2-phenyl-5-(2-propynyl)oxy-5,6,7,8-tetrahydroquinazoline | 140655-13-6

• 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: 2-phenyl-5-(2-propynyl)oxy-5,6,7,8-tetrahydroquinazoline
• 英文别名: 2-Phenyl-5-[(prop-2-yn-1-yl)oxy]-5,6,7,8-tetrahydroquinazoline；2-phenyl-5-prop-2-ynoxy-5,6,7,8-tetrahydroquinazoline
• CAS: 140655-13-6
• 化学式: C₁₇H₁₆N₂O
• 分子量: 264.327
• InChiKey: JETPKIMXQJSLOC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  20
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  35
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-phenyl-5-(2-propynyl)oxy-5,6,7,8-tetrahydroquinazoline 以 硝基苯 为溶剂， 以47%的产率得到3-(3-cyanopropyl)-1,3-dihydro-6-phenylfuro<3,4-c>pyridine
  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：

  2-phenyl-7,8-dihydro-6H-quinazolin-5-one 在 sodium tetrahydroborate 、 sodium hydride 作用下， 以 乙醇 为溶剂， 反应 24.5h， 生成 2-phenyl-5-(2-propynyl)oxy-5,6,7,8-tetrahydroquinazoline
  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

• Synthesis of 5-propynyloxycycloalkanepyrimidines and their selectivity and reactivity in intramolecular Diels-Alder reactions.
  作者：Werner A.W. Stolle、Jacqueline M. Veurink、Antonius T.M. Marcelis、Henk C. van der Plas

  DOI：10.1016/s0040-4020(01)88723-8

  日期：1992.2

  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-.