1-(4-羟基-2-甲基喹啉-3-基)乙酮 | 91569-13-0

• 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
• 中文名称: 1-(4-羟基-2-甲基喹啉-3-基)乙酮
• 英文名称: 3-Acetyl-4-hydroxy-2-methylquinoline
• 英文别名: 1-(4-hydroxy-2-methyl-[3]quinolyl)-ethanone；1-(4-Hydroxy-2-methyl-[3]chinolyl)-aethanon；1-(4-Hydroxy-2-methylquinolin-3-yl)ethanone；3-acetyl-2-methyl-1H-quinolin-4-one
• CAS: 91569-13-0
• 化学式: C₁₂H₁₁NO₂
• mdl: MFCD03266399
• 分子量: 201.225
• InChiKey: QNEXQTCWKYICPG-UHFFFAOYSA-N

物化性质

• 熔点：
  256-257 °C
• 沸点：
  338.2±37.0 °C(Predicted)
• 密度：
  1.234±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  15
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.166
• 拓扑面积：
  46.2
• 氢给体数：
  1
• 氢受体数：
  3

安全信息

• 海关编码：
  2933499090

反应信息

• 作为反应物：
  描述：

  1-(4-羟基-2-甲基喹啉-3-基)乙酮 在 三氯氧磷 作用下， 反应 2.0h， 以89%的产率得到2-甲基-3-乙酰基-4-氯喹啉
  参考文献：
  名称：

  Anand, Ramesh C.; Sinha, Arun K., Journal of the Chemical Society. Perkin transactions I, 1991, # 10, p. 2339 - 2342

  摘要：

  DOI：
• 作为产物：
  描述：

  ethyl 2-acetyl-3-anilinobut-2-enoate 以 二苯醚 为溶剂， 反应 1.0h， 以619 mg的产率得到1-(4-羟基-2-甲基喹啉-3-基)乙酮
  参考文献：
  名称：

  Structure−Activity Relationship of Quinoline Derivatives as Potent and Selective α_2C-Adrenoceptor Antagonists

  摘要：

  Starting from two acridine compounds identified in a high-throughput screening campaign (1 and 2, Table 1), a series of 4-aminoquinolines was synthesized and tested for their properties on the human alpha(2)-adrenoceptor subtypes (alpha(2A), alpha(2B), and alpha(2C.)). A number of compounds with good antagonist potencies against the alpha(2C)-adrenoceptor and excellent subtype selectivities over the other two subtypes were discovered. For example, (R)-{4-[4-(3,4-dimethylpiperazin-1-yl) phenylamino] quinolin- 3- yl} methanol 6j had an antagonist potency of 8.5 nM against, and a subtype selectivity of more than 200-fold for, the alpha(2C)-adrenoceptor. Investigation of the structure-activity relationship identified a number of structural features, the most critical of which was an absolute need for a substituent in the 3-position of the quinoline ring. The 3-position on the piperazine ring was also found to play an appreciable role, as substitutions in that position exerted a significant and stereospecific beneficial effect on the alpha(2C)-adrenoceptor affinity and potency. Replacing the piperazine ring proved difficult, with 1,4-diazepanes representing the only viable alternative.

  DOI：

  10.1021/jm060262x

文献信息

• Eco-friendly decarboxylative cyclization in water: practical access to the anti-malarial 4-quinolones
  作者：Yue Ma、Yongping Zhu、Dong Zhang、Yuqing Meng、Tian Tang、Kun Wang、Ji Ma、Jigang Wang、Peng Sun

  DOI：10.1039/c8gc03570a

  日期：——

  An eco-friendly decaboxylative cyclization in water has been developed to construct 4-quinolones from readily available isatoic anhydrides and 1,3-dicarbonyl compounds.

  已经开发出一种在水中进行的环化脱羧反应，用于从易得的异安酸酐和1,3-二羰基化合物构建4-喹啉酮。
• Tandem aza-Michael addition–vinylogous aldol condensation: synthesis of <i>N</i>-bridged pyridine fused quinolones
  作者：Lalitha Gummidi、Altaf Muddassar、Gangavaram V. M. Sharma、V. Murugesh、Surisetti Suresh

  DOI：10.1039/d1ob02087k

  日期：——

  addition–vinylogous aldol condensation strategy for the synthesis of N-bridged pyridine fused quinolone derivatives from quinolones and ynones. The presented tandem transformation features the construction of C–N and CC bonds in a single operation, under transition metal-free conditions. The wide substrate scope and gram scale synthesis of pyridine fused quinolone derivatives expand the synthetic value of

  在此，我们提出了一种串联氮杂-迈克尔加成-乙烯醇醛缩合策略，用于从喹诺酮类和炔诺酮类合成N-桥联吡啶稠合喹诺酮衍生物。所提出的串联转变的特点是在无过渡金属条件下，在一次操作中构建 C-N 和 C C 键。吡啶融合喹诺酮衍生物的广泛底物范围和克级合成扩大了所提出协议的合成价值。
• Use of Cinnamoyl Compound
  申请人：Shiraki Hiroaki

  公开号：US20090143368A1

  公开（公告）日：2009-06-04

  A composition for inhibiting the extracellular matrix gene transcription comprising a cinnamoyl compound represented by the formula (I): and an inert carrier, or the like.

  一种用于抑制细胞外基质基因转录的组合物，包括由式（I）表示的肉桂酰化合物和惰性载体等。
• N-(2-Aminobenzoyl)benzotriazole Mediated Synthesis of 3- Acyl-2-alkyl(aryl)-4-hydroxyquinolines and 3-Acylamino-4(3H) quinazolinones
  作者：İlbilge Merve ŞENOL、Sevtem Gökbulut SATIOĞLU、İlhami ÇELİK

  DOI：10.55730/1300-0527.3642

  日期：——

  New methods have been developed for the synthesis of the substituted quinolines and quinazolinones derivatives by utilizing N-(2-aminobenzoyl)benzotriazoles under mild reaction conditions. 3-Acyl-2-alkyl(aryl)-4-hydroxyquinolines were obtained in modarete yields by the reaction of N-(2-aminobenzoyl)benzotriazoles and diketones in the presence of tert-BuOK. 3-Acylamino-4(3H) quinazolinones were obtained

  开发了利用N-(2-氨基苯甲酰基)苯并三唑在温和反应条件下合成取代喹啉和喹唑啉酮衍生物的新方法。通过 N-(2-氨基苯甲酰基)苯并三唑和二酮在叔丁醇钾存在下反应，以中等产率获得 3-酰基-2-烷基（芳基）-4-羟基喹啉。通过N-(2-氨基苯甲酰基)苯并三唑、原酸酯和酰肼一锅法以良好的收率获得3-酰氨基-4(3H)喹唑啉酮。
• USE OF CINNAMOYL COMPOUND
  申请人：Sumitomo Chemical Company, Limited

  公开号：EP1857104A1

  公开（公告）日：2007-11-21

  A composition for inhibiting the extracellular matrix gene transcription comprising a cinnamoyl compound represented by the formula(I): and an inert carrier, or the like.

  一种抑制细胞外基质基因转录的组合物，包含由式(I)代表的肉桂酰化合物： 和惰性载体或类似物。