1-(3,5-dimethoxyphenyl)-4-(4-methoxyphenyl)-1H-1,2,3-triazole | 876012-78-1

• 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-(3,5-dimethoxyphenyl)-4-(4-methoxyphenyl)-1H-1,2,3-triazole
• 英文别名: 1-(3,5-Dimethoxyphenyl)-4-(4-methoxyphenyl)triazole
• CAS: 876012-78-1
• 化学式: C₁₇H₁₇N₃O₃
• 分子量: 311.34
• InChiKey: QUUUNDORFHNTQN-UHFFFAOYSA-N

物化性质

• 沸点：
  524.9±60.0 °C(Predicted)
• 密度：
  1.20±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  23
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  58.4
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  1-(3,5-dimethoxyphenyl)-4-(4-methoxyphenyl)-1H-1,2,3-triazole 在 三溴化硼 作用下， 以 二氯甲烷 为溶剂， 以93%的产率得到5-(4-(4-hydroxyphenyl)-1H-1,2,3-triazol-1-yl)benzene-1,3-diol
  参考文献：
  名称：

  Rapid Synthesis of Triazole-Modified Resveratrol Analogues via Click Chemistry

  摘要：

  Resveratrol is a phytoalexin able to display an array of biological activities. We decided to replace the double bond with a triazole ring using the archetypical click reaction: the Huisgen [3 + 2] cycloaddition. Seventy-two triazole derivatives were synthesized via a parallel combinatorial approach. Preliminary data suggest that this procedure can lead to the synthesis of compounds that display some, but not all, of resveratrol's actions with increased potency.

  DOI：

  10.1021/jm051118z
• 作为产物：
  描述：

  3,5-二甲氧基苯胺 在 盐酸 、 copper(II) sulfate 、 sodium ascorbate 、 sodium nitrite 作用下， 以 叔丁醇 为溶剂， 反应 26.17h， 生成 1-(3,5-dimethoxyphenyl)-4-(4-methoxyphenyl)-1H-1,2,3-triazole
  参考文献：
  名称：

  Rapid Synthesis of Triazole-Modified Resveratrol Analogues via Click Chemistry

  摘要：

  Resveratrol is a phytoalexin able to display an array of biological activities. We decided to replace the double bond with a triazole ring using the archetypical click reaction: the Huisgen [3 + 2] cycloaddition. Seventy-two triazole derivatives were synthesized via a parallel combinatorial approach. Preliminary data suggest that this procedure can lead to the synthesis of compounds that display some, but not all, of resveratrol's actions with increased potency.

  DOI：

  10.1021/jm051118z

文献信息

• Regioselective Conversion of Arenes to<i>N</i>-aryl-1,2,3-triazoles Using CH Borylation
  作者：Rajavel Srinivasan、Anthony G. Coyne、Chris Abell

  DOI：10.1002/chem.201403021

  日期：2014.9.8

  A one‐pot protocol for the synthesis of N‐aryl 1,2,3‐triazoles from arenes by an iridium‐catalyzed CH borylation/copper catalyzed azidation/click sequence is described. 1 mol % of Cu(OTf)2 was found to efficiently catalyze both the azidation and the click reaction. The applicability of this method is demonstrated by the late‐stage chemoselective installation of 1,2,3‐triazole moiety into unactivated

  的单釜协议用于合成Ñ -芳基的1,2,3-三唑从芳烃通过铱催化的Ç  ħ硼化/铜催化的叠氮化/击序列进行说明。发现1mol％的Cu（OTf）2有效地催化了叠氮化和点击反应。1,2,3-三唑部分在化学上重要的未活化分子的后期化学选择性安装证明了该方法的适用性。
• A Bioorthogonal Small Molecule Selective Polymeric “Clickase”
  作者：Junfeng Chen、Ke Li、Sarah E. Bonson、Steven C. Zimmerman

  DOI：10.1021/jacs.0c06553

  日期：2020.8.12

  extracellular click chemistry to be performed. We describe two proof of principle applications that illustrate the utility of the bioorthogonal activity. First, the SCNP catalyst is able to screen for ligands that bind proteins, including PROTAC-like molecules. Second, the non-membrane permeable SCNP can efficiently catalyze the click reaction extracellularly, thereby enabling in situ anticancer drug

  合成聚合物支架可作为防止生物大分子粘附的守门人。在此，我们使用门控来开发含铜单链纳米颗粒 (SCNP) 催化剂作为人工“点击酶”，它选择性地作用于能够穿透聚合物壳的小分子。具有表面铵基团的类似点击酶对炔基化蛋白质和小分子底物进行高效的铜 (I) 催化的炔-叠氮化物环加成 (CuAAC) 反应，而具有聚乙二醇 (PEG) 基团的新型 SCNP 点击酶仅具有活性在小分子上。此外，新的 SCNP 可抵抗细胞摄取，从而可以进行细胞外点击化学。我们描述了两个原理应用证明，说明了生物正交活动的效用。第一的，SCNP 催化剂能够筛选结合蛋白质的配体，包括 PROTAC 样分子。其次，非膜渗透性SCNP可以有效地在细胞外催化点击反应，从而在不干扰细胞内功能的情况下实现原位抗癌药物合成和筛选。
• Rapid Synthesis of Triazole-Modified Resveratrol Analogues via Click Chemistry
  作者：Francesca Pagliai、Tracey Pirali、Erika Del Grosso、Riccardo Di Brisco、Gian Cesare Tron、Giovanni Sorba、Armando A. Genazzani

  DOI：10.1021/jm051118z

  日期：2006.1.1

  Resveratrol is a phytoalexin able to display an array of biological activities. We decided to replace the double bond with a triazole ring using the archetypical click reaction: the Huisgen [3 + 2] cycloaddition. Seventy-two triazole derivatives were synthesized via a parallel combinatorial approach. Preliminary data suggest that this procedure can lead to the synthesis of compounds that display some, but not all, of resveratrol's actions with increased potency.