(2,4-diphenylpyrimidin-5-yl)(phenyl)methanone | 87379-51-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (2,4-diphenylpyrimidin-5-yl)(phenyl)methanone
• 英文别名: (2,4-Diphenylpyrimidin-5-yl)-phenylmethanone
• CAS: 87379-51-9
• 化学式: C₂₃H₁₆N₂O
• 分子量: 336.393
• InChiKey: QLAYGZDVSBBNKV-UHFFFAOYSA-N

物化性质

• 熔点：
  100 °C(Solv: ethyl ether (60-29-7))
• 沸点：
  475.7±37.0 °C(Predicted)
• 密度：
  1.182±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.9
• 重原子数：
  26
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  42.8
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (2,4-diphenylpyrimidin-5-yl)(phenyl)methanone 在 sodium tetrahydroborate 作用下， 以 四氢呋喃 、 甲苯 为溶剂， 反应 5.0h， 生成 Imidazole-1-carboxylic acid (2,4-diphenyl-pyrimidin-5-yl)-phenyl-methyl ester
  参考文献：
  名称：

  Synthesis and biological evaluation of azole derivatives, analogues of bifonazole, with a phenylisoxazolyl or phenylpyrimidinyl moiety

  摘要：

  A series of azole derivatives, isoxazole or pyrimidine analogues of the antifungal drug bifonazole, were synthesized and tested in vitro against representative human pathogenic fungi (Candida albicans, Cryptococcus neoformans and Aspergillus fumigatus). They were also evaluated as antibacterial agents against Staphylococcus aureus and Salmonella spp. Only 5-(imidazol-1-yl-phenylmethyl)-2,4-diphenyl-pyrimidine 7c showed weak antimicrobial activity (MIC = 66 muM) against C. albicans, C. neoformans and S. aureus. Results of biological tests proved, therefore, that replacement of the biphenyl portion of the bifonazole with a phenylisoxazolyl or phenylpyrimidinyl moiety is not profitable for antimicrobial properties. (C) 2001 Elsevier Science S.A. All rights reserved.

  DOI：

  10.1016/s0014-827x(01)01117-x
• 作为产物：
  描述：

  2-dimethylaminomethylidene-1,3-diphenylpropane-1,3-dione 、 苯甲脒 以 乙醇 为溶剂， 反应 3.0h， 以80%的产率得到(2,4-diphenylpyrimidin-5-yl)(phenyl)methanone
  参考文献：
  名称：

  2-二甲基氨基亚甲基-1,3-二酮与二亲核试剂的反应。三，5-酰基嘧啶和7,8-二氢喹唑啉-5（6 H）-ones的合成

  摘要：

  在回流的乙醇中，开环和环己烷对称的-2-二甲基氨基亚甲基-1,3-二酮与am和胍的反应通常以良好的收率得到一系列的5-酰基嘧啶和7,8-二氢喹唑啉-5（6 H）-一个。与甲am（和部分为乙am）一起，通常形成2-甲酰氨基-1,3-二酮，其为单独的产物或与相应的嘧啶或二氢喹唑啉酮的混合物。

  DOI：

  10.1002/jhet.5570200328

文献信息

• Iron Catalysis for Modular Pyrimidine Synthesis through β-Ammoniation/Cyclization of Saturated Carbonyl Compounds with Amidines
  作者：Xue-Qiang Chu、Wen-Bin Cao、Xiao-Ping Xu、Shun-Jun Ji

  DOI：10.1021/acs.joc.6b02767

  日期：2017.1.20

  method for the modular synthesis of various pyrimidine derivatives by means of the reactions of ketones, aldehydes, or esters with amidines in the presence of an in situ prepared recyclable iron(II)-complex was developed. This operationally simple reaction proceeded with broad functional group tolerance in a regioselective manner via a remarkable unactivated β-C–H bond functionalization. Control experiments

  开发了一种有效的方法，用于在原位制备的可回收铁（II）络合物存在下，通过酮，醛或酯与am的反应进行模块化合成各种嘧啶衍生物。该操作简单的反应通过显着的未激活的β-C-H键官能化，以区域选择性的方式在宽泛的官能团耐受性下进行。进行了对照实验以加深对机理的了解，并且反应很可能通过设计的TEMPO络合/烯胺添加/瞬时α占据/β-TEMPO消除/环化顺序进行。
• MOSTI, L.;MENOZZI, G.;SCHENONE, P., J. HETEROCYCL. CHEM., 1983, 20, N 3, 649-654
  作者：MOSTI, L.、MENOZZI, G.、SCHENONE, P.

  DOI：——

  日期：——
• Synthesis and biological evaluation of azole derivatives, analogues of bifonazole, with a phenylisoxazolyl or phenylpyrimidinyl moiety
  作者：Giulia Menozzi、Luisa Mosti、Paola Fossa、Chiara Musiu、Chiara Murgioni、Paolo La Colla

  DOI：10.1016/s0014-827x(01)01117-x

  日期：2001.8

  A series of azole derivatives, isoxazole or pyrimidine analogues of the antifungal drug bifonazole, were synthesized and tested in vitro against representative human pathogenic fungi (Candida albicans, Cryptococcus neoformans and Aspergillus fumigatus). They were also evaluated as antibacterial agents against Staphylococcus aureus and Salmonella spp. Only 5-(imidazol-1-yl-phenylmethyl)-2,4-diphenyl-pyrimidine 7c showed weak antimicrobial activity (MIC = 66 muM) against C. albicans, C. neoformans and S. aureus. Results of biological tests proved, therefore, that replacement of the biphenyl portion of the bifonazole with a phenylisoxazolyl or phenylpyrimidinyl moiety is not profitable for antimicrobial properties. (C) 2001 Elsevier Science S.A. All rights reserved.
• Reaction of 2-dimethylaminomethylene-1,3-diones with dinucleophiles. III. Synthesis of 5-acylpyrimidines and 7,8-dihydroquinazolin-5(6<i>H</i> )-ones
  作者：Luisa Mosti、Giulia Menozzi、Pietro Schenone

  DOI：10.1002/jhet.5570200328

  日期：1983.5

  The reaction of open-chain and cyclohexane sym-2-dimethylaminomethylene-1,3-diones with amidines and guanidine in refluxing ethanol gave, generally in good yields, a series of 5-acylpyrimidines and 7,8-dihydroquinazolin-5(6H)-ones, respectively. With formamidine (and in part acetamidine), 2-formylimino-1,3-diones were formed in general, as sole products or mixtures with the corresponding pyrimidines

  在回流的乙醇中，开环和环己烷对称的-2-二甲基氨基亚甲基-1,3-二酮与am和胍的反应通常以良好的收率得到一系列的5-酰基嘧啶和7,8-二氢喹唑啉-5（6 H）-一个。与甲am（和部分为乙am）一起，通常形成2-甲酰氨基-1,3-二酮，其为单独的产物或与相应的嘧啶或二氢喹唑啉酮的混合物。