4-(4-甲氧基苯基)-2,6-二甲基吡啶-3,5-二羧酸二甲酯 | 119789-09-2

• 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
• 中文名称: 4-(4-甲氧基苯基)-2,6-二甲基吡啶-3,5-二羧酸二甲酯
• 英文名称: 3,5-dimethoxycarbonyl-4-(4-methoxyphenyl)-2,6-dimethylpyridine
• 英文别名: dimethyl 4-(4-methoxyphenyl)-2,6-dimethylpyridine-3,5-dicarboxylate
• CAS: 119789-09-2
• 化学式: C₁₈H₁₉NO₅
• 分子量: 329.353
• InChiKey: NKKFNUJHUBOXNM-UHFFFAOYSA-N

物化性质

• 溶解度：
  >49.4 [ug/mL]

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：
  0.277
• 拓扑面积：
  74.7
• 氢给体数：
  0
• 氢受体数：
  6

安全信息

• 海关编码：
  2933399090

反应信息

• 作为反应物：
  描述：

  氨基硫脲 、 4-(4-甲氧基苯基)-2,6-二甲基吡啶-3,5-二羧酸二甲酯 在 吡啶 作用下， 以 乙醇 为溶剂， 以68%的产率得到2,2'-(4-(4-methoxyphenyl)-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：

  4-甲氧基苄醇 在 sodium nitrate 、 3-(N,N-dimethyldodecylammonium)propanesulfonic acid hydrogen sulfate 、 ammonium acetate 作用下， 反应 1.0h， 生成 4-(4-甲氧基苯基)-2,6-二甲基吡啶-3,5-二羧酸二甲酯
  参考文献：
  名称：

  通过串联氧化过程直接从醇开始的 Hantzsch 反应

  摘要：

  布朗斯台德酸性离子液体 3-(N,N-二甲基十二烷基铵) 丙磺酸硫酸氢盐 ([DDPA][HSO4]) 已成功应用于催化芳香醇与 NaNO3 的顺序氧化，然后与二羰基化合物和铵缩合醋酸盐。Hantzsch 1,4-二氢吡啶的相应吡啶类似物可以通过多组分反应以高产率获得作为主要产物。目前在 Hantzsch 反应中使用醇代替醛的工作是 Hantzsch 1,4-二氢吡啶相应吡啶类似物的经典合成的有效且绿色的替代方法。

  DOI：

  10.1155/2017/5646908

文献信息

• Reactivity of 1,4-Dihydropyridines toward Alkyl, Alkylperoxyl Radicals, and ABTS Radical Cation
  作者：C. López-Alarcón、P. Navarrete、C. Camargo、J. A. Squella、L. J. Núñez-Vergara

  DOI：10.1021/tx025579o

  日期：2003.2.1

  tested for potential scavenger effects toward alkyl, alkylperoxyl radicals, and ABTS radical cation in aqueous media at pH 7.4. Kinetic rate constants were assessed either by UV/vis spectroscopy or GC/MS techniques. Tested compounds reacted faster toward alkylperoxyl radicals and ABTS radical cation than alkyl ones. N-Ethyl-substituted DHPs showed the lowest reactivity. Kinetic results were compared with

  合成了一系列在二氢吡啶环中具有仲氮或叔氮的C4取代的1,4-二氢吡啶（DHP）。测试了所有这些化合物以及一些商业DHP衍生物在pH 7.4的水性介质中对烷基，烷基过氧自由基和ABTS自由基阳离子的潜在清除作用。动力学速率常数通过紫外/可见光谱或GC / MS技术进行评估。被测化合物对烷基过氧自由基和ABTS自由基阳离子的反应比烷基化合物更快。N-乙基取代的DHP显示最低的反应活性。动力学结果与trolox或尼索地平进行了比较。使用氘动力学同位素效应研究，我们证明了DHP环1位的氢参与了拟议的机理。在烷基的情况下，这一事实最为明显。在所有情况下，各自的吡啶衍生物被检测为反应的主要产物。
• Microwave-Assisted Oxidative Aromatization of Hantzsch 1,4-Dihydro­pyridines using Manganese Dioxide
  作者：Mark Bagley、M. Lubinu

  DOI：10.1055/s-2006-926407

  日期：2006.4

  4-Aryl- and 4-alkyl-1,4-dihydropyridines, prepared by microwave-assisted Hantzsch reaction, are readily and efficiently aromatized in only one minute using commercial manganese dioxide in the absence of an inorganic support at 100 °C under microwave irradiation. This rapid procedure is more efficient than microwave-assisted aromatization using Pd/C, iodine or o-iodoxybenzoic acid (IBX) and gives the dehydrogenated or 4-dealkylated product in 91-100% yield (13 examples).

  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）。
• 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。