吡啶-2,4,6-三羧酸三甲酯 | 25309-39-1

• 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: 吡啶-2,4,6-三羧酸三甲酯
• 英文名称: trimethyl pyridine-2,4,6-tricarboxylate
• CAS: 25309-39-1
• 化学式: C₁₁H₁₁NO₆
• 分子量: 253.211
• InChiKey: RJRVGJDUSQEIGG-UHFFFAOYSA-N

物化性质

• 熔点：
  148-150 °C
• 沸点：
  385.0±37.0 °C(Predicted)
• 密度：
  1.289±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  18
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  91.8
• 氢给体数：
  0
• 氢受体数：
  7

安全信息

• 危险性防范说明：
  P261,P305+P351+P338
• 危险性描述：
  H302,H315,H319,H335

反应信息

• 作为反应物：
  描述：

  吡啶-2,4,6-三羧酸三甲酯 在 一水合肼 、 溶剂黄146 作用下， 以 乙醇 为溶剂， 反应 9.0h， 生成 N’-2,N’-4,N’-6-tris(4-(dimethylamino)benzylidene)pyridine-2,4,6-tricarbohydrazide
  参考文献：
  名称：

  Novel pyridine-2,4,6-tricarbohydrazide derivatives: Design, synthesis, characterization and in vitro biological evaluation as α- and β-glucosidase inhibitors

  摘要：

  A range of novel pyridine 2,4,6-tricarbohydrazide derivatives (4a-4h) were synthesized and its biological inhibition towards alpha- and beta-glucosidases was studied. Most of the compounds demonstrate to be active against a-glucosidase, and quite inactive/completely inactive against beta-glucosidase. A number of compounds were found to be more active against alpha-glucosidase than the reference compound acarbose (IC50 38.25 +/- 0.12 mu M); being compound 4d with the p-hydroxy phenyl motive the most active (IC50 20.24 +/- 0.72 mu M). Molecular modeling studies show the interactions of compound 4d with the active site of target alpha-glucosidase kinase. (C) 2014 Elsevier Inc. All rights reserved.

  DOI：

  10.1016/j.bioorg.2014.10.007
• 作为产物：
  描述：

  2,4-二乙基-6-甲基-吡啶 在 盐酸 、 permanganate(VII) ion 作用下， 生成 吡啶-2,4,6-三羧酸三甲酯
  参考文献：
  名称：

  Eckert; Loria, Monatshefte fur Chemie, 1917, vol. 38, p. 239

  摘要：

  DOI：

文献信息

• Synthesis of ubiquinone and menaquinone analogues by oxidative demethylation of alkenylhydroquinone ethers with argentic oxide or ceric ammonium nitrat
  作者：L. Syper、K. Kloc、J. Mz.xl;lochowski

  DOI：10.1016/0040-4020(80)85034-4

  日期：1980.1

  It was found that alkenylhydroquinone ethers demethylated with argentic oxide or ceric ammonium nitrate in the presence of 2,4,6-pyridinetricarboxylic acid as a catalyst and afforded ubiquinone-2, menaquinone-2 and their analogs in yields of 53 to 89%. The new approach to the synthesis of starting alkenylhydroquinone ethers as well as 2,4,6-pyridinetricarboxylic acid and its derivatives has been reported

  发现在2,4,6-吡啶三甲酸作为催化剂的存在下，用氧化亚铁或硝酸铈铵对甲基化的烯基对苯二酚醚进行脱甲基，得到的泛醌2，甲萘醌2及其类似物的产率为53％至89％。已经报道了合成起始烯基氢醌醚以及2,4,6-吡啶三羧酸及其衍生物的新方法。
• Syntheses and Properties of<i>N</i>-Fluoropyridinium Salts
  作者：Teruo Umemoto、Kikuko Harasawa、Ginjiro Tomizawa、Kosuke Kawada、Kyoichi Tomita

  DOI：10.1246/bcsj.64.1081

  日期：1991.4

  counter anion displacement reactions of unstable pyridine-F2 compounds, fluorination of salts of pyridines with protonic acids or silyl esters with F2, and/ or fluorination of Lewis acid complexes of pyridines. The scope of each method was examined in detail. Each of the N-fluoropyridinium salts was assigned as the first stable 1 : 1 salt structure of the pyridine nucleus and halogen atom on the basis

