1,2,2,4-tetramethyl-1,2-dihydroquinoline-6-carbaldehyde | 292819-60-4

• 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-6-carbaldehyde
• 英文别名: 1,2,2,4-tetramethylquinoline-6-carbaldehyde
• CAS: 292819-60-4
• 化学式: C₁₄H₁₇NO
• mdl: MFCD09035416
• 分子量: 215.295
• InChiKey: YVUBWDXUKWCIDC-UHFFFAOYSA-N

物化性质

• 沸点：
  348.3±42.0 °C(Predicted)
• 密度：
  1.031±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  16
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  20.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1,2,2,4-tetramethyl-1,2-dihydroquinoline-6-carbaldehyde 在 盐酸 、 二异丁基氢化铝 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 正己烷 、 1,2-二氯乙烷 、 甲苯 为溶剂， 反应 5.33h， 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：

  2,2,4-三甲基-1,2-二氢喹啉 在 potassium carbonate 、 三氯氧磷 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成 1,2,2,4-tetramethyl-1,2-dihydroquinoline-6-carbaldehyde
  参考文献：
  名称：

  Synthesis of a dihydroquinoline based merocyanine as a ‘naked eye’ and ‘fluorogenic’ sensor for hydrazine hydrate in aqueous medium and hydrazine gas

  摘要：

  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。

  DOI：

  10.1039/c4ra02426e

文献信息

• Bioinspired Fluorescent Dyes Based on a Conformationally Locked Chromophore of the Fluorescent Protein Kaede
  作者：Nadezhda S. Baleeva、Ksenia A. Myannik、Ilia V. Yampolsky、Mikhail S. Baranov

  DOI：10.1002/ejoc.201500721

  日期：2015.9

  A novel class of fluorescent dyes based on the conformationally locked heterocyclic core of the chromophore of the fluorescent protein Kaede was discovered. Introduction of a single conformational lock at the benzylidene fragment of the Kaede chromophore resulted in an increase in the fluorescence quantum yield (FQY) by one order of magnitude and a redshift of ca. 60 nm in the emission spectrum. Imposing

  发现了一类基于荧光蛋白 Kaede 发色团的构象锁定杂环核心的新型荧光染料。在 Kaede 发色团的亚苄基片段处引入单一构象锁导致荧光量子产率 (FQY) 增加一个数量级，红移约。发射光谱中的 60 nm。在 Kaede 发色团的乙烯片段上施加第二个锁进一步增加了 FQY。锁定类似物在广泛的溶剂中表现出明亮的红移发射，这使它们成为广泛荧光标记应用的理想选择。
• 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。
• Multiple fluorescence ΔCIE and ΔRGB codes for sensing volatile organic compounds with a wide range of responses
  作者：Kaijun Tian、Dehui Hu、Rui Hu、Shuangqing Wang、Shayu Li、Yi Li、Guoqiang Yang

  DOI：10.1039/c1cc13056k

  日期：——

  A highly luminescent compound, stilbene-2,4-dimethyl-6-(1,2,2,4-tetramethyl-1,2-dihydroquinolin-6-yl)-1,3,5-s-triazine (MQT), exhibits solvent polarity-induced emission enhancement. A fluorescent sensor array was fabricated with MQT and porous polymer substrates. The colorimetric changes of the array exposed to VOCs can be readily distinguished by the naked eye. Post-processing procedures proved the high selectivity of the array for VOCs.

  一种高发光化合物，即2,4-二甲基-6-(1,2,2,4-四甲基-1,2-二氢喹啉-6-基)-1,3,5-三嗪（MQT），具有溶剂极性诱导的发光增强特性。利用MQT和多孔聚合物基底制作了荧光传感器阵列。肉眼即可轻松分辨出暴露于挥发性有机化合物（VOC）下的阵列的色度变化。后处理程序证明了该阵列对挥发性有机化合物（VOC）的高选择性。
• Photosensitive recording material suited for use in electrophotography
  申请人：AGFA-GEVAERT naamloze vennootschap

  公开号：EP0347960A1

  公开（公告）日：1989-12-27

  An electrophotographic recording material which comprises an electrically conductive support having thereon a double layer of a charge generating layer in contiguous relationship with a charge transporting layer comprising a positive charge transporting compound corresponding to the following general formula (I) : wherein : R represents hydrogen or an aliphatic or cycloaliphatic group including these groups substituted by non-ionic substituents, each of R¹ and R² (same or different) represents a C₁-C₆ alkyl group or an aryl group, and Z represents the atoms necessary to close an adjacent aromatic nucleus or aromatic ring system including such nucleus or ring system substituted with one or more substituents of non-ionic character.

  一种电致发光记录材料，它包括一个导电支架，支架上有双层电荷产生层和电荷传输层，电荷产生层和电荷传输层相邻，电荷传输层由符合下通式(I)的正电荷传输化合物组成： 其中 ： R 代表氢或脂族或环脂族基团，包括被非离子取代基取代的这些基团、 R¹ 和 R²（相同或不同）各自代表 C₁-C₆ 烷基或芳基，以及 Z 代表关闭相邻芳香核或芳香环系所需的原子，包括被一个或多个非离子性取代基取代的芳香核或芳香环系。
• ——
  作者：M. Yu. Krysin、Kh. S. Shikhaliev、I. K. Anokhina、Zh. V. Shmyreva

  DOI：10.1023/a:1017523701357

  日期：——