4-hydroxy-1-methyl-2-oxo-1,2-dihydroquinoline-3-carbaldehyde | 65740-49-0

• 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-hydroxy-1-methyl-2-oxo-1,2-dihydroquinoline-3-carbaldehyde
• 英文别名: 1-methyl-3-formyl-4-hydroxy-2(1H)-quinolinone；4-hydroxy-1-methyl-2-oxoquinoline-3-carbaldehyde
• CAS: 65740-49-0
• 化学式: C₁₁H₉NO₃
• mdl: MFCD00100780
• 分子量: 203.197
• InChiKey: VMDBJBQFGBVZKR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  15
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.09
• 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：

  4-hydroxy-1-methyl-2-oxo-1,2-dihydroquinoline-3-carbaldehyde 在 盐酸羟胺 、 sodium acetate 、 溶剂黄146 作用下， 生成 4-hydroxy-1-methyl-2-oxo-1,2-dihydroquinoline-3-carbonitrile
  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：

  3-(N-甲基-N-苯基氨基)-3-氧代丙腈 在 三氟乙酸酐 作用下， 以 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 反应 26.0h， 生成 4-hydroxy-1-methyl-2-oxo-1,2-dihydroquinoline-3-carbaldehyde
  参考文献：
  名称：

  α-Dimethylaminomethylenation-induced Houben–Hoesch-type cyclization of cyanoacetanilides: a practical synthesis of 3-formyl-4-hydroxyquinolin-2(1H)-ones

  摘要：

  The tandem reaction of cyanoacetanilides with triflic anhydride in DMF proceeded at room temperature to afford 3-formyl-4-hydroxyquinolin-2(1H)-ones in good to high yields. A detailed mechanistic study revealed that the tandem reaction proceeded via alpha-dimethylaminomethylenation, which promoted the subsequent Houben-Hoesch-type cyclization. Both alpha-functionalization and the cyclization steps were optimized, and a multi-gram scale synthesis of 3-formyl-4-hydroxyquinolin-2(1H)-one was achieved. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2011.03.040

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。
• Acyl and alkoxy substituted quinolines
  申请人：Schering Corporation

  公开号：US05378694A1

  公开（公告）日：1995-01-03

  Compounds useful as antiviral agents against DNA-containing viruses, such as herpes group viruses, are disclosed. The compounds are are represented by compounds of Formula 1.0: ##STR1## and their pharmaceutically acceptable salts and solvates. Pharmaceutical compositions containing compounds represented by Formula 1.0 and methods of treating a viral infection using compounds represented by Formula 1.0 are disclosed. Also disclosed are compounds useful as antihypertensive agents and methods of treating hypertension using such compounds. The antihypertensive agents are compounds represented by Formula 1.0 wherein R.sup.4 is selected from the group consisting of alkyl and aminoalkyl. Preferably R.sup.1 is H.

  抗DNA病毒药物化合物，如单纯疱疹病毒等DNA含量病毒的抗病毒剂被披露。这些化合物由Formula 1.0表示。其中包括Formula 1.0代表的化合物及其药用可接受的盐和溶剂。披露了含有Formula 1.0代表的化合物的药物组合物以及使用Formula 1.0代表的化合物治疗病毒感染的方法。还披露了作为降压药物的化合物以及使用这些化合物治疗高血压的方法。降压药物是由Formula 1.0代表的化合物，其中R.sup.4从由烷基和氨基烷基组成的群体中选择。最好R.sup.1是H。
• 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。
• Alkyl and acyl substituted quinolines
  申请人：Schering Corporation

  公开号：US05382572A1

  公开（公告）日：1995-01-17

  Compounds useful as antiviral agents against DNA-containing viruses, such as herpes group viruses, are disclosed. The compounds are represented by Formula 1.0: ##STR1## and their pharmaceutically acceptable salts and solvates; wherein: (A) X is selected from the group consisting of N--R.sup.3, O, S, and C(R.sup.3).sub.2 ; (B) R.sup.3 is selected from H and a range of substituents; (C) R.sup.1 is an etherifying or esterifying group; (D) R.sup.2 is selected from a range of substituents; (E) m is 0 or an integer from 1 to 4; and (F) R.sup.4 and R.sup.5 are the same and are selected from alkyl and acyl groups; together with the pharmaceutically acceptable salts of the compounds of Formula 1.0 that are acidic or basic. Pharmaceutical compositions containing compounds represented by Formula 1.0 are disclosed. Also disclosed are methods of treating a viral infection using compounds represented by Formula 1.0.

  抗DNA病毒药物化合物，如疱疹病毒群，被揭示。这些化合物由Formula 1.0表示：##STR1##及其药学上可接受的盐和溶剂；其中：（A）X选自N-R.sup.3，O，S和C(R.sup.3).sub.2组；（B）R.sup.3选自H和一系列取代基；（C）R.sup.1是醚化或酯化基团；（D）R.sup.2选自一系列取代基；（E）m为0或1至4之间的整数；（F）R.sup.4和R.sup.5相同，选自烷基和酰基；以及Formula 1.0化合物的酸性或碱性药学上可接受的盐。揭示了含有Formula 1.0化合物的药物组合物。还揭示了使用Formula 1.0化合物治疗病毒感染的方法。

表征谱图