1-ethyl-4-hydroxy-2-oxo-1,2-dihydroquinoline-3-carbaldehyde | 65740-50-3

• 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-ethyl-4-hydroxy-2-oxo-1,2-dihydroquinoline-3-carbaldehyde
• 英文别名: 3-Quinolinecarboxaldehyde, 1-ethyl-1,2-dihydro-4-hydroxy-2-oxo-；1-ethyl-4-hydroxy-2-oxoquinoline-3-carbaldehyde
• CAS: 65740-50-3
• 化学式: C₁₂H₁₁NO₃
• 分子量: 217.224
• InChiKey: BLCBANRNSXYIEB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  57.6
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1-ethyl-4-hydroxy-2-oxo-1,2-dihydroquinoline-3-carbaldehyde 在 盐酸羟胺 、 sodium acetate 、 sodium carbonate 、 溶剂黄146 、 三氯氧磷 作用下， 以 乙醇 为溶剂， 反应 12.25h， 生成 Methyl 3-amino-5-ethyl-4-oxothieno[3,2-c]quinoline-2-carboxylate
  参考文献：
  名称：

  Jayashree; Darbarwar, Malleshwar, Journal of the Indian Chemical Society, 2010, vol. 87, # 3, p. 325 - 330

  摘要：

  DOI：
• 作为产物：
  描述：

  1-ethyl-4-hydroxy-N'-[(4-methylphenyl)sulfonyl]-2-oxo-1,2-dihydroquinoline-3-carbohydrazide 在 sodium carbonate 作用下， 以 乙二醇 为溶剂， 生成 1-ethyl-4-hydroxy-2-oxo-1,2-dihydroquinoline-3-carbaldehyde
  参考文献：
  名称：

  4-hydroxy-2-quinolones 165*. 1-R-4-hydroxy-2-oxo-1,2-dihydro-quinoline-3-carbaldehydes and their thiosemicarbazones. Synthesis, structure, and biological properties

  摘要：

  Two variants are discussed of the synthesis of 1-R-4-hydroxy-2-oxo-1,2-dihydroquinoline-3-carboxylic acid beta-N-tosylhydrazides which undergo a McFayden-Stevens reaction to give 1-R-4-hydroxy-2-oxo-1,2-dihydroquinoline-3-carbaldehydes in high yields. It was shown that the thiosemicarbazones prepared from them exist in the solid state exclusively in the syn-form while in solution a hydrazone. <-> enhydrazine tautomerism is observed. The results of a study of the antitubercular activity of the synthesized compounds are reported.

  DOI：

  10.1007/s10593-009-0327-2

文献信息

• Chemistry of Substituted Quinolinones. Part II Synthesis of Novel 4-Pyrazolylquinolinone Derivatives
  作者：Mohamed Abass

  DOI：10.1080/00397910008086898

  日期：2000.8

  Abstract 4-Hydrazino-1-methyl-2(1H)quinolinone (2) was treated with chlorophthalazine, nitrous acid, isothiocyanates and isatines, and also utilized as' a precursor for some new 4-pyrazolylquinolinones. Reaction of 2 with certain 3-acylquinolinones afforded quinolinylpyrazoloquinolinones and/or quinolinylpyrazolylquinolinones.

  摘要 4-Hydrazino-1-methyl-2(1H)quinolinone (2) 用氯酞嗪、亚硝酸、异硫氰酸盐和靛红处理，并用作一些新的4-吡唑基喹啉酮的前体。2与某些3-酰基喹啉酮反应得到喹啉基吡唑并喹啉酮和/或喹啉基吡唑基喹啉酮。
• Synthesis and colon anticancer activity of some novel thiazole/-2-quinolone derivatives
  作者：Ashraf A. Aly、Asmaa H. Mohamed、Mohamed Ramadan

  DOI：10.1016/j.molstruc.2020.127798

  日期：2020.5

  Abstract We direct for the synthesis of 1,6,7-trisubstituted-4-phenylthiazol-2(3H)-ylidene)hydrazono)methyl)quinolin-2-one derivatives by the reaction of corresponding thiosemicarbazone derived by 2-quinolone derivatives with 2-bromoacetophenones in presence of triethylamine at room temperature. The mechanism of the formed products was discussed. The structure of the obtained products was fully characterized

