5-(chloro)-2-(pyridin-3-yl)benzo[d]oxazole | 92059-24-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并恶唑类
• 英文名称: 5-(chloro)-2-(pyridin-3-yl)benzo[d]oxazole
• 英文别名: 5-chloro-2-(pyridin-3-yl)benzo[d]oxazole；5-chloro-2-(pyridin-3-yl)benzoxazole；5-chloro-2-pyridine-3-ylbenzoxazole；2-(3-Pyridyl)-5-chlorbenzoxazol；5-Chloro-2-pyridin-3-yl-1,3-benzoxazole
• CAS: 92059-24-0
• 化学式: C₁₂H₇ClN₂O
• mdl: MFCD03773341
• 分子量: 230.653
• InChiKey: OXTDBAQSCKLANI-UHFFFAOYSA-N

物化性质

• 熔点：
  194-195 °C
• 沸点：
  354.8±22.0 °C(Predicted)
• 密度：
  1.356±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  16
• 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：
  38.9
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  4-氯-2-氨基苯酚 在 palladium diacetate 、 sodium t-butanolate 、 4,6-二(二苯基膦)吩嗪 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 12.0h， 生成 5-(chloro)-2-(pyridin-3-yl)benzo[d]oxazole
  参考文献：
  名称：

  Room-temperature palladium-catalyzed direct 2-arylation of benzoxazoles with aryl and heteroaryl bromides

  摘要：

  第一个室温下使用Pd(OAc)₂/NiXantphos基催化剂对苯并噁唑与芳基溴化物进行直接2-芳基化反应的研究结果已经报道。

  DOI：

  10.1039/c4cc05307a

文献信息

• Regiodivergent Cross-Dehydrogenative Coupling of Pyridines and Benzoxazoles: Discovery of Organic Halides as Regio-Switching Oxidants
  作者：Shuya Yamada、Kei Murakami、Kenichiro Itami

  DOI：10.1021/acs.orglett.6b00932

  日期：2016.5.20

  regio-divergent heterocyclic CDCs is considered crucial. In this Letter, the unprecedented use of organic halides as an oxidant to achieve the CDC reaction of pyridines and benzoxazoles with palladium catalyst is described. Moreover, the regioselectivity of the pyridine functionalization site can be controlled by the choice of organic halides.

  两种未官能化的杂芳烃的交叉脱氢偶联（CDC）已被认为是合成特权杂二芳基支架的理想转化。然而，除其他键外，特定的两个杂环CH键之间的区域选择性激活和转化一直是极富挑战性的。因此，发现新的控制元件以实现区域控制和区域发散的杂环CDC被认为是至关重要的。在这封信中，描述了前所未有地使用有机卤化物作为氧化剂来实现吡啶和苯并恶唑与钯催化剂的CDC反应。此外，可以通过选择有机卤化物来控制吡啶官能化位点的区域选择性。
• Pd/Cu bimetallic co-catalyzed direct 2-arylation of benzoxazole with aryl chloride
  作者：Ling-Li Zheng、Bo Yin、Xing-Chuan Tian、Ming-Yong Yuan、Xiao-Huan Li、Feng Gao

  DOI：10.1016/j.tetlet.2019.151316

  日期：2019.12

  An efficient Palladium/Copper bimetallic co-catalyzed direct 2-arylation of benzoxazoles with aryl chlorides is presented. The Pd(OAc)2/CuI/NiXantphos-based catalyst enables the installation of various aryl and heteroaryl groups in good to excellent yields (75–99%). Preliminary mechanism investigation indicates that Pd/Nixantphos complex activates C-Cl bond of aryl chlorides via oxidative addition

  提出了一种有效的钯/铜双金属共催化的苯并恶唑与芳基氯化物的2-芳基化反应。基于Pd（OAc）2 / CuI / NiXantphos的催化剂能够以优异的产率（75-99％）安装各种芳基和杂芳基。初步的机理研究表明，Pd / Nixantphos配合物通过氧化加成激活芳基氯的C-Cl键，而Cu / Nixantphos配合物与氮原子螯合以降低苯并恶唑中2-H的pK a。
• Nano CuO-catalyzed C–H functionalization of 1,3-azoles with bromoarenes and bromoalkenes
  作者：Wu Zhang、Yujie Tian、Na Zhao、Yuanyuan Wang、Jia Li、Zhenghua Wang

  DOI：10.1016/j.tet.2014.04.065

  日期：2014.9

  Copper oxide catalyzed direct C–H arylation and alkenylation of aromatic heterocycles using aryl and alkenyl bromides have been developed and have been applied to the C–H functionalization of a variety of 1,3-azoles like benzoxazole, benzothiazole, 1-methylbenzimidazole, and 1-methylimidazole, with moderate to excellent yields. The best performance has been achieved in the presence of PPh3 when average

  已经开发出使用芳基和烯基溴化物的氧化铜催化芳族杂环的直接C–H芳基化和烯基化反应，并将其应用于各种1,3-唑类的C–H官能化，如苯并恶唑，苯并噻唑，1-甲基苯并咪唑和1-甲基咪唑，具有中等至优异的收率。当Cuh纳米粒子的平均尺寸为6.5 nm时，在PPh 3的存在下已实现了最佳性能。该催化剂可以回收和再利用而不会显着降低其催化活性。
• Borane complexes of 2-(1-Methyl-1,2,5,6-tetra-hydropyridin-3-yl)benzoxazoles
  作者：Myung Hee Jung、Jewn-Giew Park、Bok-Sim Ryu、Kui-Woong Cho

  DOI：10.1002/jhet.5570360215

  日期：1999.3

  and substituted o-aminophenols in the presence of iodobenzene diacetate. The resulting benzoxazoles 3 were treated with methyl iodide to give the corresponding pyridinium salts 4 which underwent the hydride reduction with sodium borohydride or sodium cyanoborohydride to produce 2-(1-methyl-1,2,5,6-tetrahy-dropyridin-3-yl)benzoxazole borane complex derivatives.

  通过3-吡啶甲醛与取代的邻氨基苯酚在碘代苯二乙酸酯存在下的反应合成2-吡啶-3-基苯并恶唑。用甲基碘处理所得的苯并恶唑3，得到相应的吡啶鎓盐4，将其用硼氢化钠或氰基硼氢化钠还原氢化，得到2-（1-甲基-1,2,5,6-四氢吡啶-3- yl）苯并恶唑硼烷配合物衍生物。
• Iodine (III)-mediated synthesis of some 2-aryl/hetarylbenzoxazoles as antibacterial/antifungal agents
  作者：Ravi Kumar、Reshmi R. Nair、Saurabh Sudha Dhiman、Jitender Sharma、Om Prakash

  DOI：10.1007/s00044-009-9211-y

  日期：2010.7

  Ten 2-aryl/hetarylbenzoxazoles (5a, 5b, and 6a-h) were synthesized via oxidative cyclization of Schiff bases (3a, 3b, and 4a-h) with 1.1 equivalent of iodobenzene diacetate (IBD) in methanol. All of these 2-aryl/hetarylbenzoxazoles (5a, 5b, and 6a-h) were tested in vitro for their antibacterial and antifungal activities against Bacillus subtilis, Bacillus stearothermophilus, Escherichia coli, and Pseudomonas putida. These compounds also were screened for their antifungal activity against Aspergillus flavus and Aspergillus niger. Biological activity of these compounds was compared with those of commercially available antibiotics, chloramphenicol and antifungal agent cycloheximide. Most of these compounds, 5a, 5b, 6a, 6b, 6d, 6e, 6g, 6h, were equipotent or more potent than these commercial drugs at concentration 100 mu g/ml.

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