5H-2-phenyl-6,7,8,9-tetrahydrocycloheptapyrimidin-5-one | 140655-01-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 5H-2-phenyl-6,7,8,9-tetrahydrocycloheptapyrimidin-5-one
• 英文别名: 2-phenyl-6,7,8,9-tetrahydro-5H-cyclohepta[d]pyrimidin-5-one；5h-Cycloheptapyrimidin-5-one,6,7,8,9-tetrahydro-2-phenyl-；2-phenyl-6,7,8,9-tetrahydrocyclohepta[d]pyrimidin-5-one
• CAS: 140655-01-2
• 化学式: C₁₅H₁₄N₂O
• mdl: MFCD28163538
• 分子量: 238.289
• InChiKey: FZSSPFIOOZJBMH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  18
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.266
• 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：

  5H-2-phenyl-6,7,8,9-tetrahydrocycloheptapyrimidin-5-one 在 sodium tetrahydroborate 作用下， 以 乙醇 为溶剂， 反应 0.5h， 以99%的产率得到5H-5-hydroxy-2-phenyl-6,7,8,9-tetrahydrocycloheptapyrimidine
  参考文献：
  名称：

  Synthesis of 5-propynyloxycycloalkanepyrimidines and their selectivity and reactivity in intramolecular Diels-Alder reactions.

  摘要：

  The 5-propynyloxycycloalkane pyrimidines IIIA (17 - 20), IIIB (21 - 24), and IIIC (25, 26) and the 5-(1-propynyloxyethyl)pyrimidines IIID (27, 28), easily undergo intramolecular Diels-Alder reactions with inverse electron demand and a subsequent retro Diels-Alder reaction in which R1CN (R1 = H, Me) or X-CH2CN (X = -CH2, -CH2CH2, -H) is expelled. For the compounds IIIA and IIIB the extrusion of X-CH2CN is favoured, yielding 3-(3-cyanopropyl)-1,3-dihydro-6-phenyl-R1-R2-furo[3,4-c]pyridines (29 - 36). The compounds 17 and 21 also yielded 4-phenyl-2H-6,7,8,8a-tetrahydro-furo[4,3,2-de]quinoline (38), by expulsion of HCN or MeCN respectively, which constitute a new class of heterocyclic compounds. For the compounds IIIC and IIID the extrusion of HCN is favoured as compared to the extrusion of X-CH2CN. In case of IIIC this also gives a hitherto unknown class of heterocyclic ring systems namely 2H-1,6,7,8,9,9a-hexahydro-4-phenyl-9a-R1-5-aza-1-oxo-benz[c,d]azulenes (39, 40). The reactivity of the compounds III towards the cycloaddition appears to be strongly influenced by the nature of the substituent R2 if R1 = H. However, if R1 = Me the effect of R2 on the reactivity was very small. The ratio of the products V and VI appears to depend mainly on the nature of -X-.

  DOI：

  10.1016/s0040-4020(01)88723-8
• 作为产物：
  描述：

  1,3-环庚二酮 、 N,N-二甲基甲酰胺二甲基缩醛 、 苯甲脒 以78%的产率得到5H-2-phenyl-6,7,8,9-tetrahydrocycloheptapyrimidin-5-one
  参考文献：
  名称：

  Synthesis of 5-propynyloxycycloalkanepyrimidines and their selectivity and reactivity in intramolecular Diels-Alder reactions.

  摘要：

  The 5-propynyloxycycloalkane pyrimidines IIIA (17 - 20), IIIB (21 - 24), and IIIC (25, 26) and the 5-(1-propynyloxyethyl)pyrimidines IIID (27, 28), easily undergo intramolecular Diels-Alder reactions with inverse electron demand and a subsequent retro Diels-Alder reaction in which R1CN (R1 = H, Me) or X-CH2CN (X = -CH2, -CH2CH2, -H) is expelled. For the compounds IIIA and IIIB the extrusion of X-CH2CN is favoured, yielding 3-(3-cyanopropyl)-1,3-dihydro-6-phenyl-R1-R2-furo[3,4-c]pyridines (29 - 36). The compounds 17 and 21 also yielded 4-phenyl-2H-6,7,8,8a-tetrahydro-furo[4,3,2-de]quinoline (38), by expulsion of HCN or MeCN respectively, which constitute a new class of heterocyclic compounds. For the compounds IIIC and IIID the extrusion of HCN is favoured as compared to the extrusion of X-CH2CN. In case of IIIC this also gives a hitherto unknown class of heterocyclic ring systems namely 2H-1,6,7,8,9,9a-hexahydro-4-phenyl-9a-R1-5-aza-1-oxo-benz[c,d]azulenes (39, 40). The reactivity of the compounds III towards the cycloaddition appears to be strongly influenced by the nature of the substituent R2 if R1 = H. However, if R1 = Me the effect of R2 on the reactivity was very small. The ratio of the products V and VI appears to depend mainly on the nature of -X-.

  DOI：

  10.1016/s0040-4020(01)88723-8

文献信息

• Aqueous One-Pot Synthesis of Pyrazoles, Pyrimidines and Isoxazoles Promoted by Microwave Irradiation
  作者：Valentina Molteni、Matthew M. Hamilton、Long Mao、Christine M. Crane、Andreas P. Termin、Dean M. Wilson

  DOI：10.1055/s-2002-33650

  日期：——

  Microwave irradiation promotes the conversion of enaminoketones formed in situ into a variety of heterocycles by reaction with the appropriate bidentate nucleophile. The advantages of the method over previous approaches are short reaction times and facile purification by precipitation of the products in aqueous media. Moreover the convenient one-pot procedure makes these syntheses particularly suitable for library production. Organic reactions in aqueous media have become of great interest as water is not only more environmentally friendly, but also because organic reactions in water often display unique reactivity and selectivity.

  微波辐射促进了现场形成的烯胺酮与适当的二齿亲核试剂反应，转化为多种杂环化合物。与之前的方案相比，该方法的优势在于反应时间短，且通过产品在水介质中的沉淀实现简便纯化。此外，便捷的一锅法工艺使得这些合成特别适合于库的生产。水相中的有机反应备受关注，不仅因为水更为环保，还因为在水中进行的有机反应常常展现出独特的反应性和选择性。