N-acetyl-4-biphenylmethanamine

• 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-acetyl-4-biphenylmethanamine
• 英文别名: N-[4-phenylbenzyl]acetamide；N-(4-phenyl-benzyl)-acetamide；N-(4-Phenyl-benzyl)-acetamid；Acetyl-(4-phenyl-benzylamin)；4-Acetaminomethyl-diphenyl；N-[(4-phenylphenyl)methyl]acetamide
• 化学式: C₁₅H₁₅NO
• 分子量: 225.29
• InChiKey: GHIHPTLFNVRIAL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.13
• 拓扑面积：
  29.1
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  N-acetyl-4-biphenylmethanamine 在 2-氯蒽醌 、 氧气 作用下， 以 乙酸乙酯 为溶剂， 反应 20.0h， 以99%的产率得到N-acetyl-[1,1'-biphenyl]-4-carboxamide
  参考文献：
  名称：

  2-Chloroanthraquinone-catalyzed aerobic photo-oxidative synthesis of diacylamines from benzylamides

  摘要：

  In this Letter, we report the aerobic photo-oxidative synthesis of diacylamines from benzylamides in the presence of molecular oxygen and catalytic amounts of 2-chloroanthraquinones under visible light irradiation from a fluorescent lamp. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2014.03.123
• 作为产物：
  描述：

  S-methyl 4-biphenyl-4-methyl dithiocarbamate 在 Leptosphaeria maculans 作用下， 以 乙腈 为溶剂， 反应 72.0h， 以21%的产率得到N-acetyl-4-biphenylmethanamine
  参考文献：
  名称：

  Metabolism and Metabolites of Dithiocarbamates in the Plant Pathogenic Fungus Leptosphaeria maculans

  摘要：

  Synthetic compounds containing a dithiocarbamate group are known to have a variety of biological effects and applications including antifungal, herbicidal, and insecticidal application. Leptosphaeria maculans is a fungal pathogen of crucifers able to detoxify efficiently the only plant natural product containing a dithiocarbamate group, the phytoalexin brassinin. To evaluate the effects of dithiocarbamates on L. maculans, a number of structurally diverse S-methyl dithiocarbamates containing indolyl, biphenyl, and benzimidazolyl moieties were synthesized, and their antifungal activities and metabolism by L. maculans were investigated. All dithiocarbamates were transformed by L. maculans through hydrolysis to the corresponding amines, which were less antifungal than the parent compounds. Two dithiocarbonates were shown to be much less antifungal than the corresponding dithiocarbamates. Results of this investigation indicate that S-methyl dithiocarbamates are not useful inhibitors of L. maculans and that their rates of transformation by L. maculans did not correlate with the antifungal activity of the particular compound.

  DOI：

  10.1021/jf302038a

文献信息

• Synergy between chemo- and bio-catalysts in multi-step transformations
  作者：Aldo Caiazzo、Paula M. L. Garcia、Ron Wever、Jan C. M. van Hest、Alan E. Rowan、Joost N. H. Reek

  DOI：10.1039/b901592b

  日期：——

  Cascade synthetic pathways, which allow multi-step conversions to take place in one reaction vessel, are crucial for the development of biomimetic, highly efficient new methods of chemical synthesis. Theoretically, the complexity introduced by combining processes could lead to an improvement of the overall process; however, it is the current general belief that it is more efficient to run processes separately. Inspired by natural cascade procedures we successfully combined a lipase catalyzed amidation with palladium catalyzed coupling reactions, simultaneously carried out on the same molecule. Unexpectedly, the bio- and chemo-catalyzed processes show synergistic behaviour, highlighting the complexity of multi-catalyst systems.

