(2-(4-nitrophenyl)-5-phenyl-2H-1,2,3-triazol-4-yl)(phenyl)methanone | 1083311-17-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (2-(4-nitrophenyl)-5-phenyl-2H-1,2,3-triazol-4-yl)(phenyl)methanone
• 英文别名: [2-(4-Nitrophenyl)-5-phenyltriazol-4-yl]-phenylmethanone
• CAS: 1083311-17-4
• 化学式: C₂₁H₁₄N₄O₃
• 分子量: 370.367
• InChiKey: HSCKWOBULFWANT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.1
• 重原子数：
  28
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  93.6
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  phenyl-(5-phenyl-2H-[1,2,3]triazol-4-yl)-methanone 、 对硝基氯苯 在 monopotassium carbonate 作用下， 以 二甲基亚砜 为溶剂， 反应 50.0h， 以60%的产率得到(2-(4-nitrophenyl)-5-phenyl-2H-1,2,3-triazol-4-yl)(phenyl)methanone
  参考文献：
  名称：

  Facile One-Pot Synthesis of 4,5-Disubstituted 1,2,3-(NH)-Triazoles through Sonogashira Coupling/1,3-Dipolar Cycloaddition of Acid Chlorides, Terminal Acetylenes, and Sodium Azide

  摘要：

  A novel and efficient way of synthesizing 4,5-disubstituted-1,2,3-(NH)-triazoles through palladium-catalyzed and ultrasonic promoted Sonogashira coupling/1,3-dipolar cycloaddition of acid chlorides, terminal acetylenes, and sodium azide in one pot is developed. The reaction scope is quite general, and the methodology can produce excellent yields. The regioselective 1,4,5-trisubstituted-1,2,3-(NH)-triazoles can be made easily from 4,5-disubstituted-1,2,3-(NH)-triazoles.

  DOI：

  10.1021/ol901040d

文献信息

• Metal- and Base-Free Three-Component Reaction of Ynones, Sodium Azide, and Alkyl Halides: Highly Regioselective Synthesis of 2,4,5-Trisubstituted 1,2,3-NH-Triazoles
  作者：Baohua Chen、Jihui Li、Yuanqing Zhang、Dong Wang、Wen Wang、Tingting Gao、Lu Wang、Jiting Li、Guosheng Huang

  DOI：10.1055/s-0030-1258086

  日期：2010.7

  A base- and metal-free three-component reaction of ynones, sodium azide, and alkyl halides is developed for the ­regioselective synthesis of 2,4,5-trisubstituted-1,2,3-triazoles. The method is general, convenient, environmentally benign, atom-­economical, and high-yielding.

  开发了一种无基底和金属的三组分反应，将炔酮、叠氮化钠和烷基卤化物用于2,4,5-三取代-1,2,3-三唑的区域选择性合成。该方法具有通用性、便利性、环保性、原子经济性和高产率。
• One-pot synthesis of 2,4,5-trisubstituted 1,2,3-triazoles through the cascade reactions of acid chlorides, terminal acetylenes, sodium azide and aryl halides
  作者：Xiang Liu、Jihui Li、Baohua Chen

  DOI：10.1039/c3nj40912k

  日期：——

  An efficient one-pot reaction of acid chlorides, terminal acetylenes, sodium azide and aryl halides is developed for the regioselective synthesis of 2,4,5-trisubstituted 1,2,3-triazoles. The method is general, convenient, eco-friendly, atom-economical, and could provide excellent yields and regioselectivities.

  酰基氯，末端乙炔的有效一锅反应， 叠氮化钠开发了芳基卤化物用于区域选择性合成2,4,5-三取代的1,2,3-三唑。该方法是通用的，方便的，环境友好的，原子经济的，并且可以提供优异的产率和区域选择性。
• A binuclear Cu(<scp>i</scp>) complex as a novel catalyst towards the direct synthesis of N-2-aryl-substituted-1,2,3-triazoles from chalcones
  作者：Divya Pratap Singh、Bharat Kumar Allam、Rahul Singh、Krishna Nand Singh、Vinod Prasad Singh

  DOI：10.1039/c5ra27907k

  日期：——

  A binuclear Cu(I) complex containing a N′,N′-bis(1H-indol-3-yl)methylene}oxalohydrazide (H2bioh) ligand has been synthesized and characterized. The molecular structures of the synthesized compounds have been determined by single crystal X-ray diffraction. The crystal structures are stabilized by inter- and intra-molecular π–π stacking and C–H⋯π interactions. The Cu(I)-complex has successfully been

  合成并表征了含有N '，N'-双（1 H-吲哚-3-基）亚甲基}草酰肼（H 2 bioh）配体的双核Cu（I）配合物。合成的化合物的分子结构已经通过单晶X射线衍射确定。分子间和分子内π-π堆积和CH-H⋯π相互作用稳定了晶体结构。铜（我复合物已成功用作涉及叠氮化物-查耳酮点击反应的一锅操作的有效催化剂，并开发了随后的芳基化反应。该配合物表现出优异的催化活性，而催化剂的负载量却大大降低。整个过程对空气和湿气不敏感，可以在环境温度下轻松操作。
• Efficient Synthesis of <i>N</i>-2-Aryl-1,2,3-Triazole Fluorophores via Post-Triazole Arylation
  作者：Yuxiu Liu、Wuming Yan、Yunfeng Chen、Jeffrey L. Petersen、Xiaodong Shi

  DOI：10.1021/ol802246q

  日期：2008.12.4

  Efficient post-triazole regloselective N-2 arylation was developed from C-4, C-5 disubstituted-1,2,3-NH-triazoles. Three different approaches had been investigated, including SNAr, Cu(I) catalyzed aryl amidation and Cu(II) mediated boronic acid coupling. The N-2-aryl triazoles were successfully synthesized with excellent yields. The structures were characterized by X-ray crystallography and some N-2-triazole products gave strong fluorescence with various emission controlled by the C-5 groups.
• Facile One-Pot Synthesis of 4,5-Disubstituted 1,2,3-(NH)-Triazoles through Sonogashira Coupling/1,3-Dipolar Cycloaddition of Acid Chlorides, Terminal Acetylenes, and Sodium Azide
  作者：Jihui Li、Dong Wang、Yuanqing Zhang、Jiting Li、Baohua Chen

  DOI：10.1021/ol901040d

  日期：2009.7.16

  A novel and efficient way of synthesizing 4,5-disubstituted-1,2,3-(NH)-triazoles through palladium-catalyzed and ultrasonic promoted Sonogashira coupling/1,3-dipolar cycloaddition of acid chlorides, terminal acetylenes, and sodium azide in one pot is developed. The reaction scope is quite general, and the methodology can produce excellent yields. The regioselective 1,4,5-trisubstituted-1,2,3-(NH)-triazoles can be made easily from 4,5-disubstituted-1,2,3-(NH)-triazoles.