1,2,2,4-tetramethyl-1,2-dihydroquinoline | 46255-82-7

• 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: 1,2,2,4-tetramethyl-1,2-dihydroquinoline
• 英文别名: 1,2,2,4-tetramethylquinoline
• CAS: 46255-82-7
• 化学式: C₁₃H₁₇N
• mdl: MFCD09954743
• 分子量: 187.285
• InChiKey: BWVDOMYGBPMGKV-UHFFFAOYSA-N

物化性质

• 沸点：
  131-132 °C(Press: 3 Torr)
• 密度：
  0.950±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 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：
  3.2
• 氢给体数：
  0
• 氢受体数：
  1

安全信息

• 海关编码：
  2933499090

反应信息

• 作为反应物：
  描述：

  1,2,2,4-tetramethyl-1,2-dihydroquinoline 在 盐酸 、 二异丁基氢化铝 、 lithium diisopropyl amide 、 三氯氧磷 作用下， 以 四氢呋喃 、 正己烷 、 1,2-二氯乙烷 、 甲苯 为溶剂， 反应 29.33h， 生成 (2Z,4E)-3-methyl-5-(1,2,2,4-tetramethyl-(1,2-dihydroquinolin-6-yl))penta-2,4-dienal
  参考文献：
  名称：

  Novel Heteroarotinoids as Potential Antagonists of Mycobacterium bovis BCG

  摘要：

  A series of 15 heteroarotinoids has been prepared and evaluated for activity against Mycobacterium bovis BCG with the thiourea-containing isoxyl (7) (0.5 mug/mL) as the standard. 2,2,4-Trimethyl-2H-chromen-7-yl 4-(methoxycarbonyl)benzoate (8) displayed the most significant activity (2.0-4.0 mug/mL) in terms of the lowest concentration (mug/mL) (MIC, minimum inhibitory concentration) required to produce a 99% reduction in the number of colonies on a plate as compared to that system free of the agent at the same dilution of the culture suspension. Ethyl 4-{[N-(2,2,4,4-tetramethylchroman-6-yl)thiocarbamoyl] amino}benzoate (9) and {[(1E,3Z,5E)-1-aza-4-methyl-6-(1,2,2,4-tetramethyl(1,2-dihydroquinolyl))hexa-1,3,5-trienyl]-amino}aminomethane-1-thione (10) exhibited activity at 5.0-10.0 and 10.0-20.0 mug/mL, respectively, while the other examples had MIC values of 20 mug/mL or greater. The inhibitory ability of 8 may occur via the inhibition of mycolic acid synthesis in a like manner as found with 7, but this requires further study. The heteroarotinoids are the first examples to exhibit inhibitory ability against the growth of Mycobacterium bovis BCB.

  DOI：

  10.1021/jm0303453
• 作为产物：
  描述：

  1,2,4-trimethylquinolinium iodide 在 甲基碘化镁 、 乙醚 作用下， 生成 1,2,2,4-tetramethyl-1,2-dihydroquinoline
  参考文献：
  名称：

  Kalnin, Justus Liebigs Annalen der Chemie, 1936, vol. 523, p. 118,129

  摘要：

  DOI：

文献信息

• [EN] CARBOPYRONONE COMPOUNDS USEFUL AS DIAGNOSTIC ADJUVANTS<br/>[FR] COMPOSÉS CARBOPYRONINE UTILES EN TANT QU'ADJUVANTS DE DIAGNOSTIC
  申请人：LIFE TECHNOLOGIES CORP

  公开号：WO2015175870A1

  公开（公告）日：2015-11-19

  Described herein are fluorescent compounds and methods and comprising these compounds. The compounds disclosed herein are carbopyronine reagents that fluoresce in the red portion of the UV/VIS spectrum and provide bright fluorescence intensity, uniform cell staining, and good retention within live cells as well as low toxicity toward cells.

