2,2-dimethyl-1,2,3,4-tetrahydrobenzphenanthridin-4-one | 64869-21-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 英文名称: 2,2-dimethyl-1,2,3,4-tetrahydrobenzphenanthridin-4-one
• 英文别名: 2,2-dimethyl-2,3-dihydro-1H-benzo[a]phenanthridin-4-one；2,2-Dimethyl-4-oxo-1,2,3,4-tetrahydrobenzophenanthridin；2,2-Dimethyl-1,3-dihydrobenzo[a]phenanthridin-4-one
• CAS: 64869-21-2
• 化学式: C₁₉H₁₇NO
• 分子量: 275.35
• InChiKey: VFHPHBGZIZTJDN-UHFFFAOYSA-N

物化性质

• 熔点：
  171 °C
• 沸点：
  468.0±14.0 °C(Predicted)
• 密度：
  1.183±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  21
• 可旋转键数：
  0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.26
• 拓扑面积：
  30
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2,2-dimethyl-1,2,3,4-tetrahydrobenzphenanthridin-4-one 在 盐酸羟胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 2.0h， 生成 2,2-dimethyl-2,3-dihydro-1H-benzo[a]phenanthridin-4-one oxime
  参考文献：
  名称：

  摘要：

  2-Methyleneaminonaphthalene smoothly reacts with cyclic beta-diketones to afford azaphenanthrene derivatives in high yield. The dihydropyridine ring in the products can be oxidized to pyridine ring. The oxidation products, unlike their precursors and analogs having an aryl substituent in the a-position with respect to the nitrogen atom, react with hydroxylamine at the carbonyl group to give the corresponding oximes and in some cases undergo Knoevenagel condensation with malononitrile. Hydrolysis of the condensation product yields the respective diamide.

  DOI：

  10.1023/a:1015375313521
• 作为产物：
  描述：

  2,2-dimethyl-2,3,5,6-tetrahydro-1H-benzo[a]phenanthridin-4-one 在 哌啶 、 sulfur 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 6.0h， 以75%的产率得到2,2-dimethyl-1,2,3,4-tetrahydrobenzphenanthridin-4-one
  参考文献：
  名称：

  摘要：

  2-Methyleneaminonaphthalene smoothly reacts with cyclic beta-diketones to afford azaphenanthrene derivatives in high yield. The dihydropyridine ring in the products can be oxidized to pyridine ring. The oxidation products, unlike their precursors and analogs having an aryl substituent in the a-position with respect to the nitrogen atom, react with hydroxylamine at the carbonyl group to give the corresponding oximes and in some cases undergo Knoevenagel condensation with malononitrile. Hydrolysis of the condensation product yields the respective diamide.

  DOI：

  10.1023/a:1015375313521

文献信息

• Synthesis of tetrahydrobenzophenanthridinones.<b>V</b>
  作者：Roberto Martínez、Rubén A. Toscano、Irma E. Linzaga、Hanani Sánchez

  DOI：10.1002/jhet.5570290603

  日期：1992.10

  The preparation of tetrahydrobenzophenanthridinones 4 and 5, potential useful intermediates for the synthesis of Dynemicin A models, is described. The structure of all products was corroborated by ir, 1H-nmr, ms and X-ray spectroscopy.

  描述了四氢二苯并菲基吡啶酮4和5的制备方法，这是合成Dynemicin A模型的潜在有用中间体。红外，1 H-nmr，ms和X射线光谱证实了所有产品的结构。
• WOLFBEIS O. S., SYNTHESIS, 1977, NO 10, 723-
  作者：WOLFBEIS O. S.

  DOI：——

  日期：——
• ——
  作者：N. G. Kozlov、A. P. Kadutskii

  DOI：10.1023/a:1015375313521

  日期：——

  2-Methyleneaminonaphthalene smoothly reacts with cyclic beta-diketones to afford azaphenanthrene derivatives in high yield. The dihydropyridine ring in the products can be oxidized to pyridine ring. The oxidation products, unlike their precursors and analogs having an aryl substituent in the a-position with respect to the nitrogen atom, react with hydroxylamine at the carbonyl group to give the corresponding oximes and in some cases undergo Knoevenagel condensation with malononitrile. Hydrolysis of the condensation product yields the respective diamide.