2-(4-methyl-2-nitrophenyl)benzo[d]oxazole

• 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-(4-methyl-2-nitrophenyl)benzo[d]oxazole
• 英文别名: 2-(4-Methyl-2-nitrophenyl)-1,3-benzoxazole；2-(4-methyl-2-nitrophenyl)-1,3-benzoxazole
• 化学式: C₁₄H₁₀N₂O₃
• 分子量: 254.245
• InChiKey: IZQDHPKBWRMZFC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  19
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  71.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  2-(4-甲基苯基)苯并噁唑; 2-(4-甲基苯基)-1,3-苯并噁唑 在 dipotassium peroxodisulfate 、 silver(I) nitrite 、 氧气 、 palladium diacetate 作用下， 反应 42.0h， 以96%的产率得到2-(4-methyl-2-nitrophenyl)benzo[d]oxazole
  参考文献：
  名称：

  Palladium-catalyzed ortho-nitration of 2-arylbenzoxazoles

  摘要：

  An efficient and general protocol for palladium-catalyzed chelation-assisted ortho-nitration of 2-arylbenzoxazoles has been developed. This nitration exhibits high regioselectivity for the substrates, and the reaction could tolerate many functional groups such as F, Cl, Br, CH3, CH3O, affording ortho-nitration products in moderate to good yields. Moreover, some 2-arylbenzoxazole heterocyclic analogues proceed well under this catalytic system. Further studies have been performed to obtain insight into the mechanism. (C) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2015.10.035

文献信息

• Cobalt-Catalyzed Decarboxylative C–H (Hetero)Arylation for the Synthesis of Arylheteroarenes and Unsymmetrical Biheteroaryls
  作者：Yanrong Li、Fen Qian、Mengshi Wang、Hongjian Lu、Guigen Li

  DOI：10.1021/acs.orglett.7b02730

  日期：2017.10.20

  benzothiazoles or benzoxazoles is reported. This represents a first example of metal-catalyzed decarboxylative C–H heteroarylation of benzo-fused heterocycles. The transformation provides a convenient route, with good yields and functional group tolerance, to various important arylheteroaryl and unsymmetrical biheteroaryl structural motifs.

  报道了（杂）芳基羧酸与苯并噻唑或苯并恶唑的钴催化的脱羧交叉偶联反应。这代表了金属催化的苯并稠合杂环的脱羧CH杂杂芳基化反应的第一个例子。该转化为各种重要的芳基杂芳基和不对称的双杂芳基结构基序提供了一条方便的途径，具有良好的收率和官能团耐受性。
• Copper-catalyzed oxidative decarboxylative C–H arylation of benzoxazoles with 2-nitrobenzoic acids
  作者：Lijun Chen、Lin Ju、Katelyn A. Bustin、Jessica M. Hoover

  DOI：10.1039/c5cc06645j

  日期：——

  A copper-catalyzed oxidative decarboxylative coupling of benzoxazoles with 2-nitrobenzoic acids was developed. This methodology favors electron-rich benzoxazoles and electron-deficient benzoic acids and enables the preparation of a variety of arylated...

  建立了铜催化的苯并恶唑与2-硝基苯甲酸的氧化脱羧偶联反应。这种方法学偏爱富含电子的苯并恶唑和缺乏电子的苯甲酸，并能够制备各种芳基化的...
• Nickel-Catalyzed Decarboxylative Arylation of Heteroarenes through sp²C-H Functionalization
  作者：Ke Yang、Peng Wang、Cheng Zhang、Adnan A. Kadi、Hoong-Kun Fun、Yan Zhang、Hongjian Lu

  DOI：10.1002/ejoc.201403234

  日期：2014.12

  The direct decarboxylative arylation of hetereoarenes with benzoic acids through a nickel-catalyzed sp2 C–H functionalization process was developed. This process provides the first examples of decarboxylative cross-coupling reactions with aromatic acids through nickel catalysis and tolerates a variety of functional groups. Moreover, this method provides efficient access to 2-aryl-substituted azoles

  通过镍催化的 sp2 C-H 功能化过程，杂芳烃与苯甲酸直接脱羧芳基化。该过程提供了通过镍催化与芳香酸进行脱羧交叉偶联反应的第一个例子，并且可以耐受各种官能团。此外，该方法提供了对 2-芳基取代唑的有效获取，2-芳基取代唑是天然产物、药用化合物和功能材料中的重要结构单元。
• Palladium-catalyzed ortho-nitration of 2-arylbenzoxazoles
  作者：Hui-Jie Qiao、Fan Yang、Shi-Wei Wang、Yu-Ting Leng、Yang-Jie Wu

  DOI：10.1016/j.tet.2015.10.035

  日期：2015.12

  An efficient and general protocol for palladium-catalyzed chelation-assisted ortho-nitration of 2-arylbenzoxazoles has been developed. This nitration exhibits high regioselectivity for the substrates, and the reaction could tolerate many functional groups such as F, Cl, Br, CH3, CH3O, affording ortho-nitration products in moderate to good yields. Moreover, some 2-arylbenzoxazole heterocyclic analogues proceed well under this catalytic system. Further studies have been performed to obtain insight into the mechanism. (C) 2015 Elsevier Ltd. All rights reserved.