Dimethyl 4-(2-methoxyphenyl)-2,6-dimethylpyridine-3,5-dicarboxylate | 112010-43-2

• 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: Dimethyl 4-(2-methoxyphenyl)-2,6-dimethylpyridine-3,5-dicarboxylate
• CAS: 112010-43-2
• 化学式: C₁₈H₁₉NO₅
• 分子量: 329.353
• InChiKey: LIHAEKXYZKBDOV-UHFFFAOYSA-N

物化性质

• 熔点：
  80-81 °C(Solv: methanol (67-56-1))
• 沸点：
  400.1±45.0 °C(Predicted)
• 密度：
  1.175±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  24
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.28
• 拓扑面积：
  74.7
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  Dimethyl 4-(2-methoxyphenyl)-2,6-dimethylpyridine-3,5-dicarboxylate 在 盐酸 、 氢溴酸 作用下， 反应 2.0h， 生成 Methyl 2,4-dimethyl-5-oxo-5H-<1>benzopyrano<3,4-c>pyridine-1-carboxylate
  参考文献：
  名称：

  Synthesis of Dialkyl 2-(2-Hydroxyphenyl)-4,6-dimethyl-1,2-dihydropyridine-3,5-dicarboxylates and Alkyl 2,4-Dimethyl-5-oxo-5H-[1]benzopyrano[4,3-b]-pyridine-3-carboxylates

  摘要：

  2-羟基苯甲醛与3-氧代丁酸酯和过量氨在室温下的醋酸中反应，生成二烷基2-(2-羟基苯基)-4,6-二甲基-1,2-二氢吡啶-3,5-二羧酸酯及其2-(3,5-二烷氧羧基-4,6-二甲基-1,2,3-三氢吡啶离子-2-基)-苯氧负离子。对这些化合物的温和氧化伴随有内酯化，形成之前被错误表述的烷基2,4-二甲基-5-氧代-5H-[1]苯并吡喃[4,3-b]吡啶-3-羧酸酯。其他o-取代苯甲醛与烷基3-氨基克罗通酸酯在室温下的醋酸中反应同样生成二烷基2-芳基-4,6-二甲基-1,2-二氢吡啶-3,5-二羧酸酯，以及常见的1,4-二氢吡啶汉兹施酯。

  DOI：

  10.1055/s-1987-27984
• 作为产物：
  描述：

  β-氨基巴豆酸甲酯 在 chromium(VI) oxide 作用下， 以 水 、 溶剂黄146 为溶剂， 反应 25.0h， 生成 Dimethyl 4-(2-methoxyphenyl)-2,6-dimethylpyridine-3,5-dicarboxylate
  参考文献：
  名称：

  Synthesis of Dialkyl 2-(2-Hydroxyphenyl)-4,6-dimethyl-1,2-dihydropyridine-3,5-dicarboxylates and Alkyl 2,4-Dimethyl-5-oxo-5H-[1]benzopyrano[4,3-b]-pyridine-3-carboxylates

  摘要：

  2-羟基苯甲醛与3-氧代丁酸酯和过量氨在室温下的醋酸中反应，生成二烷基2-(2-羟基苯基)-4,6-二甲基-1,2-二氢吡啶-3,5-二羧酸酯及其2-(3,5-二烷氧羧基-4,6-二甲基-1,2,3-三氢吡啶离子-2-基)-苯氧负离子。对这些化合物的温和氧化伴随有内酯化，形成之前被错误表述的烷基2,4-二甲基-5-氧代-5H-[1]苯并吡喃[4,3-b]吡啶-3-羧酸酯。其他o-取代苯甲醛与烷基3-氨基克罗通酸酯在室温下的醋酸中反应同样生成二烷基2-芳基-4,6-二甲基-1,2-二氢吡啶-3,5-二羧酸酯，以及常见的1,4-二氢吡啶汉兹施酯。

  DOI：

  10.1055/s-1987-27984

文献信息

• Superparamagnetic core‐shell metal–organic framework Fe ₃ O ₄ @Ni‐MOF as efficient catalyst for oxidation of 1,4‐dihydropyridines using hydrogen peroxide
  作者：Marzieh Janani、Masumeh Abdoli Senejani、Tahereh Momeni Isfahani

