2-(benzoxazol-2-yl)benzonitrile | 54175-73-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 2-(benzoxazol-2-yl)benzonitrile
• 英文别名: 2-benzooxazol-2-yl-benzonitrile；2-(2-cyanophenyl)benzoxazole；2-(benzo[d]oxazol-2-yl)benzonitrile；2-(1,3-Benzoxazol-2-yl)benzonitrile
• CAS: 54175-73-4
• 化学式: C₁₄H₈N₂O
• 分子量: 220.23
• InChiKey: AKFAWVJVWNTLGE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  17
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  49.8
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  1H-2,1-苯并恶唑-3-酮 在 吡啶 作用下， 以 二氯甲烷 为溶剂， 20.0~520.0 ℃ 、6.67 Pa 条件下， 反应 7.5h， 生成 2-(benzoxazol-2-yl)benzonitrile
  参考文献：
  名称：

  A Comparison of the Flash Vacuum Pyrolysis Products of Some N-Acylbenzotriazoles and N-Acylbenzisoxazolones

  摘要：

  以下物质的闪速真空热解（f.v.p.）产物 2-(1H-苯并三唑-1-羰基)苯腈、2-(1H-苯并三唑-1-羰基)苯甲酸甲酯和 2-(1H-苯并三唑-1-羰基)苯甲酸甲酯和 1-(2-氯甲基苯甲酰基)-1H-苯并三唑和相应的苯并异噁唑酮类化合物。 苯并异噁唑酮的特征。苯并三唑 衍生物所产生的化合物，其来源表明主要是自由基过程。 过程。在较低温度下，苯并异噁唑酮产生的苯并异噁唑 产物与单碳原子中间体一致，但在较高温度下具有三重 但在较高温度下，它们具有三重二极性质，从而导致 吖啶。氯甲基化合物的主要低温 f.v.p. (氯甲基苯甲酰基)苯并异噁唑酮的主要低温 f.v.p. 产物是 吲哚并[1,2-b]苯并恶唑。

  DOI：

  10.1071/ch99037

文献信息

• Carbonates: eco-friendly solvents for palladium-catalysed direct arylation of heteroaromatics
  作者：Jia Jia Dong、Julien Roger、Cécile Verrier、Thibaut Martin、Ronan Le Goff、Christophe Hoarau、Henri Doucet

  DOI：10.1039/c0gc00229a

  日期：——

  The palladium-catalysed direct 2-, 4- or 5-arylation of a wide range of heteroaromatics with aryl halides proceed in moderate to good yields using the eco-friendly solvents carbonates. The best yields were obtained using benzoxazole or thiazole derivatives. The arylation of furan, thiophene, pyrrole, imidazole or isoxazole derivatives was found to require a more elevated reaction temperature.

  这 钯环保型芳烃卤化物催化的各种杂芳族化合物与芳基卤化物的直接2-，4-或5-芳基化反应均能以中等至良好的收率进行 溶剂碳酸盐。使用以下方法可获得最佳产量苯并恶唑 或者 噻唑衍生品。这芳基化 的 呋喃， 噻吩， 吡咯， 咪唑 或者 异恶唑 发现衍生物需要更高的反应温度。
• Photocatalytic green synthesis of benzazoles from alcohol oxidation/toluene sp³ C–H activation over metal-free BCN: effect of crystallinity and N–B pair exposure
  作者：Heyan Jiang、Cuicui Zang、Hongmei Cheng、Bin Sun、Xue Gao

  DOI：10.1039/d1cy01623g

  日期：——

  characteristics of enhanced crystallinity and improved N–B pair exposure, was prepared with a simple KCl-assisted molten salt strategy. Efficient heterogeneous photocatalytic tandem synthesis of benzazoles from alcohol oxidation/toluene sp3 C–H activation was achieved firstly over the metal-free P-BCN using visible light and the green oxidant O2, with only water as a by-product. Various o-thio/hydroxy/aminoanilines