  摘要 我们指导了 1,6,7-三取代-4-苯基噻唑-2(3H)-ylidene)hydrazono)methyl)quinolin-2-one 衍生物的合成，通过 2-quinolone 衍生物衍生的相应缩氨基硫脲与 2 -溴苯乙酮在室温下三乙胺存在下。讨论了形成产物的机理。使用不同的光谱技术，包括红外 (IR)、核磁共振 (NMR) 和质谱 (MS) 以及元素分析，对所得产物的结构进行了全面表征。新合成的化合物显示出中等的结肠抗癌活性。
• Synthesis and evaluation of molluscicidal and larvicidal activities of some novel enaminones derived from 4-hydroxyquinolinones: Part IX
  作者：Mohamed Abass、Bayaumy B. Mostafa

  DOI：10.1016/j.bmc.2005.06.038

  日期：2005.11

  series of 10 3-(hetarylaminomethylene)quinolinediones, 12 3-(substituted aminopropenoyl)-4-hydroxyquinolinones, and 10 3-(substituted aminomethylene-5-oxo-pyrazolinyl)-4-hydroxyquinolinones were synthesized as novel enaminones derived from 3-(un)substituted 4-hydroxyquinolin-2(1H)-ones in 72-94% yields and assayed for their molluscicidal activities against Biomphalaria alexandrina and Lymnaea natalensis

  合成了一系列的10个3-（杂芳基氨基亚甲基）喹啉二酮，12个3-（取代的氨基丙烯酰基）-4-羟基喹啉酮和10个3-（取代的氨基亚甲基-5-氧代吡唑啉基）-4-羟基喹啉酮，它们是由3-衍生而来的新型烯胺酮。 （un）取代的4-羟基喹啉-2（1H）-酮的产率为72-94％，并测定了它们对Biomphalaria alexandrina和Lymnaea natalensis蜗牛的杀软体动物活性。一些测试的烯胺酮具有很高的杀软体动物活性（LC（50）20ppm）。新化合物显示出了对亚历山大藻的卵孵化率，蜗牛的感染率和有效期更强的效力。此外，这些衍生物在减少接触时间的情况下显示出对曼氏血吸虫的水acid和尾c均具有潜在的杀幼虫作用（100％死亡率）。
• One-Pot, Step-Wise, Alternative Syntheses of Quinoline-Substituted Bis(Indolyl)Methanes Using a Green Approach
  作者：Madhu Bandi、Venkata Ramana Reddy Ch.

  DOI：10.1002/jhet.2922

  日期：2017.11

  A green and highly efficient protocol for one‐pot, step‐wise, alternative syntheses of quinoline‐substituted bi(indolyl)methanes has been described by the condensation of N‐methyl or N‐ethyl quinolone‐4‐one‐3‐carbaldehydes 1a and b with indole 2a–f in water containing a catalytic amount of l‐proline to afford the title compounds 5a–l in high yields and in shorter reaction times. This reaction involves

  N-甲基或N-乙基喹诺酮4-1-3-甲醛1a的缩合反应描述了一种绿色高效的方法，用于一锅一步一步替代的喹啉取代的双（吲哚基）甲烷合成。和b与吲哚2A - ˚F在含有催化量的水升-脯氨酸，得到标题化合物5A -升以高产率和更短的反应时间。该反应涉及不使用柱色谱法的后处理。
• Novel series of dihydroquinolindihydro-spiro[indoline-3,6’-[1,3]thiazine]-5′-carbonitrile derivatives
  作者：Asmaa H. Mohamed、Mohammed B. Alshammari、Esmaat M. El-Sheref、Ashraf A. Aly

  DOI：10.1016/j.molstruc.2020.128618

  日期：2020.11

  spiro[indoline-3,6’-[1,3]thiazines] were synthesized in modest yields by refluxing of substituted (1,2-dihydroquinolin-3-yl)-methylene)hydrazinecarbothioamides with 2-(2-oxoindolin-3-ylidene)malononitrile in pyridine as a solvent. The structure assignment of all obtained products has been confirmed by 1H, 13C NMR, 2D-NMR, 15N NMR spectroscopy in addition to elemental analyses. The possible mechanism for the

  摘要 通过将取代的（1,2-二氢喹啉-3-基）-亚甲基）肼碳硫酰胺与 2-(2 -oxoindolin-3-ylidene)丙二腈在吡啶中作为溶剂。除元素分析外，所有获得的产物的结构分配均已通过 1H、13C NMR、2D-NMR、15N NMR 光谱证实。还讨论了该反应的可能机制。

表征谱图