2-formamido-3-methylbiphenyl | 14294-35-0

• 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: 2-formamido-3-methylbiphenyl
• 英文别名: N-(3-methyl-[1,1'-biphenyl]-2-yl)formamide；N-(3-methylbiphenyl-2-yl)formamide；2-Formylamino-3-methyl-biphenyl；N-(2-methyl-6-phenylphenyl)formamide
• CAS: 14294-35-0
• 化学式: C₁₄H₁₃NO
• 分子量: 211.263
• InChiKey: BBQQEAFKUQDVNG-UHFFFAOYSA-N

物化性质

• 熔点：
  159-160 °C
• 沸点：
  413.3±24.0 °C(Predicted)
• 密度：
  1.125±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.07
• 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：

  2-formamido-3-methylbiphenyl 在 盐酸 作用下， 以 乙醇 为溶剂， 反应 12.0h， 以82%的产率得到3-甲基-2-联苯胺
  参考文献：
  名称：

  Palladium-Catalyzed C(sp²)–H Arylation Using Formamide as a Transformable Directing Group

  摘要：

  A new process for the ortho arylation of formanilides through palladium-catalyzed C-H activation is described. Formamide is reported as a transformable directing group in the transition-metal-catalyzed C-H functionalization reaction. The resulting biarylformanilide products can be readily transformed to the corresponding biarylisocyanides or N-heterocycles.

  DOI：

  10.1021/jo5007043
• 作为产物：
  描述：

  3-甲基-2-硝基苯胺 在 盐酸 、 potassium acetate 、 氢气 、 铁粉 、 sodium nitrite 作用下， 反应 48.0h， 生成 2-formamido-3-methylbiphenyl
  参考文献：
  名称：

  Potential antitumor agents. 55. 6-Phenylphenanthridine-4-carboxamides: a new class of DNA-intercalating antitumor agents

  摘要：

  Derivatives of the DNA-intercalating agent N-[2-(dimethylamino)ethyl]phenanthridine-4-carboxamide have been prepared and shown to have moderate in vivo antitumor activity against both the P388 leukemia and Lewis lung carcinoma. This demonstrates that the effective pharmacophore in the broad class of tricyclic carboxamides is not limited to linear tricyclic chromophores. Both 7 and the 6-phenyl derivative 10 have identical DNA binding properties, suggesting that the phenyl ring of 10 is not involved in the DNA intercalation site. A series of phenyl-substituted derivatives of 10 was evaluated. Aza substituents led to compounds with the highest in vivo cytotoxicity and in vivo P388 activity, but the in vivo solid tumor activity of the substituted 6-phenylphenanthridine-4-carboxamides was in general low.

  DOI：

  10.1021/jm00399a015

文献信息

• Electrochemical initiation of electron-catalyzed phenanthridine synthesis by trifluoromethylation of isonitriles
  作者：M. Lübbesmeyer、D. Leifert、H. Schäfer、A. Studer

  DOI：10.1039/c7cc09302k

  日期：——

  The electron-catalyzed formation of phenanthridines starting from isonitriles initiated by an electrochemical reduction of the Togni reagent is presented. The required number of faradays per mole of starting material and the respective yields clearly show the catalytic character of the electron in this reaction. The mechanism is supported by cyclic voltammetry experiments.

  提出了由Togni试剂的电化学还原引发的由异腈开始的菲啶的电子催化形成。每摩尔起始原料所需的法拉第数和相应的产率清楚地表明了该反应中电子的催化特性。该机理得到循环伏安法实验的支持。
• Additive-Free Radical Cascade Reaction of Oxime Esters: Synthesis of Pyrroline-Functionalized Phenanthridines
  作者：Yijie Xue、Dengqi Xue、Qian He、Qianwei Ge、Wei Li、Liming Shao

  DOI：10.1021/acs.joc.0c01532

  日期：2020.10.2

  dihydropyrrole-functionalized phenanthridines were efficiently synthesized by the metal-free, radical cascade cyclization reaction of 2-isocyanobiphenyls with γ,δ-unsaturated oxime esters. The C–N/C–C/C–C bonds were formed via the oil bath method in a one-pot procedure with broad substrate applicability. The radical process was supported by kinetic isotope effect studies and radical inhibition studies.

  通过2-异氰基联苯与γ，δ-不饱和肟酯的无金属自由基级联环化反应，可以有效地合成各种二氢吡咯官能化的菲啶。C–N / C–C / C–C键是通过油浴法在一锅法中形成的，具有广泛的底物适用性。自由基过程得到动力学同位素效应研究和自由基抑制研究的支持。
• 6-Trifluoromethyl-Phenanthridines through Radical Trifluoromethylation of Isonitriles
  作者：Bo Zhang、Christian Mück-Lichtenfeld、Constantin Gabriel Daniliuc、Armido Studer

  DOI：10.1002/anie.201306082

  日期：2013.10.4

  A radical approach toward 6‐perfluoroalkylphenanthridines employs the Togni reagent or derivatives thereof as radical precursors and occurs in the absence of a transition metal. Bu4NI is applied as radical initiator and phenanthridines are formed in good to excellent yields. In contrast to the currently intensively investigated trifluoromethylation of arenes, the arene core is formed during the trifluoromethylation

  对6-全氟烷基菲啶的自由基方法采用Togni试剂或其衍生物作为自由基前体，并且在不存在过渡金属的情况下发生。将Bu 4 NI用作自由基引发剂，并以良好至极好的收率形成菲啶。与目前深入研究的芳烃三氟甲基化相反，在这种方法中，芳烃核是在三氟甲基化过程中形成的。
• Preparation of 6-Difluoromethylphosphonated Phenanthridines by Visible-Light-Driven Radical Cyclization of 2-Isocyanobiphenyls
  作者：Shuang Wang、Wen-Liang Jia、Lin Wang、Qiang Liu

  DOI：10.1002/ejoc.201500988

  日期：2015.11

  A protocol to obtain a variety of 6-difluoromethylenephosphonated phenanthridines through a radical cyclization process was explored. These reactions, performed with the use of diethyl bromodifluoromethylphosphonate as a radical resource and 2-isocyanobiphenyls as radical acceptors, were smoothly triggered by visible-light photocatalysis. Electron-withdrawing and electron-donating groups were well

  探索了通过自由基环化过程获得多种 6-二氟亚甲基膦酸化菲啶的方案。这些反应以溴二氟甲基膦酸二乙酯为自由基源，2-异氰基联苯为自由基受体，在可见光光催化下顺利触发。吸电子和给电子基团具有良好的耐受性，并且以优异到中等的产率获得了目标分子。
• A ratiometric probe for the selective time-gated luminescence detection of potassium in water
  作者：Evan A. Weitz、Valérie C. Pierre

  DOI：10.1039/c0cc02637a

  日期：——

  A europium probe for the ratiometric detection of potassium in water is presented. This probe demonstrates high sensitivity, with an affinity for K+ in the mM range, and high selectivity for K+ over Na+, Ca2+, Mg2+ and Li+. The long luminescence lifetime of the probe and its large Stokes shift further enable accurate determination of the concentration of K+ in complex aqueous media.

  介绍了一种用于水中钾的比率检测的铕探针。该探针具有高灵敏度，对K+的亲和力在毫摩尔范围内，并且对K+相较于Na+、Ca2+、Mg2+和Li+具有高选择性。该探针的长发光寿命和较大的斯托克斯位移进一步使其能够在复杂水性介质中准确测定K+的浓度。