2-甲基-6-氧代-1H-吡啶-4-羧酸丙酯 | 40975-42-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 中文名称: 2-甲基-6-氧代-1H-吡啶-4-羧酸丙酯
• 英文名称: propyl 6-methylpyridin-2-one-4-carboxylate
• 英文别名: propyl 6-methyl-2-oxo-1, 2-dihydropyridine-4-carboxylate；Propyl 2-hydroxy-6-methylisonicotinate；propyl 2-methyl-6-oxo-1H-pyridine-4-carboxylate
• CAS: 40975-42-6
• 化学式: C₁₀H₁₃NO₃
• 分子量: 195.218
• InChiKey: JXVAWCDXLDAUAX-UHFFFAOYSA-N

物化性质

• 沸点：
  360.3±42.0 °C(Predicted)
• 密度：
  1.133±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  14
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  55.4
• 氢给体数：
  1
• 氢受体数：
  3

安全信息

• 海关编码：
  2933399090

反应信息

• 作为反应物：
  描述：

  2-甲基-6-氧代-1H-吡啶-4-羧酸丙酯 在 吡啶 作用下， 以 二氯甲烷 、 二甲基亚砜 为溶剂， 反应 16.0h， 生成
  参考文献：
  名称：

  Practical and Scalable Synthesis of S1P₁ Receptor Agonist ACT-209905

  摘要：

  A practical and scalable route for the fast delivery of 12 kg of S1P(1) agonist (ACT-209905) has been developed. ACT-209905 is composed of an amino pyridine group, an oxadiazole spacer, a 2-ethyl-5-methylphenol moiety and a chiral 1-amino-2-propanol side chain. The convergent synthesis consists of 16 steps with 9 isolated intermediates and is chromatography-free. Key building blocks are accessed from low-cost starting materials, such as acetone, diethyl oxalate, cyanoacetamide, and 2-ethyl-5-methyl aniline. A Negishi coupling that was troubled by the use of metal reagents and concomitant metal waste streams has been replaced by a less expensive Guareschi-Thorpe reaction to build up an amino isonicotinic acid. The chiral 1-amino-2-propanol moiety was secured by selective ring-opening of an epoxide with lithium hexamethyldisilazide as an ammonia surrogate, thus omitting the notorious double alkylated byproduct.

  DOI：

  10.1021/op200326s
• 作为产物：
  描述：

  3-氰基-1,2-二氢-6-甲基-2-氧代-4-吡啶羧酸乙酯 在 盐酸 、 水 、 caesium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 37.0h， 生成 2-甲基-6-氧代-1H-吡啶-4-羧酸丙酯
  参考文献：
  名称：

  Construction and functionalization of fused pyridine ring leading to novel compounds as potential antitubercular agents

  摘要：

  A series of fused and functionalized pyridine derivatives were designed, synthesized and tested for their potential antitubercular properties. All these novel compounds were prepared by using multistep methods involving the construction of pyridine ring as a key synthetic step. Some of these compounds were found to be interesting when tested for their antitubercular properties in vitro and one of them appeared as an attractive and potential antitubercular agent. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2012.05.096

文献信息

• 一种甲基酮衍生物及其制备方法与应用
  申请人：苏州大学

  公开号：CN106496130B

  公开（公告）日：2019-09-20

  本发明公开了一种甲基酮衍生物及其制备方法与应用，将酮衍生物、有机过氧化物溶于溶剂中，于80‑130℃反应，获得甲基嘧啶酮和甲基吡啶酮衍生物。本发明使用酮衍生物为起始物，原料易得、种类很多；利用本发明的方法得到的产物类型多样，既可以直接使用、又可以用于其他进一步的反应。本发明方法无金属参与，适合于制药工艺。本发明方法路线简短、反应条件温和、反应操作和后处理过程简单、产率较高，适合于规模化生产。
• Metal-free radical C–H methylation of pyrimidinones and pyridinones with dicumyl peroxide
  作者：Pei-Zhi Zhang、Jian-An Li、Ling Zhang、Adedamola Shoberu、Jian-Ping Zou、Wei Zhang

  DOI：10.1039/c6gc03355e

  日期：——

  A new method for free radical methylation of pyrimidinones and pyridinones with dicumyl peroxide (DCP) under metal-free condition is introduced. A 50 g-scale reaction could be performed safely at desired...

  介绍了一种在无金属条件下用过氧化二枯基（DCP）与嘧啶酮和吡啶酮进行自由基甲基化的新方法。50 g规模的反应可以在所需的条件下安全地进行...
• Mn(OAc)3-Mediated Regioselective Radical Alkoxycarbonylation of Indoles, Pyrimidinones, and Pyridinones
  作者：Jian-Ping Zou、Wei Zhang、Cheng-Kun Li、Dong-Liang Zhang、Ogundipe Olamiji、Pei-Zhi Zhang、Adedamola Shoberu

  DOI：10.1055/s-0037-1610039

  日期：2018.8

  alkoxycarbonylation of indoles, pyrimidinones, and pyridinones with alkyl carbazates is reported. The reactions proceed through a radical process to afford regioselectively 3-carboxylated indoles, 5-carboxylated pyrimidinones, and 3-carboxylated pyridin­ones in moderate to good yields under mild reaction conditions. Mn(OAc)3-mediated alkoxycarbonylation of indoles, pyrimidinones, and pyridinones with alkyl

  作为特别主题“现代自由基方法及其在合成中的战略应用”的一部分发布 抽象的 Mn（OAc）3介导的吲哚，嘧啶酮和吡啶酮与烷基咔唑的烷氧基羰基化反应。反应通过自由基过程进行，以在温和的反应条件下以中等至良好的产率提供区域选择性的3-羧化吲哚，5-羧化嘧啶酮和3-羧化吡啶酮。 Mn（OAc）3介导的吲哚，嘧啶酮和吡啶酮与烷基咔唑的烷氧基羰基化反应。反应通过自由基过程进行，以在温和的反应条件下以中等至良好的产率提供区域选择性的3-羧化吲哚，5-羧化嘧啶酮和3-羧化吡啶酮。
• Direct regioselective Csp2–H trifluoromethylation of pyrimidinones and pyridinones
  作者：Pei-Zhi Zhang、Cheng-Kun Li、Guo-Yu Zhang、Ling Zhang、Yao-Jia Jiang、Jian-Ping Zou

  DOI：10.1016/j.tet.2016.04.048

  日期：2016.6

  pyrimidinones and 3-trifluoromethyl pyridinones in moderate to good yields was described. The reaction showed that the steric hindrance due to bulky groups adjacent to the position of attack by the trifluoromethyl radical had important influence on the yield.

  描述了使用CF 3 SO 2 Na / Mn（OAc）3进行嘧啶酮和吡啶酮的直接区域选择性C sp2- H三氟甲基化，以中等至良好的产率提供了5-三氟甲基嘧啶酮和3-三氟甲基吡啶酮。该反应表明，由于三氟甲基自由基的进攻位置附近的庞大基团而引起的位阻对产率有重要影响。