4-(4-chlorophenyl)-5-methyl-1H-1,2,3-triazole

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 4-(4-chlorophenyl)-5-methyl-1H-1,2,3-triazole
• 英文别名: 4-(4-chlorophenyl)-5-methyl-2H-triazole
• 化学式: C₉H₈ClN₃
• mdl: MFCD28383843
• 分子量: 193.636
• InChiKey: IIPOQCXWGRGHQM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  13
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.111
• 拓扑面积：
  41.6
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  4-(4-chlorophenyl)-5-methyl-1H-1,2,3-triazole 、 sodium 4-methylbenzenesulfinate 在 碘 作用下， 以 乙酸乙酯 为溶剂， 反应 16.0h， 以74%的产率得到4-(4-chlorophenyl)-5-methyl-2-p-tosyl-2H-1,2,3-triazole
  参考文献：
  名称：

  Metal-free, highly regioselective sulfonylation of NH-1,2,3-triazoles with sodium sulfinates and thiosulfonates

  摘要：

  A convenient and metal-free protocol for the highly regioselective sulfonylation of NH-1,2,3-triazoles is described. A range of readily accessible NH-1,2,3-triazoles were sulfonylated with various aryl sulfinates in the presence of molecular iodine. The scope was extended to thiosulfonates as an efficient sulfonylating agent and nitrochromene derived triazoles were also explored for selective N-sulfonylation. A variety of synthetically viable N-2-sulfonyl triazoles were obtained in moderate to high yields with excellent regioselectivities via N-S bond construction under mild reaction conditions. (C) 2018 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2018.04.023
• 作为产物：
  描述：

  1-chloro-4-(2-nitropropenyl)benzene 在 sodium azide 、 对甲苯磺酸 作用下， 生成 4-(4-chlorophenyl)-5-methyl-1H-1,2,3-triazole
  参考文献：
  名称：

  Metal-free, highly regioselective sulfonylation of NH-1,2,3-triazoles with sodium sulfinates and thiosulfonates

  摘要：

  A convenient and metal-free protocol for the highly regioselective sulfonylation of NH-1,2,3-triazoles is described. A range of readily accessible NH-1,2,3-triazoles were sulfonylated with various aryl sulfinates in the presence of molecular iodine. The scope was extended to thiosulfonates as an efficient sulfonylating agent and nitrochromene derived triazoles were also explored for selective N-sulfonylation. A variety of synthetically viable N-2-sulfonyl triazoles were obtained in moderate to high yields with excellent regioselectivities via N-S bond construction under mild reaction conditions. (C) 2018 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2018.04.023

文献信息

• Synthesis, Antiproliferative and Pro-Apoptotic Effects of Nitrostyrenes and Related Compounds in Burkitt's Lymphoma
  作者：Andrew J. Byrne、Sandra A. Bright、Darren Fayne、James P. McKeown、Thomas McCabe、Brendan Twamley、Clive Williams、Mary J. Meegan

  DOI：10.2174/1573406413666171002123907

  日期：2018.2.6

  identified as a lead target structure for the development of particularly effective compounds targeting Burkitt's lymphoma (BL). OBJECTIVES The aims of the curent study were to synthesise a panel of nitrostyrene compounds and to evaluate their activity in Burkitt's lymphoma (BL). METHODS A panel of structurally varied compounds were designed and synthesised using Henry Knoevenagel condensation reactions.

  背景技术淋巴细胞癌（淋巴瘤）约占全世界恶性疾病的12％。硝基苯乙烯支架被认为是开发针对Burkitt淋巴瘤（BL）的特别有效的化合物的主要靶标结构。目的目前的研究目的是合成一组硝基苯乙烯化合物并评估其在伯基特氏淋巴瘤（BL）中的活性。方法使用Henry Knoevenagel缩合反应设计和合成一组结构变化的化合物。单晶X射线分析证实了这些新颖结构的六个实例的E构型。还研究了许多与硝基苯乙烯有关的化合物，包括1，3-双（芳基）-2-硝基丙烯与含有硝基乙烯基药效团的杂环支架，例如3-硝基-2-苯基-2H-色烯。使用BL细胞系EBV-MUTU-1和EBV + DG-75（耐化学性）评估化合物的抗增殖活性，以建立初步的结构活性关系。结果成功建立了具有优化的硝基苯乙烯骨架和3-硝基-2-苯基-2Hchromne结构的铅化合物，在MUTU-1细胞中的典型IC50值分别为0.45 µM和0.47 µM，
• Aluminium(III) Chloride-Catalyzed Three-Component Condensation of Aromatic Aldehydes, Nitroalkanes and Sodium Azide for the Synthesis of 4-Aryl-<i>NH</i>-1,2,3-triazoles
  作者：Qinquan Hu、Yi Liu、Xiaocong Deng、Yanjun Li、Yunfeng Chen

  DOI：10.1002/adsc.201600098

  日期：2016.5.19

  three‐component reaction of aromatic aldehydes, nitroalkanes, and sodium azide has been developed; this reaction sequence can be applied to a broad substrate scope and affords the corresponding 4‐aryl‐NH‐1,2,3‐triazoles in good to excellent yields. The milder reaction conditions and easier operation make this AlCl3‐catalyzed protocol more advantageous for the synthesis of 4‐aryl‐NH‐1,2,3‐triazoles.

