2-(2,6-dimethoxyphenyl)benzo[d]oxazole | 404365-75-9

• 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-(2,6-dimethoxyphenyl)benzo[d]oxazole
• 英文别名: 2-(2,6-dimethoxyphenyl)benzoxazole；DMHBO；2-(2,6-Dimethoxyphenyl)-1,3-benzoxazole；2-(2,6-dimethoxyphenyl)-1,3-benzoxazole
• CAS: 404365-75-9
• 化学式: C₁₅H₁₃NO₃
• 分子量: 255.273
• InChiKey: CHKPRMHRCZIOFL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  19
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.13
• 拓扑面积：
  44.5
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-(2,6-dimethoxyphenyl)benzo[d]oxazole 在 三溴化硼 作用下， 以 正己烷 、 二氯甲烷 为溶剂， 反应 48.0h， 以82%的产率得到MHBO
  参考文献：
  名称：

  Rotational Energy Barrier of 2-(2′,6′-Dihydroxyphenyl)benzoxazole: A Case Study by NMR

  摘要：

  2-(2'-Hydroxyphenyl)benzoxazole (HBO) derivatives represent an important class of luminescent materials, as they can undergo excited state intramolecular proton transfer (ESIPT). The material's ESIPT properties are dependent on the ratio of two different rotamers, whose interconversion is poorly understood. By using HBO derivative 4, the rotational energy barrier of 2- (2;6'-hydroxyphenyl)benzoxazole is determined to be 10.5 kcal/mol by variable-temperature NMR. Although a HBO derivative typically exhibits two rotamers with O center dot center dot center dot H-O (e.g., 1a) and N center dot center dot center dot H-O bonding (e.g., 1b), correlation of NMR with fluorescence data reveals that the rotamer with N center dot center dot center dot H-O bonding is predominant in the solution.

  DOI：

  10.1021/jo201890f
• 作为产物：
  描述：

  2,6-二甲氧基苯甲醛 在 氧气 、 palladium diacetate 、 caesium carbonate 作用下， 以 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 反应 8.0h， 生成 2-(2,6-dimethoxyphenyl)benzo[d]oxazole
  参考文献：
  名称：

  Rotational Energy Barrier of 2-(2′,6′-Dihydroxyphenyl)benzoxazole: A Case Study by NMR

  摘要：

  2-(2'-Hydroxyphenyl)benzoxazole (HBO) derivatives represent an important class of luminescent materials, as they can undergo excited state intramolecular proton transfer (ESIPT). The material's ESIPT properties are dependent on the ratio of two different rotamers, whose interconversion is poorly understood. By using HBO derivative 4, the rotational energy barrier of 2- (2;6'-hydroxyphenyl)benzoxazole is determined to be 10.5 kcal/mol by variable-temperature NMR. Although a HBO derivative typically exhibits two rotamers with O center dot center dot center dot H-O (e.g., 1a) and N center dot center dot center dot H-O bonding (e.g., 1b), correlation of NMR with fluorescence data reveals that the rotamer with N center dot center dot center dot H-O bonding is predominant in the solution.

  DOI：

  10.1021/jo201890f

文献信息

• Pd-Catalyzed Decarboxylative Arylation of Thiazole, Benzoxazole, and Polyfluorobenzene with Substituted Benzoic Acids
  作者：Kai Xie、Zhiyong Yang、Xingjian Zhou、Xiujian Li、Sizhuo Wang、Ze Tan、Xiangyu An、Can-Cheng Guo

  DOI：10.1021/ol100296b

  日期：2010.4.2

  with various substituted benzoic acids is developed. The reaction is compatible with both electron-rich and electron-poor benzoic acids. It can also be extended to the synthesis of polyfluoro-substituted biaryls using polyfluorobenzenes as the starting materials.