  级联合成路径允许在一个反应容器中进行多步转化，这对于开发仿生的高效新型化学合成方法至关重要。理论上，通过结合过程引入的复杂性可能会改善整体过程；然而，目前普遍认为单独进行各个过程更为高效。受自然级联过程的启发，我们成功地将脂肪酶催化的酰胺化与钯催化的偶联反应结合在一起，同时在同一分子上进行。意外的是，生物催化和化学催化过程显示出协同效应，突显了多催化剂系统的复杂性。
• Organopotassium‐Catalyzed Silylation of Benzylic C(<i>sp</i>³)−H Bonds
  作者：Baptiste Neil、Lamine Saadi、Louis Fensterbank、Clément Chauvier

  DOI：10.1002/anie.202306115

  日期：2023.8

  Benzylsilanes have found increasing applications in organic synthesis as bench‐stable synthetic intermediates, yet are mostly produced by stoichiometric procedures. Catalytic alternatives based on the atom‐economical silylation of benzylic C(sp³)−H bonds remain scarcely available as specialized directing groups and catalytic systems are needed to outcompete the kinetically‐favored silylation of C(sp²)−H bonds. Herein, we describe the first general and catalytic‐in‐metal undirected silylation of benzylic C(sp³)−H bonds under ambient, transition metal‐free conditions using stable tert‐butyl‐substituted silyldiazenes (tBu−N=N−SiR₃) as silicon source. The high activity and selectivity of the catalytic system, exemplified by the preparation of various mono‐ or gem‐bis benzyl(di)silanes, originates from the facile generation of organopotassium reagents, including tert‐butylpotassium.

  摘要苄基硅烷作为稳定的合成中间体，在有机合成中的应用日益广泛，但大多是通过化学计量法生产的。基于苄基 C（sp3）-H 键原子经济硅烷化的催化替代品仍然很少，因为需要专门的定向基团和催化系统才能与动力学上有利的 C（sp2）-H 键硅烷化竞争。在本文中，我们首次介绍了以稳定的叔丁基取代的硅二氮（tBu-N=N-SiR3）为硅源，在无过渡金属的环境条件下，对苄基 C(sp3)-H 键进行的通用金属内催化非定向硅烷化反应。该催化系统的高活性和高选择性源于有机钾试剂（包括叔丁基钾）的简便生成，以制备各种单苄基或双苄基（二）硅烷为例。
• A General Photocatalytic Strategy for Nucleophilic Amination of Primary and Secondary Benzylic C–H Bonds
  作者：Madeline E. Ruos、R. Garrison Kinney、Oliver T. Ring、Abigail G. Doyle

  DOI：10.1021/jacs.3c04912

  日期：2023.8.23

  intercepted by a variety of N-centered nucleophiles, including nitriles (Ritter reaction), amides, carbamates, sulfonamides, and azoles, for the construction of pharmaceutically relevant C(sp3)–N bonds under unified reaction conditions. Mechanistic studies indicate that HAT is amidyl radical-mediated and that the photocatalyst operates via a reductive quenching pathway. These findings establish a mild, metal-free

  我们报告了一种可见光光氧化还原催化的方法，该方法能够使伯和仲苄基 C(sp 3 )–H 键发生亲核胺化。一种新型酰胺基自由基前体和有机光催化剂串联作用，通过顺序氢原子转移（HAT）和氧化自由基-极性交叉将伯和仲苄基C(sp 3 )–H键转化为碳正离子。生成的碳正离子可以被各种以N为中心的亲核试剂拦截，包括腈（Ritter 反应）、酰胺、氨基甲酸酯、磺酰胺和唑类，以便在统一的反应条件下构建药物相关的 C(sp 3 ) –N键。机理研究表明，HAT 是酰胺自由基介导的，并且光催化剂通过还原猝灭途径发挥作用。这些发现建立了一种温和、无金属和模块化的方案，用于将 C(sp 3 )–H 键快速多样化至胺化产物库。
• 13. Symmetrical triad prototropic systems. Part IX. The influence of polynuclear aryl groups upon mobility and equilibrium in the αγ-diarylmethyleneazomethine system
  作者：Charles W. Shoppee

  DOI：10.1039/jr9330000037

  日期：——
• Silica Gel Supported Ferric Perchlorate: A New and Efficient Reagent for One Pot Synthesis of Amides from Benzylic Alcohols
  作者：Peyman Salehi、Aghamorad Rostamian Motlagh

  DOI：10.1080/00397910008087369

  日期：2000.2

  Benzylic alcohols react efficiently with nitriles in the presence of silica gel supported ferric perchlorate to produce amides in high yields.