2-甲基-6-溴-1,4-二氢-4-氧代-3-喹啉羧酸乙酯 | 120420-50-0

• 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: 2-甲基-6-溴-1,4-二氢-4-氧代-3-喹啉羧酸乙酯
• 英文名称: 2-methyl-6-bromo-1,4-dihydro-4-oxo-3-quinolinecarboxylic acid, ethyl ester
• 英文别名: Ethyl 6-bromo-4-hydroxy-2-methylquinoline-3-carboxylate；ethyl 6-bromo-2-methyl-4-oxo-1H-quinoline-3-carboxylate
• CAS: 120420-50-0
• 化学式: C₁₃H₁₂BrNO₃
• 分子量: 310.147
• InChiKey: OWQFPNVJMALXNK-UHFFFAOYSA-N

物化性质

• 熔点：
  271-273 °C
• 沸点：
  401.2±45.0 °C(Predicted)
• 密度：
  1.488±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  55.4
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-甲基-6-溴-1,4-二氢-4-氧代-3-喹啉羧酸乙酯 在 sodium hydroxide 作用下， 反应 8.0h， 以93%的产率得到6-Bromo-2-methyl-4-oxo-1,4-dihydro-quinoline-3-carboxylic acid
  参考文献：
  名称：

  几种2-取代的1,4-二氢-4-氧代-3-喹啉羧酸衍生物的合成及异构体转化

  摘要：

  DOI：

  10.1007/bf00633172
• 作为产物：
  描述：

  乙酰基丙二酸二乙酯 在 对甲苯磺酸 作用下， 以 二苯醚 、 正戊烷 为溶剂， 反应 25.0h， 生成 2-甲基-6-溴-1,4-二氢-4-氧代-3-喹啉羧酸乙酯
  参考文献：
  名称：

  4-Quinolone Derivatives:  High-Affinity Ligands at the Benzodiazepine Site of Brain GABA_A Receptors. Synthesis, Pharmacology, and Pharmacophore Modeling

  摘要：

  The 3-ethoxycarbonyl-4-quinolone compound I has previously been identified via a database search as an interesting lead compound for ligand binding at the benzodiazepine site of GABA(A) receptors (Kahnberg et al. J. Mol. Graphics Modelling 2004, 23, 253-261). Pharmacophore-guided optimization of this lead compound yielded a number of high-affinity ligands for the benzodiazepine site including compounds 20 and 23-25 displaying sub-nanomolar affinities. A few of the compounds have been tested on the alpha(1)beta(2)gamma(2s) and alpha(3)beta(2)gamma(2s) GABA(A) receptor subtypes, and two of the compounds (5 and 19) display selectivity for alpha(1) versus alpha(3)-containing receptors by a factor of 22 and 27, respectively. This selectivity for alpha(1)beta(2)gamma(2s) is in the same range as that for the well-known alpha(1) subunit selective compound zolpidem.

  DOI：

  10.1021/jm058057p

文献信息

• Cascade Knoevenagel and aza-Wittig reactions for the synthesis of substituted quinolines and quinolin-4-ols
  作者：Xiaofeng Zhang、Xiaoming Ma、Weiqi Qiu、Jason Evans、Wei Zhang

  DOI：10.1039/c8gc03180k

  日期：——

  A [4 + 2] annulation involving cascade Knoevenagel, aza-Wittig and dehydrofluorination reactions is developed for the synthesis of substituted quinolin-4-ols including analogs bearing CF2H, CF3, and C2F5 groups. This simple and highly efficient method is also applicable for the synthesis of substituted quinolines. A number of reported biologically active compounds can be readily prepared by this one-pot

  开发了一种包括级联Knoevenagel，aza-Wittig和脱氟化氢反应的[4 + 2]环合反应，用于合成取代的喹啉-4-醇，包括带有CF 2 H，CF 3和C 2 F 5基团的类似物。这种简单而高效的方法也适用于取代喹啉的合成。通过一锅法合成可以容易地制备许多报道的生物活性化合物。新反应过程的绿色化学指标分析提供了令人满意的结果。
• 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。
• Quinolines from the cyclocondensation of isatoic anhydride with ethyl acetoacetate: preparation of ethyl 4-hydroxy-2-methylquinoline-3-carboxylate and derivatives
  作者：Nicholas G Jentsch、Jared D Hume、Emily B Crull、Samer M Beauti、Amy H Pham、Julie A Pigza、Jacques J Kessl、Matthew G Donahue

  DOI：10.3762/bjoc.14.229

  日期：——

  A convenient two-step synthesis of ethyl 4-hydroxy-2-methylquinoline-3-carboxylate derivatives has been developed starting from commercially available 2-aminobenzoic acids. In step 1, the anthranilic acids are smoothly converted to isatoic anhydrides using solid triphosgene in THF. In step 2, the anhydride electrophiles are reacted with the sodium enolate of ethyl acetoacetate, generated from sodium

  已经从市售的 2-氨基苯甲酸开始开发了一种方便的两步合成 4-羟基-2-甲基喹啉-3-羧酸乙酯衍生物的方法。在步骤 1 中，使用 THF 中的固体三光气将邻氨基苯甲酸平稳地转化为靛红酸酐。在步骤 2 中，酸酐亲电试剂与由氢氧化钠生成的乙酰乙酸乙酯的烯醇钠在温热的 N,N-二甲基乙酰胺中反应，从而形成取代的喹啉。乙酯在 3 位的降解累积策略允许构建参与 HIV 整合酶项目的关键芳基喹啉合成所需的 α-羟基乙酸残基。
• Derivatives of 4-hydroxyquinoline-3-carboxylic acid
  作者：N. M. Sukhova、T. V. Lapina、M. Yu. Lidak

  DOI：10.1007/bf00515358

  日期：1983.11
• CYXOBA, N. M.;LAPINA, T. V.;LIDAK, M. YU., XIMIYA GETEROTSIKL. SOEDIN., 1983, N 11, 1521-1523
  作者：CYXOBA, N. M.、LAPINA, T. V.、LIDAK, M. YU.

  DOI：——

  日期：——