偶氮苯-4-基异氰酸酯 | 1942-61-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 偶氮苯
• 中文名称: 偶氮苯-4-基异氰酸酯
• 中文别名: (E)-1-(4-异氰酸基苯基)-2-苯基重氮基烯
• 英文名称: 4-(phenylazo)phenylisocyanate
• 英文别名: p-azobenzene isocyanate；Diazene, (4-isocyanatophenyl)phenyl-；(4-isocyanatophenyl)-phenyldiazene
• CAS: 1942-61-6
• 化学式: C₁₃H₉N₃O
• mdl: MFCD00152743
• 分子量: 223.234
• InChiKey: HICXYNWIRHBSKQ-UHFFFAOYSA-N

物化性质

• 熔点：
  97-98 °C
• 沸点：
  359.2±25.0 °C(Predicted)
• 密度：
  1.13±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.9
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  54.2
• 氢给体数：
  0
• 氢受体数：
  4

安全信息

• 海关编码：
  2929109000

反应信息

• 作为反应物：
  描述：

  memantine hydrochloride 、 偶氮苯-4-基异氰酸酯 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 17.0h， 以50 mg的产率得到1-((1r,3R,5S,7r)-3,5-dimethyladamantan-1-yl)-3-(4-(phenyldiazenyl)phenyl)urea
  参考文献：
  名称：

  NMDA受体的光开关拮抗剂的开发

  摘要：

  N-甲基-d天冬氨酸受体（NMDAR）对于神经系统过程（例如学习，记忆和突触可塑性）至关重要。这样，调节其功能的小分子在许多神经系统疾病的研究中受到关注。我们已经合成了一个小的光电开关库，可调节NMDAR功能。迄今为止，最有效的光开关是基于甘氨酸结合位点的已知配体，并且显示出显着的亚型选择性。

  DOI：

  10.1016/j.tet.2017.06.056
• 作为产物：
  描述：

  三光气 、 对氮蒽蓝 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 6.0h， 生成 偶氮苯-4-基异氰酸酯
  参考文献：
  名称：

  NMDA受体的光开关拮抗剂的开发

  摘要：

  N-甲基-d天冬氨酸受体（NMDAR）对于神经系统过程（例如学习，记忆和突触可塑性）至关重要。这样，调节其功能的小分子在许多神经系统疾病的研究中受到关注。我们已经合成了一个小的光电开关库，可调节NMDAR功能。迄今为止，最有效的光开关是基于甘氨酸结合位点的已知配体，并且显示出显着的亚型选择性。

  DOI：

  10.1016/j.tet.2017.06.056

文献信息

• Introducing a photo-switchable azo-functionality inside Cr-MIL-101-NH2 by covalent post-synthetic modification
  作者：Antje Modrow、Dordaneh Zargarani、Rainer Herges、Norbert Stock

  DOI：10.1039/c2dt30672g

  日期：——

  For the first time an azo functionality was covalently introduced into a MOF by post-synthetic modification. The reaction of Cr-MIL-101-NH2 with p-phenylazobenzoylchloride (1) and 4-(phenylazo)phenylisocyanate (2) as the reactants led to the compounds Cr-MIL-101_amide and Cr-MIL-101_urea, with the azo groups protruding into the mesoporous cages. XRPD and N2 sorption measurements confirm the intactness of the framework and the successful covalent modification was proven by IR- and NMR-spectroscopy. Furthermore, cis/trans isomerisation upon irradiation with light was demonstrated by UV/Vis spectroscopy. More distinct changes in the UV/Vis spectra were observed for Cr-MIL-101_amide compared to Cr-MIL-101_urea, while the degree of functionalization, i.e. the number of reacted NH2-groups, seems to have a less pronounced effect. The variation of the sorption properties due to the cis/trans isomerisation was proven by methane adsorption measurements.

  这是首次通过合成后修饰将偶氮官能团共价引入 MOF。Cr-MIL-101-NH2 与对苯基偶氮苯甲酰氯 (1) 和 4-（苯基偶氮）苯基异氰酸酯 (2) 反应，生成了 Cr-MIL-101_amide 和 Cr-MIL-101_urea，偶氮基团突出到介孔笼中。XRPD 和 N2 吸附测量证实了框架的完整性，红外光谱和核磁共振光谱也证明了共价修饰的成功。此外，紫外/可见光谱也证明了光照射时顺式/反式异构化。与 Cr-MIL-101_脲相比，Cr-MIL-101_酰胺的紫外/可见光谱变化更为明显，而官能化程度（即反应的 NH2 基团数量）的影响似乎不那么明显。甲烷吸附测量证明了顺式/反式异构化导致的吸附特性变化。
• Postpolymerization Modification of Hydroxyl-Functionalized Polymers with Isocyanates
  作者：Frank Biedermann、Eric A. Appel、Jesús del Barrio、Till Gruendling、Christopher Barner-Kowollik、Oren A. Scherman

  DOI：10.1021/ma2008018

  日期：2011.6.28

  The postpolymerization functionalization of hydroxyl-group terminated polymers (M-n in the range of 1000-6000 g mol(-1)) such as poly(ethylene glycol) (PEG), poly(N-isopropylacrylamide) (PNIPAM), poly(N,N-dimethylacrylamide) (PDMAM), and poly(tert-butyl acrylate) (PtBA) with a wide range of functional isocyanate derivatives such as azobenzene, and anthracene has been investigated. It was shown by H-1 and C-13 NMR, GPC, Fourier transform infrared spectroscopy (FTIR), and electrospray ionization mass spectrometry (ESI-MS) that a high degree of end-group conversion, typically >98%, with little or no formation of side products can be achieved at ambient temperature. PNIPAM, PDMAM, PtBA, and PHEAM polymers have been obtained by reversible addition-fragmentation chain transfer (RAFT) radical polymerization from a hydroxyl-group containing chain transfer agent (CTA). The formation of the carbamate has been shown to be compatible with the trithiocarbonate end-group of the RAFT polymers. Additionally, this approach allows for the direct functionalization of RAFT polymers without the need of additional steps such as deprotection or aminolysis of the CTA. This route was subsequently used for the preparation of a variety of side-chain functional polymers from poly(N-hydroxyethyl acrylamide) (PHEAM). Three different high yielding methods have been employed to prepare the isocyanates (R-NCO). Either amino or carboxylic acid precursors have been converted into the desired R NCO or hydroxyl group moieties have been reacted with an excess of 1,6-hexamethylene diisocyanate (HDI) to statistically form the monofunctional product.