N-(4-methoxyphenyl) 4-methoxybenzamidine | 138240-22-9

• 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-(4-methoxyphenyl) 4-methoxybenzamidine
• 英文别名: 4-methoxy-N'-(4-methoxyphenyl)benzenecarboximidamide
• CAS: 138240-22-9
• 化学式: C₁₅H₁₆N₂O₂
• 分子量: 256.304
• InChiKey: KBZXAVMPHRLMPC-UHFFFAOYSA-N

物化性质

• 熔点：
  150 °C
• 沸点：
  378.3±52.0 °C(Predicted)
• 密度：
  1.11±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  19
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.13
• 拓扑面积：
  56.8
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  N-(4-methoxyphenyl) 4-methoxybenzamidine 在 溴 、 三溴化硼 作用下， 以 1,4-二氧六环 、 二氯甲烷 为溶剂， 反应 66.33h， 生成 5-ethyl-1,2-bis(4-hydroxyphenyl)-1H-imidazole
  参考文献：
  名称：

  Structure−Activity Relationship Study To Understand the Estrogen Receptor-Dependent Gene Activation of Aryl- and Alkyl-Substituted 1H-Imidazoles

  摘要：

  A series of C5-substituted 1,2,4-triaryl-1H-imidazoles was synthesized. Their gene-activating properties were determined on estrogen receptor alpha positive MCF-7 breast cancer cells, stably transfected with the plasmid ERE(wtc)luc (MCF-7-2a cells). The influence of 4-OH and 2-Cl substituents on the phenyl rings as well as the significance of a methyl, ethyl, or phenyl group at C5 on the estrogen receptor binding and the resulting gene activation in MCF-7-2a cells was studied. The alkyl and aryl groups at C5 of 1,2,4-tris(4-hydroxyphenyl)-1H-imidazole 1 increased the transactivation, while chlorine atoms on the phenyl rings diminished this effect. 5-Ethyl-1,2,4-tris(4-hydroxyphenyl)-1H-imidazole 9 was identified as the most active compound. Its excellent transcriptional activity did not only depend on the C5 ethyl group, but also on the three hydroxyl groups of the phenyl rings. Compounds (11-14) with a reduced number of hydroxyl groups displayed distinctly lower gene activation.

  DOI：

  10.1021/jm061106t
• 作为产物：
  描述：

  3,4-bis(4-methoxyphenyl)-5-(4-nitrophenyl)-4,5-dihydro-1,2,4-oxadiazole 在 氢气 作用下， 以 甲醇 为溶剂， 以82%的产率得到N-(4-methoxyphenyl) 4-methoxybenzamidine
  参考文献：
  名称：

  从 4,5-二氢-1,2,4-恶二唑合成单取代 N-芳基脒的有效途径

  摘要：

  使用亚胺与腈氧化物的 1,3-偶极环加成反应制备二氢-1,2,4-恶二唑。进一步的还原性 NO 键裂解以良好的收率提供单取代的 N-芳基脒。因此，已开发出合成单取代的 N-芳基脒的有效途径。

  DOI：

  10.3998/ark.5550190.0011.220

文献信息

• Reactions of Aryliminodimagnesium with Some<i>N</i>,<i>N</i>-Dimethylcarboxamides and Benzonitriles Affording Various Types of Amidines. Correction of Previous Results on Formamidine Formation from<i>N</i>,<i>N</i>-Dimethylformamide
  作者：Masao Okubo、Mikio Tanaka、Yuri Murata、Nobuyuki Tsurusaki、Yasumasa Omote、Yukinobu Ikubo、Koji Matsuo

  DOI：10.1246/cl.1991.1965

  日期：1991.11

  Some symmetrical and unsymmetrical form- and benzamidines were prepared by the reaction of ArN(MgBr)2 with Ar’CN, HCONMe2 and related compounds in tetrahydrofurn.

  通过在四氢呋喃中将ArN(MgBr)2与Ar’CN、HCONMe2及相关化合物反应制备了一些对称和非对称的形式和苯胺。
• Calcium mediated efficient synthesis of <i>N</i>-arylamidines from organic nitriles and amines
  作者：Indrani Banerjee、Shweta Sagar、Tarun K. Panda

  DOI：10.1039/d0ob00805b

  日期：——

  electron-withdrawing to electron-donating substitutions as well as heterocyclic substitution. The reaction was carried out in a solvent-free medium under ambient conditions. The nucleophilic addition of aromatic amines to aryl nitriles led to good to excellent yields of the corresponding amidines. The reactivity of the amidines was further examined and the respective urea derivatives were achieved in excellent yields

  idine是在各种工业中具有广泛应用的主要有机化合物。在这里，我们已经开发了一种简单的一步反应方案，用于由双（六甲基二硅叠氮化钙）[Ca N（SiMe 3）2 } 2（THF）2催化的N-芳酰胺的合成]。organic的合成很容易由有机腈和胺实现，它们提供了从吸电子到给电子取代以及杂环取代的广泛底物范围。反应在环境条件下在无溶剂介质中进行。芳族胺向芳基腈的亲核加成导致相应am的产率良好至优异。进一步检查了idine的反应性，并以优异的产率获得了相应的脲衍生物。可能的机理涉及活性氨基酰胺钙预催化剂的产生，该催化剂有助于反应过程中腈的活化。
• Synthesis of 2-Arylquinazolin-4(3<i>H</i>)-ones by<i>N</i>-Aryl Benzamidines with Aromatic Carbonates
  作者：Shunichi Aikawa、Chiharu Sekiguchi、Yuko Yamazaki、Mika Hattori、Tatsuya Isaka、Yasuhiko Yoshida、Shogo Ihara

