2,2,4,6-四甲基-1H-喹啉 | 1810-78-2

• 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
• 中文名称: 2,2,4,6-四甲基-1H-喹啉
• 英文名称: 2,2,4,6-tetramethyl-1,2-dihydroquinoline
• 英文别名: 2,2,4,6-Tetramethyl-1,2-dihydro-chinolin；2,2,4,6-tetramethyl-1H-quinoline
• CAS: 1810-78-2
• 化学式: C₁₃H₁₇N
• mdl: MFCD00087597
• 分子量: 187.285
• InChiKey: DTMCOYOYXVFCKJ-UHFFFAOYSA-N

物化性质

• 熔点：
  42 °C
• 沸点：
  114-118 °C(Press: 2.3 Torr)
• 密度：
  0.944±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  14
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.384
• 拓扑面积：
  12
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  2,2,4,6-四甲基-1H-喹啉 在 盐酸 作用下， 生成 2,4,6-三甲基喹啉
  参考文献：
  名称：

  DE363582

  摘要：

  公开号：
• 作为产物：
  描述：

  4-羟基-2,2,4,6-四甲基-1,2,3,4-四氢喹啉 以 水 为溶剂， 生成 2,2,4,6-四甲基-1H-喹啉
  参考文献：
  名称：

  Photoaddition of water and methanol to 2,2,4,6-tetramethyl-1,2-dihydroquinoline

  摘要：

  Products of the steady-state photolysis of 2,2,4,6-tetramethyl-1,2-dihydroquinoline (1) in water, methanol, and water-ethanol were isolated for the first time and identified by H-1 and C-13 NMR spectroscopy, IR spectroscopy, and mass spectrometry. As a result of the photolysis, the molecule of the solvent is added to the double bond of the heterocycle with formation of 4-hydroxy- (2) or 4-methoxy-2,2,4,6-tetramethyl-1,2,3,4-tetrahydroquinoline (3) in water and methanol, respectively. Compounds 2 and 3 are converted gradually into 1 in the dark. The rate of the back reaction depends on the solvent and the concentration of the product. Comparison of the products of the photolysis in methanol and hexane at 45 degrees C and of the azoisobutyronitrile-initiated oxidation of 1 at the same temperature has shown that unlike the photolysis in hexane, aminyl radicals are not precursors of the product of the photolysis in methanol. The reaction proceeds via an excited singlet state.

  DOI：

  10.1007/bf02494844

文献信息

• Design of new hybrid template by linking quinoline, triazole and dihydroquinoline pharmacophoric groups: A greener approach to novel polyazaheterocycles as cytotoxic agents
  作者：Koduru Sri Shanthi Praveena、Edupuganti Veera Venkat Shivaji Ramarao、Nandula Yadagiri Sreenivasa Murthy、Surekha Akkenapally、C. Ganesh Kumar、Ravikumar Kapavarapu、Sarbani Pal

  DOI：10.1016/j.bmcl.2015.01.012

  日期：2015.3

  A new hybrid template designed by linking three pharmacophoric groups, for example, quinoline, triazole and dihydroquinoline moieties have been used for the generation of a library of molecules as potential cytotoxic agents. Synthesis of these polyazaheterocycles were carried out by using a strategy that involved one-pot sequential azidation and CuAAC in water under mild conditions. A number of 1,4-disubstituted

  通过连接三个药效基团（例如喹啉，三唑和二氢喹啉部分）设计的新杂合模板已用于生成分子库，作为潜在的细胞毒性剂。这些聚氮杂环杂环化合物的合成是通过在温和条件下于水中进行一锅顺序叠氮化和CuAAC的策略进行的。合成了许多在N -1上具有喹啉基亚甲基和在C-4上具有1,2-二氢喹啉基亚甲基作为不同取代基的1,4-二取代的1,2,3-三唑，并评估了其对各种癌细胞的细胞毒性作用。其中一些对肺癌细胞显示出令人鼓舞的活性，其中之一显示对PDE4的抑制，表明这些新型多氮杂环化合物具有潜在的药用价值。
• Enantioselective Organocatalytic Transfer Hydrogenation of 1,2-Dihydroquinoline through Formation of Aza-<i>o</i>-xylylene
  作者：Guangxun Li、Hongxin Liu、Gang Lv、Yingwei Wang、Qingquan Fu、Zhuo Tang

