pyridine-2,6-diylbis(methylene) diacrylate

• 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-2,6-diylbis(methylene) diacrylate
• 英文别名: [6-(Prop-2-enoyloxymethyl)pyridin-2-yl]methyl prop-2-enoate；[6-(prop-2-enoyloxymethyl)pyridin-2-yl]methyl prop-2-enoate
• 化学式: C₁₃H₁₃NO₄
• 分子量: 247.251
• InChiKey: ATTHEJRCDHEDLT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  18
• 可旋转键数：
  8
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.15
• 拓扑面积：
  65.5
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  吡啶-2.6-二羧酸二甲酯 在 sodium tetrahydroborate 、 三乙胺 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 11.75h， 生成 pyridine-2,6-diylbis(methylene) diacrylate
  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

文献信息

• Curable liquids and inkjet inks for food packaging applications
  申请人：Agfa Graphics N.V.

  公开号：EP2604663A1

  公开（公告）日：2013-06-19

  A radiation curable liquid including at least one free radical polymerizable monomer or oligomer, at least one diffusion hindered acetalysation catalyst and at least one diffusion hindered hydroxyl containing compound. The radiation curable liquid applied to a substrate prevents migration of very low viscous monomers, such as vinyl ether acrylate monomers, into the substrate.

  一种辐射固化液，包括至少一种可自由基聚合的单体或低聚物、至少一种扩散受阻乙醛化催化剂和至少一种扩散受阻含羟基化合物。将辐射固化液涂在基材上，可防止粘度极低的单体（如丙烯酸乙烯基醚单体）迁移到基材中。
• EP2604663B1
  申请人：——

  公开号：EP2604663B1

  公开（公告）日：2017-08-09
• US9718971B2
  申请人：——

  公开号：US9718971B2

  公开（公告）日：2017-08-01
• [EN] CURABLE LIQUIDS AND INKJET INKS FOR FOOD PACKAGING APPLICATIONS<br/>[FR] LIQUIDES DURCISSABLES ET ENCRES À JET D'ENCRE POUR DES APPLICATIONS D'EMBALLAGE ALIMENTAIRE
  申请人：AGFA GRAPHICS NV

  公开号：WO2013087427A1

  公开（公告）日：2013-06-20

  A radiation curable liquid including at least one free radical polymerizable monomer or oligomer, at least one diffusion hindered acetalysation catalyst and at least one diffusion hindered hydroxyl containing compound. The radiation curable liquid applied to a substrate prevents migration of very low viscous monomers, such as vinyl ether acrylate monomers, into the substrate.
• 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.