3,5-吡啶二羧酸,1,4-二氢-2,6-二甲基-4-(2-甲基丙基)-,二甲基酯 | 121195-86-6

• 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: 3,5-吡啶二羧酸,1,4-二氢-2,6-二甲基-4-(2-甲基丙基)-,二甲基酯
• 英文名称: 4-isobutyl-3,5-dimethoxycarbonyl-2,6-dimethyl-1,4-dihydropyridine
• 英文别名: Dimethyl 4-isobutyl-2,6-dimethyl-1,4-dihydropyridine-3,5-dicarboxylate；dimethyl 2,6-dimethyl-4-(2-methylpropyl)-1,4-dihydropyridine-3,5-dicarboxylate
• CAS: 121195-86-6
• 化学式: C₁₅H₂₃NO₄
• 分子量: 281.352
• InChiKey: QKJJLHREYPDKJH-UHFFFAOYSA-N

物化性质

• 熔点：
  124-126 °C
• 沸点：
  369.6±42.0 °C(Predicted)
• 密度：
  1.052±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  20
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  64.6
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  3,5-吡啶二羧酸,1,4-二氢-2,6-二甲基-4-(2-甲基丙基)-,二甲基酯 在 sodium perchlorate 作用下， 以 乙腈 为溶剂， 以36.7%的产率得到dimethyl 2,6-dimethyl-4-(2-methylpropyl)-3,5-pyridinedicarboxylate
  参考文献：
  名称：

  Electrochemical oxidation of 4-monoalkyl-substituted 1,4-dihydropyridines

  摘要：

  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.

  DOI：

  10.1007/s10593-009-0211-0
• 作为产物：
  描述：

  异戊醛 、 乙酰乙酸甲酯 在 乙酸铵 、 四丁基溴化铵 作用下， 以 水 为溶剂， 反应 0.17h， 以81%的产率得到3,5-吡啶二羧酸,1,4-二氢-2,6-二甲基-4-(2-甲基丙基)-,二甲基酯
  参考文献：
  名称：

  微波辐照下相转移催化剂在水中合成取代的1,4-二氢吡啶

  摘要：

  摘要 在微波辐射下，使用相转移催化剂，醛、乙酰乙酸乙酯和乙酸铵在水中反应合成了各种取代的 1,4-二氢吡啶。与经典的 Hantzsch 反应条件相比，这种新方法始终具有收率好和反应时间短的优点。已经使用二醛作为前体以良好的产率合成了含有两个单元的双功能化合物。

  DOI：

  10.1081/scc-200039409

文献信息

• Synthesis of Substituted 1,4‐Dihydropyridines in Water Using Phase‐Transfer Catalyst Under Microwave Irradiation
  作者：Hojatollah Salehi、Qing‐Xiang Guo

  DOI：10.1081/scc-200039409

  日期：2004.12.31

  Abstract The synthesis of various substituted 1,4‐dihydropyridines has been achieved by the reaction of aldehydes, ethyl/methyl acetoacetates, and ammonium acetate in water using phase‐transfer catalyst under microwave irradiation. Compared to the classical Hantzsch's reaction conditions, this new method consistently has the advantage of good yields and short reaction times. Bifunctional compounds containing

  摘要 在微波辐射下，使用相转移催化剂，醛、乙酰乙酸乙酯和乙酸铵在水中反应合成了各种取代的 1,4-二氢吡啶。与经典的 Hantzsch 反应条件相比，这种新方法始终具有收率好和反应时间短的优点。已经使用二醛作为前体以良好的产率合成了含有两个单元的双功能化合物。
• Magnetic Fe3O4 nanoparticles: Efficient and recoverable nanocatalyst for the synthesis of polyhydroquinolines and Hantzsch 1,4-dihydropyridines under solvent-free conditions
  作者：Masoud Nasr-Esfahani、S. Jafar Hoseini、Morteza Montazerozohori、Rasool Mehrabi、Hasan Nasrabadi

  DOI：10.1016/j.molcata.2013.11.010

  日期：2014.2

  A green approach for efficient and rapid synthesis of biologically active substituted Hantzsch 1,4-dihydropyridine and polyhydroquinoline derivatives using magnetic Fe3O4 nanoparticles (Fe3O4 MNPs) as a recyclable catalyst under solvent-free conditions was reported. The catalyst was characterized by FT-IR, XRD, and TEM analysis. Compared to the classical reactions, this method consistently has the

  报道了在无溶剂条件下使用磁性Fe 3 O 4纳米颗粒（Fe 3 O 4 MNPs）作为可循环利用催化剂高效，快速合成生物活性取代的Hantzsch 1,4-二氢吡啶和聚氢喹啉衍生物的绿色方法。通过FT-IR，XRD和TEM分析对催化剂进行了表征。与经典反应相比，该方法始终具有反应时间短，催化剂负载少，收率高，易于磁分离和催化剂可重复使用的优点。
• LiBr as an Efficient Catalyst for One-pot Synthesis of Hantzsch 1,4-Dihydropyridines under Mild Conditions
  作者：D. K. Yadav、R. Patel、V. P. Srivastava、G. Watal、L. D. S. Yadav

  DOI：10.1002/cjoc.201190036

  日期：2011.1

  A simple, inexpensive and efficient one‐pot synthesis of 1,4‐dihydropyridines has been accomplished via lithium bromide‐catalyzed Hantzsch three‐component condensation reaction of an aldehyde, α,β‐ketoester and ammonium acetate in acetonitrile at room temperature in good to excellent yields. The present protocol is applicable to wide range of substrates including aliphatic, aromatic and heterocyclic

  通过溴化锂催化的Hantzsch三组分醛，α，β-酮酸酯和乙酸铵在乙腈中于室温下进行的简单，廉价且有效的一锅合成，已完成。优异的产量。本协议适用于多种底物，包括脂族，芳族和杂环醛，可提供1,4-二氢吡啶。
• 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.