3-(4-phenyl-1H-1,2,3-triazol-1-yl)dihydrofuran-2(3H)-one | 1319721-86-2

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: 3-(4-phenyl-1H-1,2,3-triazol-1-yl)dihydrofuran-2(3H)-one
• 英文别名: 3-(4-phenyl-1H-1,2,3-triazol-1yl)dihydrofuran-2(3H)-one；3-(4-Phenyltriazol-1-yl)oxolan-2-one
• CAS: 1319721-86-2
• 化学式: C₁₂H₁₁N₃O₂
• 分子量: 229.238
• InChiKey: IDCXIPUWCDAKED-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  57
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  苯乙炔 、 3-azidodihydrofuran-2(3H)-one 在 2-{4-[(dimethylamino)methyl]-1,2,3-triazol-1-yl}cyclohexan-1-ol 、 copper(II) sulfate 、 sodium ascorbate 作用下， 以 乙醇 、 水 为溶剂， 反应 24.0h， 以69%的产率得到3-(4-phenyl-1H-1,2,3-triazol-1-yl)dihydrofuran-2(3H)-one
  参考文献：
  名称：

  一种新型的水溶性配体，可有效催化铜催化脂肪族叠氮化物和炔烃的惠斯根环加成反应

  摘要：

  使用新型水溶性催化配体2- {4-[（（二甲基氨基）甲基] -1,2,3-三唑-1-基}环己基- 1-ol（AMTC）。测试了一系列脂族和芳族底物，并将其与众所周知的三（三唑）胺配体（TBTA和THPTA）进行了比较。还研究了溶剂组成的影响。

  DOI：

  10.1016/j.tetlet.2015.09.110

文献信息

• Acid–Base Jointly Promoted Copper(I)-Catalyzed Azide–Alkyne Cycloaddition
  作者：Changwei Shao、Xinyan Wang、Qun Zhang、Sheng Luo、Jichen Zhao、Yuefei Hu

  DOI：10.1021/jo200869a

  日期：2011.8.19

  In this novel acid–base jointly promoted CuAAC, the combination of CuI/DIPEA/HOAc was developed as a highly efficient catalytic system. The functions of DIPEA and HOAc have been assigned, and HOAc was recognized to accelerate the conversions of the C–Cu bond-containing intermediates and buffer the basicity of DIPEA. As a result, all drawbacks occurring in the popular catalytic system CuI/NR3 were overcome

  在这种新型的酸碱共同促进的CuAAC中，CuI / DIPEA / HOAc的结合被开发为一种高效的催化体系。已经指定了DIPEA和HOAc的功能，HOAc被认为可以加速含C–Cu键的中间体的转化并缓冲DIPEA的碱性。结果，容易克服了流行的催化体系CuI / NR 3中发生的所有缺点。
• Alkyne-Azide Cycloadditions with Copper Powder in a High-Pressure Continuous-Flow Reactor: High-Temperature Conditions versus the Role of Additives
  作者：Sándor B. Ötvös、István M. Mándity、Lóránd Kiss、Ferenc Fülöp

  DOI：10.1002/asia.201201125

  日期：2013.4

  procedure is presented for 1,3‐dipolar cycloaddition reactions between organic azides and acetylenes. This simple and inexpensive technique eliminates the need for costly special apparatus and utilizes Cu powder as a plausible CuI source. To maximize the reaction rates, high‐pressure/high‐temperature conditions are utilized; alternatively, the harsh reaction conditions can be moderated at room temperature

  针对有机叠氮化物和乙炔之间的1,3-偶极环加成反应，提出了一种安全，高效的基于流化学的方法。这种简单而廉价的技术消除了对昂贵的专用设备的需求，并利用了铜粉作为合理的铜I。来源。为了使反应速率最大化，利用了高压/高温条件。或者，可以在室温下通过联合应用碱性和酸性添加剂来缓解苛刻的反应条件。在一系列模型反应中对这两种方法的性能进行比较，发现形成了有用的1,4-二取代的1,2,3-三唑类，产率极高。得益于流程处理的好处，与叠氮化物处理相关的风险得以降低，并且克级生产已得到安全实施。高效合成抗真菌顺喷菌素的一些高度功能化衍生物证明了这种连续流动技术的合成能力。
• [EN] DERIVATIVES OF 1,2,3-TRIAZOLYL CYCLOHEXAN-1-OL AND ITS USE<br/>[FR] DÉRIVÉS DE 1,2,3-TRIAZOLYLE CYCLOHEXAN-1-OL ET LEUR UTILISATION
  申请人：UNIV JAGIELLONSKI

  公开号：WO2016200283A1

  公开（公告）日：2016-12-15

  1,2,3-triazolyl cyclohexanol derivatives have been disclosed and their use as ligands accelerating the copper(I)-catalyzed azide-alkyne cycloaddition and the zinc(II)-catalyzed azide-nitrile cycloaddition.

  已经披露了1,2,3-三唑基环己醇衍生物，并且它们被用作加速铜(I)催化的叠氮-炔烃环加成和锌(II)催化的叠氮-腈环加成的配体。
• Synthesis and evaluation of the quorum sensing inhibitory effect of substituted triazolyldihydrofuranones
  作者：Gilles Brackman、Martijn Risseeuw、Shari Celen、Paul Cos、Louis Maes、Hans J. Nelis、Serge Van Calenbergh、Tom Coenye

  DOI：10.1016/j.bmc.2012.06.009

  日期：2012.8

  Acylhomoserine lactone (AHL) analogues in which the amide function is replaced by a triazole group were synthesized and evaluated for their effect on quorum sensing (QS) and biofilm formation in Burkholderia cenocepacia and Pseudomonas aeruginosa. In addition, the influence of the length of the acyl-mimicking chain was investigated. The compounds showed selectivity between two different AHL QS systems. 3-(1H-1,2,3-Triazol-1-yl)dihydrofuran-2(3H)-ones, in which the 4-substituent best resembled the acyl chain of the native AHL molecule exhibited significant QS agonistic and antagonistic activities. Replacing this aliphatic substituent by a phenyl-containing moiety resulted in active inhibitors of QS. The most active compounds showed biofilm inhibitory as well as biofilm eradicating activities in both test organisms. (C) 2012 Elsevier Ltd. All rights reserved.
• A layered double hydroxide, a synthetically useful heterogeneous catalyst for azide−alkyne cycloadditions in a continuous-flow reactor
  作者：Sándor B. Ötvös、Ádám Georgiádes、Mónika Ádok-Sipiczki、Rebeka Mészáros、István Pálinkó、Pál Sipos、Ferenc Fülöp

  DOI：10.1016/j.apcata.2015.05.003

  日期：2015.7