4-(4-tolyl)-6-chloroquinoline | 749916-89-0

• 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-(4-tolyl)-6-chloroquinoline
• 英文别名: 4-chloro-6-(4-tolyl)quinoline；4-chloro-6-(4-methylphenyl)quinoline
• CAS: 749916-89-0
• 化学式: C₁₆H₁₂ClN
• 分子量: 253.731
• InChiKey: XNLVUTKTXPYMFM-UHFFFAOYSA-N

物化性质

• 沸点：
  387.6±32.0 °C(Predicted)
• 密度：
  1.206±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  18
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  12.9
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  2,3-二甲基苯胺 、 4-(4-tolyl)-6-chloroquinoline 以 N-甲基吡咯烷酮 为溶剂， 生成 N-(2,3-dimethylphenyl)-6-p-tolylquinolin-4-amine
  参考文献：
  名称：

  4-Anilino-6-phenyl-quinoline inhibitors of mitogen activated protein kinase-activated protein kinase 2 (MK2)

  摘要：

  A class of inhibitors of mitogen activated protein kinase-activated kinase 2 (MK2) was discovered via high-throughput screening. This compound class demonstrates activity against the enzyme with sub-mu M IC(50) values, and suppresses LPS-induced TNF alpha levels in THP-1 cells. MK2 inhibition kinetic measurements indicated mixed binding approaching non-ATP competitive inhibition. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2010.06.107
• 作为产物：
  描述：

  6-溴-4-氯喹啉 、 4-甲苯硼酸 在 palladium bis[bis(diphenylphosphino)ferrocene] dichloride 、 sodium carbonate 作用下， 以 乙醇 、 甲苯 为溶剂， 生成 4-(4-tolyl)-6-chloroquinoline
  参考文献：
  名称：

  4-Anilino-6-phenyl-quinoline inhibitors of mitogen activated protein kinase-activated protein kinase 2 (MK2)

  摘要：

  A class of inhibitors of mitogen activated protein kinase-activated kinase 2 (MK2) was discovered via high-throughput screening. This compound class demonstrates activity against the enzyme with sub-mu M IC(50) values, and suppresses LPS-induced TNF alpha levels in THP-1 cells. MK2 inhibition kinetic measurements indicated mixed binding approaching non-ATP competitive inhibition. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2010.06.107

文献信息

• The successive substitution of halogens in 4-chloro-6-iodoquinoline by aryl groups in cross-coupling reactions with arylboronic acids
  作者：Alexey V. Tsvetkov、Gennadij V. Latyshev、Nikolai V. Lukashev、Irina P. Beletskaya

  DOI：10.1016/s0040-4039(02)01516-2

  日期：2002.9

  The conditions for selective stepwise substitution of iodine and chlorine atoms in 4-chloro-6-iodoquinoline which allow the synthesis of the corresponding diarylquinolines with different aryl groups in the 4- and 6-positions, in a one-pot procedure, in high yields are reported. A significant effect of the addition of water or Bu4NBr on the rate and yield of both stages was discovered.

  在4-氯-6-碘喹啉中选择性逐步取代碘和氯原子的条件，可以一锅法以高收率合成相应的在4-位和6-位带有不同芳基的二芳基喹啉被报道。发现添加水或Bu 4 NBr对两个阶段的速率和产率都有显着影响。
• Successive Replacement of Halogen Atoms in 4,6-Dihaloquinolines in Cross-coupling Reactions with Arylboronic Acids Catalyzed by Palladium and Nickel Complexes
  作者：I. P. Beletskaya、A. V. Tsvetkov、G. V. Latyshev、N. V. Lukashev

  DOI：10.1023/b:rujo.0000013144.15578.2d

  日期：2003.11

  Conditions were found where in 6-halo-4-quinolines (halogen = iodine, bromine, or chlorine) the halo-en atoms were replaced in succession by similar or different aryl groups in cross-coupling reactions with arylboric acids catalyzed by palladium and nickel complexes. Basing on successive Suzuki reaction a convenient procedure was developed for preparation of diarylquinolines that did not require isolation of the intermediate monoarylation product and afforded almost quantitative yields of diarylquinolines.