1-(oxiran-2-ylmethyl)-4-phenyl-1H-1,2,3-triazole | 124940-27-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 1-(oxiran-2-ylmethyl)-4-phenyl-1H-1,2,3-triazole
• 英文别名: 1-(Oxiran-2-ylmethyl)-4-phenyl-1h-1,2,3-tri-azole；1-(oxiran-2-ylmethyl)-4-phenyltriazole
• CAS: 124940-27-8
• 化学式: C₁₁H₁₁N₃O
• 分子量: 201.228
• InChiKey: KWPMIOQERMQBBI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  15
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  43.2
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  1-chloro-3-(4-phenyl-1H-1,2,3-triazol-1-yl)propan-2-ol 在 sodium hydroxide 作用下， 以 水 、 丙酮 为溶剂， 反应 1.0h， 以96%的产率得到1-(oxiran-2-ylmethyl)-4-phenyl-1H-1,2,3-triazole
  参考文献：
  名称：

  Synthesis of N-(oxyran-2-ylmethyl)triazoles and -tetrazoles

  摘要：

  The alkylation of 5-phenyl-1H-tetrazole and 4-nitro-2H-1,2,3-triazole with 1-chloro-2,3-epoxypropane and cycloaddition of 1-azido-3-chloropropan-2-ol to acetylenic dipolarophiles gave the corresponding N-(3-chloro-2-hydroxypropyl)azoles as intermediate products in the synthesis of N-(oxiran-2-ylmethyl)azoles.

  DOI：

  10.1134/s1070428015090171

文献信息

• Copper(I) Acetate: A Structurally Simple but Highly Efficient Dinuclear Catalyst for Copper-Catalyzed Azide-Alkyne Cycloaddition
  作者：Changwei Shao、Guolin Cheng、Deyong Su、Jimin Xu、Xinyan Wang、Yuefei Hu

  DOI：10.1002/adsc.200900768

  日期：——

  this article, the structurally well‐defined dinuclear complex copper(I) acetate was studied in detail and was developed as a highly practical and efficient catalyst for the copper(I)‐catalyzed azide‐alkyne cycloaddition. The “bare” phenylethynylcopper(I) (i.e., with no exogeneous ligands) was isolated as an intermediate, which can be converted into an active catalytic species by treatment with acetic

  在本文中，对结构明确的双核络合乙酸铜（I）进行了详细研究，并将其开发为铜（I）催化的叠氮化物-炔烃环加成反应的一种高度实用且高效的催化剂。分离出“裸露的”苯基乙炔基铜（I）（即没有外源性配体）作为中间体，可以通过用乙酸处理（反应中原位产生）以有效催化叠氮化物的方式将其转化为活性催化物质。炔烃在温和条件下的环加成反应。
• Cu ion-exchanged and Cu nanoparticles decorated mesoporous ZSM-5 catalysts for the activation and utilization of phenylacetylene in a sustainable chemical synthesis
  作者：Bhaskar Sarmah、Biswarup Satpati、Rajendra Srivastava

  DOI：10.1039/c6ra19606c

  日期：——

  SBA-15, and Al2O3 samples were also prepared. A sustainable catalytic process was developed for the selective synthesis of indolizine, chalcone, and triazole derivatives using a mesoporous ZSM-5 based heterogeneous catalyst. A multi-component synthetic strategy is reported here for the selective synthesis of the above mentioned chemicals that involves phenylacetylene as one of the building blocks. Control

  使用1，4-二氮杂双环[2.2.2]辛烷基多阳离子表面活性剂作为结构导向剂合成介孔ZSM-5。通过离子交换法制备了Cu 2+交换介孔ZSM-5。使用NaBH 4作为还原剂，制备了装饰有介孔ZSM-5的Cu纳米粒子。通过X射线衍射，N 2吸附，紫外可见光和扫描/透射电子显微镜技术的互补组合来表征材料。为了进行比较，Cu 2+交换了ZSM-5，HY和NaY。和铜纳米颗粒装饰了常规的ZSM-5，SBA-15和Al 2 O 3还准备了样品。开发了一种可持续的催化方法，用于使用介孔ZSM-5基非均相催化剂选择性合成吲哚嗪，查尔酮和三唑衍生物。本文报道了一种多组分合成策略，用于上述涉及苯乙炔作为结构单元之一的化学品的选择性合成。进行对照实验以确定提出的反应途径。进行了回收和浸出实验，以证明催化过程的可持续性和稳健性。在这些催化剂中，装饰有中孔ZSM-5的Cu纳米颗粒在所有这些反应中均表现出最高的活性。
• Zeo-Click Chemistry: Copper(I)-Zeolite-Catalyzed Cascade Reaction; One-Pot Epoxide Ring-Opening and Cycloaddition
  作者：Thirupathi Boningari、Andrea Olmos、Benjaram M. Reddy、Jean Sommer、Patrick Pale

