4-(2,3-dichlorophenyl)-1H-1,2,3-triazole | 1378976-06-7

• 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-(2,3-dichlorophenyl)-1H-1,2,3-triazole
• 英文别名: 4-(2,3-dichlorophenyl)-2H-triazole
• CAS: 1378976-06-7
• 化学式: C₈H₅Cl₂N₃
• 分子量: 214.054
• InChiKey: OPIGATGRUCISOI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  13
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 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：

  2-环己烯-1-酮 、 4-(2,3-dichlorophenyl)-1H-1,2,3-triazole 在 三乙烯二胺 作用下， 以 乙腈 为溶剂， 反应 96.0h， 以56%的产率得到3-(4-(2,3-dichlorophenyl)-2H-1,2,3-triazol-2-yl)cyclohexanone
  参考文献：
  名称：

  DABCO-mediated aza-Michael addition of 4-aryl-1H-1,2,3-triazoles to cycloalkenones. Regioselective synthesis of disubstituted 1,2,3-triazoles

  摘要：

  Aza-Michael addition of 4-aryl-1H-1,2,3-triazoles to 2-cycloalken-1-ones has been studied in the presence of DABCO as organic base. The reactions were carried out in acetonitrile at room temperature to provide 2,4-disubstituted 2H-1,2,3-triazoles as major adducts and 1,4-disubstituted 1H-1,2,3-triazoles as minor adducts. Though the reaction times are longer (4-8 days), the two regioisomers were separated by using column chromatography and the adducts were obtained in very good to excellent combined chemical yields. The electron-rich and electron-poor substituents on aryl moiety of 4-aryl-triazoles could tolerate the reaction conditions to afford the title adducts. (C) 2016 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2016.11.125
• 作为产物：
  描述：

  2,3-二氯碘苯 在 bis-triphenylphosphine-palladium(II) chloride 、 potassium fluoride 、 copper(l) iodide 、 叠氮基三甲基硅烷 、 三乙胺 作用下， 以 1,4-二氧六环 、 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 8.0h， 生成 4-(2,3-dichlorophenyl)-1H-1,2,3-triazole
  参考文献：
  名称：

  Rational Design of 4-Aryl-1,2,3-Triazoles for Indoleamine 2,3-Dioxygenase 1 Inhibition

  摘要：

  Indoleamine 2,3-dioxygenase 1 (IDO1) is an important therapeutic target treatment of diseases such as cancer that involve pathological immune escape. Starting from the scaffold of our previously discovered IDO1 inhibitor 4-phenyl-1,2,3-triazole, we used computational structure-based methods to design more potent ligands. This approach yielded highly efficient low molecular weight inhibitors, the most active being of nanomolar potency both in an enzymatic and in a cellular assay, while showing no cellular toxicity and a high selectivity for IDO1 over tryptophan 2,3-dioxygenase (TDO). A quantitative structure-activity relationship based on the electrostatic ligand-protein interactions in the docked binding modes and on the quantum chemically derived charges of the triazole ring demonstrated a good explanatory power for the observed activities.

  DOI：

  10.1021/jm300260v

文献信息

• Asymmetric Organocatalytic Approach to 2,4-Disubstituted 1,2,3-Triazoles by N2-Selective Aza-Michael Addition
  作者：Ujjawal Kumar Bhagat、Rama Krishna Peddinti

  DOI：10.1021/acs.joc.7b02793

  日期：2018.1.19

  of this reaction have only recently been developed. Nevertheless, functionalization at the N2-position of NH-1,2,3-triazoles leading to optically active N2-substituted triazoles is not yet developed. In this article, we report, for the first time, the asymmetric aza-Michael reaction of 4-aryl-NH-1,2,3-triazoles to cyclic enones under the catalytic influence of chiral bifunctional thiourea organocatalysts

