1,2,3,4-tetrahydro-benzo[g]quinoline-5,10-dione | 18710-11-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 1,2,3,4-tetrahydro-benzo[g]quinoline-5,10-dione
• 英文别名: 5,10-Dioxo-1,2,3,4,5,10-hexahydro-benzochinolin；1,2,3,4-Tetrahydro-1-aza-anthrachinon-(9,10)；1,2,3,4-Tetrahydrobenzo[g]quinoline-5,10-dione
• CAS: 18710-11-7
• 化学式: C₁₃H₁₁NO₂
• 分子量: 213.236
• InChiKey: WWSBPWZIYSWZJO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  16.0
• 可旋转键数：
  0.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  46.17
• 氢给体数：
  1.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  1,2,3,4-tetrahydro-benzo[g]quinoline-5,10-dione 在 2,3-二氯-5,6-二氰基-1,4-苯醌 作用下， 以 苯 为溶剂， 反应 1.5h， 以69%的产率得到苯并[g]喹啉-5,10-二酮
  参考文献：
  名称：

  Synthesis of quinolinoquinones and 1,2,3,4-tetrahydroquinolinoquinones via cyclobutenediones

  摘要：

  N-Benzyl-1,2,3,4-tetrahydrocyclobuta[b]pyridine-5,6-dione is easily synthesized and functions as a synthetic equivalent of the unstable pyridiocyclobutenedione. Regiospecific introduction of unsaturated nucleophiles at the more reactive carbonyl group, followed by thermolysis in xylene in vessels open to air, rapidly establishes the tetrahydroquinolinequinone system which can be oxidized to the corresponding quinolinequinone with 2,3-dichloro-5,6-dicyanoquinone.

  DOI：

  10.1021/jo00022a031
• 作为产物：
  描述：

  N-benzyl-1,2,3,4-tetrahydroquinolinequinone-5,8-dione 在 palladium on activated charcoal 作用下， 以 乙醇 为溶剂， 反应 2.0h， 以94%的产率得到1,2,3,4-tetrahydro-benzo[g]quinoline-5,10-dione
  参考文献：
  名称：

  Synthesis of quinolinoquinones and 1,2,3,4-tetrahydroquinolinoquinones via cyclobutenediones

  摘要：

  N-Benzyl-1,2,3,4-tetrahydrocyclobuta[b]pyridine-5,6-dione is easily synthesized and functions as a synthetic equivalent of the unstable pyridiocyclobutenedione. Regiospecific introduction of unsaturated nucleophiles at the more reactive carbonyl group, followed by thermolysis in xylene in vessels open to air, rapidly establishes the tetrahydroquinolinequinone system which can be oxidized to the corresponding quinolinequinone with 2,3-dichloro-5,6-dicyanoquinone.

  DOI：

  10.1021/jo00022a031

文献信息

• Synthesis of Heterocyclic Quinones by Aza-Diels-Alder Reaction of a 4-Stannyl-1-azadiene
  作者：Juan Cuerva、Antonio Echavarren

  DOI：10.1055/s-1997-735

  日期：1997.2

  4-Stannyl-1-azadiene 2 undergoes aza-Diels-Alder reactions with activated dienophiles. Selective oxidation of the adducts proceeds with allylic inversion allowing for the efficient preparation of new heterocyclic quinones.

  4-Stannyl-1-azadiene 2 与活化的亲二烯体发生 aza-Diels-Alder 反应。加合物的选择性氧化通过烯丙基反转进行，从而可以有效制备新的杂环醌。