  DOI：10.1002/ejoc.201000802

  日期：2010.11

  Copper(I)-modified zeolites, especially Cu I -USY, proved to be very efficient catalysts in multi-component reactions of epoxides with sodium azide and terminal alkynes. Such catalysts allow highly regio- and stereoselective syntheses of hydroxymethylated triazoles. These heterogeneous, modified zeolites can easily be recovered and reused. Moreover, the cascade reaction was best performed in water

  铜 (I) 改性沸石，尤其是 Cu I -USY，被证明是环氧化物与叠氮化钠和末端炔烃的多组分反应中非常有效的催化剂。这种催化剂允许羟甲基化三唑的高度区域和立体选择性合成。这些异质改性沸石可以很容易地回收和再利用。此外，级联反应最好在室温下在水中进行，使所有过程真正绿色。详细研究揭示了 Cu I 改性沸石在环氧化物开环和环加成步骤中所起的作用。
• Inhibiting a dynamic viral protease by targeting a non-catalytic cysteine
  作者：Kaitlin R. Hulce、Priyadarshini Jaishankar、Gregory M. Lee、Markus-Frederik Bohn、Emily J. Connelly、Kristin Wucherer、Chayanid Ongpipattanakul、Regan F. Volk、Shih-Wei Chuo、Michelle R. Arkin、Adam R. Renslo、Charles S. Craik

  DOI：10.1016/j.chembiol.2022.03.007

  日期：2022.5

  (HHV) infection by covalently inactivating the HHV maturational protease via a conserved, non-catalytic cysteine (C161). Using human cytomegalovirus protease (HCMV Pr) as a model, we screened a library of disulfides to identify molecules that tether to C161 and inhibit proteolysis, then elaborated hits into irreversible HCMV Pr inhibitors that exhibit broad-spectrum inhibition of other HHV Pr homologs

  病毒是一些最致命的人类疾病的罪魁祸首，但现有的疫苗和抗病毒药物只能解决一小部分潜在的人类病毒病原体。在这里，我们提供了一种通过保守的非催化半胱氨酸 (C161) 共价灭活 HHV 成熟蛋白酶来管理人类疱疹病毒 (HHV) 感染的方法。使用人巨细胞病毒蛋白酶 (HCMV Pr) 作为模型，我们筛选了二硫键文库，以鉴定与 C161 相连并抑制蛋白水解的分子，然后将其精心设计成不可逆的 HCMV Pr 抑制剂，对其他 HHV Pr 同源物表现出广谱抑制作用。我们进一步开发了一种针对 HCMV Pr 的优化工具化合物，并使用综合结构生物学和生化方法来证明 HCMV Pr 同二聚化的抑制剂稳定性，利用构象平衡来阻止蛋白水解。不可逆的 HCMV Pr 抑制破坏了细胞中的 HCMV 感染性，为通过非催化半胱氨酸靶向蛋白水解来控制病毒感染提供了原理证明。
• Copper(I) oxide and benzoic acid ‘on water’: a highly practical and efficient catalytic system for copper(I)-catalyzed azide–alkyne cycloaddition
  作者：Changwei Shao、Rui Zhu、Sheng Luo、Qun Zhang、Xinyan Wang、Yuefei Hu

  DOI：10.1016/j.tetlet.2011.05.061

  日期：2011.7

  A simple combination of Cu2O and PhCO2H 'on H2O' has been developed as a highly practical and efficient catalytic system for copper(I)-catalyzed azide-alkyne cycloaddition (CuAAC). It not only provides a further evidence for the strategy of carboxylic acids-promoted CuAAC, but also offers significant advantages to CuAAC because Cu2O is one of the most stable and cheapest Cu(I) sources; PhCO2H is one of the structurally simplest bidentate ligands; and water is the most 'green' solvent. (C) 2011 Elsevier Ltd. All rights reserved.