2-(6-methylpyridin-2-yl)-benzooxazole | 64819-72-3

• 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: 2-(6-methylpyridin-2-yl)-benzooxazole
• 英文别名: 2-(6-methylpyridin-2-yl)-benzoxazole；2-(2-benzoxazolyl)-6-methylpyridine；2-(6-methylpyridin-2-yl)benzoxazole；2-(6-methyl-pyridin-2-yl)-benzooxazole；Benzoxazole, 2-(6-methyl-2-pyridinyl)-；2-(6-methylpyridin-2-yl)-1,3-benzoxazole
• CAS: 64819-72-3
• 化学式: C₁₃H₁₀N₂O
• 分子量: 210.235
• InChiKey: AFEQKTSLKHQAKK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  16
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  38.9
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  tetrakis(actonitrile)copper(I) hexafluorophosphate 、 2-(6-methylpyridin-2-yl)-benzooxazole 以 乙腈 为溶剂， 反应 0.33h， 以100%的产率得到[Cu(2-(6-methylpyridin-2-yl)oxazole)₂][PF₆]
  参考文献：
  名称：

  Exploring simple ancillary ligands in copper-based dye-sensitized solar cells: effects of a heteroatom switch and of co-sensitization

  摘要：

  使用结构简单的异配铜（i）染料，在n型染料敏化太阳能电池中实现了达到N719铑染料40％的光电转换效率；同时介绍了使用混合铜（i）染料对DSC性能的影响。

  DOI：

  10.1039/c6ta10947k
• 作为产物：
  描述：

  2-溴-6-甲基吡啶 、 苯并恶唑 在 PdCl(C₃H₅)(dppb) caesium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 20.0h， 以78%的产率得到2-(6-methylpyridin-2-yl)-benzooxazole
  参考文献：
  名称：

  Direct arylation of oxazole and benzoxazole with aryl or heteroaryl halides using a palladium–diphosphine catalyst

  摘要：

  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.

  DOI：

  10.1016/j.jorganchem.2007.10.028

文献信息

• Palladium-catalyzed direct heteroarylation of chloropyridines and chloroquinolines
  作者：Fazia Derridj、Julien Roger、Florence Geneste、Safia Djebbar、Henri Doucet

  DOI：10.1016/j.jorganchem.2008.11.032

  日期：2009.2

  PdCl(dppb)(C3H5) as a catalyst, a range of heteroaryl derivatives undergoes coupling via C–H bond activation/functionalization reaction with chloropyridines or chloroquinolines in low to high yields. This air-stable catalyst can be used with a wide variety of substrates. The position of the chloro substituent on pyridines has a minor influence on the yields. On the other hand, the nature on the heteroaryl derivative

  芳基氯化物与杂芳烃的直接偶联将具有可持续发展的巨大优势，因为它们的成本更低，质量更轻，可用化合物的多样性更大，并且还因为仅形成了与副产物碱有关的HCl和减少制备这些化合物的步骤数。我们观察到通过使用PdCl（dppb）（C 3 H 5）作为催化剂，一系列杂芳基衍生物通过C–H键活化/官能化反应与氯吡啶或氯喹啉进行低至高收率的偶联。这种空气稳定的催化剂可与多种基材一起使用。吡啶上氯取代基的位置对收率影响很小。另一方面，杂芳基衍生物的性质具有很大的影响。使用苯并恶唑，噻吩或噻唑衍生物可获得最高的收率。氯吡啶与呋喃的偶联也得到了预期的产物，但是产率低至中等。
• Palladium‐Catalysed Direct C‐H Activation/Arylation of Heteroaromatics: An Environmentally Attractive Access to Bi‐ or Polydentate Ligands
  作者：Fazia Derridj、Aditya L. Gottumukkala、Safia Djebbar、Henri Doucet

  DOI：10.1002/ejic.200800143

  日期：2008.6

  Bi- or polydentate ligands based on heterocycles can be easily prepared by palladium-catalysed C–H bond activation of heteroaromatics followed by heteroarylation with heteroaryl bromides. A variety of heteroaromatics such as furans, thiophenes, pyridines, thiazoles or oxazole derivatives have been employed and moderate to good yields were generally obtained using the air-stable complex [PdCl(dppb)(C3H5)]

  基于杂环的双齿或多齿配体可以很容易地通过钯催化的杂芳烃的 C-H 键活化，然后用杂芳基溴化物进行杂芳基化来制备。已经使用了多种杂芳烃，例如呋喃、噻吩、吡啶、噻唑或恶唑衍生物，并且使用空气稳定的络合物 [PdCl(dppb)(C3H5)] 作为催化剂通常可以获得中等至良好的产率。可以容忍杂芳烃上的一系列功能，例如乙酰基、甲酰基、酯或腈。（© Wiley-VCH Verlag GmbH & Co. KGaA，69451 Weinheim，德国，2008）
• Synthesis of benzoxazolylpyridine nickel complexes and their efficient dimerization of ethylene to α-butene
  作者：Rong Gao、Liwei Xiao、Xiang Hao、Wen-Hua Sun、Fosong Wang

  DOI：10.1039/b807604a

  日期：——

  A series of new nickel complexes bearing benzoxazolylpyridines was synthesized and characterized by FT-IR spectroscopic and elemental analysis. The molecular structures of two representative complexes were determined by single-crystal X-ray diffraction. The complex [NiCl22-(2-benzoxazolyl)-6-methylpyridine}] (5) is a centrosymmetric dinuclear compound with two penta-coordinated Ni(II) centers, whereas the complex [NiCl22-(5-methyl-2-benzoxazolyl)-6-methylpyridine}] (6) is mononuclear exhibiting a distorted octahedral-coordination geometry around the nickel atom. Upon activation with diethylaluminium chloride (Et2AlCl), all the complexes exhibited moderate to good catalytic activity for ethylene oligomerization (27–415 g mmol−1(Ni) h−1bar−1) with high selectivity for ethylene dimerization to form α-butene. The observed variance in the catalytic activities of the complexes is attributed to the different ligand environments and effects of reaction parameters.

  合成并表征了一系列含有苯并咯唑基吡啶的新镍配合物，采用FT-IR光谱和元素分析进行表征。通过单晶X射线衍射确定了两个代表性配合物的分子结构。配合物[NiCl22-(2-benzoxazolyl)-6-methylpyridine}] (5)为中心对称的双核化合物，具有两个五配位的Ni(II)中心，而配合物[NiCl22-(5-methyl-2-benzoxazolyl)-6-methylpyridine}] (6)为单核化合物，显示出在镍原子周围的扭曲八面体配位几何构型。在用氯化二乙铝（Et2AlCl）激活后，所有配合物在乙烯低聚化反应中表现出中等至良好的催化活性（27–415 g mmol⁻¹(Ni) h⁻¹bar⁻¹），并对乙烯二聚化形成α-丁烯具有高度选择性。配合物的催化活性差异归因于不同的配体环境和反应参数的影响。
• Barni,E.; Savarino,P., Journal of Heterocyclic Chemistry, 1977, vol. 14, p. 937 - 940
  作者：Barni,E.、Savarino,P.

  DOI：——

  日期：——

表征谱图