N-(4-(trifluoromethyl)phenyl)pyridin-3-amine | 1268526-02-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: N-(4-(trifluoromethyl)phenyl)pyridin-3-amine
• 英文别名: N-[4-(trifluoromethyl)phenyl]pyridin-3-amine
• CAS: 1268526-02-8
• 化学式: C₁₂H₉F₃N₂
• 分子量: 238.212
• InChiKey: XGRBISVJHYRKIO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  24.9
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  N-(4-(trifluoromethyl)phenyl)pyridin-3-amine 在 palladium diacetate 、 sodium hydride 、 三氟乙酸 作用下， 以 乙二醇二甲醚 、 甲苯 为溶剂， 反应 42.0h， 生成 5-(5-cyclohexylpentyl)-1-methyl-8-(trifluoromethyl)-5H-pyrido[3,2-b]indol-1-ium iodide
  参考文献：
  名称：

  δ-Carbolines and their ring-opened analogs: Synthesis and evaluation against fungal and bacterial opportunistic pathogens

  摘要：

  Previous studies have indicated that the delta-carboline (2) ring system derived from the natural product cryptolepine (1) may represent a pharmacophore for anti-infective activity. This paper describes the design and synthesis of a small library of substituted delta-carbolines and the evaluation of the anti-fungal and anti-bacterial activities. An evaluation of the anti-bacterial activity of a previously reported library of ring-opened analogs was also conducted to provide an opportunity to test the hypothesis that both group of compounds may have the same biological target. Results indicate that against a selected group of fungal pathogens, substituted delta-carbolinium analogs displayed higher potency and several fold lower cytotoxicity than cryptolepine the parent natural product. Both the delta-carbolinium compounds and their ring-opened analogs, exhibited equally high anti-bacterial activity against the selected pathogens and especially against the gram positive bacteria evaluated. Published by Elsevier Masson SAS.

  DOI：

  10.1016/j.ejmech.2011.03.021
• 作为产物：
  描述：

  3-氯吡啶 、 对三氟甲基苯胺 在 potassium tert-butylate 、 [bis-1,3-(2,4,6-triisopropylbenzyl)-5,6-dimethylbenzimidazol-2-ylidene]-N-(3-Chloropyridine)dichloropalladium(II) 作用下， 以 甲苯 为溶剂， 反应 3.25h， 以89%的产率得到N-(4-(trifluoromethyl)phenyl)pyridin-3-amine
  参考文献：
  名称：

  立体富集的大体积1,3-双（N，N'-芳烷基）苯并咪唑鎓基Pd-PEPPSI复合物用于Buchwald–Hartwig胺化反应

  摘要：

  Pd-PEPPSI（钯-吡啶增强的预催化剂制备过程的稳定和引发）配合物现已成为定义为C–C和C–N键形成的催化剂。与此相关，我们准备了一个由六个空气和水分稳定的，简单到大体积的苄基取代基组成的系列，这些取代基带有苯并咪唑核心Pd-PEPPSI复合物C1-C6。通过X射线衍射（XRD）研究证实了C6的结构，并通过％V Bur确定了N杂环卡宾的空间压力计算。值得注意的是，这些NHC-Pd-Py骨架表现出苯并咪唑NHCs良好的σ供体和π扩展电子性质，这是催化的基本要求。与先前报道的其他催化剂在温和的反应条件下，在3-氯吡啶和各种芳基/杂芳基胺之间进行布赫瓦尔德-哈特维格交叉偶联反应相比，已证明所制备的配合物具有出色的压倒性。另一方面，不需要外部添加剂或配体将铅母体分子完全转化为产物。更值得注意的是，与其他配合物C1-C5相比，C6具有明显的催化活性用于C–N键的形成。此外，底物的范围可以扩展到其

  DOI：

  10.1039/d0nj01294g

文献信息

• C–N Cross-Coupling via Photoexcitation of Nickel–Amine Complexes
  作者：Chern-Hooi Lim、Max Kudisch、Bin Liu、Garret M. Miyake

  DOI：10.1021/jacs.8b03744

  日期：2018.6.20

  science, biology, and medicine. Transition metal complexes can elegantly orchestrate diverse aminations but typically require demanding reaction conditions, precious metal catalysts, or oxygen-sensitive procedures. Here, we introduce a mild nickel-catalyzed C-N cross-coupling methodology that operates at room temperature using an inexpensive nickel source (NiBr2·3H2O), is oxygen tolerant, and proceeds

  CN 交叉偶联是一类重要的反应，在化学、材料科学、生物学和医学领域都具有深远的影响。过渡金属配合物可以巧妙地协调不同的胺化，但通常需要苛刻的反应条件、贵金属催化剂或氧敏感程序。在这里，我们介绍了一种温和的镍催化 CN 交叉偶联方法，该方法使用廉价的镍源 (NiBr2·3H2O) 在室温下运行，具有耐氧性，并通过镍-胺配合物的直接照射进行。通过辐照含有胺、芳基卤化物、和催化量的 NiBr2·3H2O，在室温下使用市售的 365 nm LED，无需添加光氧化还原催化剂和作为配体和碱的额外作用的胺基质。进行了密度泛函理论计算和动力学同位素效应实验，以阐明观察到的 CN 交叉偶联反应性。
• METHODS FOR FORMING ARYL CARBON-NITROGEN BONDS USING LIGHT AND PHOTOREACTORS USEFUL FOR CONDUCTING SUCH REACTIONS
  申请人：Colorado State University Research Foundation

