methyl 4-acetylquinaldate | 150147-06-1

• 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: methyl 4-acetylquinaldate
• 英文别名: methyl 4-acetylquinolne-2-carboxylate；methyl 4-acetylquinoline-2-carboxylate；methyl 1-acetylisoquinoline-3-carboxylate
• CAS: 150147-06-1
• 化学式: C₁₃H₁₁NO₃
• 分子量: 229.235
• InChiKey: HINPYZDNDZWAMY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.15
• 拓扑面积：
  56.3
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  methyl 4-acetylquinaldate 在 吡啶 、 sodium tetrahydroborate 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 3.0h， 生成 4-(1-Hexanoyloxy-ethyl)-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
• 作为产物：
  描述：

  Methyl 4-acetyl-5,6,7,8-tetrahydroquinoline-2-carboxylate 在 4-苯基吡啶-N-氧化物 、 R,R-Jacobsen's catalyst 、 亚碘酰苯 、 trifluoromethanesulfonic acid anhydride 、 三乙胺 、 间氯过氧苯甲酸 作用下， 以 二氯甲烷 、 乙腈 为溶剂， 反应 24.0h， 生成 methyl 4-acetylquinaldate
  参考文献：
  名称：

  肽类抗生素链霉菌素家族的合成研究：硫链菌素，西霉素和硫肽素的二氢喹啉部分的合成

  摘要：

  巯基链霉菌素，西霉素和肽肽的巯基链霉菌素家族的成员硫肽素的二氢喹啉部分的合成已通过“使用三氟甲烷磺酸酐和三乙胺”通过Matsumura-Boekelheide重排进行一锅法烯烃化而实现。由周围位置的立体中心控制的反应。

  DOI：

  10.1016/j.tetlet.2005.07.121

文献信息

• Discovery and efficient synthesis of a biologically active alkaloid inspired by thiostrepton biosynthesis
  作者：Qingfei Zheng、Shoufeng Wang、Wen Liu

  DOI：10.1016/j.tet.2014.06.076

  日期：2014.10

  numerous biological activities, including anti-bacterial, anti-tumor, and anti-plasmodial activities. The quinaldic acid (QA) moiety-containing side ring (loop 2) was proven to play an important role in carrying out these functions. Previously, we proposed biosynthetic logic for thiostrepton loop 2 and demonstrated the formation mechanism of QA. Herein, we report the discovery and efficient synthesis of

  硫排蛋白（Thiostrepton）是一种天然的肽大环化合物，由于其结构复杂性和众多的生物活性（包括抗菌，抗肿瘤和抗疟原虫活性）而备受关注。包含奎纳酸（QA）部分的侧环（环2）被证明在执行这些功能中起着重要的作用。以前，我们提出了硫代链霉菌环2的生物合成逻辑，并证明了QA的形成机理。在本文中，我们报告了生物活性生物碱的发现和有效合成，该生物活性生物碱即是硫代链霉菌素生物合成途径中的关键中间体。进行化学酶联法合成该分子，并制备了一系列类似物用于生物测定，其中包括检查抗菌和抗肿瘤活性。
• Biosynthesis of the modified peptide antibiotic thiostrepton in Streptomyces azureus and Streptomyces laurentii
  作者：Ursula Mocek、Zhaopie Zeng、David O'Hagan、Pei Zhou、Lai Duen G. Fan、John M. Beale、Heinz G. Floss

  DOI：10.1021/ja00071a009

  日期：1993.9

  Experiments with (S)-[1,2- 13 C 2 ]- and (S)-[2,3- 13 C 2 ]serine showed intact incorporation of serine into the thiazoline and thiazole rings as well as the dehydroalanine, alanine, and tetrahydropyridine moieties. (S)-[3- 13 C, 2 H 2 ]Serine and (2S,3S)-[3- 13 C, 2 H 1 ]serine were used to elucidate the stereochemistry of the various transformations of serine

  已通过向 Streptomyces azureus 和 Streptomyces laurentii 的培养物施用同位素标记的前体来研究硫肽抗生素 thiostrepton (1) 的生物合成。证明了抗生素所有成分的氨基酸来源。(S)-[1,2- 13 C 2 ]- 和 (S)-[2,3- 13 C 2 ] 丝氨酸的实验表明丝氨酸完整地掺入噻唑啉和噻唑环以及脱氢丙氨酸、丙氨酸、和四氢吡啶部分。(S)-[3- 13 C, 2 H 2 ]丝氨酸和(2S,3S)-[3- 13 C, 2 H 1 ]丝氨酸用于阐明丝氨酸各种转化的立体化学
• HAT-Mediated Electrochemical C(sp²)–H Acylation of Quinolines with Alcohols
  作者：Yujie Liao、Cong Jiang、Congcong Qiang、Ping Liu、Peipei Sun

  DOI：10.1021/acs.orglett.3c02668

  日期：2023.10.13

  Herein, an electrochemical hydrogen atom transfer (HAT) strategy for C(sp2)–H formylation of electron-deficient quinolines and isoquinolines is described. The cheap methanol acts as a formyl source with a catalytic amount of N-hydroxyphthalimide (NHPI) as the hydrogen atom transfer (HAT) catalyst. The advantages of this reaction are transition-metal-catalyst- and chemical-oxidant-free conditions, and

  本文描述了缺电子喹啉和异喹啉的C(sp 2 )–H 甲酰化的电化学氢原子转移 (HAT) 策略。廉价的甲醇作为甲酰源，催化量的N-羟基邻苯二甲酰亚胺 (NHPI) 作为氢原子转移 (HAT) 催化剂。该反应的优点是无过渡金属催化剂和化学氧化剂的条件，并且该方案也可以应用于喹啉的直接C(sp 2 )–H乙酰化或丙酰化。