1-苯基-N-(吡嗪-2-基)甲亚胺 | 127438-20-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪类
• 中文名称: 1-苯基-N-(吡嗪-2-基)甲亚胺
• 英文名称: N-benzylidenepyrazin-2-amine
• 英文别名: NBPA；1-phenyl-N-pyrazin-2-ylmethanimine
• CAS: 127438-20-4
• 化学式: C₁₁H₉N₃
• 分子量: 183.213
• InChiKey: WJCXYPMQTZXRBU-UHFFFAOYSA-N

物化性质

• 沸点：
  332.6±22.0 °C(Predicted)
• 密度：
  1.09±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  38.1
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1-苯基-N-(吡嗪-2-基)甲亚胺 在 lithium hydroxide 、 sodium hydroxide 、 sodium tetrahydroborate 、 正丁基锂 、 1-羟基苯并三唑 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 三乙胺 作用下， 以 四氢呋喃 、 甲醇 、 乙醇 、 正己烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 32.5h， 生成 (2S)-2-[[4-[[benzyl(pyrazin-2-yl)amino]methyl]-2-(2-methylphenyl)benzoyl]amino]-4-methylsulfanylbutanoic acid
  参考文献：
  名称：

  Second-Generation Peptidomimetic Inhibitors of Protein Farnesyltransferase Demonstrating Improved Cellular Potency and Significant in Vivo Efficacy

  摘要：

  The synthesis and evaluation of analogues of previously reported farnesyltransferase inhibitors, pyridyl benzyl ether 3 and pyridylbenzylamine 4, are described. Substitution of 3 at the 5-position of the core aryl ring resulted in inhibitors of equal or less potency against the enzyme and decreased efficacy in a cellular assay against Ras processing by the enzyme. Substitution of 4 at the benzyl nitrogen yielded 26, which showed improved efficacy and potency and yet presented a poor pharmacokinetic profile. Further modification afforded 30, which demonstrated a dramatically improved pharmacokinetic profile. Compounds 26 and 29 demonstrated significant in vivo efficacy in nude mice inoculated with MiaPaCa-2, a human pancreatic tumorderived cell line.

  DOI：

  10.1021/jm9901935
• 作为产物：
  描述：

  氨基吡嗪 、 苯甲醇 在 氧气 作用下， 以 甲苯 为溶剂， 130.0 ℃ 、101.33 kPa 条件下， 反应 18.0h， 以52%的产率得到1-苯基-N-(吡嗪-2-基)甲亚胺
  参考文献：
  名称：

  有氧条件下用于选择性氧化脱氢偶联的功能性POM催化剂

  摘要：

  在良性条件下为可持续的化学生产开发选择性和有效的可重复使用的催化系统是有吸引力的，并引起了广泛关注。在这里，我们报告杆状的十八烷基三甲基铵官能化的Keggin型多金属氧酸盐[PMO 12 O 40 ]杂化物（OTA-POM）作为有效的非均相催化剂，用于在有氧条件下选择性氧化脱氢偶联反应，无需任何添加剂或外部碱。混合POM的催化剂回收率和随后的五次连续可回收性研究证实了当前催化体系的非均质性。

  DOI：

  10.1016/j.mcat.2021.111396

文献信息

• Co(OAc)₂-Catalyzed Trifluoromethylation and C(3)-Selective Arylation of 2-(Propargylamino)pyridines via a 6-<i>Endo-Dig</i> Cyclization
  作者：Jianjun Li、Yifan Lei、Yang Yu、Cong Qin、Yiwei Fu、Hao Li、Wei Wang

  DOI：10.1021/acs.orglett.7b02759

  日期：2017.11.17

  arylation of 2-(propargylamino)pyridines has been developed. A new 6-endo-dig cyclization involving an unprecedented C(3) selective arylation of the pyridines instead of a commonly observed 5-exo-dig cyclization with “N” is realized. Moreover, the study presents the first case of the installation of a trifluoromethyl group into electron-deficient azaarenes. The process delivers an efficient cascade approach

  已经开发了Co（OAc）2催化的三氟甲基化和随后的2-（炔丙基氨基）吡啶的C（3）-选择性芳基化。一个新的6 -end-dig环化涉及前所未有的吡啶的C（3）选择性芳基化，而不是通常观察到的带有“ N”的5 -exo-dig环化。此外，该研究提出了在缺乏电子的氮杂芳烃中安装三氟甲基的第一种情况。该方法为具有宽底物范围的新型三氟甲基化1,8-萘啶结构提供了一种有效的级联方法。
• <i>N</i>-(Alkyl)-2-amino-1,4-pyrazine Derivatives: Synthesis and Antioxidative Properties of 3- and 3,5-<i>p</i>-Hydroxyphenyl-Substituted Compounds
  作者：Jacqueline Marchand-Brynaert、Paul Jeanjot、Frédéric Bruyneel、Axelle Arrault、Sonia Gharbi、Jean-François Cavalier、Agnès Abels、Cécile Marchand、Roland Touillaux、Jean-François Rees

