Bis(2-(acryloyloxy)ethyl) pyridine-3,5-dicarboxylate

• 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: Bis(2-(acryloyloxy)ethyl) pyridine-3,5-dicarboxylate
• 英文别名: bis(2-prop-2-enoyloxyethyl) pyridine-3,5-dicarboxylate
• 化学式: C₁₇H₁₇NO₈
• 分子量: 363.324
• InChiKey: AYODGZFULZDQNM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  26
• 可旋转键数：
  14
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  118
• 氢给体数：
  0
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  Bis(2-(acryloyloxy)ethyl) pyridine-3,5-dicarboxylate 、 碘甲烷 在 crude product 、 Acetonitrile ethyl acetate 作用下， 以 乙腈 为溶剂， 反应 16.0h， 以to give a red oil (632 mg, 1.25 mmol, yield: 91%)的产率得到3,5-bis((2-(acryloyloxy)ethoxy)carbonyl)-1-methylpyridin-1-ium iodide
  参考文献：
  名称：

  NOVEL CROSS-LINKERS FOR HYDROGELS, HYDROGELS INCLUDING THESE CROSS-LINKERS AND APPLICATIONS THEREOF

  摘要：

  本发明涉及新型的交联剂，特别是用于透明质酸水凝胶的交联剂，包括所述交联剂的对应水凝胶及其各种应用。该发明的交联剂是一种双或多功能的交联剂，包括或由具有3-6个碳原子的芳香或杂芳环系统组成，该环系统通过至少2个环位置的功能基团与至少2个末端基团耦合，能够与巯基或氨基形成共价键，特别是与巯基在巯基-烯丙基反应中形成共价键。交联剂可以带电或不带电。在特定的实施例中，末端基团通过酯或酰胺键与芳香或杂芳环系统的羧基耦合。更具体地说，该发明的交联剂是吡啶-3,5-二羧酸或其相应的吡啶盐衍生物，其中2个末端基团通过酯或酰胺键与吡啶或吡啶核心的羧基耦合，例如（2-氨基乙基）-氨基甲酰基）-1-甲基吡啶-1-ium-卤化物。

  公开号：

  US20150240037A1
• 作为产物：
  描述：

  3,5-吡啶二甲酸 在 氯化亚砜 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 6.0h， 生成 Bis(2-(acryloyloxy)ethyl) pyridine-3,5-dicarboxylate
  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

• "NOVEL CROSS-LINKERS FOR HYDROGELS, HYDROGELS INCLUDING THESE CROSS-LINKERS AND APPLICATIONS THEREOF"
  申请人：Max-Planck-Gesellschaft zur Förderung der Wissenschaften e.V.

  公开号：EP2900636A1

  公开（公告）日：2015-08-05
• US9644076B2
  申请人：——

  公开号：US9644076B2

  公开（公告）日：2017-05-09