N-(tert-butyl)quinolin-2-amine

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 英文名称: N-(tert-butyl)quinolin-2-amine
• 英文别名: N-tert-butylquinolin-2-amine
• 化学式: C₁₃H₁₆N₂
• mdl: MFCD22083164
• 分子量: 200.283
• InChiKey: JZGDQSBAUSQBAD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.307
• 拓扑面积：
  24.9
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  N-(tert-butyl)quinolin-2-amine 在 三氟乙酸 作用下， 以 various solvent(s) 为溶剂， 生成 2-氨基喹啉
  参考文献：
  名称：

  A General and Efficient 2-Amination of Pyridines and Quinolines

  摘要：

  Pyridine N-oxides were converted to 2-aminopyridines in a one-pot fashion using Ts2O-t-BuNH2 followed by in situ deprotection with TFA. The amination proceeded in high yields, excellent 2-/4-selectivity, and with good functional group compatibility. 2-Amino (iso)quinolines were also obtained in the same manner. Combined with the simple oxidation of pyridines to pyridine N-oxides, this method provides a general and efficient way for amination of 2-unsubstituted pyridines.

  DOI：

  10.1021/jo070189y
• 作为产物：
  描述：

  甲基硝基苯 在 sodium phenoxide 、 palladium diacetate 、 silver carbonate 、 calcium chloride 、 potassium hydroxide 、 锌 作用下， 以 1,4-二氧六环 、 水 、 二甲基亚砜 为溶剂， 反应 17.5h， 生成 N-(tert-butyl)quinolin-2-amine
  参考文献：
  名称：

  Palladium-catalyzed direct coupling of 2-vinylanilines and isocyanides: an efficient synthesis of 2-aminoquinolines

  摘要：

  一系列2-氨基喹啉以良好至优异的产率制备完成。

  DOI：

  10.1039/c5ob01659b

文献信息

• HETEROBICYCLIC COMPOUNDS
  申请人：Amgen Inc.

  公开号：US20130225552A1

  公开（公告）日：2013-08-29

  Heterobicyclic compounds of Formula (I): or a pharmaceutically-acceptable salt, tautomer, or stereoisomer thereof, as defined in the specification, and compositions containing them, and processes for preparing such compounds. Provided herein also are methods of treating disorders or diseases treatable by inhibition of PDE10, such as obesity, non-insulin dependent diabetes, schizophrenia, bipolar disorder, obsessive-compulsive disorder, Huntington's Disease, and the like.

  Formula (I)的杂环化合物： 或其药用可接受的盐、互变异构体或立体异构体，如规范中所定义，并含有它们的组合物，以及制备这种化合物的方法。本文还提供了通过抑制PDE10来治疗由此可治疗的疾病或疾病的方法，如肥胖症、非胰岛素依赖型糖尿病、精神分裂症、躁郁症、强迫症、亨廷顿病等。
• Iodine Catalyzed C2‐H Formamidation of Quinoline <i>N</i> ‐Oxides using Isocyanides: A Metal‐Free Approach
  作者：Naveenkumar Anugu、Sanjeeva Thunga、Sivaparwathi Golla、Hari Prasad Kokatla

  DOI：10.1002/adsc.202100883

  日期：2022.1.4

  A molecular iodine catalyzed regioselective insertion of isocyanide into C2-H of quinoline N-oxides has been developed. The reaction proceeds through the nucleophilic addition of isocyanide on quinoline N-oxides followed by rearrangement in presence of iodine. This metal-free reaction affords rapid access to quinoline 2-formamides with exceptional functional group tolerance, broad substrate scope and

  已经开发了分子碘催化异氰化物区域选择性插入到喹啉N-氧化物的C2-H 中。该反应通过异氰化物在喹啉N-氧化物上的亲核加成然后在碘存在下重排进行。这种无金属反应可快速获得具有优异官能团耐受性、广泛底物范围和 100% 原子经济性的喹啉 2-甲酰胺。合成了 33 个N -（2-喹啉基）甲酰胺库 ，可用于药物和合成化学。
• [EN] AMINO HETEROARYL COMPOUNDS AS BETA-SECRETASE MODULATORS AND METHODS OF USE<br/>[FR] COMPOSÉS AMINO HÉTÉROARYLES COMME MODULATEURS DE LA BÊTA-SECRÉTASE ET PROCÉDÉS D'UTILISATION
  申请人：AMGEN INC