  建立了Pd催化的噻唑和苯并恶唑与各种取代的苯甲酸的脱羧偶联反应。该反应与富电子和贫电子的苯甲酸都相容。它也可以扩展到以多氟苯为原料合成多氟取代的联芳基。
• Intramolecular O‐arylation using nano‐magnetite supported <i>N</i> ‐heterocyclic carbene‐copper complex with wingtip ferrocene
  作者：Altafhusen Naikwade、Megha Jagadale、Dolly Kale、Shivanand Gajare、Prakash Bansode、Gajanan Rashinkar

  DOI：10.1002/aoc.5066

  日期：——

  Nano‐magnetite supported N‐heterocyclic carbene‐copper complex with wingtip ferrocene has been prepared via multi‐step procedure. The complex has been characterized by various analytical techniques such as fourier transform infrared (FT‐IR), fourier transform Raman (FT‐Raman), X‐ray photoelectron spectroscopy (XPS), X‐ray diffraction (XRD), transmission electron microscopy (TEM) and vibrating sample

  纳米磁铁矿负载的N-杂环卡宾-铜与翼尖二茂铁配合物已通过多步程序制备。该复合物具有多种分析技术的特征，例如傅立叶变换红外（FT-IR），傅立叶变换拉曼（FT-Raman），X射线光电子能谱（XPS），X射线衍射（XRD），透射电子显微镜（ TEM）和振动样品磁力计（VSM）分析。该复合物的催化活性已在异质条件下的邻碘苯胺的分子内芳基化中得到了利用。该复合物可以成功回收多达十二个连续循环。
• Excited-state intramolecular proton transfer in 2-(2′,6′-dihydroxyphenyl)benzoxazole: effect of dual hydrogen bonding on the optical properties
  作者：Wei-Hua Chen、Yi Pang

  DOI：10.1016/j.tetlet.2010.02.043

  日期：2010.4

  O–H···O bonds to ensure a coplanar structure between the benzoxazole and phenol fragments. Optical comparison with the parent compound 2-(2′-hydroxyphenyl)benzoxazole (HBO) reveals that the dual hydrogen bonding in DHBO plays an essential role in raising the desirable keto emission for ESIPT and tuning the polarity sensitivity toward the molecular environment. DHBO also exhibits a higher quantum yield

  通过使用钯催化的氧化环化反应合成了2-（2'，6'-二羟基苯基）苯并恶唑（DHBO）。该化合物利用O - H ··· N和O – H ··· O两种键来确保苯并恶唑和酚片段之间的共面结构。与母体化合物2-（2'-羟基苯基）苯并恶唑（HBO）的光学比较表明，DHBO中的双氢键在提高ESIPT所需的酮基发射量和调整对分子环境的极性敏感性方面起着至关重要的作用。DHBO还表现出更高的量子产率（φ FL 比HBO =甲醇0.108）（φ FL = 0.0025）在相同的溶剂中。
• Magnetic Nanoparticle Decorated N-Heterocyclic Carbene–Nickel Complex with Pendant Ferrocenyl Group for C–H Arylation of Benzoxazole
  作者：Altafhusen Naikwade、Megha Jagadale、Dolly Kale、Shivanand Gajare、Gajanan Rashinkar

  DOI：10.1007/s10562-018-2514-1

  日期：2018.10

  Magnetic nanoparticle decorated N-heterocyclic carbene-nickel complex with pendant ferrocenyl group has been prepared by multi-step procedure. The formation of complex was confirmed on the basis of analytical techniques such as Fourier transform infrared (FT-IR), Fourier transform Raman (FT-Raman) and X-ray photoelectron spectroscopy (XPS) as well as by X-ray diffraction (XRD), transmission electron microscopy (TEM) and vibrating sample magnetometer (VSM) analysis. The complex proved to be an efficient heterogeneous catalyst for C-H arylation of benzoxazole with aryl boronic acids. The recycling studies revealed that complex could be reused for six times without significant decrease in catalytic activity.[GRAPHICS].
• Rotational Energy Barrier of 2-(2′,6′-Dihydroxyphenyl)benzoxazole: A Case Study by NMR
  作者：Weihua Chen、Eric B. Twum、Linlin Li、Brian D. Wright、Peter L. Rinaldi、Yi Pang

  DOI：10.1021/jo201890f

  日期：2012.1.6

  2-(2'-Hydroxyphenyl)benzoxazole (HBO) derivatives represent an important class of luminescent materials, as they can undergo excited state intramolecular proton transfer (ESIPT). The material's ESIPT properties are dependent on the ratio of two different rotamers, whose interconversion is poorly understood. By using HBO derivative 4, the rotational energy barrier of 2- (2;6'-hydroxyphenyl)benzoxazole is determined to be 10.5 kcal/mol by variable-temperature NMR. Although a HBO derivative typically exhibits two rotamers with O center dot center dot center dot H-O (e.g., 1a) and N center dot center dot center dot H-O bonding (e.g., 1b), correlation of NMR with fluorescence data reveals that the rotamer with N center dot center dot center dot H-O bonding is predominant in the solution.