4-methyl-2-phenyl-5,6,7,8-tetrahydroquinazolin-5-one | 27653-52-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氮杂萘
• 英文名称: 4-methyl-2-phenyl-5,6,7,8-tetrahydroquinazolin-5-one
• 英文别名: 4-methyl-2-phenyl-7,8-dihydro-6H-quinazolin-5-one
• CAS: 27653-52-7
• 化学式: C₁₅H₁₄N₂O
• 分子量: 238.289
• InChiKey: ADHDTWLSTVLZPR-UHFFFAOYSA-N

物化性质

• 沸点：
  336.7±42.0 °C(Predicted)
• 密度：
  1.186±0.06 g/cm3(Predicted)

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：
  0.27
• 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：

  4-methyl-2-phenyl-5,6,7,8-tetrahydroquinazolin-5-one 在 sodium hydride 作用下， 以 四氢呋喃 为溶剂， 反应 26.0h， 生成 Quinazoline,5-ethyl-5,6,7,8-tetrahydro-4-methyl-2-phenyl-5-(2-propynyloxy)-
  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-环己二酮 、 alkaline earth salt of/the/ methylsulfuric acid 在 potassium carbonate 作用下， 以 甲醇 为溶剂， 反应 3.15h， 生成 4-methyl-2-phenyl-5,6,7,8-tetrahydroquinazolin-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