  各种稳定的 N-氟吡啶鎓盐，带有非亲核性或弱亲核性抗衡阴离子，例如 TfO−、FSO3−、BF4−、SbF6−、ClO4−、CH3SO3− 等，或带有给电子或吸电子取代基合成了吡啶环上的化合物并研究了它们的性质。还合成了 N-氟吡啶鎓-2-磺酸盐、N-氟喹啉鎓三氟甲磺酸盐和高度受阻的 N-氟-2,6-二-叔丁基吡啶鎓盐。它们是通过不稳定的吡啶-F2 化合物的抗衡阴离子置换反应、吡啶盐与质子酸或甲硅烷基酯与 F2 的氟化和/或吡啶的路易斯酸络合物的氟化来合成的。详细检查了每种方法的范围。每种 N-氟吡啶鎓盐都被指定为第一个稳定的 1：1 基于光谱和元素分析的吡啶核和卤素原子的盐结构。稳定性取决于抗衡阴离子的亲核性或碱性以及环的电子性质或位置...
• Factors Influencing the Course of the Macrocyclization ofα,ω-Diamines with Esters ofα,ω-Dicarboxylic Acids
  作者：Dorota Gryko、Daniel T. Gryko、Hanna Sierzputowska-Gracz、Piotr Pi??tek、Janusz Jurczak

  DOI：10.1002/hlca.200490004

  日期：2004.1

  The efficient synthesis of eight new macrocyclic amides (lactams) via reaction of diesters with diamines under normal dilution conditions is described. The role of intermolecular H-bond formation and steric hindrance is discussed based on 1H- and 15N-NMR studies of appropriate model compounds. Principles for the optimal choice of esters that can be efficiently transformed into diamides have been developed

  描述了通过二酯与二胺在正常稀释条件下的反应有效合成八种新的大环酰胺（内酰胺）。基于适当模型化合物的1 H-和15 N-NMR研究，讨论了分子间H键形成和位阻的作用。已经开发出可以有效转化为二酰胺的最佳选择酯的原理。
• Synthetic Approaches to the Bifunctional Chelators for Radio­nuclides Based On Pyridine-Containing Azacrown Compounds
  作者：Anastasia D. Zubenko、Anna A. Shchukina、Olga A. Fedorova

  DOI：10.1055/s-0039-1691540

  日期：——

  Synthetic ways to introduce functional groups (CO2Me, CO2H, OCH2CO2H, OCH2C≡CH, CH2OH, CH2Cl, CH2N3) into the pyridine ring of pyridine-containing azacrown compounds are described. These groups were introduced at position-4 of the pyridine ring, while keeping the macrocyclic carboxylate groups available for metal chelation. The derivatives were obtained by macrocyclization reaction of 4-substituted

  合成的方式引进的官能团（CO 2 Me中，CO 2 H，OCH 2 CO 2 H，OCH 2 C≡CH，CH 2 OH，CH 2氯，CH 2 Ñ 3）描述了将含吡啶的氮杂冠化合物引入吡啶环中的方法。这些基团被引入吡啶环的4位，同时保持大环羧酸盐基团可用于金属螯合。所述衍生物通过4-取代的三甲基吡啶-2,4,6-三羧酸酯的大环化反应或通过修饰大环吡啶片段中的甲酯基而获得。通过与不同的载体生物分子缀合，可以将获得的衍生物用于制备放射治疗剂，以将药物靶向性递送至癌细胞而不会损害健康组织。
• Remote electronic control in asymmetric cyclopropanation with chiral Ru-pybox catalysts
  作者：Soon-Bong Park、Kiyoshi Murata、Hideki Matsumoto、Hisao Nishiyama

  DOI：10.1016/0957-4166(95)00324-i

  日期：1995.10

  Electronic control by remote substitents far from a catalytically active center was found in an asymmetric cyclopropanation of olefins and diazoacetates with the ruthenium catalysts of chiral 4-substituted bis(4′-isopropyloxazolinyl)pyridine, 4-X-pybox. It was found that electron-withdrawing groups increase the catalytic activity, but electron-donating groups decrease it. The enantiomer ratios of the

  在远距离的取代基催化活性中心进行电子控制的过程中，发现烯烃和重氮乙酸酯的不对称环丙烷化是通过手性4-取代的双（4'-异丙基恶唑啉基）吡啶，4-X-pybox的钌催化剂进行的。发现吸电子基团增加了催化活性，但是给电子基团降低了它的催化活性。具有吸电子基团X ＝ Cl和COOMe的产物环丙烷的对映体比率高于具有供电子基团X ＝ OMe和NMe 2的对映异构体比率。乙基和对映异构体比率升-薄荷基环丙烷被朝向哈米特corelated σ对位值，得到正ρ值，为0.365反式-乙基酯，为0.486顺-乙基酯，为0.517反式-升-薄荷基酯，和0.517为顺式-升-薄荷基酯。但是，产品的反式：顺式比例不受其取代基ca的影响。90:10重氮乙酸乙酯和约。96：4升-薄荷基重氮基。分子内环丙烷化显然给出了类似的趋势。