4-Hydroxymethyl-quinoline-2-carboxylic acid methyl ester | 179764-70-6

• 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-Hydroxymethyl-quinoline-2-carboxylic acid methyl ester
• 英文别名: Methyl 4-(hydroxymethyl)quinoline-2-carboxylate
• CAS: 179764-70-6
• 化学式: C₁₂H₁₁NO₃
• 分子量: 217.224
• InChiKey: HQLHMBNYIWSZNP-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：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  59.4
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  4-Hydroxymethyl-quinoline-2-carboxylic acid methyl ester 在 sodium hydroxide 作用下， 以 四氢呋喃 为溶剂， 反应 0.17h， 以87.9%的产率得到4-hydroxymethylquinoline-2-carboxylic acid
  参考文献：
  名称：

  Studies on the biosynthesis of thiostrepton: 4-(1-hydroxyethyl)quinoline-2-carboxylate as a free intermediate on the pathway to the quinaldic acid moiety

  摘要：

  Specifically C-13-labeled quinoline-2-carboxylate derivatives were synthesized from quinoline and used to study the biosynthesis of thiostrepton in a strain of Streptomyces laurentii. C-13 NMR analysis of thiostrepton recovered after feeding methyl (RS)-[11-C-13]-4-(1-hydroxyethyl)quinoline-2-carboxylate or methyl [11-C-13]-4-acetylquinoline-2-carboxylate showed conclusively that these compounds are specifically and efficiently incorporated into thiostrepton. Both compounds were also detected in cultures of the producing organism by isotope dilution analysis. The significance of the relative endogenous concentrations of the two compounds and of the relative extent of the incorporation of exogenously added labeled material into thiostrepton are discussed in terms of the biosynthetic pathway linking tryptophan and 4-(1-hydroxyethyl)quinoline-2-carboxylate in S. laurentii. A highly specific enzyme activity was detected in cell-free extracts of S. laurentii that was capable of adenylating (12S)-4-(1-hydroxyethyl)quinoline-2-carboxylic acid. Partial purification of the enzyme was achieved. The enzyme was found to be specific for the enantiomer of the substrate which has the same absolute configuration as found in the natural antibiotic structure. The presence of one specific enzyme catalysing the adenylation process in S. laurentii was shown by photoaffinity labeling with [alpha-P-32]-8-azido-ATP and subsequent SDS PAGE analysis of the labeled products. The native molecular weight of the active enzyme, determined by gel permeation chromatography, was found to be approximately 47 kDa, compared with a denatured weight of 50 kDa estimated for the photoaffinity-labeled protein. The enzyme is thus probably monomeric. Copyright (C) 1996 Elsevier Science Ltd

  DOI：

  10.1016/0968-0896(96)00126-5
• 作为产物：
  描述：

  喹哪啶酸 在 氯化亚砜 、 双氧水 、 iron(II) sulfate 、 三氟乙酸 作用下， 反应 25.0h， 生成 4-Hydroxymethyl-quinoline-2-carboxylic acid methyl ester
  参考文献：
  名称：

  Studies on the biosynthesis of thiostrepton: 4-(1-hydroxyethyl)quinoline-2-carboxylate as a free intermediate on the pathway to the quinaldic acid moiety

  摘要：

  Specifically C-13-labeled quinoline-2-carboxylate derivatives were synthesized from quinoline and used to study the biosynthesis of thiostrepton in a strain of Streptomyces laurentii. C-13 NMR analysis of thiostrepton recovered after feeding methyl (RS)-[11-C-13]-4-(1-hydroxyethyl)quinoline-2-carboxylate or methyl [11-C-13]-4-acetylquinoline-2-carboxylate showed conclusively that these compounds are specifically and efficiently incorporated into thiostrepton. Both compounds were also detected in cultures of the producing organism by isotope dilution analysis. The significance of the relative endogenous concentrations of the two compounds and of the relative extent of the incorporation of exogenously added labeled material into thiostrepton are discussed in terms of the biosynthetic pathway linking tryptophan and 4-(1-hydroxyethyl)quinoline-2-carboxylate in S. laurentii. A highly specific enzyme activity was detected in cell-free extracts of S. laurentii that was capable of adenylating (12S)-4-(1-hydroxyethyl)quinoline-2-carboxylic acid. Partial purification of the enzyme was achieved. The enzyme was found to be specific for the enantiomer of the substrate which has the same absolute configuration as found in the natural antibiotic structure. The presence of one specific enzyme catalysing the adenylation process in S. laurentii was shown by photoaffinity labeling with [alpha-P-32]-8-azido-ATP and subsequent SDS PAGE analysis of the labeled products. The native molecular weight of the active enzyme, determined by gel permeation chromatography, was found to be approximately 47 kDa, compared with a denatured weight of 50 kDa estimated for the photoaffinity-labeled protein. The enzyme is thus probably monomeric. Copyright (C) 1996 Elsevier Science Ltd

  DOI：

  10.1016/0968-0896(96)00126-5

文献信息

• One-pot synthesis of heteroaromatic acetals via selectfluor-mediated tandem reaction of methyl quinoline-2-carboxylate and methanol
  作者：Wengui Wang、Zhenqiang Chen、Yingying Zhang、Wei Zeng、Shoufeng Wang

  DOI：10.1016/j.tet.2021.132607

  日期：2022.1

  report a mild Ag-catalyzed domino acetalization reaction using quinoline-2-carboxylates, which were substructures in a number of natural products. Methanol was directly utilized as the source of the acetal part. The main features of the domino reaction include the Minisci reaction, oxidation, and acetalization. Hydrogen fluoride generated in-situ participates in the Minisci reaction, and no external acids

  在这里，我们报告了使用 quinoline-2-carboxylates 的温和 Ag 催化的多米诺缩醛化反应，它是许多天然产物的亚结构。甲醇直接用作缩醛部分的来源。多米诺骨牌反应的主要特征包括 Minisci 反应、氧化和缩醛化。原位产生的氟化氢参与Minisci反应，无需外加酸。这种多米诺骨牌反应为在温和条件下使用甲醇生成杂芳族缩醛提供了一种简单而通用的途径，具有良好的官能团耐受性。