3,3'-(1H-1,2,3-triazole-1,4-diyl)diphenol | 942202-08-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 3,3'-(1H-1,2,3-triazole-1,4-diyl)diphenol
• 英文别名: 1,4-bis(3-hydroxyphenyl)-1,2,3-triazole；1,4-bis(3-hydroxyphenyl)-1H-1,2,3-triazole；3-[1-(3-hydroxyphenyl)triazol-4-yl]phenol
• CAS: 942202-08-6
• 化学式: C₁₄H₁₁N₃O₂
• 分子量: 253.26
• InChiKey: KRTBMWIULWLCTM-UHFFFAOYSA-N

物化性质

• 熔点：
  207.1-207.6 °C
• 沸点：
  564.8±60.0 °C(Predicted)
• 密度：
  1.35±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  19
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  71.2
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  溴化氰 、 3,3'-(1H-1,2,3-triazole-1,4-diyl)diphenol 在 三乙胺 作用下， 以 丙酮 、 乙腈 为溶剂， 反应 1.0h， 以90%的产率得到1,4-bis(3-cyanooxyphenyl)-1H-1,2,3-triazole
  参考文献：
  名称：

  HALOGEN-FREE FLAME RETARDING MATERIALS BASED ON BISPHENOL TRIAZOLE RESINS AND POLYMERS

  摘要：

  这项发明提供了无卤、双酚三唑树脂和聚合物，具有优异的阻燃性能，相关的组合物、制备方法和使用方法。

  公开号：

  US20120316313A1
• 作为产物：
  描述：

  3-碘苯酚 在 bis-triphenylphosphine-palladium(II) chloride 2,2'-联吡啶 、 copper(l) iodide 、 N,N-二异丙基乙胺 、 copper(I) bromide 作用下， 以 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 反应 48.0h， 生成 3,3'-(1H-1,2,3-triazole-1,4-diyl)diphenol
  参考文献：
  名称：

  HALOGEN-FREE FLAME RETARDING MATERIALS BASED ON BISPHENOL TRIAZOLE RESINS AND POLYMERS

  摘要：

  这项发明提供了无卤、双酚三唑树脂和聚合物，具有优异的阻燃性能，相关的组合物、制备方法和使用方法。

  公开号：

  US20120316313A1

文献信息

• Design, Synthesis, Biological Evaluation and Pharmacokinetics of Bis(hydroxyphenyl) substituted Azoles, Thiophenes, Benzenes, and Aza-Benzenes as Potent and Selective Nonsteroidal Inhibitors of 17β-Hydroxysteroid Dehydrogenase Type 1 (17β-HSD1)
  作者：Emmanuel Bey、Sandrine Marchais-Oberwinkler、Ruth Werth、Matthias Negri、Yaseen A. Al-Soud、Patricia Kruchten、Alexander Oster、Martin Frotscher、Barbara Birk、Rolf W. Hartmann

  DOI：10.1021/jm8006917

  日期：2008.11.13

  activation of the estrogen receptor alpha (ERalpha). 17beta-Hydroxysteroid dehydrogenase type 1 (17beta-HSD1), which is responsible for the catalytic reduction of the weakly active estrogen estrone (E1) into E2, is therefore discussed as a novel drug target. Recently, we have discovered a 2,5-bis(hydroxyphenyl) oxazole to be a potent inhibitor of 17beta-HSD1. In this paper, further structural optimizations were

  最有效的女性性激素17beta-Estradiol（E2）通过激活雌激素受体α（ERalpha）刺激乳腺肿瘤的生长和子宫内膜异位症。因此，将17beta-羟基类固醇脱氢酶1型（17beta-HSD1）负责将弱活性雌激素雌酮（E1）催化还原为E2，作为一种新型药物靶标进行了讨论。最近，我们发现2，5-双（羟苯基）恶唑是17beta-HSD1的有效抑制剂。在本文中，进行了进一步的结构优化：合成了39个双（羟基苯基）唑，噻吩，苯和氮杂苯，并对其生物学特性进行了评估。这项研究最有前途的化合物显示出在低纳摩尔范围内提高的IC 50值，对17beta-HSD2的高选择性，对ERalpha的低结合亲和力，在大鼠肝微粒体中具有良好的代谢稳定性，并且经口应用后具有合理的药代动力学特征。分子静电势的计算揭示了17beta-HSD1抑制与电子密度分布之间的相关性。
• Thermally Induced Structural Transformation of Bisphenol-1,2,3-triazole Polymers: Smart, Self-Extinguishing Materials
  作者：Beom-Young Ryu、Todd Emrick

  DOI：10.1002/anie.201005456

  日期：2010.12.10

  Safer plastics: A novel class of polymers, termed bisphenol‐1,2,3‐triazole (BPT) polyarylates, was prepared by polycondensation chemistry. They exhibit high‐performance and self‐extinguishing properties as a result of their heterocyclic nature and a thermally induced structural transformation (see picture).

  更安全的塑料：通过缩聚化学制备了一类新型的称为双酚-1,2,3-三唑（BPT）聚芳酯的聚合物。由于它们的杂环性质和热诱导的结构转变，它们表现出高性能和自熄性（参见图片）。
• Halogen-free flame retarding materials based on bisphenol triazole resins and polymers
  申请人：Emrick Todd

  公开号：US08895688B2

  公开（公告）日：2014-11-25

  The invention provides halogen-free, bisphenol triazole resins and polymers having exceptional flame retarding properties, related compositions and methods of making and use thereof.

  该发明提供了具有优异阻燃性能的无卤联苯三唑树脂和聚合物，相关组合物的制备方法和使用方法。
• Bisphenol-1,2,3-triazole (BPT) Epoxies and Cyanate Esters: Synthesis and Self-Catalyzed Curing
  作者：Beom-Young Ryu、Todd Emrick

  DOI：10.1021/ma200767j

  日期：2011.7.26

  Novel bisphenol-1,2,3-triazole (BPT) resins, including epoxy (DGE-BPT) and cyanate ester (BPTCE) systems, were prepared and used in curing chemistry with no added reagents or catalysts. The materials were characterized relative to conventional epoxies and cyanate esters, in terms of curing and thermal properties, and the curing process and products were characterized by differential scanning calorimetry (DSC), thermogravimetric analysis (TGA), pyrolysis combustion flow calorimetry (PCFC), and small scale flame tests. These novel BPT-based resins cure in the absence of added catalysts and exhibit exceptionally low heat release and high char residue. Despite the absence of antiflammable additives (either halogenated or inorganic compounds), BPTCE itself was found to be nonignitable, with extremely high char residue value (67%) and extraordinarily low heat release capacity (HRC of similar to 10 J/(g K)).
• US8895688B2
  申请人：——

  公开号：US8895688B2

  公开（公告）日：2014-11-25