3-(2-甲基-5-吡啶基)-3-氧代丙酸乙酯 | 21683-58-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: 3-(2-甲基-5-吡啶基)-3-氧代丙酸乙酯
• 英文名称: ethyl 3-(6-methylpyridin-3-yl)-3-oxopropanoate
• 英文别名: ethyl 3-(2-methyl-5-pyridinyl)-3-oxopropanoate
• CAS: 21683-58-9
• 化学式: C₁₁H₁₃NO₃
• 分子量: 207.229
• InChiKey: CSTIAWJADKPHBF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  15
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  56.3
• 氢给体数：
  0
• 氢受体数：
  4

安全信息

• 海关编码：
  2933399090

反应信息

• 作为反应物：
  描述：

  3-(2-甲基-5-吡啶基)-3-氧代丙酸乙酯 在 哌啶 、 盐酸 、 2,2'-联吡啶 、 sodium hydroxide 、 sodium tetrahydroborate 、 硫酸 、 sodium hydride 、 三苯基膦 、 cobalt(II) chloride 、 偶氮二甲酸二乙酯 作用下， 以 四氢呋喃 、 甲醇 、 乙醇 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 96.0h， 生成 Hydroxypioglitazone
  参考文献：
  名称：

  Synthesis and Biological Activity of Metabolites of the Antidiabetic, Antihyperglycemic Agent Pioglitazone

  摘要：

  Pioglitazone (5-(4-(2-(5-ethyl-2-pyridyl)ethoxy)benzyl)-2,4-thiazolidinedione, 2) is a prototypical antidiabetic thiazolidinedione that had been evaluated for possible; clinical development. Metabolites 6-9 have been identified after dosing of rats and dogs. Ketone 10 has not yet been identified as a metabolite but has been added to the list as a putative metabolite by analogy to alcohol 6 and ketone 7. We have developed improved syntheses of pioglitazone (2) metabolites 6-9 and the putative metabolite ketone 10. These entities have been compared in the KKA(y) mouse model of human type-II diabetes to pioglitazone (2). Ketone 10 has proven to be the most potent of these thiazolidinediones in this in, vivo assay. When 6-10 were compared in vitro in the 3T3-L1 cell line to 2, for their ability to augment insulin-stimulated lipogenesis, 10 was again the most potent compound with 6, 7, and 9 roughly equivalent to 2. These data suggest that metabolites 6, 7, and 9 are likely to contribute to the pharmacological activity of pioglitazone (2), as had been previously reported for ciglitazone (1).

  DOI：

  10.1021/jm9605694
• 作为产物：
  描述：

  4-二甲氨基吡啶 在 palladium on activated carbon sodium hydroxide 、 乙酸酐 、 溶剂黄146 作用下， 以 甲醇 、 二氯甲烷 、 水 、 甲苯 为溶剂， 以97%的产率得到2-甲基吡啶-5-丙酸甲酯
  参考文献：
  名称：

  3-hydroxy-3-(2-methyl-5-pyridyl)-propionic acid alkyl esters

  摘要：

  3-羟基-3-(2-甲基-5-吡啶基)-丙酸烷基酯是工业上可以简单制备的中间产物，可用于生产2-甲基吡啶-5-丙酸烷基酯。

  公开号：

  US04687856A1

文献信息

• Efficient one-pot selective reduction of esters in β-ketoesters using LiHMDS and lithium aluminium hydride
  作者：K. Sivagurunathan、S. Raja Mohamed Kamil、S. Syed Shafi、F. Liakth Ali Khan、R. Venkat Ragavan

  DOI：10.1016/j.tetlet.2011.01.030

  日期：2011.3

  The ester functionality in β-keto esters is selectively reduced in one-pot, first by enolization using LiHMDS and then reduced with lithium aluminium hydride. This method produces β-hydroxyl ketones from the corresponding β-keto esters in high yield.

  首先通过使用LiHMDS烯醇化，然后用氢化锂铝将β-酮酯中的酯官能团一锅选择性地还原。该方法从相应的β-酮酯高产率地产生β-羟基酮。
• [EN] NAPHTHYRIDINE AND PYRIDO[3,4-c]PYRIDAZINE DERIVATIVES AS GABAA α5 RECEPTOR MODULATORS<br/>[FR] DÉRIVÉS DE NAPHTYRIDINE ET DE PYRIDO[3,4-C]PYRIDAZINE SERVANT DE MODULATEURS DU RÉCEPTEUR GABAA α5
  申请人：RICHTER GEDEON NYRT

  公开号：WO2021191838A1

  公开（公告）日：2021-09-30

  The present invention provides compounds of formula (I) and/or salts thereof and/or biologically active metabolites thereof and/or prodrugs thereof and/or solvates thereof and/or hydrates thereof and/or polymorphs thereof having affinity and selectivity for the gamma-aminobutyric acid A receptor subunit alpha 5 and act as GABAA α5 positive allosteric modulators, thereby useful in the treatment or prevention of diseases related to the GABAA α5 receptor, process for the preparation and intermediates of the preparation process thereof, pharmaceutical compositions comprising them alone or in combination with one or more other active ingredients and their use as medicaments.

