N-(imino(phenyl)methyl)-4-methylbenzamide | 68167-55-5

• 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-(imino(phenyl)methyl)-4-methylbenzamide
• 英文别名: N-(benzenecarboximidoyl)-4-methylbenzamide
• CAS: 68167-55-5
• 化学式: C₁₅H₁₄N₂O
• 分子量: 238.289
• InChiKey: HURZSKAFOCDZLH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  18
• 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：
  55.4
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  N-(imino(phenyl)methyl)-4-methylbenzamide 在 盐酸羟胺 、 溶剂黄146 作用下， 以60 %的产率得到5-(4-甲基苯基)-3-苯基-1,2,4-恶二唑
  参考文献：
  名称：

  Pd 催化的氨基羰基化酰基脒：一锅法环化和 11C 标记

  摘要：

  本文报道了由 Pd(0) 催化的芳基卤化物、脒和一氧化碳羰基合成酰基脒的方案。值得注意的是，一氧化碳是从固体 CO 来源非原位产生的，并且确定了几种具有互补优势和底物范围的高效钯配体。此外，还报道了通过酰基脒中间体合成 1,2,4-三唑和 1,2,4-恶二唑的连续一锅法、两步法方案。此外，该方法还扩展到使用 [ 11 C] 一氧化碳进行同位素标记，从而首次合成11 C 标记的酰基脒以及11 C 标记的 1,2,4-恶二唑。

  DOI：

  10.1021/acs.joc.2c02115
• 作为产物：
  描述：

  对甲基苯甲酸 在 乙醇 、 三氯氧磷 作用下， 生成 N-(imino(phenyl)methyl)-4-methylbenzamide
  参考文献：
  名称：

  Titherley; Stubbs, Journal of the Chemical Society, 1914, vol. 105, p. 306

  摘要：

  DOI：

文献信息

• NBS-mediated practical cyclization of N-acyl amidines to 1,2,4-oxadiazoles via oxidative N‒O bond formation
  作者：Ertong Li、Manman Wang、Zhen Wang、Wenquan Yu、Junbiao Chang

  DOI：10.1016/j.tet.2018.07.036

  日期：2018.8

  A reaction involving an efficient NBS-mediated oxidative N‒O bond formation has been established for the synthesis of 1,2,4-oxadiazoles from readily accessible N-acyl amidines. The features of this synthetic method include simplicity of operation, mild reaction conditions, short reaction times, high yields, and eco-friendliness. The reaction also works well with crude N-acyl amidines obtained by amidation

  已经建立了涉及有效的NBS介导的氧化N ＝ O键形成的反应，用于由容易获得的N-酰基am合成1,2,4-恶二唑。这种合成方法的特点包括操作简单，反应条件温和，反应时间短，产率高和环保。该反应还适用于通过简单的苯甲酸和mid酰胺化而获得的粗制N-酰基s，以可扩展的方式生产生物学上相关的1,2,4-恶二唑。
• Ammonium Formate-Pd/C as a New Reducing System for 1,2,4-Oxadiazoles. Synthesis of Guanidine Derivatives and Reductive Rearrangement to Quinazolin-4-Ones with Potential Anti-Diabetic Activity
  作者：Paola Marzullo、Sonya Vasto、Silvestre Buscemi、Andrea Pace、Domenico Nuzzo、Antonio Palumbo Piccionello

  DOI：10.3390/ijms222212301

  日期：——

  heterocycle with wide reactivity and many useful applications. The reactive O-N bond is usually reduced using molecular hydrogen to obtain amidine derivatives. NH4CO2H-Pd/C is here demonstrated as a new system for the O-N reduction, allowing us to obtain differently substituted acylamidine, acylguanidine and diacylguanidine derivatives. The proposed system is also effective for the achievement of a

  1,2,4-恶二唑是一种杂环化合物，具有广泛的反应活性和许多有用的应用。通常使用分子氢还原反应性ON键以获得脒衍生物。NH 4 CO 2 H-Pd/C在这里被证明是一种新的ON还原系统，使我们能够获得不同取代的酰基脒、酰基胍和二酰基胍衍生物。该系统还可有效实现 5-(2'-氨基苯基)-1,2,4-恶二唑还原重排为 1-烷基喹唑啉-4(1 H )-酮。生物碱糖苷也用此方法获得。初步测试了所得化合物的细胞毒性、诱导氧化应激、α-葡萄糖苷酶和 DPP4 抑制等生物活性，显示出作为抗糖尿病药物的潜在应用。
• Unsaturated Hetero Chains, VI. ω-alkoxy- and ω-Amino-Substituted Oligonitriles – Synthesis, Structures, and Reactivity
  作者：Nicola C. Aust、Roland Fröhlich、Jürgen Hecht、Ernst-Ulrich Würthwein