  公开号：US20190345122A1

  公开（公告）日：2019-11-14

  The disclosure relates to a method for forming aryl carbon-nitrogen bonds and to photoreactors useful in these and other light-driven reactions. The method comprises contacting an aryl halide with an amine in the presence of a Ni salt catalyst solution and an optional base, thereby forming a reaction mixture; exposing the reaction mixture to light under reaction condition sufficient to produce the aryl carbon-nitrogen bonds. In certain embodiments, the amine may be present in a molar excess to the aryl halide. In certain embodiments, the Ni salt catalyst solution includes a Ni(II) salt and a polar solvent, wherein the Ni(II) salt is dissolved in the polar solvent. In certain embodiments, the reactions conditions include holding the reaction mixture at between about room temperature and about 80° C. for between about 1 hour and about 20 hours such that at least about 50% yield is obtained.

  该披露涉及一种形成芳基碳氮键的方法，以及在这些和其他光驱动反应中有用的光反应器。该方法包括在存在Ni盐催化剂溶液和可选碱的情况下，将芳基卤化物与胺接触，从而形成反应混合物；将反应混合物暴露在充分产生芳基碳氮键的反应条件下的光下。在某些实施例中，胺可能以摩尔过量存在于芳基卤化物中。在某些实施例中，Ni盐催化剂溶液包括Ni(II)盐和极性溶剂，其中Ni(II)盐溶解在极性溶剂中。在某些实施例中，反应条件包括将反应混合物保持在室温和80°C之间，持续1小时至20小时，使得至少获得约50%的产率。
• Energy Transfer to Ni-Amine Complexes in Dual Catalytic, Light-Driven C–N Cross-Coupling Reactions
  作者：Max Kudisch、Chern-Hooi Lim、Pall Thordarson、Garret M. Miyake

  DOI：10.1021/jacs.9b11049

  日期：2019.12.11

  from the excited state [Ru(bpy)3]Cl2 PC to Ni-amine complexes. The structure and speciation of Ni-amine com-plexes that are the proposed EnT acceptors was elucidated by crystallography and spectroscopic binding studies. With the acceptors known, quantitative Förster theory was utilized to predict the ratio of quenching rate constants upon changing the PC, enabling selection of an organic phenoxazine

  利用 Ni(II) 盐和光催化剂 (PC) 的双催化光驱动交叉偶联方法已成为在温和条件下形成芳基 CN 键的有前途的方法。最近发现 PC 可以被省略并且 Ni(II) 复合物直接被光激发表明 PC 可以执行能量转移 (EnT) 到 Ni(II) 复合物，这是最近在其他系统中提出的一种机制可能性。镍光催化。在这里，我们报告了该领域中能够区分 EnT 和电子转移 (ET) 的第一项研究，结果与 Förster 型 EnT 从激发态 [Ru(bpy)3]Cl2 PC 到 Ni-胺配合物一致。通过晶体学和光谱结合研究阐明了作为提议的 EnT 受体的 Ni-胺复合物的结构和形态。
• NEW COMPOUNDS
  申请人：SERRANO-WU Michael H.

  公开号：US20130018054A1

  公开（公告）日：2013-01-17

  The present invention provides organic compounds of the following structure; A-L1-B—C-D-L2-E that are useful for treating or preventing conditions or disorders associated with DGAT1 activity in animals, particularly humans.

  本发明提供了以下结构的有机化合物；A-L1-B-C-D-L2-E，用于治疗或预防与动物DGAT1活性相关的疾病或疾病，特别是人类。
• Identification of 3-phenylaminoquinolinium and 3-phenylaminopyridinium salts as new agents against opportunistic fungal pathogens
  作者：Tryphon K. Mazu、Jagan R. Etukala、Xue Y. Zhu、Melissa R. Jacob、Shabana I. Khan、Larry A. Walker、Seth Y. Ablordeppey

  DOI：10.1016/j.bmc.2010.10.065

  日期：2011.1

  Previous studies on the indoloquinoline alkaloid, cryptolepine (2), revealed that it has antii-nfective properties among other activities. Using Structure-activity relationship (SAR) techniques, several ring-opened analogs of cryptolepine (3-phenylaminopyridinium and 3-phenylaminoquinolinium derivatives) were designed to improve the potency and lower the cytotoxicity shown by several of the precursor agents. Results indicate that these ring-opened analogs constitute new anti-infective agents with over a 100-fold potency and several fold lower cytotoxicity than cryptolepine from which they are derived. Published by Elsevier Ltd.