2-苯基吡啶-4-羧酸甲酯 | 4634-14-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 中文名称: 2-苯基吡啶-4-羧酸甲酯
• 中文别名: 2-苯基异烟酸甲酯；2-苯基-4-吡啶羧酸甲酯
• 英文名称: methyl 2-phenylisonicotinate
• 英文别名: 2-phenylisonicotinic acid methyl ester；2-Phenyl-pyridin-4-carbonsaeure-methylester；methyl 2-phenylpyridine-4-carboxylate
• CAS: 4634-14-4
• 化学式: C₁₃H₁₁NO₂
• 分子量: 213.236
• InChiKey: PKPOOQVXKJROPY-UHFFFAOYSA-N

物化性质

• 熔点：
  90 °C
• 沸点：
  115-125 °C(Press: 0.005 Torr)
• 密度：
  1.147±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  39.2
• 氢给体数：
  0
• 氢受体数：
  3

安全信息

• 海关编码：
  2933399090

反应信息

• 作为反应物：
  描述：

  2-苯基吡啶-4-羧酸甲酯 在 lithium hydroxide 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 2.0h， 生成 2-苯基-吡啶-4-甲酸
  参考文献：
  名称：

  Start Selective and Rigidify: The Discovery Path toward a Next Generation of EGFR Tyrosine Kinase Inhibitors

  摘要：

  The epidermal growth factor receptor (EGFR), when carrying an activating mutation like del19 or L858R, acts as an oncogenic driver in a subset of lung tumors. While tumor responses to tyrosine kinase inhibitors (TKIs) are accompanied by marked tumor shrinkage, the response is usually not durable. Most patients relapse within two years of therapy often due to acquisition of an additional mutation in EGFR kinase domain that confers resistance to TKIs. Crucially, oncogenic EGFR harboring both resistance mutations, T790M and C797S, can no longer be inhibited by currently approved EGFR TKIs. Here, we describe the discovery of BI-4020, which is a noncovalent, wild-type EGFR sparing, macro-cyclic TKI. BI-4020 potently inhibits the above-described EGFR variants and induces tumor regressions in a cross-resistant EGFR(del19 T790M C797S) xenograft model. Key was the identification of a highly selective but moderately potent benzimidazole followed by complete rigidification of the molecule through macrocyclization.

  DOI：

  10.1021/acs.jmedchem.9b01169
• 作为产物：
  描述：

  2-溴-4-甲基吡啶 在 potassium phosphate 、 potassium permanganate 、 四(三苯基膦)钯 作用下， 以 乙二醇二甲醚 、 水 、 丙酮 为溶剂， 反应 55.67h， 生成 2-苯基吡啶-4-羧酸甲酯
  参考文献：
  名称：

  Design and synthesis of non-symmetric phenylpyridine type ligands. Experimental and theoretical studies of their corresponding iridium complexes

  摘要：

  In this work three non-symmetric phenylpyridine type ligands, L1, L2 and 13, were designed, and their corresponding Iridium complexes, C1, C2 and C3, synthetized, in order to understand the effect of ligand asymmetry on the properties of the complexes, and to explore their potentiality in devices. The complexes were structurally characterized by NMR experiments and by X-ray Diffraction, and physicochemically by technics as UV/Vis and cyclic voltammetry. Theoretical DFT calculations of the energy and electronic density of the frontier orbitals of the complexes under study were also performed. The energy of the HOMO and LUMO correlated well with the experimental electrochemical data, and supported the understanding of the processes observed. (C) 2016 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.poly.2016.07.029

文献信息

• Recent Developments in the Chemistry of Heteroaromatic N-Oxides
  作者：Liming Zhang、Youliang Wang

  DOI：10.1055/s-0034-1379884

  日期：——

  ortho-Alkyl C–H Functionalization 4.3.3 N-Oxide Directed Remote C–H Functionalization 4.4 1,3-Dipolar Cycloaddition 5 Conclusion and Outlook Selected developments in the chemistry of heteroaromatic N-oxides since 2001 are presented in this review. The use of these N-oxides, both in late-transition-metal-catalyzed oxidations of carbon–carbon triple bonds and in regioselective C–H functionalizations of the heteroarene