  本发明提供了式（I）的化合物和/或其盐和/或其生物活性代谢物和/或其前药和/或其溶剂和/或其水合物和/或其多晶体，具有亲和力和选择性，用于γ-氨基丁酸A受体亚单位α5，并作为GABAA α5正向变构调节剂，因此有用于治疗或预防与GABAA α5受体相关的疾病，制备过程及制备过程中间体，包括它们的药物组合物，单独或与一个或多个其他活性成分组合使用作为药物。
• Process for preparing 3-hydroxy-3-(2-methyl-5-pyridyl)-propionic acid
  申请人：Lonza Ltd.

  公开号：US04723017A1

  公开（公告）日：1988-02-02

  3-Hydroxy-3-(2-methyl-5-pyridyl)-propionic acid alkyl esters which, as intermediate products that can be industrially produced in a simple manner, can be used for the production of 2-methylpyridine-5-propionic acid alkyl ester.

  3-羟基-3-(2-甲基-5-吡啶基)-丙酸烷基酯是一种可用于工业生产的中间产物，可简单地用于生产2-甲基吡啶-5-丙酸烷基酯。
• 3-(Pyridinyl)-2-cyclohexen-1-ones
  申请人：Sterling Drug Inc.

  公开号：US04026900A1

  公开（公告）日：1977-05-31

  3-(4 OR 3-Pyridinyl)-2-cyclohexen-1-ones (I) and their oxime derivatives are useful in preparing (3-aminophenyl)-pyridines, in turn, useful in preparing known antibacterial agents. Also shown is the preparation of I by starting with the reaction of methyl vinyl ketone with either 1-(pyridinyl)-1-(lower-tertiary-amino)-ethylene (II) or lower-alkyl 3-(pyridinyl)-3-oxopropanoate. Also shown is the process of converting I to its oxime, acylating the oxime and heating the acylated oxime under acidic conditions to produce N-(lower-acyl)-3-(pyridinyl)-aniline (VII), and hydrolyzing VII under aqueous alkaline conditions to produce the corresponding 3-(pyridinyl)aniline.

  3-(4或3-吡啶基)-2-环己烯-1-酮(I)及其肟衍生物在制备(3-氨基苯基)-吡啶类化合物方面有用，进而有用于制备已知的抗菌剂。还显示了通过甲基乙烯酮与1-(吡啶基)-1-(低级三级胺)-乙烯(II)或低烷基3-(吡啶基)-3-氧代丙酸酯反应制备I的过程。还显示了将I转化为其肟衍生物，酰化肟衍生物并在酸性条件下加热产生N-(低酰基)-3-(吡啶基)-苯胺(VII)，并在水性碱性条件下水解VII以产生相应的3-(吡啶基)苯胺的过程。
• Conversion of 3-(pyridinyl)-2-cyclohexen-1-one to 3-(pyridinyl)anilines
  申请人：Sterling Drug Inc.

  公开号：US04075217A1

  公开（公告）日：1978-02-21

  3-(4- OR 3-Pyridinyl)-2-cyclohexen-1-ones (I) and their oxime derivatives are useful in preparing (3-aminophenyl)-pyridines, in turn, useful in preparing known antibacterial agents. Also shown is the preparation of I by starting with the reaction of methyl vinyl ketone with either 1-(pyridinyl)-1-(lower-tertiary-amino)-ethylene (II) or lower-alkyl 3-(pyridinyl)-3-oxopropanoate. Also shown is the process of converting I to its oxime, acylating the oxime and heating the acylated oxime under acidic conditions to produce N-(lower-acyl)-3-(pyridinyl)-aniline (VII), and hydrolyzing VII under aqueous alkaline conditions to produce the corresponding 3-(pyridinyl)aniline.

  3-(4- OR 3-Pyridinyl)-2-cyclohexen-1-ones (I)及其肟衍生物可用于制备(3-氨基苯基)吡啶，后者又可用于制备已知的抗菌剂。同时，通过甲基乙烯酮与1-(吡啶基)-1-(低三级胺基)-乙烯(II)或较低烷基3-(吡啶基)-3-氧代丙酸酯反应制备I。此外，通过将I转化为其肟，酰化肟并在酸性条件下加热以产生N-(低酰基)-3-(吡啶基)苯胺(VII)，并在水性碱性条件下水解VII以产生相应的3-(吡啶基)苯胺。