2-amino-6-phenyl-5,6-dihydro-4(3H)-pyrimidinone | 6340-72-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪类
• 英文名称: 2-amino-6-phenyl-5,6-dihydro-4(3H)-pyrimidinone
• 英文别名: 2-amino-6-phenyl-5,6-dihydropyrimidin-4(3H)-one；2-amino-6-phenyl-5,6-dihydro-3H-pyrimidin-4-one；2-Amino-6-phenyl-5,6-dihydro-3H-pyrimidin-4-on；4(1H)-Pyrimidinone, tetrahydro-2-imino-6-phenyl-；2-amino-4-phenyl-4,5-dihydro-1H-pyrimidin-6-one
• CAS: 6340-72-3
• 化学式: C₁₀H₁₁N₃O
• mdl: MFCD12827657
• 分子量: 189.217
• InChiKey: AXWXBNVCXSTOSJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.1
• 重原子数：
  14
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  67.5
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-amino-6-phenyl-5,6-dihydro-4(3H)-pyrimidinone 在 nitrogen oxides 、 溶剂黄146 作用下， 生成 6-苯基尿嘧啶
  参考文献：
  名称：

  Warmington, Journal fur praktische Chemie (Leipzig 1954), 1893, vol. <2> 47, p. 203

  摘要：

  DOI：
• 作为产物：
  描述：

  DL-3-氨基-3-苯基丙酸 在 盐酸 、 甲醇 、 水 作用下， 生成 2-amino-6-phenyl-5,6-dihydro-4(3H)-pyrimidinone
  参考文献：
  名称：

  Rodionow; Urbanskaja, Zhurnal Obshchei Khimii, 1948, vol. 18, p. 2028

  摘要：

  DOI：

文献信息

• An Eco-Friendly and Highly Efficient Synthesis of Pyrimidinones Using a TiO2-CNTs Nanocomposite Catalyst
  作者：Shahin Khalilian、Shahrzad Abdolmohammadi、Fereshteh Nematolahi

  DOI：10.2174/1570178614666170321113926

  日期：2017.6.14

  nanocomposite catalyzed procedure for the synthesis of 2-amino-6-aryl-5,6-dihydro-4(3H)-pyrimidinones from a one-pot threecomponent coupling reaction of Meldrum’s acid, aromatic aldehydes, and guanidine nitrate with high yields under solvent-free conditions. This new protocol has revealed several advantages such as recyclability of catalyst, short reaction times, high to excellent yields of products

  背景：在有机合成中使用非均相催化剂的最新发展增加了对精细金属氧化物纳米颗粒的需求。纳米级的二氧化钛纳米颗粒（TiO2 NPs）具有优异的性能，例如高催化活性，无毒，易于获得，水分稳定性和可重复使用性，因此可用于多种有机和无机转化。嘧啶酮是药物和制药工业领域中的特权杂环。 方法：在催化量的合成的TiO2-CNTs纳米复合材料存在下，当前方法学解决了Meldrum酸，芳族醛和硝酸胍的直接组装，可用于提供2-氨基-6-芳基-5,6 -dihydro-4（3H）-嘧啶酮在无溶剂条件下2-3小时内。 结果：通过简单的一锅三组分偶联反应，合成了一系列2-氨基-6-芳基-5,6-二氢-4（3H）-嘧啶酮，高产率（90-98％）重量比为50:50的TiO2-CNTs纳米复合材料是一种有效且可回收的催化剂。所有合成的化合物均通过令人满意的元素分析，IR，1H和13C NMR光谱进行了很好的表征。通过XRD，
• Application of Fragment-Based Lead Generation to the Discovery of Novel, Cyclic Amidine β-Secretase Inhibitors with Nanomolar Potency, Cellular Activity, and High Ligand Efficiency
  作者：Philip D. Edwards、Jeffrey S. Albert、Mark Sylvester、David Aharony、Donald Andisik、Owen Callaghan、James B. Campbell、Robin A. Carr、Gianni Chessari、Miles Congreve、Martyn Frederickson、Rutger H. A. Folmer、Stefan Geschwindner、Gerard Koether、Karin Kolmodin、Jennifer Krumrine、Russell C. Mauger、Christopher W. Murray、Lise-Lotte Olsson、Sahil Patel、Nate Spear、Gaochao Tian

  DOI：10.1021/jm070829p

  日期：2007.11.1

  Fragment-based lead generation has led to the discovery of a novel series of cyclic amidine-based inhibitors of beta-secretase (BACE-1). Initial fragment hits with an isocytosine core having millimolar potency were identified via NMR affinity screening. Structure-guided evolution of these fragments using X-ray crystallography together with potency determination using surface plasmon resonance and functional enzyme inhibition assays afforded micromolar inhibitors. Similarity searching around the isocytosine core led to the identification of a related series of inhibitors, the dihydroisocytosines. By leveraging the knowledge of the ligand-BACE-1 recognition features generated from the isocytosines, the dihydroisocytosines were efficiently optimized to submicromolar potency. Compound 29, with an IC50 of 80 nM, a ligand efficiency of 0.37, and cellular activity of 470 nM, emerged as the lead structure for future optimization.
• Reaction of polyfluorinated chalcones with guanidine
  作者：E. A. Borodina、N. A. Orlova、Yu. V. Gatilov、O. I. Sal’nikova

  DOI：10.1134/s1070428015120143

  日期：2015.12

  Reactions of polyfluorinated chalcones with guanidine in the presence of bases are accompanied by elimination of the polyfluorophenyl group. 3-(Pentafluorophenyl)-1-phenylprop-2-en-1-one and its derivatives reacted with guanidine under basic conditions to give 4-phenylpyrimidin-2-amine, polyfluorobenzenes, and Michael adducts, 3-(2-amino-4-phenylpyrimidin-5-yl)-3-(4-R-2,3,5,6-tetrafluorophenyl)-1-phenylpropan-1-ones. 1-(Pentafluorophenyl)-3-phenylprop-2-en-1-one and 1,3-bis(pentafluorophenyl)prop-2-en-1-one were converted into cinnamic acid derivatives whose reaction with guanidine afforded 2-amino-6-aryl-5,6-dihydropyrimidin-4(1H)-ones.
• Amino-Functionalized MCM-41 base-Catalyzed one-Pot synthesis of 2-Amino-5,6-dihydropyrimidin-4(3H)-ones
  作者：M. Mirza-Aghayan、T. Baie Lashaki、M. Rahimifard、R. Boukherroub、A. A. Tarlani

  DOI：10.1007/bf03246225

  日期：2011.3

  A simple and efficient one-pot method for the preparation of 2-amino-5,6-dihydropyrimidin-4(3H)-one from the cyclocondensation of Meldrum's acid, aldehydes and guanidinium carbonate using a catalytic amount of amino-functionalized MCM-41 is described. This efficient technique has the advantage of giving 2-NH2-DHPM building blocks using a base catalyst in good to high yields, being completed in short reaction times and offering a simple product isolation procedure.
• Mohammadnejad, Mahdieh; Hashtroudi, Mehri S.; Balalaie, Saeed, Heterocyclic Communications, 2009, vol. 15, # 6, p. 459 - 465
  作者：Mohammadnejad, Mahdieh、Hashtroudi, Mehri S.、Balalaie, Saeed

  DOI：——

  日期：——