N-[(2-hydroxy-3-phenoxy)propyl]-(3-aminopropyl)triethoxysilane | 791783-26-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: N-[(2-hydroxy-3-phenoxy)propyl]-(3-aminopropyl)triethoxysilane
• 英文别名: 1-Phenoxy-3-(3-triethoxysilylpropylamino)propan-2-ol；1-phenoxy-3-(3-triethoxysilylpropylamino)propan-2-ol
• CAS: 791783-26-1
• 化学式: C₁₈H₃₃NO₅Si
• 分子量: 371.549
• InChiKey: ZVTKSQAWVPKWMX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.45
• 重原子数：
  25
• 可旋转键数：
  15
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  69.2
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  3-氨基丙基三乙氧基硅烷 、 苯基缩水甘油醚 反应 24.0h， 生成 N-[(2-hydroxy-3-phenoxy)propyl]-(3-aminopropyl)triethoxysilane
  参考文献：
  名称：

  Poly(silsesquioxanes) derived from the hydrolytic condensation of organotrialkoxysilanes containing hydroxyl groups

  摘要：

  Organotrialkoxysilanes containing secondary hydroxyl groups were synthesized by reacting 1 mole of (3-aminopropyl)triethoxysilane (APS) with 1 or 2 mole of phenylglycidylether (PGE). Resulting products, APS-PGE and APS-PGE(2), respectively, were subjected to hydrolytic condensation at 50 degreesC during 24 h. For APS-PGE, the reaction was performed using a molar ratio [H2O]/Si = 3, without addition of an external catalyst. For APS-PGE(2), the reaction was catalyzed by HCOOH or NaOH. Resulting poly(silsesquioxanes) (PSSO) were characterized by size exclusion chromatography, Fourier-transformed infrared spectroscopy and matrix-assisted ultraviolet laser desorption/ionization time-of-flight mass spectrometry (UV-MALDI-TOF MS). PSSO derived from APS-PGE and APS-PGE(2), catalyzed by HCOOH, exhibited a relatively narrow distribution of polyhedral structures. This constitutes a simple one-step synthesis of polyhedral oligomeric silsesquioxanes (POSS) functionalized with amine and/or hydroxyl groups. The directionality of the reaction pathway towards the formation of polyhedral structures was ascribed to the formation of intramolecular Si-O-C bonds through the reaction of SiOEt or SiOH groups with secondary hydroxyl groups. Intramolecular Si-O-C bonds were found in the structures of APS-PGE and APS-PGE(2), and in most of the species of the PSSO obtained from the NaOH-catalyzed reaction of APS-PGE(2). A small fraction of surviving Si-O-C bonds was also found in the polyhedral structures of the PSSO derived from the hydrolytic condensation of APS-PGE and APS-PGE(2) catalyzed by formic acid. By usual organic reactions transforming hydroxyl groups into other functional groups, it is possible to generate narrow distribution of multi-functionalized POSS starting from an OH-functionalized organotrialkoxysilane. (C) 2003 Elsevier Science B.V. All rights reserved.

  DOI：

  10.1016/s0022-328x(03)00377-2

文献信息

• Poly(silsesquioxanes) derived from the hydrolytic condensation of organotrialkoxysilanes containing hydroxyl groups
  作者：Ignacio E. dell’ Erba、Diana P. Fasce、Roberto J.J. Williams、Rosa Erra-Balsells、Yuko Fukuyama、Hiroshi Nonami

  DOI：10.1016/s0022-328x(03)00377-2

  日期：2003.11

  Organotrialkoxysilanes containing secondary hydroxyl groups were synthesized by reacting 1 mole of (3-aminopropyl)triethoxysilane (APS) with 1 or 2 mole of phenylglycidylether (PGE). Resulting products, APS-PGE and APS-PGE(2), respectively, were subjected to hydrolytic condensation at 50 degreesC during 24 h. For APS-PGE, the reaction was performed using a molar ratio [H2O]/Si = 3, without addition of an external catalyst. For APS-PGE(2), the reaction was catalyzed by HCOOH or NaOH. Resulting poly(silsesquioxanes) (PSSO) were characterized by size exclusion chromatography, Fourier-transformed infrared spectroscopy and matrix-assisted ultraviolet laser desorption/ionization time-of-flight mass spectrometry (UV-MALDI-TOF MS). PSSO derived from APS-PGE and APS-PGE(2), catalyzed by HCOOH, exhibited a relatively narrow distribution of polyhedral structures. This constitutes a simple one-step synthesis of polyhedral oligomeric silsesquioxanes (POSS) functionalized with amine and/or hydroxyl groups. The directionality of the reaction pathway towards the formation of polyhedral structures was ascribed to the formation of intramolecular Si-O-C bonds through the reaction of SiOEt or SiOH groups with secondary hydroxyl groups. Intramolecular Si-O-C bonds were found in the structures of APS-PGE and APS-PGE(2), and in most of the species of the PSSO obtained from the NaOH-catalyzed reaction of APS-PGE(2). A small fraction of surviving Si-O-C bonds was also found in the polyhedral structures of the PSSO derived from the hydrolytic condensation of APS-PGE and APS-PGE(2) catalyzed by formic acid. By usual organic reactions transforming hydroxyl groups into other functional groups, it is possible to generate narrow distribution of multi-functionalized POSS starting from an OH-functionalized organotrialkoxysilane. (C) 2003 Elsevier Science B.V. All rights reserved.