2-(4-bromophenyl)-6-chlorobenzo[d]oxazole | 1315571-18-6

• 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-bromophenyl)-6-chlorobenzo[d]oxazole
• 英文别名: 2-(4-bromophenyl)-6-chlorobenzoxazole；6-chloro-2-(4-bromophenyl)benzoxazole；2-(4-Bromophenyl)-6-chloro-1,3-benzoxazole
• CAS: 1315571-18-6
• 化学式: C₁₃H₇BrClNO
• 分子量: 308.562
• InChiKey: VHAZXMTXNWUQCY-UHFFFAOYSA-N

物化性质

• 熔点：
  168-170 °C
• 沸点：
  370.5±22.0 °C(Predicted)
• 密度：
  1.598±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 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：
  26
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  2-Hydroxy-4-chloro-(p-bromobenzylideno)-anilin 在 sodium iodide 作用下， 以 二氯甲烷 为溶剂， 以70%的产率得到2-(4-bromophenyl)-6-chlorobenzo[d]oxazole
  参考文献：
  名称：

  以碘化钠为介质高效间接电化学合成2-取代的苯并恶唑

  摘要：

  AbstractAn electrochemical strategy for the efficient synthesis of 2‐substituted benzoxazoles was developed using a catalytic amount of sodium iodide (NaI) as a redox catalyst in a two‐phase buffer system.magnified image

  DOI：

  10.1002/adsc.201300502

文献信息

• Chlorination and ortho-acetoxylation of 2-arylbenzoxazoles
  作者：Yuting Leng、Fan Yang、Weiguo Zhu、Yangjie Wu、Xiang Li

  DOI：10.1039/c1ob05223c

  日期：——

  Efficient and facile catalytic protocols for chlorination and ligand-directed ortho-acetoxylation of 2-arylbenzoxazoles have been developed. The chlorination is not a ligand-directed ortho-functionalization, but an electrophilic substitution process in the benzo ring of the benzoxazole moiety. Meanwhile, the acetoxylation exhibited high regioselectivity for the substrates containing a meta-substituent and occurred at the less sterically hindered ortho-C–H bond of the directing group.

  针对 2-芳基苯并恶唑的氯化和配体定向正乙酰氧基化，我们开发出了高效、简便的催化方案。氯化反应不是配体定向的正官能化，而是苯并恶唑分子苯环上的亲电取代过程。同时，乙酰氧基化对含有元取代基的底物具有很高的区域选择性，并且发生在指导基团的立体阻碍较小的正交-C-H 键上。
• Mesoporous Poly(melamine-formaldehyde): A Green and Recyclable Heterogeneous Organocatalyst for the Synthesis of Benzoxazoles and Benzothiazoles Using Dioxygen as Oxidant
  作者：Daoshan Yang、Peng Liu、Ning Zhang、Wei Wei、Mingbo Yue、Jinmao You、Hua Wang

  DOI：10.1002/cctc.201402628

  日期：2014.12

  simple, highly efficient, and sustainable strategy for the synthesis of benzoxazole and benzothiazole derivatives was developed by using inexpensive, green, readily available, and recyclable mesoporous poly(melamine–formaldehyde) as a green, heterogeneous organocatalyst. The corresponding substituted benzoxazoles and benzothiazoles were obtained in good to excellent yields by aerobic oxidation of o‐substituted

  通过使用廉价，绿色，易得且可回收的中孔聚（三聚氰胺-甲醛）作为绿色，多相有机催化剂，开发了一种简单，高效且可持续的苯并恶唑和苯并噻唑衍生物合成策略。通过在双氧气氛下用各种醛类对邻位取代的氨基苯进行好氧氧化，可以得到良好至优异的收率，得到相应的取代苯并恶唑和苯并噻唑。催化剂可以通过简单的过滤完全回收，可以重复使用六次以上，而不会显着降低催化活性。
• Magnetically recoverable and reusable CuFe₂O₄nanoparticle-catalyzed synthesis of benzoxazoles, benzothiazoles and benzimidazoles using dioxygen as oxidant
  作者：Daoshan Yang、Xiao Zhu、Wei Wei、Nana Sun、Li Yuan、Min Jiang、Jinmao You、Hua Wang

  DOI：10.1039/c4ra00559g

  日期：——

  A green and efficient strategy for the synthesis of benzoxazoles, benzothiazoles and benzimidazoles has been developed by using inexpensive, readily available, dioxygen-stable and recyclable CuFe₂O₄as the nanocatalyst.

  通过使用廉价、易获得、稳定于二氧化碳并可循环利用的CuFe2O4纳米催化剂，已经开发出一种合成苯并噁唑、苯并噻唑和苯并咪唑的绿色高效策略。
• Cyclopalladated Ferrocenylimine Catalyzed Chlorination of 2-Arylbenzoxazoles
  作者：Yuting Leng、Fan Yang、Yangjie Wu、Ke Li

  DOI：10.1002/cjoc.201180245

  日期：2011.8

  An efficient and facile protocol for palladacycle‐catalyzed chlorination of 2‐arylbenzoxazoles was developed. The results represent the first examples involving the palladacycle as the catalyst for such chlorination. This chlorination was not a ligand‐directed ortho‐CH activation, but an electrophilic substitution process at the para‐position of the nitrogen atom in the benzo ring of benzoxazole moiety

  开发了一种高效且简便的方案，可用于Palladacycle催化的2-芳基苯并恶唑的氯化反应。结果代表了涉及保拉达环作为这种氯化催化剂的第一个实例。该氯化不是配体引导邻-C  ħ激活，但在电取代过程对在苯并恶唑部分的苯并环的氮原子的-位，的区域化学其中已被HMBC谱分析确认。催化体系可以耐受各种卤素原子，例如F，Cl和Br，以中等至极好的收率提供相应的产物。
• Efficient Indirect Electrochemical Synthesis of 2-Substituted Benzoxazoles using Sodium Iodide as Mediator
  作者：Wei-Cui Li、Cheng-Chu Zeng、Li-Ming Hu、Hong-Yu Tian、R. Daniel Little

  DOI：10.1002/adsc.201300502

  日期：2013.10.11

  AbstractAn electrochemical strategy for the efficient synthesis of 2‐substituted benzoxazoles was developed using a catalytic amount of sodium iodide (NaI) as a redox catalyst in a two‐phase buffer system.magnified image