  DOI：10.1021/acs.orglett.5b02025

  日期：2015.9.4

  A new way of forming the aza-o-xylylene with easily accessible 1,2-dihydroquinolines as precursor has been developed. The presence of an electron-donating group at the proper position of 1,2-dihydroquinoline was crucial for protonation of the alkene through dearomatization with a simple Brønsted acid. The in situ forming reactive intermediate was trapped with Hantzsch ester to afford tetrahydroquinolines

  已开发出一种以容易获得的1,2-二氢喹啉为前体形成氮杂邻二甲苯的新方法。在1,2-二氢喹啉的适当位置上存在一个供电子基团，这对于通过简单的布朗斯台德酸进行脱芳构作用使烯烃的质子化至关重要。用Hantzsch酯捕获原位形成的反应性中间体，从而以优异的收率和对映选择性提供四氢喹啉。
• The catalytic enantioselective synthesis of tetrahydroquinolines containing all-carbon quaternary stereocenters via the formation of aza-ortho-xylylene with 1,2-dihydroquinoline as a precursor
  作者：Guangxun Li、Hongxin Liu、Yingwei Wang、Shiqi Zhang、Shujun Lai、Ling Tang、Jinzhong Zhao、Zhuo Tang

  DOI：10.1039/c5cc07752d

  日期：——

  Tetrahydroquinolines (THQs) with an all-carbon quaternary stereocenter were effectively obtained via the in situ formation of aza-ortho-xylylene (AOX) with easily accessible 1,2-dihydroquinolines as precursors.

  四氢喹啉（THQs）具有全碳季铵立体中心，通过易于获得的1,2-二氢喹啉作为前体，有效地通过现场形成氮杂-邻位-二甲苯亚基（AOX）而获得。
• A Facile Synthesis of 2,2,4-Trisubstituted-1,2-Dihydroquinolines Catalyzed by Zinc Triflate under Solvent-Free Conditions
  作者：Dhiman Kundu、Shrishnu Kumar Kundu、Adinath Majee、Alakananda Hajra

  DOI：10.1002/jccs.200800175

  日期：2008.10

  An efficient process has been developed for the synthesis of 2,2,4-trisubstituted-1,2-dihydroquinolines in good yields through a simple one-pot condensation between anilines and ketones in the presence of zinc triflate as a catalyst at room temperature under solvent-free conditions.

  在三氟甲磺酸锌作为催化剂的条件下，在室温下，苯胺和酮之间的简单一锅缩合反应，开发了一种高效合成 2,2,4-三取代-1,2-二氢喹啉的方法。无溶剂条件。
• Kinetic description of the oxidation of hydrocarbons inhibited by sulfur-containing hydrogenated quinolines
  作者：O. T. Kasaikina、N. A. Golovina、Kh. S. Shikhaliev、Zh. V. Shmyreva

  DOI：10.1007/bf00717333

  日期：1994.5

  The inhibiting effect of dithiolthione derivatives of hydrogenated quinolines (DTT) on the oxidation of various hydrocarbons (n-decane,n-decene, ethylbenzene, β-carotene) was investigated. The inhibiting effect of the DTTs is greater at high temperatures (>100 °C) than that of the parent hydrogenated quinolines and weaker at moderate temperatures. The DTTs do not affect the decomposition of hydroperoxides

  研究了氢化喹啉（DTT）的二硫醇硫酮衍生物对各种烃（正癸烷、正癸烯、乙苯、β-胡萝卜素）氧化的抑制作用。DTTs 的抑制作用在高温（> 100 °C）下比母体氢化喹啉的抑制作用更大，而在中等温度下则更弱。DTT 不影响氢过氧化物的分解。可能，将二硫醇硫酮循环引入氢喹啉分子会降低其对 O2 和过氧化物自由基的反应性，这有利于提高 DTT 在升高的温度下的抗氧化活性。