2-(4-methylpiperidin-1-yl)benzoxazole | 452346-92-8

• 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-(4-methylpiperidin-1-yl)benzoxazole
• 英文别名: 2-(4-methylpiperdin-1-yl)benzoxazole；2-(4-Methylpiperidin-1-yl)-1,3-benzoxazole
• CAS: 452346-92-8
• 化学式: C₁₃H₁₆N₂O
• 分子量: 216.283
• InChiKey: OWILTSNQFQOGDL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 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：

  C₁₃H₁₈N₂O 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-(4-methylpiperidin-1-yl)benzoxazole
  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

• [EN] AMIDO-THIOPHENE COMPOUNDS AND THEIR USE AS 11-BETA-HSD1 INHIBITORS<br/>[FR] COMPOSÉS AMIDO-THIOPHÈNE ET LEUR UTILISATION EN TANT QU'INHIBITEURS DE 11-BÊTA-HSD1
  申请人：UNIV EDINBURGH

  公开号：WO2009074789A1

  公开（公告）日：2009-06-18

  The present invention pertains generally to the field of therapeutic compounds. More specifically the present invention pertains to certain amido-thiophene compounds that, inter alia, inhibit 11β-hydroxysteroid dehydrogenase type 1 (11β-HSD1). The present invention also pertains to pharmaceutical compositions comprising such compounds, and the use of such compounds and compositions, both in vitro and in vivo, to inhibit 11β-hydroxysteroid dehydrogenase type 1; to treat disorders that are ameliorated by the inhibition of 11β-hydroxysteroid dehydrogenase type 1; to treat the metabolic syndrome, which includes disorders such as type 2 diabetes and obesity, and associated disorders including insulin resistance, hypertension, lipid disorders and cardiovascular disorders such as ischaemic (coronary) heart disease; to treat CNS disorders such as mild cognitive impairment and early dementia, including Alzheimer's disease; etc. Formula (I).

  本发明一般涉及治疗化合物领域。更具体地，本发明涉及某些酰胺噻吩化合物，其中包括抑制11β-羟基类固醇脱氢酶1（11β-HSD1）。本发明还涉及包含这些化合物的药物组合物，以及利用这些化合物和组合物在体外和体内抑制11β-羟基类固醇脱氢酶1；治疗通过抑制11β-羟基类固醇脱氢酶1而得到改善的疾病；治疗代谢综合征，其中包括2型糖尿病和肥胖等疾病，以及相关疾病，包括胰岛素抵抗、高血压、脂质紊乱和心血管疾病，如缺血性（冠状）心脏病；治疗中枢神经系统疾病，如轻度认知障碍和早期痴呆，包括阿尔茨海默病等。公式（I）。
• Copper-Catalyzed Direct Oxidative C–H Amination of Benzoxazoles with Formamides or Secondary Amines under Mild Conditions
  作者：Yaming Li、Yusheng Xie、Rong Zhang、Kun Jin、Xiuna Wang、Chunying Duan

  DOI：10.1021/jo200447x

  日期：2011.7.1

  A facile, efficient, and practical method for copper-catalyzed direct C–H amination of benzoxazoles with formamides or secondary amines has been developed. The system can be performed in the absence of external base and only requires O2 or even air as oxidant. A variety of substituted benzoxazol-2-amines were synthesized with moderate to excellent yield.

  已经开发了一种简便，有效且实用的方法，用于铜催化的苯甲恶唑与甲酰胺或仲胺的CH–H氨化反应。该系统可以在没有外部碱的情况下进行，仅需要O 2或什至空气作为氧化剂。合成了各种取代的苯并恶唑-2-胺，产率中等至优异。
• 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。
• 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。