  多孔硼碳氮化物 (P-BCN) 具有增强的结晶度和改进的 N-B 对暴露的特性，是用简单的 KCl 辅助熔盐策略制备的。首先使用可见光和绿色氧化剂 O 2在不含金属的 P-BCN 上实现了乙醇氧化/甲苯 sp 3 C-H 活化对苯并唑的高效多相光催化串联合成，只有水作为副产物。各种o-硫基/羟基/氨基苯胺和醇或甲苯可以转化为相应的2-取代苯并噻唑、苯并恶唑和苯并咪唑，具有良好至优异的光催化性能。与本体 BCN 相比，改进的光催化性能应归因于结晶度增强诱导的电荷分离和传输改进。由于富含电子的 N 原子，增加的 N-B 对暴露促进了超氧化物自由基的产生，以及由于 B 2p 轨道构建的价带提高了氧化能力。这项工作提出了一种通过无金属多相光催化合成苯并唑和其他精细化学品的绿色高效合成策略。
• Cu(OAc)₂-Mediated benzimidazole-directed C–H cyanation using 2-(4-methylpiperazin-1-yl)acetonitrile as the cyano source
  作者：Tianyou Zhang、Jingyi Qiao、He Song、Feng Xu、Xiaochong Liu、Chunzhao Xu、Junjie Ma、Hao Liu、Zhizhong Sun、Wenyi Chu

  DOI：10.1039/c9nj00776h

  日期：——

  the Cu(OAc)2-mediated cyanation of arenes using benzimidazole as the directing group with 2-(4-methylpiperazin-1-yl)acetonitrile as the cyano source was developed. A series of cyano derivatives were facilely and conveniently obtained in moderate to good yields by using this method. The C–H activation catalytic system was originally applied to the C(sp2)–H cyanation of the aryl/heteroaryl to synthesize

  提出了一种新的协议，以苯并咪唑为导向基团，以2-（4-甲基哌嗪-1-基）乙腈为氰源，用Cu（OAc）2介导的芳烃氰化。使用此方法可以轻松，方便地以中等到良好的收率获得一系列氰基衍生物。C–H活化催化体系最初应用于芳基/杂芳基的C（sp 2）–H氰化反应，以合成2-（1 H-苯并[ d ]咪唑-2-基）芳基腈。合成的20种氰化物产品中有19种新化合物。在该反应中，最初将2-（4-甲基哌嗪-1-基）乙腈作为氰基源用于芳烃的C（sp 2）-H氰化反应。另外，荧光材料通过所获得的氰化物产物3的衍生反应获得5a。
• Direct C–H Bond Arylation of (Benzo)oxazoles with Aryl Chlorides Catalyzed by <i>N</i>-Heterocyclic Carbene–Palladium(II)–1-Methylimidazole Complex
  作者：Xiao-Bao Shen、Yun Zhang、Wen-Xin Chen、Zheng-Kang Xiao、Ting-Ting Hu、Li-Xiong Shao

  DOI：10.1021/ol500531m

  日期：2014.4.4

  The direct C-H bond arylation of (benzo)oxazoles with aryl chlorides was achieved catalyzed by a well-defined NHC-Pd(II)-Im complex. Under the optimal conditions, various aryl chlorides were successfully applied as the arylating reagents to achieve the 2-aryl (benzo)oxazoles in acceptable to high yields, providing a convenient and alternative method for the direct C-H bond arylation of (benzo)oxazoles and enriching the chemistry of the NHC-Pd(II) complex in organic synthesis.
• Direct arylation of oxazole and benzoxazole with aryl or heteroaryl halides using a palladium–diphosphine catalyst
  作者：Fazia Derridj、Safia Djebbar、Ouassini Benali-Baitich、Henri Doucet

  DOI：10.1016/j.jorganchem.2007.10.028

  日期：2008.1

  Through the use of PdCl(dppb)(C3H5) as a catalyst, a range of aryl bromides and chlorides undergoes coupling via C-H bond activation/flunctionalization reaction with oxazole or benzoxazole in good yields. This air-stable catalyst can be used at low loadings with several substrates. Surprisingly, better results in terms of substrate/catalyst ratio were obtained in several cases using electron-excessive aryl bromides than with the electron-deficient ones. This seems to be mainly due to the relatively low thermal stability of some of the 2-arylbenzoxazoles formed with electron -deficient aryl halides. With these substrates, in order to obtain higher yields of product, the reactions had to be performed at a lower temperature (100-120 degrees C) using a larger amount of catalyst. On the other hand, in the presence of the most stable products, the reactions were performed at 150 degrees C using as little as 0.2 mol% catalyst. Arylation of benzoxazole with heteroaryl bromides also gave the coupling products in moderate to high yields using 0.2-5 mol% catalyst. With this catalyst, electron-deficient aryl chloride such as 4-chlorobenzonitrile, 4-chloroacetophenone or 2-chloronitrobenzene have also been used successfully. (c) 2007 Elsevier B.V. All rights reserved.