2-(4-fluorophenyl)-6-methylbenzo[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-fluorophenyl)-6-methylbenzo[d]oxazole
• 英文别名: 2-(4-Fluorophenyl)-6-methyl-1,3-benzoxazole
• 化学式: C₁₄H₁₀FNO
• mdl: MFCD07114507
• 分子量: 227.238
• InChiKey: VSKGJUFNILBUHI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  17
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  26
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  2-溴-4-甲基苯胺 在 四甲基乙二胺 、 copper(II) bis(trifluoromethanesulfonate) 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 24.0h， 生成 2-(4-fluorophenyl)-6-methylbenzo[d]oxazole
  参考文献：
  名称：

  Copper-catalysed intramolecular O-arylation of aryl chlorides and bromides: a straightforward approach to benzo[d]oxazoles in water

  摘要：

  A general, efficient and more sustainable protocol for the copper-catalysed intramolecular O-arylation of o'- haloanilides leading to the benzo[d]oxazole core is reported. Remarkably, the optimised conditions allowed for the use of inexpensive and easily available aryl chlorides as arylating agents. Moreover, all reactions were carried out employing exclusively water as the solvent, rendering the methodology presented herein highly valuable from both environmental and economic points of view. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2007.08.013

文献信息

• Zr and Hf-metal-organic frameworks: Efficient and recyclable heterogeneous catalysts for the synthesis of 2-arylbenzoxazole via ring open pathway acylation reaction
  作者：Linh Ho Thuy Nguyen、Trang Thi Thu Nguyen、Phuong Hoang Tran、Yoshiyuki Kawazoe、Hung Minh Le、Tan Le Hoang Doan

  DOI：10.1016/j.jcat.2019.04.023

  日期：2019.6

  2-arylbenzoxazole under solvent free conditions. Owning the wide opening spaces structures and inherent formate sites, MOFs based on 6-connected Zr6/Hf6 node were able to identify a significantly enhanced yield in Brønsted acid catalyzed reactions under conventional heating and microwave irradiation. In addition, the detailed mechanism of active sites of the ring opening acylation reaction was confirmed

  由锆和ha组成的由12个配位簇和6个配位簇组成的金属有机骨架被证明是在无溶剂条件下将苯并恶唑开环酰化为2-芳基苯并恶唑的高效多相催化剂。拥有宽阔的开放空间结构和固有的甲酸酯位点，基于6个连接的Zr 6 / Hf 6节点的MOF能够识别出在常规加热和微波辐射下布朗斯台德酸催化的反应中产率的显着提高。此外，通过使用密度泛函理论（DFT）计算，证实了开环酰化反应活性位点的详细机理。
• Unexpected Decarboxylation-Triggered <i>o</i> -Hydroxyl-Controlled Redox Condensation of Phenylglycines with 2-Nitrophenols in Aqueous Media
  作者：Lin Tang、Zhen Yang、Tian Sun、Di Zhang、Xiantao Ma、Weihao Rao、Yuqiang Zhou

  DOI：10.1002/adsc.201800586

  日期：2018.8.17

  o‐hydroxyl‐controlled hydrogen‐transfer strategy for the one‐pot synthesis of benzoxazoles from readily available amino acids and 2‐nitrophenols is reported. On the basis of this autoredox reaction, the C−N bond can be efficiently constructed to afford the desired products in moderate to good yields under transition‐metal‐free conditions in aqueous media.

  据报道，采用脱羧触发和邻羟基控制的氢转移策略，可以从容易获得的氨基酸和2-硝基酚一锅法合成苯并恶唑。在这种自动氧化还原反应的基础上，可以在水性介质中在无过渡金属的条件下有效构建CN键，以中等至良好的产率获得所需的产物。
• 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。
• Synthesis of benzoxazoles <i>via</i> an iron-catalyzed domino C–N/C–O cross-coupling reaction
  作者：Bo Yang、Weiye Hu、Songlin Zhang

  DOI：10.1039/c7ra13080e

  日期：——

  An eco-friendly and efficient method has been developed for the synthesis of 2-arylbenzoxazoles via a domino iron-catalyzed C–N/C–O cross-coupling reaction. Some of the issues typically encountered during the synthesis of 2-arylbenzoxazoles in the presence of palladium and copper catalysts, including poor substrate scope and long reaction times have been addressed using this newly developed iron-catalyzed

  开发了一种通过多米诺铁催化的 C-N/C-O 交叉偶联反应合成 2-芳基苯并恶唑的环保高效方法。使用这种新开发的铁催化方法已经解决了在钯和铜催化剂存在下合成 2-芳基苯并恶唑的过程中通常遇到的一些问题，包括底物范围差和反应时间长。