  公开号：WO2011063233A1

  公开（公告）日：2011-05-26

  The present invention comprises a new class of compounds useful for the modulation of Beta-secretase enzyme activity and for the treatment of Beta-secretase mediated diseases, including Alzheimer's disease (AD) and related conditions. In one embodiment, the compounds have a general Formula I wherein ring A, B1, B2, B3, L, R1, R4, R5 and m of Formula I are defined herein. The invention also includes use of these compounds in pharmaceutical compositions for treatment, prophylactic or therapeutic, of disorders and conditions related to the activity of beta-secretase protein. Such disorders include, for example, Alzheimer's Disease (AD), cognitive deficits, cognitive impairment, schizophrenia and other central nervous system conditions related to and/or caused by the formation and/or deposition of plaque on the brain. The invention also comprises further embodiments of Formula I, intermediates and processes useful for the preparation of compounds of Formula I.

  本发明涵盖了一类新化合物，用于调节β-分泌酶酶活性，治疗由β-分泌酶介导的疾病，包括阿尔茨海默病（AD）和相关疾病。在一个实施例中，这些化合物具有一般的化学式I，其中化合物I的环A、B1、B2、B3、L、R1、R4、R5和m在此定义。该发明还包括将这些化合物用于制备药物组合物，用于治疗与β-分泌酶蛋白活性相关的疾病和症状，包括例如阿尔茨海默病（AD）、认知缺陷、认知损害、精神分裂症和其他与大脑斑块形成和/或沉积有关和/或由此引起的中枢神经系统疾病。该发明还包括化合物I的进一步实施例、中间体和用于制备化合物I的过程。
• Buttressing Effect as a Key Design Principle towards Highly Efficient Palladium/N-Heterocyclic Carbene Buchwald-Hartwig Amination Catalysts
  作者：Yin Zhang、Guy Lavigne、Noël Lugan、Vincent César

  DOI：10.1002/chem.201702859

  日期：2017.10.4

  The backbone substitution of the standard 1,3‐bis(2,6‐diisopropylphenyl)‐2H‐imidazol‐2‐ylidene (IPr) ligand by dimethylamino groups was previously shown to induce a dramatic improvement in the catalytic efficiency of the corresponding Pd–PEPPSI (pyridine‐enhanced pre‐catalyst preparation, stabilization, and initiation) pre‐catalysts in N‐arylation reactions. Herein, a thorough structure/activity study

  先前显示标准的1,3-双（2,6-二异丙基苯基）-2 H-咪唑-2-亚基（IPr）配体被二甲氨基取代的主链可显着提高相应Pd的催化效率N-芳基化反应中的–PEPPSI（吡啶增强的前催化剂的制备，稳定和引发）。在此，已经描述了用于合理化该有益效果的详尽的结构/活性研究。除了先前报道的IPr和IPr配体之外，新的IPr和IPr研究中设计并分析了分别带有一个较大的二异丙基氨基和二甲基氨基和氯取代基的组合的配体。发现主链取代的影响起源是空间性的，并且与芳烃化学中遇到的众所周知的支撑效应有关。通过开发一种高效的催化体系，用于庞大的α，α，α-三取代伯胺的芳基化反应，证明了这种方法的实用性和多功能性。根据[的PdCl（η优化系统3 -cinnamyl）（IPR ）]或[的PdCl（η 3 -cinnamyl）（IPR ）]预催化剂可在前所未有的温和条件下（催化剂负载量：0.5–2 mol％，反应温度：
• Rational Ligand Design for the Arylation of Hindered Primary Amines Guided by Reaction Progress Kinetic Analysis
  作者：Paula Ruiz-Castillo、Donna G. Blackmond、Stephen L. Buchwald

  DOI：10.1021/ja512903g

  日期：2015.3.4

  We report the Pd-catalyzed arylation of very hindered α,α,α-trisubstituted primary amines. Kinetics-based mechanistic analysis and rational design have led to the development of two biarylphosphine ligands that allow the transformation to proceed with excellent efficiency. The process was effective in coupling a wide range of functionalized aryl and heteroaryl halides under mild conditions.

  我们报告了受阻非常大的 α,α,α-三取代伯胺的 Pd 催化芳基化。基于动力学的机械分析和合理设计导致了两种联芳基膦配体的开发，使转化能够以优异的效率进行。该方法在温和条件下有效地偶联了广泛的官能化芳基和杂芳基卤化物。