  DOI：10.1002/jlac.199719970742

  日期：1997.7

  1,5-dialkoxy-2,4-diazapentadienylium salts (8) with N-acyl- and N-alkoxycarbonylamidines (4). It is the nature of the leaving group which mainly determines the chain length of the products obtained. – Compounds 7 show ring-chain tautomerism involving the cyclic form 6 in dependence of the substitution pattern. All ω-alkoxy substituted oligontriles 5, 7 and 9 may easily converted to the corresponding

  ω-烷氧基取代的1-oxa-3,5-二氮杂六烯（5），1-oxa-3,5,7-三氮杂辛酸酯（7）和1-oxa-3,5,7,9-四氮杂十八碳烯（9）通过将1，3-二烷氧基-2-氮杂丙烯鎓盐（3）或1，5-二烷氧基-2，4-二氮杂戊二烯鎓盐（8）与N-酰基-和N-烷氧基羰基am （4）缩合来合成。离去基团的性质主要决定获得的产物的链长。–化合物7显示环取代互变异构现象，其中环状形式6取决于取代模式。所有ω-烷氧基取代的杂多酚5、7通过与仲胺10反应，可以容易地将α1和9 9转化为相应的ω-氨基化合物11、14和15。的反应5a，5b中与伯胺12个通向三嗪酮13。锂化的酮亚胺16将5b和7d转化为相应的1-oxa-3,5,7-三氮杂十八碳四烯17和1-oxa-3,5,7,9-四氮杂十八碳烯18。从化合物5a，7c，9a和18的X射线分析得出，在新的晶体状态下，螺旋形几何结构占主导地位。推挽替代效
• Schulte, Norbert; Froehlich, Roland; Hecht, Juergen, Liebigs Annalen, 1996, # 3, p. 371 - 380
  作者：Schulte, Norbert、Froehlich, Roland、Hecht, Juergen、Wuerthwein, Ernst-Ulrich

  DOI：——

  日期：——
• 1,3-Diaza-1,3-butadienes. Synthesis and Conversion into Pyrimidines by [4π + 2π] Cycloaddition with Electron Deficient Acetylenes. Synthetic Utility of 2-(Trichloromethyl)pyrimidines¹
  作者：Angel Guzmán、Moisés Romero、Francisco X. Talamás、Rene Villena、Robert Greenhouse、Joseph M. Muchowski

  DOI：10.1021/jo952106w

  日期：1996.1.1

  Methods have been devised to generate 1H-1,3-diaza-1,3-butadienes bearing a leaving group at position-4 in latent, masked, and unprotected forms. A hallmark of these azadienes is that they undergo thermal [4 pi + 2 pi] cycloaddition reactions with electron deficient acetylenes to give adducts which are aromatized to pyrimidine derivatives under the reaction conditions. Thus, 1-(methoxycarbonyl)-3-acylamidines 17 on beating in solution are converted in situ into the 1,3-diaza-1,3-dienes 18 and/or 19 which react with dimethyl acetylenedicarboxylate (DMAD) to produce the pyrimidines 20. The 1-Boc-1,3-diaza-1,3-dienes 24 are masked forms of the LH-dienes inasmuch as they react with DMAD under relatively mild conditions to give the dihydropyrimidine adducts 25, which are easily detectable by H-1 NMR spectroscopy, and which aromatize to pyrimidines 26 at higher temperatures. The 4-methylthio compounds 31 and 33, and the 2-(trichloromethyl) compounds 37, are isolable, relatively stable, 1H-1,3-diaza-1,3-butadienes, These easily prepared compounds react with electron deficient acetylenes under mild conditions to provide the pyrimidines 20, 34, and 38, respectively, in fair to excellent yields. The 2-(trichloromethyl)pyrimidines 38 are very useful precursors of a wide variety of other 2-substituted pyrimidines 46-52.