pyridine-2,4,6-tricarbonyl dichloride | 77533-77-8

• 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: pyridine-2,4,6-tricarbonyl dichloride
• 英文别名: pyridine-2,4,6-tricarbonyl chloride；Pyridin-tricarbonsaeure-(2,4,6)-trichlorid；Pyridine-2,4,6-tricarbonyl chloride
• CAS: 77533-77-8
• 化学式: C₈H₂Cl₃NO₃
• 分子量: 266.468
• InChiKey: RGOGKQDMWCYPOV-UHFFFAOYSA-N

物化性质

• 熔点：
  89-91 °C(Solv: benzene (71-43-2); ligroine (8032-32-4))
• 沸点：
  364.9±37.0 °C(Predicted)
• 密度：
  1.646±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  15
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  64.1
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  N-羟乙基丙烯酰胺 、 pyridine-2,4,6-tricarbonyl dichloride 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 以22%的产率得到tris(2-acrylamidoethyl) pyridine-2,4,6-tricarboxylate
  参考文献：
  名称：

  Synthesis of Pyridine Acrylates and Acrylamides and Their Corresponding Pyridinium Ions as Versatile Cross-Linkers for Tunable Hydrogels

  摘要：

  A small library of cross-linkers for hydrogels was synthesized. The cross-linkers consisted of 2,6- and 3,5-diacylpyridine or 2,4,6-triacylpyridine as the core unit, which were tethered via ethylene glycol, amino ethanol, and 1,n-diamine spacers to terminal acrylate or acrylamide moieties. Esterification and amide formation of the terminal acryl units were found to be dependent on the ratio of NH/O in the spacer, the constitution pattern of the pyridine ring, and the total number of acryl groups. Thus, esters generally gave higher yields than amides decreasing with increasing number of NH in the spacer and with increasing number of acryl units. In the case of 3,5-diacylpyridine derivatives, these trends were less prominent as compared to the 2,6-diacylpyridine series, indicating that steric hindrance and unfavorable hydrogen bonding interaction of the spacers might influence the observed reactivity differences. The 3,5-diacylpyridines were converted to the N-methylpyridinium salts and selected members of both neutral and cationic 3,5-diacylpyridinium derivatives were submitted to hydrogelations with synthetic polymer poly(1-glycidylpiperazine) via aza-Michael addition and thiolated natural hyaluronan via thio-Michael reaction, respectively. Rheological properties of the resulting hydrogels were studied, revealing that both spacer type as well as charge affected elastic moduli and degree of swelling.

  DOI：

  10.1055/s-0033-1338614
• 作为产物：
  描述：

  2,4,6-三甲基吡啶 在 chromium(VI) oxide 、 氯化亚砜 、 硫酸 作用下， 生成 pyridine-2,4,6-tricarbonyl dichloride
  参考文献：
  名称：

  含吡啶的氮杂皇冠化合物的放射性核素双功能螯合剂的合成方法

  摘要：

  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。

  DOI：

  10.1055/s-0039-1691540

文献信息

• A Convenient One-Pot Synthesis of Arene-Centered Tris(thiazoline) Compounds
  作者：Bin Fu、Xuhong Lu、Qingqing Qi、Yumei Xiao、Nan Li

  DOI：10.3987/com-08-11586

  日期：——

  A simple and practical one-pot synthesis of novel enantiopure tris(thiazoline) compounds was documented. The desired products were obtained in moderate to good yields through three steps from commercially available 1, 3, 5-benzenetricarboxylic acid or 2, 4, 6-pyridinetricarboxylic acid, and chiral amino alcohols. Only one column chromatographic purification was needed for the three steps.
• Synthesis of Pyridine Acrylates and Acrylamides and Their Corresponding Pyridinium Ions as Versatile Cross-Linkers for Tunable Hydrogels
  作者：Günter Tovar、Heike Boehm、Sabine Laschat、Markus Mateescu、Isabell Nuss、Alexander Southan、Hayley Messenger、Seraphine Wegner、Julia Kupka、Monika Bach

  DOI：10.1055/s-0033-1338614

  日期：——

  A small library of cross-linkers for hydrogels was synthesized. The cross-linkers consisted of 2,6- and 3,5-diacylpyridine or 2,4,6-triacylpyridine as the core unit, which were tethered via ethylene glycol, amino ethanol, and 1,n-diamine spacers to terminal acrylate or acrylamide moieties. Esterification and amide formation of the terminal acryl units were found to be dependent on the ratio of NH/O in the spacer, the constitution pattern of the pyridine ring, and the total number of acryl groups. Thus, esters generally gave higher yields than amides decreasing with increasing number of NH in the spacer and with increasing number of acryl units. In the case of 3,5-diacylpyridine derivatives, these trends were less prominent as compared to the 2,6-diacylpyridine series, indicating that steric hindrance and unfavorable hydrogen bonding interaction of the spacers might influence the observed reactivity differences. The 3,5-diacylpyridines were converted to the N-methylpyridinium salts and selected members of both neutral and cationic 3,5-diacylpyridinium derivatives were submitted to hydrogelations with synthetic polymer poly(1-glycidylpiperazine) via aza-Michael addition and thiolated natural hyaluronan via thio-Michael reaction, respectively. Rheological properties of the resulting hydrogels were studied, revealing that both spacer type as well as charge affected elastic moduli and degree of swelling.
• 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。