[3-[3-[[Diethoxy(oxido)phosphaniumyl]methylamino]propanoyloxy]-2-hydroxypropyl] 2-methylprop-2-enoate | 1345977-44-7

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: [3-[3-[[Diethoxy(oxido)phosphaniumyl]methylamino]propanoyloxy]-2-hydroxypropyl] 2-methylprop-2-enoate
• 英文别名: [3-[3-[[diethoxy(oxido)phosphaniumyl]methylamino]propanoyloxy]-2-hydroxypropyl] 2-methylprop-2-enoate
• CAS: 1345977-44-7
• 化学式: C₁₅H₂₈NO₈P
• 分子量: 381.363
• InChiKey: PMQZEOSPPMMPEV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.1
• 重原子数：
  25
• 可旋转键数：
  16
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.73
• 拓扑面积：
  126
• 氢给体数：
  2
• 氢受体数：
  9

反应信息

• 作为产物：
  描述：

  二乙基氨基甲烷膦酸酯 、 3-(丙烯酰氧基)-2-羟基丙基甲基丙烯酸酯 反应 24.0h， 生成 [3-[3-[[Diethoxy(oxido)phosphaniumyl]methylamino]propanoyloxy]-2-hydroxypropyl] 2-methylprop-2-enoate
  参考文献：
  名称：

  Synthesis and polymerizations of six aminophosphonate-containing methacrylates

  摘要：

  AbstractTwo different groups of novel aminophosphonate‐containing methacrylates were synthesized. The route to the first group involves reactions of ethyl α‐bromomethacryate (EBBr) and t‐butyl α‐bromomethacryate (TBBr) with diethyl aminomethylphosphonate and diethyl 2‐aminoethylphosphonate. Bulk and solution polymerizations at 60–80 °C with 2,2′‐azobis(isobutyronitrile) (AIBN) gave crosslinked or soluble polymers depending on monomer structure and polymerization conditions. Increasing bulkiness from ethyl to t‐butyl decreases the polymerization rate, correlated well with the chemical shift differences of double bond carbons and consistent with the lower molecular weights of t‐butyl ester polymers (Mn = 1800–7900 vs. 50,000–72,000). The route to the second group involves the Michael addition reaction between diethyl aminomethylphosphonate and diethyl 2‐aminoethylphosphonate with 3‐(acryloyloxy)‐2‐hydroxypropyl methacrylate (AHM) to give secondary amines. The photopolymerization using differential scanning calorimeter showed that these monomers have similar or higher reactivities than AHM, even though AHM has two double bonds. The high rates of polymerization of these monomers were attributed to both hydrogen bonding interactions due to additional NH groups as well as chain transfer reactions. All the homopolymers obtained produced char (17–35%) on combustion. © 2011 Wiley Periodicals, Inc. J Polym Sci Part A: Polym Chem, 2011.

  DOI：

  10.1002/pola.24965

文献信息

• Synthesis and polymerizations of six aminophosphonate-containing methacrylates
  作者：Zeynep Sarayli Bilgici、Oznur Demir Ordu、Mehtap Isik、Duygu Avci

  DOI：10.1002/pola.24965

  日期：2011.12.1

  AbstractTwo different groups of novel aminophosphonate‐containing methacrylates were synthesized. The route to the first group involves reactions of ethyl α‐bromomethacryate (EBBr) and t‐butyl α‐bromomethacryate (TBBr) with diethyl aminomethylphosphonate and diethyl 2‐aminoethylphosphonate. Bulk and solution polymerizations at 60–80 °C with 2,2′‐azobis(isobutyronitrile) (AIBN) gave crosslinked or soluble polymers depending on monomer structure and polymerization conditions. Increasing bulkiness from ethyl to t‐butyl decreases the polymerization rate, correlated well with the chemical shift differences of double bond carbons and consistent with the lower molecular weights of t‐butyl ester polymers (Mn = 1800–7900 vs. 50,000–72,000). The route to the second group involves the Michael addition reaction between diethyl aminomethylphosphonate and diethyl 2‐aminoethylphosphonate with 3‐(acryloyloxy)‐2‐hydroxypropyl methacrylate (AHM) to give secondary amines. The photopolymerization using differential scanning calorimeter showed that these monomers have similar or higher reactivities than AHM, even though AHM has two double bonds. The high rates of polymerization of these monomers were attributed to both hydrogen bonding interactions due to additional NH groups as well as chain transfer reactions. All the homopolymers obtained produced char (17–35%) on combustion. © 2011 Wiley Periodicals, Inc. J Polym Sci Part A: Polym Chem, 2011.