  摘要 这篇综述介绍了自2001年以来杂芳族N-氧化物化学的部分发展。这些N-氧化物在后期过渡金属催化的碳-碳三键的氧化中以及在杂芳烃的区域选择性CH-H官能化中的使用，都是当代关注的话题，也是讨论的重点。 1引言 2杂芳族氮氧化物的合成 2.1受阻杂芳烃的直接氧化 2.2通过杂芳环的构建 3种杂芳族N-氧化物作为氧化剂 3.1炔烃氧化 3.2丙二烯氧化 3.3碳氧化 4种杂芳族氮氧化物作为底物 4.1预先活化的脱氧邻-C–H功能化 4.2带有不稳定碳的脱氧邻-C–H官能化 4.3非脱氧CHH功能化 4.3.1邻-C–H功能化 4.3.2 N氧化物定向邻烷基C–H官能化 4.3.3 N氧化物定向远程C–H功能化 4.4 1,3-偶极环加成 5结论与展望 这篇综述介绍了自2001年以来杂芳族N-氧化物化学的部分发展。这些N-氧化物在后期过渡金属催化的碳-碳三键的氧化中以及在杂芳烃的区域选择性C
• α-Halo carbonyls enable meta selective primary, secondary and tertiary C–H alkylations by ruthenium catalysis
  作者：Andrew J. Paterson、Callum J. Heron、Claire L. McMullin、Mary F. Mahon、Neil J. Press、Christopher G. Frost

  DOI：10.1039/c7ob01192j

  日期：——

  selective C–H alkylation of arenes is described using a wide range of α-halo carbonyls as coupling partners. Previously unreported primary alkylations with high meta selectivity have been enabled by this methodology whereas using straight chain alkyl halides affords ortho substituted products. Mechanistic analysis reveals an activation pathway whereby cyclometalation with a ruthenium(II) complex activates

  描述了使用多种α-卤代羰基作为偶联伙伴的芳烃催化间选择性CH烷基化反应。通过该方法可以实现以前未报道的具有高间位选择性的伯烷基化反应，而使用直链烷基卤化物则可以得到邻位取代的产物。机理分析揭示了一种活化途径，其中用钌（II）配合物进行环金属化会活化底物分子，并负责观察到的间位选择性。偶联配偶体的独特的第二次活化使两个组分之间发生位点选择性反应。
• Iron-Catalyzed Direct C-H Arylation of Heterocycles and Quinones with Arylboronic Acids
  作者：Arghya Deb、Srimanta Manna、Arun Maji、Uttam Dutta、Debabrata Maiti

  DOI：10.1002/ejoc.201300743

  日期：2013.8

  The arylation of C–H bonds to generate heteroaryl–aryl (Het–Ar) and arylated quinone (Quin–Ar) compounds has received great attention to achieve sustainable goals in synthetic chemistry. Despite significant advances, arylation of a broad range of Het–Ar and Quin–Ar derivatives remains a challenging task. Herein, a variety of heterocycles are arylated by using arylboronic acids in the presence of catalytic

  C-H键的芳基化生成杂芳基-芳基（Het-Ar）和芳基化醌（Quin-Ar）化合物在合成化学中实现可持续目标方面受到了极大的关注。尽管取得了重大进展，广泛的 Het-Ar 和 Quin-Ar 衍生物的芳基化仍然是一项具有挑战性的任务。在本文中，在催化量的廉价 Fe(NO3)3 存在下，使用芳基硼酸将各种杂环芳基化。C-芳基化醌化合物可以通过芳基硼酸与醌或氢醌反应来制备。本方法操作简单，可扩展，不需要杂环或醌的预官能化，并且可以容忍偶联伙伴中的多种官能团。这些品质有望使这种方法对学术和工业用途具有吸引力。
• Cyclic derivatives as modulators of chemokine receptor activity
  申请人：Carter H. Percy

  公开号：US20050054627A1

  公开（公告）日：2005-03-10

  The present application describes modulators of MCP-1 of formula (I): or pharmaceutically acceptable salt forms thereof, useful for the treatment of rheumatoid arthritis, multiple sclerosis, atherosclerosis and asthma.

  当前申请描述了MCP-1的调节剂，其化学公式为(I):或其药用可接受的盐形式，用于治疗类风湿性关节炎、多发性硬化症、动脉粥样硬化和哮喘。
• Simple mixed Fe–Zn catalysts for the Suzuki couplings of tetraarylborates with benzyl halides and 2-halopyridines
  作者：Robin B. Bedford、Mark A. Hall、George R. Hodges、Michael Huwe、Mark C. Wilkinson

  DOI：10.1039/b915945b

  日期：——

  Employing co-catalytic zinc reagents facilitates the iron-catalysed Suzuki cross-coupling of tetraarylborates with both benzyl and 2-heteroaryl halides.

  使用协同催化锌试剂可促进铁催化下的Suzuki交叉偶联反应，实现四芳基硼酸酯与苯甲基及2-杂芳基卤化物的偶联。