N-[bis[diethoxy(oxido)phosphaniumyl]methyl]-2-[2-[bis[diethoxy(oxido)phosphaniumyl]methylcarbamoyl]prop-2-enoxymethyl]prop-2-enamide | 1422155-22-3

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 有机膦酸及其衍生物
• 英文名称: N-[bis[diethoxy(oxido)phosphaniumyl]methyl]-2-[2-[bis[diethoxy(oxido)phosphaniumyl]methylcarbamoyl]prop-2-enoxymethyl]prop-2-enamide
• CAS: 1422155-22-3
• 化学式: C₂₆H₅₂N₂O₁₅P₄
• 分子量: 756.598
• InChiKey: MUKGYQLKDWPVTL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.1
• 重原子数：
  47
• 可旋转键数：
  28
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.77
• 拓扑面积：
  234
• 氢给体数：
  2
• 氢受体数：
  15

反应信息

• 作为反应物：
  描述：

  N-[bis[diethoxy(oxido)phosphaniumyl]methyl]-2-[2-[bis[diethoxy(oxido)phosphaniumyl]methylcarbamoyl]prop-2-enoxymethyl]prop-2-enamide 在 三甲基溴硅烷 、 甲醇 作用下， 以 二氯甲烷 为溶剂， 反应 4.0h， 以58%的产率得到[[2-[2-(Diphosphonomethylcarbamoyl)prop-2-enoxymethyl]prop-2-enoylamino]-phosphonomethyl]phosphonic acid
  参考文献：
  名称：

  Synthesis and evaluations of bisphosphonate-containing monomers for dental materials

  摘要：

  AbstractTwo new bismethacrylamide (1, 2) and two new methacrylamide (3, 4) dental monomers were synthesized. In each group, one monomer contains a bisphosphonate group, the other a bisphosphonic acid group. Monomer 1 and 3 were synthesized by amidation of 2‐(2‐chlorocarbonyl‐allyloxymethyl)‐acryloylchloride and methacryloyl chloride with tetraethyl aminomethyl‐bis(phosphonate) and converted to the bisphosphonic acid monomers 2 and 4 by hydrolysis with trimethylsilyl bromide. Monomer 1 (m.p.: 71–72 °C), monomer 3 (33–34 °C), and monomer 4 (no m.p.) were obtained as white solids and monomer 2 a viscous liquid, soluble in water. Homopolymerization of 1 gave crosslinked polymers, indicating its low cyclization tendency. The photopolymerization studies indicated that its copolymerizability with 2,2‐bis[4‐(2‐hydroxy‐3‐methacryloyloxy propyloxy) phenyl] propane and 2‐hydroxyethyl methacrylate (HEMA) without changing their rates and conversions significantly means that it could be used as a biocompatible crosslinker. Although monomer 2 showed low polymerizability, because of its good performance in terms of solubility, hydrolytic stability, hydroxyapatite interaction, acidity, and copolymerizability with HEMA, it shows potential to be used in self‐etching dental adhesives. The thermal polymerization of 3 resulted in soluble polymers and evaluation of monomer 4 in terms of solubility, acidity, and copolymerizability with HEMA indicated its potential as an adhesive monomer. © 2012 Wiley Periodicals, Inc. J Polym Sci Part A: Polym Chem, 2012

  DOI：

  10.1002/pola.26305
• 作为产物：
  描述：

  di-tert-butyl 2,2'-[oxybis(methylene)]diacrylate 在 吡啶 、 草酰氯 、 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 生成 N-[bis[diethoxy(oxido)phosphaniumyl]methyl]-2-[2-[bis[diethoxy(oxido)phosphaniumyl]methylcarbamoyl]prop-2-enoxymethyl]prop-2-enamide
  参考文献：
  名称：

  Synthesis and evaluations of bisphosphonate-containing monomers for dental materials

  摘要：

  AbstractTwo new bismethacrylamide (1, 2) and two new methacrylamide (3, 4) dental monomers were synthesized. In each group, one monomer contains a bisphosphonate group, the other a bisphosphonic acid group. Monomer 1 and 3 were synthesized by amidation of 2‐(2‐chlorocarbonyl‐allyloxymethyl)‐acryloylchloride and methacryloyl chloride with tetraethyl aminomethyl‐bis(phosphonate) and converted to the bisphosphonic acid monomers 2 and 4 by hydrolysis with trimethylsilyl bromide. Monomer 1 (m.p.: 71–72 °C), monomer 3 (33–34 °C), and monomer 4 (no m.p.) were obtained as white solids and monomer 2 a viscous liquid, soluble in water. Homopolymerization of 1 gave crosslinked polymers, indicating its low cyclization tendency. The photopolymerization studies indicated that its copolymerizability with 2,2‐bis[4‐(2‐hydroxy‐3‐methacryloyloxy propyloxy) phenyl] propane and 2‐hydroxyethyl methacrylate (HEMA) without changing their rates and conversions significantly means that it could be used as a biocompatible crosslinker. Although monomer 2 showed low polymerizability, because of its good performance in terms of solubility, hydrolytic stability, hydroxyapatite interaction, acidity, and copolymerizability with HEMA, it shows potential to be used in self‐etching dental adhesives. The thermal polymerization of 3 resulted in soluble polymers and evaluation of monomer 4 in terms of solubility, acidity, and copolymerizability with HEMA indicated its potential as an adhesive monomer. © 2012 Wiley Periodicals, Inc. J Polym Sci Part A: Polym Chem, 2012

  DOI：

  10.1002/pola.26305

文献信息

• Synthesis and evaluations of bisphosphonate-containing monomers for dental materials
  作者：Burcin Akgun、Duygu Avci

  DOI：10.1002/pola.26305

  日期：2012.12.1

  AbstractTwo new bismethacrylamide (1, 2) and two new methacrylamide (3, 4) dental monomers were synthesized. In each group, one monomer contains a bisphosphonate group, the other a bisphosphonic acid group. Monomer 1 and 3 were synthesized by amidation of 2‐(2‐chlorocarbonyl‐allyloxymethyl)‐acryloylchloride and methacryloyl chloride with tetraethyl aminomethyl‐bis(phosphonate) and converted to the bisphosphonic acid monomers 2 and 4 by hydrolysis with trimethylsilyl bromide. Monomer 1 (m.p.: 71–72 °C), monomer 3 (33–34 °C), and monomer 4 (no m.p.) were obtained as white solids and monomer 2 a viscous liquid, soluble in water. Homopolymerization of 1 gave crosslinked polymers, indicating its low cyclization tendency. The photopolymerization studies indicated that its copolymerizability with 2,2‐bis[4‐(2‐hydroxy‐3‐methacryloyloxy propyloxy) phenyl] propane and 2‐hydroxyethyl methacrylate (HEMA) without changing their rates and conversions significantly means that it could be used as a biocompatible crosslinker. Although monomer 2 showed low polymerizability, because of its good performance in terms of solubility, hydrolytic stability, hydroxyapatite interaction, acidity, and copolymerizability with HEMA, it shows potential to be used in self‐etching dental adhesives. The thermal polymerization of 3 resulted in soluble polymers and evaluation of monomer 4 in terms of solubility, acidity, and copolymerizability with HEMA indicated its potential as an adhesive monomer. © 2012 Wiley Periodicals, Inc. J Polym Sci Part A: Polym Chem, 2012