-四氢苯并[ b ] [1,6]对-萘啶衍生物的产率高至高。