methyl 1-octyl-1H-1,2,3-triazole-4-carboxylate | 80819-66-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: methyl 1-octyl-1H-1,2,3-triazole-4-carboxylate
• 英文别名: 4-methoxycarbonyl-1-octyl-1H-1,2,3-triazole；1-octyl-4-methoxycarbonyl-1,2,3-triazole；4-methoxycarbonyl-1-octyl-1,2,3-triazole；Methyl 1-octyltriazole-4-carboxylate
• CAS: 80819-66-5
• 化学式: C₁₂H₂₁N₃O₂
• 分子量: 239.318
• InChiKey: DAEHJSCCRDGPHZ-UHFFFAOYSA-N

物化性质

• 熔点：
  78-80 °C
• 沸点：
  348.7±34.0 °C(Predicted)
• 密度：
  1.08±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  17
• 可旋转键数：
  9
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.75
• 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：

  1-溴辛烷 在 sodium azide 、 copper(II) sulfate 、 sodium ascorbate 作用下， 以 四氢呋喃 、 二甲基亚砜 为溶剂， 生成 methyl 1-octyl-1H-1,2,3-triazole-4-carboxylate
  参考文献：
  名称：

  从苄基和烷基卤化物高效一锅法合成 1,2,3-三唑

  摘要：

  提出了一种通过原位生成的叠氮化物和炔烃的 1,3-偶极环加成制备 1,2,3-三唑的有效一锅法。这种简便的方法可应用于苄基或烷基卤化物，并且通过简单的过滤分离纯产品。

  DOI：

  10.1055/s-2005-864809

文献信息

• Polystyrene resin-supported CuI-cryptand 22 complex: a highly efficient and reusable catalyst for three-component synthesis of 1,4-disubstituted 1,2,3-triazoles under aerobic conditions in water
  作者：Barahman Movassagh、Nasrin Rezaei

  DOI：10.1016/j.tet.2014.09.092

  日期：2014.11

  resin-supported copper(I) iodide-cryptand-22 complex (PS–C22–CuI) was synthesized and characterized by FT-IR, EDX, SEM, XPS, and TG-DTA analysis. This complex was found to be a highly active and robust heterogeneous catalyst for either three-component reaction of organic halides, sodium azide, and terminal alkynes, or the reaction of organic azides and alkynes to form 1,4-disubstituted 1,2,3-triazoles in good

  合成并通过FT-IR，EDX，SEM，XPS和TG-DTA分析对聚苯乙烯树脂负载的碘化铜-I-crypTAnd-22铜（PS-C22-CuI）配合物进行表征。已发现该配合物是一种高活性且稳健的非均相催化剂，可用于有机卤化物，叠氮化钠和末端炔烃的三组分反应，或有机叠氮化物和炔烃反应以形成1,4-二取代的1,2,3使用水作为绿色溶剂，在室温下以良好或优异的收率合成-三唑。催化剂不仅可以通过过滤容易地与最终产物分离，而且可以在不显着降低催化活性的情况下重复使用。
• Antitubercular activity of 1,2,3-triazolyl fatty acid derivatives
  作者：Diego G. Ghiano、Agustina de la Iglesia、Nina Liu、Peter J. Tonge、Héctor R. Morbidoni、Guillermo R. Labadie

  DOI：10.1016/j.ejmech.2016.09.086

  日期：2017.1

  being most of them active with some of the analogs displaying activity at micromolar concentration. The most potent member of the series has the triazole moiety on the C-2 position with a carbon chain of eight or ten carbon atoms. The 1,5-isomers of the most active analog were significantly less active than the original isomer. The activity of the selected hit was assayed on several clinical MTB multi-drug

  通过点击化学有效地合成了1,2,3-三唑不饱和脂肪酸模拟物的集合。制备的1，4-二取代的类似物覆盖不同的烷基链长和三唑位置。随后测试了这些化合物对结核分枝杆菌的抵抗力，它们大多数具有活性，其中一些类似物在微摩尔浓度下显示出活性。该系列中最有效的成员在C-2位置具有三唑部分，碳原子数为8或10个碳原子。活性最高的类似物的1，5-异构体的活性明显低于原始异构体。在提供相同MIC的几种临床MTB多药耐药菌株上测定了所选基因的活性。
• ZnO Nanoparticles: Efficient and Versatile Reagents for Synthesis of 1,4-disubstituted 1,2,3-triazoles
  作者：Bahareh Sadeghi、Alireza Hassanabadi、Mohammad Kamali

  DOI：10.3184/174751912x13247429490396

  日期：2012.1

  Reaction between azides and acetylenes catalysed by ZnO nanoparticles (ZnO NPs) in solvent EtOH at room temperature provide a simple and efficient one-pot route for the synthesis of 1,4-disubstituted 1,2,3-triazoles in excellent yields. 1,2,3-Triazoles are used in various agricultural, industrial and medical fields.

  在室温下，由 ZnO 纳米颗粒 (ZnO NPs) 在溶剂 EtOH 中催化的叠氮化物和乙炔之间的反应为以优异的产率合成 1,4-二取代 1,2,3-三唑提供了一种简单有效的单锅法。1,2,3-三唑类用于各种农业、工业和医疗领域。
• Synthesis of 1,4-Disubstituted-1,2,3-trizazoles via Click Reaction in Micro Flow Reactor
  作者：Ming Lei、Ruijun Hu、Yanguang Wang、Hong Zhang

  DOI：10.3987/com-13-s(s)51

  日期：——

  A Cu (I)-catalyzed three-component click reaction of alkyl bromide, terminal alkyne and sodium azide was developed in micro flow reactor. Sodium ascorbate was added as additive to prevent the oxidative coupling of desired product with terminal alkyne. Under optimized condition, various 1,4-disubstituted-1,2,3-triazoles were obtained in 85-95% yield with exclusive 1,4-regioisomeric selectivity. The present smooth procedure greatly accelerated the reaction due to the excellent mixing and mass transfer in micro flow system.
• Hydroxyapatite-supported copper(II)-catalyzed azide–alkyne [3+2] cycloaddition with neither reducing agents nor bases in water
  作者：Yoshiro Masuyama、Kazuki Yoshikawa、Noriyuki Suzuki、Kenji Hara、Atsushi Fukuoka

  DOI：10.1016/j.tetlet.2011.10.060

  日期：2011.12

  Copper(II)-exchanged hydroxyapatite, prepared by ion-exchanging of Ca(II) in calcium hydroxyapatite [Ca-10(PO4)(6)(OH)(2)] with Cu(NO3)(2) at 70 degrees C in water, functions as a reusable heterogeneous catalyst with neither reducing agents nor bases for azide-alkyne [3+2] cycloaddition at 50 degrees C in water under air. (C) 2011 Elsevier Ltd. All rights reserved.