  已经开发出了一种氯化铝（III）催化的三元芳族醛，硝基烷和叠氮化钠反应。该反应顺序可应用于广泛的底物范围，并提供相应的4-芳基-NH -1,2,3-三唑，收率良好至极佳。较温和的反应条件和更简便的操作使此AlCl 3催化方案对于合成4芳基NH -1,2,3-三唑更有利。
• Copper-Catalyzed Cross-Dehydrogenative <i>N</i>²-Coupling of <i>NH</i>-1,2,3-Triazoles with <i>N</i>,<i>N</i> -Dialkylamides: <i>N</i>-Amidoalkylation of <i>NH</i>-1,2,3-Triazoles
  作者：Xiaocong Deng、Xue Lei、Gang Nie、Lihui Jia、Yuanxiang Li、Yunfeng Chen

  DOI：10.1021/acs.joc.7b00752

  日期：2017.6.16

  An efficient copper-catalyzed C–N bond formation by N–H/C–H cross-dehydrogenative coupling (CDC) between NH-1,2,3-triazoles and N,N-dialkylamides has been developed. The method provided N-amidoalkylated 1,2,3-triazoles with moderate to high yields, and the reactions showed high N2-selectivities when 4,5-disubstituted NH-1,2,3-triazoles served as the substrates.

  已经开发了通过NH -1,2,3-三唑与N，N-二烷基酰胺之间的NH - CH / CH-H交叉脱氢偶联（CDC）形成有效的铜催化C-N键的方法。该方法提供了中等至高产率的N-酰胺基烷基化的1,2,3-三唑，并且当以4,5-二取代的NH -1,2,3-三唑为底物时，反应显示出高的N 2-选择性。
• Zinc Oxide Nanoparticles Catalysed One-Pot Three-Component Reaction: A Facile Synthesis of 4-Aryl-NH-1,2,3-Triazoles
  作者：Parmita Phukan、Soniya Agarwal、Kalyanjyoti Deori、Diganta Sarma

  DOI：10.1007/s10562-020-03143-w

  日期：2020.8

  Abstract A facile one-pot, three component reaction has been developed using aldehydes, nitroalkane and sodium azide with zinc oxide nanocatalyst for the synthesis of 4-aryl-NH-1,2,3-triazoles. ZnO nanoparticles with controlled size (15–25 nm) and morphology were prepared using a sonochemical strategy. Structural and morphological study revealed the growth of well crystalline particles along the c

  摘要 使用醛、硝基烷烃和叠氮化钠与氧化锌纳米催化剂建立了一种简便的一锅三组分反应，用于合成 4-芳基-NH-1,2,3-三唑。使用声化学策略制备具有受控尺寸（15-25 nm）和形态的 ZnO 纳米颗粒。结构和形态研究表明，由于较高的表面能，晶体颗粒沿 c 轴即 [0001] 方向生长。由于反应在绿色溶剂聚乙二醇 (PEG) 400 中在有氧条件下顺利进行，因此本工作中使用的催化协议为现有方法提供了一种高效且经济的替代方案。该反应具有广泛的底物范围，导致所需产物的产率极好。催化剂回收部分在初期很棘手；然而，成功引入了一种替代途径来回收前者并将其重新用于下一个催化反应循环，并具有出色的催化活性保持性。使用回收的催化剂观察到的高催化效率而没有显着的活性损失主要是由于在多次催化反应后保留了 ZnO 纳米颗粒的形态和晶体结构。图形摘要
• Access to Fluoroalkylated Azoles and 2-Acylaminoketones via Fluorinated Anhydride-Mediated Cleavage of NH-1,2,3-Triazoles
  作者：Vladimir Motornov、Petr Beier

  DOI：10.1021/acs.orglett.2c00359

  日期：2022.3.18

  pentafluoropropionic anhydrides) by nitrogen acylation and acid-mediated triazole ring opening. Structurally diverse fluoroalkylated oxazoles were prepared from 4,5-disubstituted-1,2,3-triazoles. Efficient synthesis of 2-acylaminoketones was achieved from 4-substituted 1,2,3-triazoles. Finally, easy access to fluoroalkylated imidazoles and 1,2,4-triazines was developed by a one-pot two-step route from

  NH-1,2,3-三唑在与氟化酸酐（三氟乙酸、二氟乙酸、氯二氟乙酸和五氟丙酸酐）的反应中通过氮酰化和酸介导的三唑开环进行开环。结构多样的氟烷基化恶唑由 4,5-二取代-1,2,3-三唑制备。从 4-取代的 1,2,3-三唑实现了 2-酰基氨基酮的高效合成。最后，通过从 NH-三唑、氟化酸酐和胺或肼的一锅两步路线开发了易于获得氟烷基化咪唑和 1,2,4-三嗪的方法。