1,1',2,2'-tetra-hydroxyl{4'',4'''-phenylenebis[aminomethyl]}bisphenol

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: 1,1',2,2'-tetra-hydroxyl{4'',4'''-phenylenebis[aminomethyl]}bisphenol
• 英文别名: 4-[[4-[(3,4-Dihydroxyphenyl)methylideneamino]phenyl]iminomethyl]benzene-1,2-diol
• 化学式: C₂₀H₁₆N₂O₄
• 分子量: 348.358
• InChiKey: GFCCMZCNTLLOHP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  26
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  106
• 氢给体数：
  4
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  1,1',2,2'-tetra-hydroxyl{4'',4'''-phenylenebis[aminomethyl]}bisphenol 、 9,10-二氢-9-氧杂-10-磷杂菲-10-氧化物 以 乙醇 为溶剂， 反应 10.0h， 以80%的产率得到1,1',2,2'-tetra-hydroxyl-{4'',4'''-phenylenebis[amino-((10''''-O-10''''-H-9''''-oxa-10''''λ⁵-phosphaphenanthrene-10''''-yl))methyl]}bisphenol
  参考文献：
  名称：

  Syntheses of Two Dopo-Based Reactive Additives as Flame Retardants and Co-Curing Agents for Epoxy Resins

  摘要：

  Two novel phosphorus-nitrogen-containing flame retardants, 1,1 ',2,2 '-tetra-hydroxyl-4 '', 4 '''-biphenylene-bis[amino-((10 ''''-O-10 ''''-H-9 ''''-oxa-10 ''''lambda(5)-phosphaphenanthrene-10 ''''-yl))-methyl]}-bisphenol (3) and 1,1 ',2,2 '-tetra-hydroxyl-{4 '',4 '''-phenylene-bis[amino-((10 ''''- O-10 ''''- H-9 ''''- oxa-10 ''''lambda(5)-phosphaphenanthrene-10 ''''-yl))-methyl]}-bis-phenol (4) were synthesized by two steps: 1,1 ',2,2 '-tetra-hydroxyl-{4 '',4 '''- bi-phenylene-bis[amino-methyl]}-bis-phenol, imine (1), was synthesized through condensation reaction between 3,4-dihydroxybenzaldehyde and 4,4 '-diaminobiphenyl; and, 1,1 ',2,2 '-tetra-hydroxyl-{4 '',4 '''- phenylene-bis[amino-methyl]}-bis-phenol, imine (2) was synthesized by the reaction of 3,4-dihydroxybenzaldehyde and 1,4-phenylenediamine; then, addition reactions between 9,10-dihydro-9-oxa-10- phosphaphenanthrene-10-oxide and the two imines, the (3) and (4) were obtained, respectively. (1)-(4) were characterized by FTIR, NMR, and MS. (3) and (4) reacted with epoxy resins as co-curing agents with 4,4 '-diaminodiphenylmethane. Compared with control samples, (3) or (4) co-cured epoxy thermosets with phosphorus content of 1.0wt% possessed good flame retardant properties with LOI value reaching more than 36.0, higher char yields. The glass translation temperature (T-g) of thermosets containing (3) or (4) were characterized with suitable changes by DSC test.

  DOI：

  10.1080/10426507.2014.884092
• 作为产物：
  描述：

  对苯二胺 、 3,4-二羟基苯甲醛 以 乙醇 为溶剂， 反应 0.12h， 生成 1,1',2,2'-tetra-hydroxyl{4'',4'''-phenylenebis[aminomethyl]}bisphenol
  参考文献：
  名称：

  Covalent self-assembled nanoparticles with pH-dependent enhanced tumor retention and drug release for improving tumor therapeutic efficiency

  摘要：

  已经构建了一种共价苯硼酸（PBA）基自组装纳米系统，用于实现pH依赖性增强的肿瘤保留和药物释放。

  DOI：

  10.1039/c6tb02833k

文献信息

• Utilizing Reversible Interactions in Polymeric Nanoparticles To Generate Hollow Metal–Organic Nanoparticles
  作者：Longyu Li、Conghui Yuan、Dongming Zhou、Alexander E. Ribbe、Kevin R. Kittilstved、S. Thayumanavan

  DOI：10.1002/anie.201505242

  日期：2015.10.26

  The use of reversible linkers in polymers has been of interest mainly for biomedical applications. Herein, we present a novel strategy to utilize reversible interactions in polymeric nanoparticles to generate hollow metal–organic nanoparticles (MOPs). These hollow MOPs are synthesized from self‐assembled polymeric nanoparticles using a simple metal–comonomer exchange process in a single step. The control

