1-(9-蒽基甲基)-4-苯基-1H-[1,2,3]噻唑 | 1019335-75-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 蒽
• 中文名称: 1-(9-蒽基甲基)-4-苯基-1H-[1,2,3]噻唑
• 英文名称: 1-anthracen-9yl-methyl-4-phenyl-1H-[1,2,3]triazole
• 英文别名: 1-(9-Anthracenylmethyl)-4-phenyl-1H-[1,2,3]triazole；1-(anthracen-9-ylmethyl)-4-phenyltriazole
• CAS: 1019335-75-1
• 化学式: C₂₃H₁₇N₃
• 分子量: 335.408
• InChiKey: FGMISXSMUISSGY-UHFFFAOYSA-N

物化性质

• 沸点：
  604.5±58.0 °C(Predicted)
• 密度：
  1.19±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.4
• 重原子数：
  26
• 可旋转键数：
  3
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.04
• 拓扑面积：
  30.7
• 氢给体数：
  0
• 氢受体数：
  2

安全信息

• 海关编码：
  2933990090

反应信息

• 作为产物：
  描述：

  9-溴甲基蒽 、 苯乙炔 在 sodium azide 、 copper nanoparticles on activated carbon 作用下， 以 水 为溶剂， 反应 6.0h， 以90%的产率得到1-(9-蒽基甲基)-4-苯基-1H-[1,2,3]噻唑
  参考文献：
  名称：

  Click chemistry from organic halides, diazonium salts and anilines in water catalysed by copper nanoparticles on activated carbon

  摘要：

  一种易于制备、可重复使用且具有多功能性的催化剂，由氧化铜纳米颗粒负载于活性炭上构成，经过充分表征并发现其能有效促进1,2,3-三唑的多组分合成。该合成过程以有机卤化物、重氮盐和芳香胺为原料，在水相中进行，且铜的用量较低。

  DOI：

  10.1039/c1ob05735a

文献信息

• Ruthenium-Catalyzed Azide-Thioalkyne Cycloadditions in Aqueous Media: A Mild, Orthogonal, and Biocompatible Chemical Ligation
  作者：Paolo Destito、José R. Couceiro、Hélio Faustino、Fernando López、José L. Mascareñas

  DOI：10.1002/anie.201705006

  日期：2017.8.28

  metal-promoted bioorthogonal ligations remains as a major scientific challenge. Demonstrated herein is that azides undergo efficient and regioselective room-temperature annulations with thioalkynes in aqueous milieu when treated with catalytic amounts of a suitable ruthenium complex. The reaction is compatible with different biomolecules, and can be carried out in complex aqueous mixtures such as phosphate

  有效的金属促进的生物正交连接的发展仍然是主要的科学挑战。本文证明，当用催化量的合适的钌络合物处理时，叠氮化物在水溶液中与硫代炔烃进行有效的区域选择性室温环化。该反应与不同的生物分子相容，并且可以在复杂的水性混合物中进行，例如磷酸盐缓冲液，细胞裂解液，胎牛血清，甚至是活细菌（大肠杆菌）。重要的是，该反应与经典的CuAAC相互相容。
• Mesoporous graphitic carbon nitride as a heterogeneous catalyst for photoinduced copper(<scp>i</scp>)-catalyzed azide–alkyne cycloaddition
  作者：Sajjad Dadashi-Silab、Baris Kiskan、Markus Antonietti、Yusuf Yagci

  DOI：10.1039/c4ra09954k

  日期：——

  A new protocol for the photoinduced copper(I)-catalyzed azide–alkyne cycloaddition (CuAAC) was developed. The system utilizes mesoporous graphitic carbon nitride (mpg-N3C4) as a heterogeneous photocatalyst to realize the in situ formation of the required copper(I) catalyst by reducing copper(II) species upon UV or sunlight irradiation. The efficiency of the system in regard to its ability to photoinitiate

  为光诱导的铜（I）催化的叠氮化物-炔烃环加成反应（CuAAC）开发了一种新的协议。该系统利用介孔石墨碳氮化物（mpg-N 3 C 4）作为非均相光催化剂，通过还原铜（II）实现原位形成所需的铜（I）催化剂。）受到紫外线或阳光照射的物种。关于在不同溶剂中光引发各种脂族和芳族叠氮化物和炔烃的CuAAC的能力，研究了该系统的效率。光热法测量证实，反应速率取决于光强度以及连续或间歇照射。重要的是，由于光催化剂的非均质性质，mpg-C 3 N 4可以很容易地分离出来并在进一步的反应中重新使用，而不会失去活性。
• A fluorogenic ‘click’ reaction of azidoanthracene derivatives
  作者：Fang Xie、Krishnamoorthy Sivakumar、Qingbing Zeng、Michael A. Bruckman、Blake Hodges、Qian Wang

  DOI：10.1016/j.tet.2008.01.080

  日期：2008.3

  Fluorogenic reactions have broad applications in biolabeling, combinatorial synthesis of fluorescent dyes, and materials development. It was recently reported that the highly selective and efficient Cu(I)-catalyzed azide-alkyne cycloaddition (CuAAC) reaction can be employed in designing new types of fluorogenic reactions. In this study, we report a fluorogenic reaction using anthracene azides as starting materials. The fluorescence of the anthryl core can be greatly inhibited upon introducing electron-donating azido groups in the proximity. Such weakly fluorescent anthracene azides demonstrate high reactivity with a variety of alkynes under the CuAAC conditions producing a strongly fluorescent triazole product with high quantum yields. This reaction can be used in the synthesis and screening of fluorescent dyes combinatorially. Compared with most existing methods, the fluorogenic CuAAC reaction is a much milder and simpler technique to prepare large libraries of fluorescent dyes without further purification. In order to demonstrate the efficiency of using anthracene azides for biolabeling applications, both small molecules and biomolecules including the multialkyne-derivatized cowpea mosaic virus and tobacco mosaic virus had been studied. (C) 2008 Elsevier Ltd. All rights reserved.
• Click chemistry from organic halides, diazonium salts and anilines in water catalysed by copper nanoparticles on activated carbon
  作者：Francisco Alonso、Yanina Moglie、Gabriel Radivoy、Miguel Yus

  DOI：10.1039/c1ob05735a

  日期：——

  An easy-to-prepare, reusable and versatile catalyst consisting of oxidised copper nanoparticles on activated carbon has been fully characterised and found to effectively promote the multicomponent synthesis of 1,2,3-triazoles from organic halides, diazonium salts, and aromatic amines in water at a low copper loading.

  一种易于制备、可重复使用且具有多功能性的催化剂，由氧化铜纳米颗粒负载于活性炭上构成，经过充分表征并发现其能有效促进1,2,3-三唑的多组分合成。该合成过程以有机卤化物、重氮盐和芳香胺为原料，在水相中进行，且铜的用量较低。