dimethyl 4-(4-chlorophenyl)-2,6-dimethylpyridine-3,5-dicarboxylate | 201161-20-8

• 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-(4-chlorophenyl)-2,6-dimethylpyridine-3,5-dicarboxylate
• 英文别名: 2,6-dimethyl-4-(4'-chlorophenyl)-3,5-pyridinedicarboxylic acid dimethyl ester；2,6-dimethyl-4-(4-chlorophenyl)-3,5-pyridinedicarboxylic acid dimethyl ester；dimethyl 4-(4'-chlorophenyl)-2,6-dimethylpyridine-3,5-dicarboxylate；dimethyl 4-(4-chlorophenyl)-2,6-dimethyl-3,5-pyridinedicarboxylate；2,6-dimethyl-3,5-dimethoxycarbonyl-4-(p-chlorophenyl)pyridine；3,5-dimethoxycarbonyl-4-(4-chlorophenyl)-2,6-dimethylpyridine
• CAS: 201161-20-8
• 化学式: C₁₇H₁₆ClNO₄
• 分子量: 333.771
• InChiKey: YFRKKIOJROOZKZ-UHFFFAOYSA-N

物化性质

• 熔点：
  137-139 °C
• 沸点：
  416.8±45.0 °C(Predicted)
• 密度：
  1.244±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  23
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  65.5
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  氨基硫脲 、 dimethyl 4-(4-chlorophenyl)-2,6-dimethylpyridine-3,5-dicarboxylate 在 吡啶 作用下， 以 乙醇 为溶剂， 以62%的产率得到2,2'-(4-(4-chlorophenyl)-2,6-dimethylpyridine-3,5-dicarbonyl)bis(hydrazine-1-carbothioamide)
  参考文献：
  名称：

  Microwave Assisted Synthesis of Some Pyridine Derivatives Containing Mercaptotriazole and Thiazolidinone as a New Class of Antimicrobial Agents

  摘要：

  A fast and facile procedure for the synthesis of pyridomereaptotriazole 4a-e and pyridothiazolidinone 5a-e is being reported starting from diliydropyridine 1a-e. Subsequent oxidation with nitrating mixture (HNO3/H2SO4) produced the anticipated 2,6-dimethylpyridine derivatives 2a-e, which were subsequently condensed with thiosemicarbazide in ethanol to produce the key intermediate 2,2'-[4(4-substituted phenyl)- 2,6-dimethylpyridine-3,5-diyl]dicarbonyldihydrazine carbothioamides 3a-e. In the final step pyridomercaptotriazole derivatives 4a-e were synthesized by treating 3a-e in alkaline media. In parallel pyridothiazolidinone derivatives 5a-e were obtained by the reaction of 3a-e with ClCH2COOH/CH3COONa. All the reactions were carried out on microwave irradiation in good yield with short time. The structures of all the compounds have been confirmed on the basis of their analytical, IR, H-1 NMR, and Mass spectral data (Tables I and II). The potent antimicrobial effects of the synthesized compounds were also investigated.

  DOI：

  10.1080/10426500701557138
• 作为产物：
  描述：

  乙酰乙酸甲酯 在 manganese(IV) oxide 、 ammonium hydroxide 作用下， 以 二氯甲烷 为溶剂， 反应 0.19h， 生成 dimethyl 4-(4-chlorophenyl)-2,6-dimethylpyridine-3,5-dicarboxylate
  参考文献：
  名称：

  Microwave-Assisted Oxidative Aromatization of Hantzsch 1,4-Dihydro­pyridines using Manganese Dioxide

  摘要：

  4-芳基和4-烷基-1,4-二氢吡啶通过微波辅助的Hantzsch反应制备，在没有无机支持的情况下，使用商业锰氧化物在100°C的微波照射下，仅需一分钟即可高效芳香化。此快速程序比使用Pd/C、碘或邻碘代苯甲酸（IBX）的微波辅助芳香化更为高效，脱氢或4-去烷基的产物产率为91-100%（13个示例）。