  DOI：10.1055/s-2003-37652

  日期：——

  development in medicinal chemistry, the lipophilicity of these lead compounds has to be increased. Therefore various methods of N-alkylation were systematically explored. The best results were obtained by quenching aminopyrazinyl anion with alkyl iodides, and by coupling aldehydes (reductive amination) in the presence of phenylsilane and tin catalyst. Aminopyrazines equipped with linear alkyl side-chains of

  2-氨基-5-(对羟基苯基)-1,4-吡嗪和2-氨基-3,5-双(对羟基苯基)-1,4-吡嗪具有优异的抗氧化性能。为了药物化学的可能发展，必须提高这些先导化合物的亲脂性。因此，系统地探索了各种 N-烷基化方法。最好的结果是用烷基碘猝灭氨基吡嗪阴离子，并在苯基硅烷和锡催化剂存在下偶联醛（还原胺化）。配备至少六个碳的直链烷基侧链的氨基吡嗪在脂质介质中显示出改善的自由基清除性能。
• CuSO₄–Glucose for in Situ Generation of Controlled Cu(I)–Cu(II) Bicatalysts: Multicomponent Reaction of Heterocyclic Azine and Aldehyde with Alkyne, and Cycloisomerization toward Synthesis of N-Fused Imidazoles
  作者：Sankar K. Guchhait、Ajay L. Chandgude、Garima Priyadarshani

  DOI：10.1021/jo3003024

  日期：2012.5.4

  ethanol (nonanhydrous) under open air has been explored. With this catalysis, the multicomponent cascade reaction of A3-coupling of heterocyclic amidine with aldehyde and alkyne, 5-exo-dig cycloisomerization, and prototropic shift has afforded an efficient and eco-friendly synthesis of therapeutically important versatile N-fused imidazoles. Diverse heterocyclic amidines, several of which are known to

  探索了在露天条件下，葡萄糖在乙醇（无水）中部分还原CuSO 4所产生的混合Cu（I）-Cu（II）系统的催化效率。通过这种催化，杂环am与醛和炔烃的A 3偶联，5- exo-dig环异构化和质变转移的多组分级联反应提供了一种具有治疗意义的通用N-稠合咪唑的高效环保合成。不同的杂环am，其中几种已知的是反应性较差的，并且醛在该催化过程中是相容的。
• A chemoselective Ugi-type reaction in water using TMSCN as a functional isonitrile equivalent: generation of heteroaromatic molecular diversity
  作者：Sankar Kumar Guchhait、Vikas Chaudhary、Chetna Madaan

  DOI：10.1039/c2ob26733k

  日期：——

  KF-mediated nucleophilic activation of TMSCN as a functional isonitrile equivalent establishes an efficient and chemoselective Ugi-type multicomponent reaction of a heterocyclic amidine and aldehyde with TMSCN in water. In this approach, the use of isocyanide is circumvented, known competing reactions are virtually eliminated, pure products are obtained by a non-chromatographic method, and therapeutically relevant and diverse N-fused 3-aminoimidazoles can be prepared from a wide variety of aldehydes and heterocyclic amidines. This reaction coupling with cascade cyclization provides various privileged tetracyclic heteroaromatic scaffolds.

  KF催化的TMSCN亲核活化作为功能性异腈等价物，建立了羟基胺和醛与TMSCN在水中进行的高效且化学选择性的Ugi类型多组分反应。在这种方法中，避免了异氰酸酯的使用，已知的竞争反应几乎被消除，纯产品通过非色谱法获得，并且可从多种醛和杂环胺制备出具有治疗相关性和多样性的N-融合3-氨基咪唑。该反应结合级联环化提供了多种特权的四环杂芳烃骨架。
• Copper‐Catalyzed Asymmetric Arylation of <i>N</i> ‐Heteroaryl Aldimines: Elementary Step of a 1,4‐Insertion
  作者：Chunlin Wu、Xurong Qin、Adhitya Mangala Putra Moeljadi、Hajime Hirao、Jianrong Steve Zhou

  DOI：10.1002/anie.201812646

  日期：2019.2.25

  complexes of monodentate phosphoramidites efficiently promote asymmetric arylation of N‐azaaryl aldimines with arylboroxines. DFT calculations and experiments support an elementary step of 1,4‐insertion in the reaction pathway, a step in which an aryl‐copper species adds directly across four atoms of C=N−C=N in the N‐azaaryl aldimines.

  单齿亚磷酰胺的铜络合物可有效地促进N-氮杂芳基醛亚胺与芳基硼氧烷的不对称芳基化。DFT计算和实验支持1,4-插入在反应途径的基本步骤，一个步骤，其中芳基-铜物质增加了C = N-C = N的直接跨四个原子在Ñ -azaaryl醛亚胺。