  尽管N个N1-官能^ h -1,2,3-三唑已经知道了几十年，这种反应的对映选择性变种最近才开发的。然而，尚未开发出在N H -1,2,3-三唑的N2-位上的官能化导致光学活性的N2-取代的三唑。在本文中，我们首次报道了在手性双官能硫脲有机催化剂的催化作用下，4-芳基-N H -1,2,3-三唑与环烯酮的不对称氮杂-迈克尔反应，生成对映体。 2,4-二取代的1,2,3-三唑。辛可宁衍生的硫脲催化剂III 在当前的转换中有效地工作，以生产N2官能化的1,2,3-三唑为主要产品，光学收率高达> 99.9％，以及次要的1,4-二取代的1,2,3-三唑。
• On Water Cu@g‐C ₃ N ₄ Catalyzed Synthesis of NH‐1,2,3‐Triazoles via [2+3] Cycloadditions of Nitroolefins/Alkynes and Sodium Azide
  作者：Soumen Payra、Arijit Saha、Subhash Banerjee

  DOI：10.1002/cctc.201801524

  日期：2018.12.7

  CuCl2 (Cu@g‐C3N4) and characterized by powder X‐ray diffraction, field emission scanning electron microscopy, high resolution transmission electron microscopy, X‐ray photoelectron spectroscopy studies. An efficient and regioselective protocol for the on water synthesis of 4‐aryl‐NH‐1,2,3‐triazole derivatives via 1,3‐diipolar cycloaddition reactions of nitroolefins/phenylacetylenes to sodium azide were

  在这里，我们报道了石墨聚合的C 3 N 4负载的CuCl 2（Cu @ g‐C 3 N 4）的制造，其特征在于粉末X射线衍射，场发射扫描电子显微镜，高分辨率透射电子显微镜，X射线光电子能谱研究。通过使用Cu @ g-C 3证明了通过硝基烯烃/苯基乙炔与叠氮化钠的1,3-二极性环加成反应进行水合成4-芳基-NH -1,2,3-三唑衍生物的高效且区域选择性的方案N 4作为坚固且可重复使用的催化剂。
• Dipolar HCP materials as alternatives to DMF solvent for azide-based synthesis
  作者：Feng Gao、Rongxian Bai、Minghao Li、Yanlong Gu

  DOI：10.1039/d1gc02002a

  日期：——

  Hypercrosslinked polymers HCP-DMF and HCP-DMF-SO₃H containing abundant and flexible DMF moieties were designed and synthesized.

  含有丰富且灵活的DMF基团的超交联聚合物HCP-DMF和HCP-DMF-SO₃H被设计并合成。
• Base-Mediated Ring Opening of meso-Epoxides with 4-Aryl-NH-1,2,3-triazoles: Synthesis of trans-2-(Aryltriazolyl)cycloalkanols
  作者：Ujjawal Bhagat、Rama Peddinti

  DOI：10.1055/s-0036-1589045

  日期：2017.9

  A novel method of nucleophilic ring-opening of meso-epoxides with 4-aryl-NH-1,2,3-triazoles has been developed under metal-free conditions. The epoxide-ring opening process were carried out in the presence of organic bases (DABCO/Et3N) in acetonitrile at 85 °C to afford a regioisomeric mixture of trans-2-(4-aryl-2H-1,2,3-triazol-2-yl)cycloalkanols (2,4-disubstituted triazoles) as major adducts and trans-2-(4-aryl-1H-1,2,3-triazol-1-yl)cycloalkanols (1,4-disubstituted triazoles) as minor adducts in excellent combined chemical yields (isolated yield up to 99%).

  已经开发出一种新的无金属条件下，使用4-芳基-NH-1,2,3-三唑对中间环氧化合物进行亲核环开反应的方法。在乙腈中，加入有机碱（DABCO / Et3N）并在85°C下进行环氧化合物的环开过程，以得到顺式异构体混合物，其中trans-2-(4-芳基-2H-1,2,3-三唑-2-基)环己醇（2,4-二取代三唑）为主要产物，而trans-2-(4-芳基-1H-1,2,3-三唑-1-基)环己醇（1,4-二取代三唑）为次要产物，化学收率极高（分离收率高达99%）。
• The preparation, characterization and catalytic activity of porous tragacanth gum -g-poly (p-styrene sulfonamide-co-acrylamide)
  作者：Mahtab Yaghubzadeh、Sedigheh Alavinia、Ramin Ghorbani-Vaghei、Samaneh Koosha

  DOI：10.1016/j.molstruc.2023.136265

  日期：2023.12