  DOI：10.1002/jhet.1638

  日期：2014.3

  The reaction of N‐aryl benzamidines 1a, 1b, 1c, 1d, 1e, 1f, 1g, 1h, 1i, 1j, 1k, 1l, 1m, 1n with diphenyl carbonate 2a or ethyl phenyl carbonate 2b synthesized 2‐arylquinazolin‐4(3H)‐ones 3a, 3b, 3c, 3d, 3e, 3f, 3g, 3h, 3i, 3j, 3k, 3l, 3m, 3n in simple and safe process with good yields (71–90%). It was suggested that different electron‐donating substituent in N‐aryl benzamidines 1a, 1b, 1c, 1d, 1e, 1f

  的反应ñ -芳基苯甲脒1A，1B，1C，1D，1E，1F，1克，1H，1I，1J，1K，1升，1米，1N与碳酸二苯酯2A或乙基苯基酯2b中合成的2- arylquinazolin-4（ 3 H）-one 3a，3b，3c，3d，3e，3f，3g，3h，3i，3j，3k，3l，3m，3n以简单而安全的方法生产，收率良好（71–90％）。建议在N-芳基苄am 1a，1b，1c，1d，1e，1f，1g，1h，1i，1j，1k，1l，1m，1n中使用不同的供电子取代基与2-芳基喹唑啉-4（3 H）-酮3a，3b，3c，3d，3e，3f，3g，3h，3i，3j，3k，3l，3m，3n的收率相似。在这些反应中，N-芳基苄be 1a，1b，1c，1d，1e，1f，1g，1h，1i，1j，1k，1l，1m，1n通过与碳酸盐2亲核加成而形成中间体化合物，从而得到环化产物3a，3b，3c，3d，3e，3f，3
• CuI-Catalyzed Oxidative [3 + 2] Reaction of Fullerene with Amidines or Amides Using Air as the Oxidant: Preparation of Fulleroimidazole or Fullerooxazole Derivatives
  作者：Hai-Tao Yang、Xi-Chen Liang、Yan-Hong Wang、Yang Yang、Xiao-Qiang Sun、Chun-Bao Miao

  DOI：10.1021/ol401909z

  日期：2013.9.20

  CuI-catalyzed oxidative reaction of amidines with C60 using air as the oxidant has been exploited for the easy preparation of fulleroimidazole derivatives. Furthermore, this kind of CuI-catalyzed [3 + 2] reaction has also been successfully applied in the synthesis of fullerooxazole derivatives starting from amides for the first time. The substrate scope is broad, and the process is particularly cheap

  利用CuI以空气为氧化剂，催化C与C 60的氧化反应已被广泛用于制备全咪唑衍生物。此外，这种由CuI催化的[3 + 2]反应也已成功地首次用于从酰胺开始的全氟恶唑衍生物的合成中。基材范围广，并且该方法特别便宜且简单。
• Rhodium(III)-Catalyzed Cascade [5 + 1] Annulation/5-exo-Cyclization Initiated by C–H Activation: 1,6-Diynes as One-Carbon Reaction Partners
  作者：Fen Xu、Wei-Fen Kang、Yang Wang、Chun-Sen Liu、Jia-Yue Tian、Rui-Rui Zhao、Miao Du

  DOI：10.1021/acs.orglett.8b01105

  日期：2018.6.1

  n reaction of amidines with diynes is reported herein. This protocol provides highly atom-economical access to fabricate two nitrogen-containing heterocycles in one step with high efficiency and selectivity. Significantly, this reaction represents the first example of using diyne as a one-carbon reaction partner in C–H functionalization. Kinetic isotope effects suggested that the catalytic cycle of

  本文报道了with与二炔的催化[5 +1]环化/ 5-外环化反应。该方案提供了一种经济高效的原子制备方法，可一步一步高效地制备两个含氮杂环。重要的是，该反应代表了在C–H功能化中使用二炔作为单碳反应伙伴的第一个例子。动力学同位素效应表明该反应的催化循环是由N中邻位C–H键的裂解引发的idine的苯基环，可能参与限速步骤。基于密度泛函理论（DFT）的计算表明，C–H活化和通过5-exo环化形成Rh（V）物种可能是此级联转化的重要过程。