2-(3-methylpiperidin-1-yl)benzo[d]oxazole | 1604815-62-4

• 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-(3-methylpiperidin-1-yl)benzo[d]oxazole
• 英文别名: 2-(3-Methylpiperidin-1-yl)-1,3-benzoxazole；2-(3-methylpiperidin-1-yl)-1,3-benzoxazole
• CAS: 1604815-62-4
• 化学式: C₁₃H₁₆N₂O
• 分子量: 216.283
• InChiKey: SHXZVWVWHCZXGE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  16
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  29.3
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  在 N-溴代丁二酰亚胺(NBS) 、 potassium acetate 作用下， 以 1,4-二氧六环 、 水 为溶剂， 反应 0.08h， 生成 2-(3-methylpiperidin-1-yl)benzo[d]oxazole
  参考文献：
  名称：

  N-Bromosuccinimide as an oxidant for the transition-metal-free synthesis of 2-aminobenzoxazoles from benzoxazoles and secondary amines

  摘要：

  开发了一种简易且无需过渡金属的方法，通过结合苯并恶唑与二级胺的开环反应以及N-溴代琥珀酰亚胺（NBS）介导的氧化环化反应，实现了2-氨基苯并恶唑的合成。在环开酰胺的氧化环化过程中，NBS被选作强效氧化剂，以高产率（最高可达94%）提供所需的2-氨基苯并恶唑。

  DOI：

  10.1039/c4ob00386a

文献信息

• The Synthesis of 2-Aminobenzoxazoles Using Reusable Ionic Liquid as a Green Catalyst under Mild Conditions
  作者：Ya Zhou、Zhiqing Liu、Tingting Yuan、Jianbin Huang、Chenjiang Liu

  DOI：10.3390/molecules22040576

  日期：——

  A facile, green, and efficient method for the direct oxidative amination of benzoxazoles using heterocyclic ionic liquid as catalyst has been developed. The reaction proceeded smoothly at room temperature and gave the desirable 2-aminobenzoxazoles with good to excellent yields (up to 97%). The catalyst 1-butylpyridinium iodide can be easily recycled and reused with similar efficacies for at least four cycles.

  一种简便、绿色且高效的方法已被开发，用于使用杂环离子液体作为催化剂直接氧化胺化苯并噁唑。反应在室温下顺利进行，并得到理想的2-氨基苯并噁唑，产率良好到优秀（最高可达97%）。催化剂四丁基吡啶碘化物可以方便地回收并重复使用，至少可维持四个循环的相似效果。
• New topological Co₂(BDC)₂(DABCO) as a highly active heterogeneous catalyst for the amination of oxazoles via oxidative C–H/N–H couplings
  作者：Thach N. Tu、Khoa D. Nguyen、Truong N. Nguyen、Thanh Truong、Nam T. S. Phan

  DOI：10.1039/c5cy01145k

  日期：——

  Herein, we report the synthesis, structural characterization, and catalytic properties of a new cobalt-based metal–organic framework, Co2(BDC)2(DABCO) (where BDC = 1,4-benzenedicarboxylate and DABCO = 1,4-diazabicyclo[2.2.2]octane), namely VNU-10 (where VNU = Vietnam National University). Single-crystal X-ray diffraction analysis revealed that VNU-10 crystallizes in the hexagonal space group P6/mmm. The structure of this material is comprised of two-dimensional kgm layers which are interconnected by DABCO pillars to afford an overall three-dimensional porous architecture. VNU-10 exhibited exceptional catalytic activity toward the direct amination of oxazoles via C–H/N–H couplings while a previously reported topological isomer, Co2(BDC)2(DABCO), with the sql topology, displayed poor activity. Leaching tests indicated that homogeneous catalysis via leached active cobalt species is unlikely. Furthermore, the VNU-10 catalyst was facilely isolated from the reaction mixture and reused several times without degradation of the catalytic reactivity.

  在此，我们报告了一种新型钴基金属有机框架 Co2(BDC)2(DABCO)（其中 BDC = 1,4-苯二甲酸酯，DABCO = 1,4-二氮杂双环[2.2.2]辛烷），即 VNU-10（其中 VNU = 越南国立大学）的合成、结构表征和催化特性。单晶 X 射线衍射分析表明，VNU-10 晶型为六方空间群 P6/mmm。这种材料的结构由二维 kgm 层组成，这些 kgm 层通过 DABCO 柱相互连接，从而形成一个整体的三维多孔结构。VNU-10 在通过 CâH/NâH 偶联对噁唑进行直接胺化时表现出卓越的催化活性，而之前报道的具有 sql 拓扑结构的拓扑异构体 Co2(BDC)2(DABCO)则表现出很差的活性。浸出测试表明，通过浸出活性钴物种进行均相催化的可能性不大。此外，VNU-10 催化剂可以很容易地从反应混合物中分离出来并重复使用多次，而不会降低催化反应活性。
• HFIP Promoted Low-Temperature S_NAr of Chloroheteroarenes Using Thiols and Amines
  作者：Yuvraj B. Bhujabal、Kamlesh S. Vadagaonkar、Aniket Gholap、Yogesh S. Sanghvi、Rambabu Dandela、Anant R. Kapdi

  DOI：10.1021/acs.joc.9b02371

  日期：2019.12.6

  A highly efficient and an unprecedented hexafluoro-2-propanol, promoting low-temperature aromatic nucleophilic substitutions of chloroheteroarenes, has been performed using thiols and (secondary) amines under base free and metal-free conditions. The developed protocol also provides excellent regio-control for the selective functionalization of dichloroheteroarenes, while the utility of the protocol was demonstrated by the modification of a commercially available drug ceritinib.
• N-Bromosuccinimide as an oxidant for the transition-metal-free synthesis of 2-aminobenzoxazoles from benzoxazoles and secondary amines
  作者：Xiaoe Wang、Daqian Xu、Chengxia Miao、Qiaohong Zhang、Wei Sun

  DOI：10.1039/c4ob00386a

  日期：——

  A facile and transition-metal-free method was developed through merging the ring opening of benzoxazoles with secondary amines and N-bromosuccinimide (NBS) mediated oxidative cyclization toward the synthesis of 2-aminobenzoxazoles. NBS was selected as a powerful oxidant in the oxidative cyclization of ring-opening amidines to provide the desirable 2-aminobenzoxazoles in excellent yields (up to 94%).

  开发了一种简易且无需过渡金属的方法，通过结合苯并恶唑与二级胺的开环反应以及N-溴代琥珀酰亚胺（NBS）介导的氧化环化反应，实现了2-氨基苯并恶唑的合成。在环开酰胺的氧化环化过程中，NBS被选作强效氧化剂，以高产率（最高可达94%）提供所需的2-氨基苯并恶唑。