  DOI：

  10.1055/s-2006-926407

文献信息

• Multicomponent Domino Cyclization-Oxidative Aromatization on a Bifunctional Pd/C/K-10 Catalyst: An Environmentally Benign Approach toward the Synthesis of Pyridines
  作者：Béla Török、Omar De Paolis、Jonathan Baffoe、Shainaz Landge

  DOI：10.1055/s-0028-1083177

  日期：——

  A one-pot synthesis of substituted pyridines via a domino cyclization-oxidative aromatization (dehydrogenation) approach is described. The process is based on the use of a new bifunctional noble metal-solid acid catalyst, Pd/C/K-10 montmorillonite and microwave irradiation. The cyclization readily takes place on the strong solid acid while palladium dehydrogenates the dihydropyridine intermediates to the desired products.

  描述了一种通过多步环化-氧化芳构化（脱氢）方法合成取代吡啶的一锅法。该过程基于一种新型双功能贵金属-固体酸催化剂Pd/C/K-10蒙脱石和微波辐射的使用。环化反应在强固体酸上顺利进行，而钯则将二氢吡啶中间体脱氢转化为所需产物。
• An Efficient Transition-Metal-Chloride/Sodium-Nitrite/TEMPO Catalytic System for Aerobic Oxidative Aromatisation of Hantzsch 1,4-Dihydropyridines
  作者：Bin-Hui Lou、Shu-Bin Chen、Jian Wang、Ying Chen、Jing-Hua Li

  DOI：10.3184/174751913x13701832537930

  日期：2013.7

  A facile and efficient transition-metal-chloride/sodium-nitrite/TEMPO catalytic system for aerobic oxidative aromati-sation of Hantzsch 1,4-dihydropyridines in high yields under mild conditions is described.

  本文介绍了一种简便高效的过渡金属氯化物/亚硝酸钠/TEMPO 催化系统，该系统可在温和的条件下有氧氧化芳香化汉茨奇 1,4-二氢吡啶并获得高产率。
• New Strategy for the Oxidation of Hantzsch 1,4‐Dihydropyridines and Dihydropyrido[2,3‐d]pyrimidines Catalyzed by DMSO under Aerobic Conditions
  作者：Anil Saini、Sanjay Kumar、Jagir S. Sandhu

  DOI：10.1080/00397910701410442

  日期：2007.7

  novel metal‐salt‐oxidant‐free, efficient, and economical method for the oxidation of Hantzsch 1,4‐dihydropyridines that uses aerial oxygen and solvent‐grade dimethylsulfoxide is described. Also, the synthesis of pyrido[2,3‐d]pyrimidines is achieved from in situ oxidation of dihydropyrido[2,3‐d]pyrimidines that arise from the reaction of 6‐aminouracils and cyano olefins in dimethylsulfoxide.

  摘要描述了一种使用空气氧和溶剂级二甲基亚砜氧化 Hantzsch 1,4-二氢吡啶的新型无金属盐氧化剂、高效且经济的方法。此外，吡啶并[2,3-d]嘧啶的合成是通过二氢吡啶并[2,3-d]嘧啶在二甲亚砜中的反应产生的二氢吡啶并[2,3-d]嘧啶的原位氧化来实现的。
• 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
• Oxidative aromatization of Hantzsch 1,4-dihydropyridines by cupric bromide under mild heterogeneous condition
  作者：Forid Saikh、Rimpa De、Somnath Ghosh

  DOI：10.1016/j.tetlet.2014.09.025

  日期：2014.11

  A mild heterogeneous oxidizing agent, cupric bromide has been utilized for the oxidative aromatization of Hantzsch 1,4-dihydropyridines to the corresponding pyridine derivatives in excellent yields with the isolation of products by simple work-up procedure.

  一种温和的非均相氧化剂溴化铜已被用于Hantzsch 1,4-二氢吡啶氧化芳构化成相应的吡啶衍生物，并以极高的收率通过简单的后处理程序分离出产物。