4-isopropyl-3,5-dimethoxycarbonyl-2,6-dimethylpyridine | 219701-26-5

• 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
• 英文名称: 4-isopropyl-3,5-dimethoxycarbonyl-2,6-dimethylpyridine
• 英文别名: dimethyl 2,6-dimethyl-4-propan-2-ylpyridine-3,5-dicarboxylate
• CAS: 219701-26-5
• 化学式: C₁₄H₁₉NO₄
• 分子量: 265.309
• InChiKey: YRPNKZTUKSAGGP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  19
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  65.5
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  dimethyl 1,4-dihydro-4-(1-methylethyl)-2,6-dimethyl-3,5-pyridinedicarboxylate 在 potassium carbonate 作用下， 以 乙醇 、 水 为溶剂， 反应 12.0h， 以82.8%的产率得到4-isopropyl-3,5-dimethoxycarbonyl-2,6-dimethylpyridine
  参考文献：
  名称：

  用1,4-二氢吡啶化合物制备相应吡啶化合物 的方法

  摘要：

  本发明公开一种用1,4‑二氢吡啶化合物制备相应吡啶化合物的方法。本发明的方法是：将1,4‑二氢吡啶化合物、曙红Y的四正丁基铵盐、碳酸钾加入到有机溶剂与水的混合溶剂中搅拌混合均匀，通入空气在可见光照射条件下进行反应，待反应结束后，加入乙酸乙酯，分别用水、饱和氯化铵洗涤，除去无机碱并调节体系至微酸性，在有机相中加入少量活性碳除去色素，再经过无水硫酸钠干燥，旋干，重结晶获得相应的吡啶类化合物。本发明方法相比于现有技术具有以空气中的氧气作为氧化剂，便宜且方便易得；以太阳光为能源，使得工业生产更加有利；催化量的非金属光催化剂的使用，降低了合成成本，避免了贵金属在药物合成中的累积。

  公开号：

  CN104262236B

文献信息

• Remarkably fast and selective aromatization of Hantzsch esters with MoOCl4 and MoCl5: A chemical model for possible biologically relevant properties of molybdenum-containing enzymes
  作者：Mladen Litvić、Maja Regović、Karolina Šmic、Marija Lovrić、Mirela Filipan-Litvić

  DOI：10.1016/j.bmcl.2012.04.043

  日期：2012.6

  Mo(VI) and Mo(V) salts both react selectively with Hantzsch esters to produce substitute pyridines in good-to-excellent yield (75-99%). The remarkable reactivity and selectivity of MoOCl4 under reflux of acetonitrile and MoCl5 in dichloromethane at room temperature encouraged us to propose that molybdenum-containing enzymes (such as xanthine or aldehyde oxidase) also participate to some degree in the metabolism of 1,4-dihydropyridine drugs in the liver analogous to NADH in the respiratory chain. (C) 2012 Elsevier Ltd. All rights reserved.
• Electrochemical oxidation of 4-monoalkyl-substituted 1,4-dihydropyridines
  作者：B. Turovska、I. Goba、I. Turovskis、S. Grinberga、S. Belyakov、S. Stupnikova、E. Liepinsh、J. Stradins

  DOI：10.1007/s10593-009-0211-0

  日期：2008.12

  The electrochemical oxidation of 4-monoalkyl-substituted 1,4-dihydropyridines has been studied in an aprotic medium and in the presence of pyridine. In an aprotic medium the products of oxidation are both 4-alkyl-substituted and 4-unsubstituted pyridines or mixtures of them. On oxidation in acetonitrile of 4-Et-, 4-n-Pr-, and 4-i-Bu-substituted dihydropyridines, 2-methylene-1,2,3,4-tetrahydropyridines were obtained in addition to the oxidized forms. In the presence of base the products of preparative electrolysis of the studied compounds were 4-alkyl-substituted pyridines. The exception was the 4-i-Pr- substituted dihydropyridine which was dealkylated on oxidation even in the presence of base.