  本文描述了荧光化合物及包括这些化合物的方法。本文披露的化合物是在UV/VIS光谱的红色部分发出荧光的羧基吡咯烷试剂，具有明亮的荧光强度、均匀的细胞染色以及在活细胞内良好的保留性，同时对细胞具有低毒性。
• Reactions of 2,2-dialkyl-1,2-dihydroquinolines. Part IV. 4,5-Dihydro-4,4-dimethyl-1H-1,2-dithiolo[3,4-c]quinoline-1-thiones
  作者：J. P. Brown

  DOI：10.1039/j39680001074

  日期：——

  1,2-Dihydro-2,2,4-trimethylquinoline and its 1-methyl and 6-ethoxy-derivatives gave 4,5-dihydro-4,4-dimethyl-1H-1,2-dithiolo[3,4-c]quinoline-1-thiones on heating with sulphur. The products react with methyl iodide to give methylthiodithiolium salts.

  1,2-二氢-2,2,4-三甲基喹啉及其1-甲基和6-乙氧基衍生物得到4,5-二氢-4,4-二甲基-1 H -1,2-二硫代[3,4- c ]与硫一起加热的喹啉-1-硫酮。产物与碘甲烷反应，得到甲硫基二硫鎓盐。
• Laser flash photolysis study of the decay kinetics of carbocations of 1,2,2,4-tetramethyl-1,2-dihydroquinoline in the porous glass in the presence of methanol
  作者：P. P. Levin、T. D. Nekipelova、E. N. Khodot

  DOI：10.1007/s11172-006-0115-4

  日期：2005.10

  The efficiency of formation and the decay kinetics of carbocations formed under the photolysis of 1,2,2,4-tetramethyl-1,2-dihydroquinoline in methanol and in a porous glass filled with methanol or dried in air or in vacuo were studied by the laser flash photolysis techniques. In MeOH, the carbocations recombine via the second-order law in the reaction with the MeO− anion formed in an equimolar amount

  1,2,2,4-四甲基-1,2-二氢喹啉在甲醇和充满甲醇或在空气或真空中干燥的多孔玻璃中光解形成的碳正离子的形成效率和衰变动力学研究如下：激光闪光光解技术。在 MeOH 中，碳正离子在与等摩尔量的 MeO− 阴离子反应中通过二阶定律重组，并在与溶剂反应中通过一级定律衰变，速率常数为 3·108 L mol-1分别为 s−1 和 1.4·103 s−1。当溶液放入多孔玻璃中时，没有观察到碳正离子与 MeO- 复合，与溶剂的反应受到一定程度的抑制（速率常数 8·102 s-1）。观察到碳正离子与甲醇的反应被抑制到表面上的单层 MeOH 上。在真空干燥的多孔玻璃中碳正离子衰变的主要途径是与 SiO 基团的成对复合。相应的动力学根据自由扩散反应物的模型进行描述。
• Synthesis of a dihydroquinoline based fluorescent cyanine for selective, naked eye, and turn off detection of Fe³⁺ions
  作者：K. Vijay、C. Nandi、Shriniwas D. Samant

  DOI：10.1039/c6ra06642a

  日期：——

  A cyanine dye was synthesized by condensing 6-formylated 1,2,2,4-tetramethyl-1,2-dihydroquinoline (TMDQ) and 1,7-dimethyl-2-phenylimidazo[1,2-a]pyridin-1-ium iodide.

  通过将6-甲酰基化的1,2,2,4-四甲基-1,2-二氢喹啉（TMDQ）和1,7-二甲基-2-苯基咪唑[1,2-a]吡啶-1-ium碘化物缩合，合成了一种青烯染料。
• Synthesis of a dihydroquinoline based merocyanine as a ‘naked eye’ and ‘fluorogenic’ sensor for hydrazine hydrate in aqueous medium and hydrazine gas
  作者：K. Vijay、C. Nandi、Shriniwas D. Samant

  DOI：10.1039/c4ra02426e

  日期：——

  1,2,2,4-Tetramethyldihydroquinoline (TMDQ) is formylated at the 6-position and the resulting quinoline aldehyde is condensed with 3-methyl-1-phenyl-1H-pyrazol-5(4H)-one to obtain a merocyanine 6-pyrazolinyl TMDQ.

  1,2,2,4-四甲基二氢喹啉（TMDQ）在6位进行甲酰化反应，得到喹啉醛，然后与3-甲基-1-苯基-1H-吡唑-5（4H）-酮缩合，得到一种6-吡唑烷基TMDQ的美洛显色剂。