  DOI：10.1002/aoc.6350

  日期：2021.10

  Fe3O4@Ni-MOF revealed high efficiency for oxidation of various 1,4-dihydropyridines using hydrogen peroxide. The Box–Behnken design matrix and the response surface method were applied to investigate the optimization of the reaction conditions. The conditions for optimal reaction yield and time were: amount of catalyst ≈17 mmol, temperature ≈78°C and amount of hydrogen peroxide ≈ 1 ml. A variety of 3,5-diacyl

  描述了一种在超顺磁性核-壳金属-有机骨架 Fe 3 O 4 @Ni存在下使用 H 2 O 2氧化某些 3,5-二酰基或 3,5-二酯 1,4-二氢吡啶的简便有效的方法-MOF。Fe 3 O 4 @Ni-MOF 是通过 Step-by-Step 方法获得的，其中磁性 Fe 3 O 4使用巯基乙酸连接剂用 Ni-MOF 涂覆磁性纳米颗粒。使用热重分析、FT-IR 光谱、粉末 X 射线衍射、场发射扫描电子显微镜和能量色散 X 射线分析对合成的催化剂进行了表征。新型超顺磁性核壳金属有机骨架 Fe 3 O 4@Ni-MOF 显示使用过氧化氢氧化各种 1,4-二氢吡啶的效率很高。应用 Box-Behnken 设计矩阵和响应面法来研究反应条件的优化。最佳反应收率和时间的条件是：催化剂量≈17 mMOl，温度≈78°C，过氧化氢量≈1 ml。使用 H 2 O 2和 Fe 3 O 4已将各种具有不同取代官能团的
• An efficient, metal-free, room temperature aromatization of Hantzsch-1,4-dihydropyridines with urea–hydrogen peroxide adduct, catalyzed by molecular iodine
  作者：Mirela Filipan-Litvić、Mladen Litvić、Vladimir Vinković

  DOI：10.1016/j.tet.2008.04.040

  日期：2008.6

  A mild, highly efficient and metal-free synthetic method for aromatization of 1,4-dihydropyridines employing urea–hydrogen peroxide adduct as oxidant catalyzed by 20 mol % of molecular iodine was developed. The reaction was carried out in ethyl acetate at room temperature and the products were isolated in high to excellent yields. A plausible free-radical mechanism is proposed based on results obtained

  开发了一种温和，高效，无金属的合成方法，该方法以20 mol％的分子碘为催化剂，使用脲-过氧化氢加合物作为氧化剂进行1,4-二氢吡啶的芳构化。该反应在室温下在乙酸乙酯中进行，并且以高至优异的产率分离出产物。基于在1，4-二氢吡啶环中具有烷基和芳基取代基的衍生物所获得的结果，提出了一种可能的自由基机理。
• 4-Phenyl-1,2,4-triazole-3,5-dione as a novel and reusable reagent for the aromatization of 1,4-dihydropyridines under mild conditions
  作者：Mohammad Ali Zolfigol、Arash Ghorbani Choghamarani、Mozhgan Shahamirian、Maliheh Safaiee、Iraj Mohammadpoor-Baltork、Shadpour Mallakpour、Mohammad Abdollahi-Alibeik

  DOI：10.1016/j.tetlet.2005.06.031

  日期：2005.8

  4-Substituted 1,3,4-triazole-3,5-diones were used as effective and recyclable oxidizing agents for the oxidation of 1,4-dihydropyridines to the corresponding pyridine derivatives under mild conditions with good to excellent yields. (c) 2005 Elsevier Ltd. All rights reserved.
• A highly efficient biomimetic aromatization of Hantzsch-1,4-dihydropyridines with t-butylhydroperoxide, catalysed by iron(III) phthalocyanine chloride
  作者：Mirela Filipan-Litvić、Mladen Litvić、Vladimir Vinković

  DOI：10.1016/j.bmc.2008.09.004

  日期：2008.10

  Rapid aromatization of Hantzsch-1,4-DHPswith t-butylhydroperoxide catalysed by iron(III) phthalocyanine chloride is described. The reaction proceeds smoothly at room temperature within 1-35 min and the products of high purity were isolated in excellent yields. To explain the reactivity of this catalytical system plausible mechanism have been proposed to involve formation of high-valent oxoferryl species as in cytochrome P450 itself. (C) 2008 Elsevier Ltd. All rights reserved.
• 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.