4-methyl-2-oxo-6-phenyl-1,2,3,4-tetrahydro-pyrimidine-5-carboxylic acid amide | 59607-52-2

• 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: 4-methyl-2-oxo-6-phenyl-1,2,3,4-tetrahydro-pyrimidine-5-carboxylic acid amide
• 英文别名: 6-Methyl-2-oxo-4-phenyl-1,2,3,4-tetrahydropyrimidine-5-carboxamide；6-methyl-2-oxo-4-phenyl-3,4-dihydro-1H-pyrimidine-5-carboxamide
• CAS: 59607-52-2
• 化学式: C₁₂H₁₃N₃O₂
• 分子量: 231.254
• InChiKey: ZWNWOSHSDNWVNG-UHFFFAOYSA-N

物化性质

• 熔点：
  218-224 °C(Solv: hexane (110-54-3))
• 沸点：
  450.9±45.0 °C(Predicted)
• 密度：
  1.237±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  84.2
• 氢给体数：
  3
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  4-methyl-2-oxo-6-phenyl-1,2,3,4-tetrahydro-pyrimidine-5-carboxylic acid amide 在 palladium on activated charcoal 甲烷磺酸 、 四磷十氧化物 、 氢气 、 三乙胺 、 三氯氧磷 作用下， 以 甲醇 、 二苯醚 为溶剂， 反应 5.0h， 生成 4-methyl-6-phenylpyrimidine-5-carbonitrile
  参考文献：
  名称：

  Kappe, Christian Oliver; Roschger, Peter, Journal of Heterocyclic Chemistry, 1989, vol. 26, p. 55 - 64

  摘要：

  DOI：
• 作为产物：
  描述：

  乙酰乙酰胺 、 1,1'-phenylmethanediyl-bis-urea 以83%的产率得到
  参考文献：
  名称：

  KATO TETSUZO; CHIBA TAKUO; SASAKI MAKOTO, YAKUGAKU DZASSI, YAKUGAKU ZASSNI, J. PHARM. SOS. JAR., 1981, 101, NO 2, 1+

  摘要：

  DOI：

文献信息

• One Pot Synthesis of Micromolar BACE-1 Inhibitors Based on the Dihydropyrimidinone Scaffold and Their Thia and Imino Analogues
  作者：Jessica Bais、Fabio Benedetti、Federico Berti、Iole Cerminara、Sara Drioli、Maria Funicello、Giorgia Regini、Mattia Vidali、Fulvia Felluga

  DOI：10.3390/molecules25184152

  日期：——

  A library of dihydropyrimidinones was synthesized via a “one-pot” three component Biginelli reaction using different aldehydes in combination with β-dicarbonyl compounds and urea. Selected 2-thiooxo and 2-imino analogs were also obtained with the Biginelli reaction from thiourea and guanidine hydrochloride, respectively. The products were screened in vitro for their β-secretase inhibitory activity. The majority of the compounds resulted to be active, with IC50 in the range 100 nM–50 μM.

  通过使用不同的醛与β-二羰基化合物和尿素的“一锅法”三组分Biginelli反应合成了一系列二氢嘧啶酮类化合物。选择性地，也从硫脲和盐酸胍得到了2-硫氧代和2-亚氨基类似物。这些产物在体外被筛选，用于评估它们的β-分泌酶抑制活性。大多数化合物表现出活性，IC50在100 nM至50 μM范围内。
• Separation of enantiomers of 4-aryldihydropyrimidines by direct enantioselective HPLC. A critical comparison of chiral stationary phases
  作者：Oliver P. Kleidernigg、C.Oliver Kappe

  DOI：10.1016/s0957-4166(97)00214-0

  日期：1997.6

  The separation of the enantiomers of 29 racemic 4-aryldihydropyrimidine-5-carboxylates (DHPMs), aza-analogs of nifedipine-type dihydropyridine calcium channel modulators, was evaluated in direct enantioselective HPLC, employing the following commercially available chiral stationary phases (CSPs): Chiralcel OD-H, ChiraDex, Chirobiotic V and T, and Whelk-O1. In addition, a 1,2-diphenyl-1,2-diaminoethane based CSP and two quinine carbamate based chiral ion exchangers were also employed. For all 29 DHPMs separation of individual enantiomers could be achieved with at least one CSP with alpha-values ranging from 1.10 to 8.67. (C) 1997 Elsevier Science Ltd.
• KAPPE, CHRISTIAN OLIVER;ROSCHGER, PETER, J. HETEROCYCL. CHEM., 26,(1989) N, C. 55-64
  作者：KAPPE, CHRISTIAN OLIVER、ROSCHGER, PETER

  DOI：——

  日期：——
• DUBUR G. YA.; XANINA E. L., XIMIYA GETEROTSIKL. SOEDIN. <KGSS-AQ>, 1976, HO 2, 220-223
  作者：DUBUR G. YA.、 XANINA E. L.

  DOI：——

  日期：——
• Kappe, Christian Oliver; Roschger, Peter, Journal of Heterocyclic Chemistry, 1989, vol. 26, p. 55 - 64
  作者：Kappe, Christian Oliver、Roschger, Peter

  DOI：——

  日期：——