  可逆的连接基在聚合物中的使用已引起人们的关注，主要用于生物医学应用。在本文中，我们提出了一种利用聚合物纳米颗粒中可逆相互作用生成中空金属-有机纳米颗粒（MOP）的新颖策略。这些中空的MOP由自组装的聚合物纳米粒子通过简单的金属-共聚单体交换过程一步一步合成而成。对聚合物前体颗粒尺寸的控制转化为控制MOP尺寸的直接机会。可通过溶液中金属离子的浓度轻松调节MOP的壳厚度。已经提出了形成这些空心MOP的基本机理。该方法适用于具有不同配位几何形状的多种金属离子，为该方法的通用性提供了证据。
• Thermoresponsive Polymeric Nanoparticles: Nucleation from Cooperative Polymerization Driven by Dative Bonds
  作者：Longyu Li、Conghui Yuan、Lizong Dai、S. Thayumanavan

  DOI：10.1021/ma5015808

  日期：2014.9.9

  Cooperative polymerization, aided by the nucleationelongation mechanism, has the promise of providing polymers and nanostructures that are otherwise inaccessible. The molecular origin of the cooperative growth of polymers is driven by a secondary interaction, often based on polarization, electrostatics, or sterics-driven secondary structure. Here, we demonstrate that covalent dative interactions can be used to achieve cooperative polymerization. Our results suggest that the initial polymer formation serves as the nucleus for monodisperse nanoparticle assembly. The dynamic nature of the dative interaction in this equilibrium self-assembly has been shown to endow these nanoparticles with thermal responsive characteristics.
• Syntheses of Two Dopo-Based Reactive Additives as Flame Retardants and Co-Curing Agents for Epoxy Resins
  作者：Ling Xiao、De-chao Sun、Tian-li Niu、You-wei Yao

  DOI：10.1080/10426507.2014.884092

  日期：2014.10.3

  Two novel phosphorus-nitrogen-containing flame retardants, 1,1 ',2,2 '-tetra-hydroxyl-4 '', 4 '''-biphenylene-bis[amino-((10 ''''-O-10 ''''-H-9 ''''-oxa-10 ''''lambda(5)-phosphaphenanthrene-10 ''''-yl))-methyl]}-bisphenol (3) and 1,1 ',2,2 '-tetra-hydroxyl-4 '',4 '''-phenylene-bis[amino-((10 ''''- O-10 ''''- H-9 ''''- oxa-10 ''''lambda(5)-phosphaphenanthrene-10 ''''-yl))-methyl]}-bis-phenol (4) were synthesized by two steps: 1,1 ',2,2 '-tetra-hydroxyl-4 '',4 '''- bi-phenylene-bis[amino-methyl]}-bis-phenol, imine (1), was synthesized through condensation reaction between 3,4-dihydroxybenzaldehyde and 4,4 '-diaminobiphenyl; and, 1,1 ',2,2 '-tetra-hydroxyl-4 '',4 '''- phenylene-bis[amino-methyl]}-bis-phenol, imine (2) was synthesized by the reaction of 3,4-dihydroxybenzaldehyde and 1,4-phenylenediamine; then, addition reactions between 9,10-dihydro-9-oxa-10- phosphaphenanthrene-10-oxide and the two imines, the (3) and (4) were obtained, respectively. (1)-(4) were characterized by FTIR, NMR, and MS. (3) and (4) reacted with epoxy resins as co-curing agents with 4,4 '-diaminodiphenylmethane. Compared with control samples, (3) or (4) co-cured epoxy thermosets with phosphorus content of 1.0wt% possessed good flame retardant properties with LOI value reaching more than 36.0, higher char yields. The glass translation temperature (T-g) of thermosets containing (3) or (4) were characterized with suitable changes by DSC test.
• Covalent self-assembled nanoparticles with pH-dependent enhanced tumor retention and drug release for improving tumor therapeutic efficiency
  作者：Yongwei Hao、Cuixia Zheng、Lei Wang、Yujie Hu、Haochen Guo、Qingling Song、Hongling Zhang、Zhenzhong Zhang、Yun Zhang

  DOI：10.1039/c6tb02833k

  日期：——

  A covalent phenylboronic acid (PBA)-based self-assembly nanosystem has been constructed for achieving pH-dependent enhanced tumor retention and drug release.

  已经构建了一种共价苯硼酸（PBA）基自组装纳米系统，用于实现pH依赖性增强的肿瘤保留和药物释放。