5,8-dihydroxy-1,4-dimethyl-2(1H)quinolinone | 157463-87-1

• 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: 5,8-dihydroxy-1,4-dimethyl-2(1H)quinolinone
• 英文别名: 5,8-Dihydroxy-1,4-dimethylquinolin-2(1H)-one；5,8-dihydroxy-1,4-dimethylquinolin-2-one
• CAS: 157463-87-1
• 化学式: C₁₁H₁₁NO₃
• 分子量: 205.213
• InChiKey: BZEILIQWQRQWMJ-UHFFFAOYSA-N

物化性质

• 沸点：
  385.4±42.0 °C(Predicted)
• 密度：
  1.350±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  15
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  60.8
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  5,8-dihydroxy-1,4-dimethyl-2(1H)quinolinone 在 potassium dichromate 、 硫酸 作用下， 以 水 为溶剂， 反应 0.17h， 以74%的产率得到1,4-dimethylquinoline-2,5,8(1H)-trione
  参考文献：
  名称：

  Regioselectivity of the Diels-Alder reactions of 2,5,8(1H)-quinolinetriones

  摘要：

  Diels-Alder reactions of 2,5,8(1H)-quinolinetriones were completely regioselective for all the unsymmetrical dienes tested, except in the case of isoprene. This corresponds to a level of regioselectivity higher than the one found by previous workers for 5,8-quinolinequinone.

  DOI：

  10.1016/s0040-4020(01)85276-5
• 作为产物：
  描述：

  N-(2,5-二甲氧基苯基)甲酰胺 在 lithium aluminium tetrahydride 、 硫酸 、 氢溴酸 作用下， 以 乙醚 、 xylene 为溶剂， 反应 54.0h， 生成 5,8-dihydroxy-1,4-dimethyl-2(1H)quinolinone
  参考文献：
  名称：

  Regioselectivity of the Diels-Alder reactions of 2,5,8(1H)-quinolinetriones

  摘要：

  Diels-Alder reactions of 2,5,8(1H)-quinolinetriones were completely regioselective for all the unsymmetrical dienes tested, except in the case of isoprene. This corresponds to a level of regioselectivity higher than the one found by previous workers for 5,8-quinolinequinone.

  DOI：

  10.1016/s0040-4020(01)85276-5

文献信息

• Regioselective Diels–Alder reactions of 3-indolylquinones
  作者：Miguel Ángel Alonso、Pilar López-Alvarado、Carmen Avendaño、J.Carlos Menéndez

  DOI：10.1016/s0040-4020(03)00340-5

  日期：2003.4

  6-(3-Indolyl)quinolinequinone derivatives gave regioselective Diels–Alder reactions with a variety of dienophiles, yielding polycyclic carbazole derivatives. One-pot reactions, proceeding through a cascade of reactions including regioselective Michael and Diels–Alder steps, gave heptacyclic derivatives starting from indoles and 2,5,8(1H)-quinolinetriones. Double Diels–Alder reactions of 6-(3-indolyl)quinolinequinones

  6-（3-吲哚基）喹啉醌衍生物可与多种亲二烯体进行区域选择性Diels-Alder反应，生成多环咔唑衍生物。一锅式反应通过一系列反应（包括区域选择性Michael和Diels-Alder步骤）进行，从吲哚和2,5,8（1 H）-喹啉三酮类化合物开始生成七环衍生物。Double Diels-6-（3-吲哚基）喹啉醌和二卤代苯醌的阿尔德反应一步生成11个环的产物。
• Perez Jose Maria, Vidal Luis, Grande Mercedes T., Menendez J. Carlos, Ave+, Tetrahedron, 50 (1994) N 26, S 7923-7932
  作者：Perez Jose Maria, Vidal Luis, Grande Mercedes T., Menendez J. Carlos, Ave+

  DOI：——

  日期：——
• Synthesis of Casimiroin and Optimization of Its Quinone Reductase 2 and Aromatase Inhibitory Activities
  作者：Arup Maiti、P. V. Narasimha Reddy、Megan Sturdy、Laura Marler、Scott D. Pegan、Andrew D. Mesecar、John M. Pezzuto、Mark Cushman

  DOI：10.1021/jm801335z

  日期：2009.4.9

  An efficient method has been developed to synthesize casimiroin (1), a component of the edible fruit of Casimiroa edulis, on a multigram scale in good overall yield. The route was versatile enough to provide an array of compound 1 analogues that were evaluated as QR2 and aromatase inhibitors. In addition, X-ray crystallography studies of QR2 in complex with compound 1 and one of its more potent analogues has provided insight into the mechanism of action of this new series of QR2 inhibitors. The initial biological investigations suggest that compound 1 and its analogues merit further investigation as potential chemopreventive or chemotherapeutic agents.
• Regioselectivity of the Diels-Alder reactions of 2,5,8(1H)-quinolinetriones
  作者：José María Pérez、Luis Vidal、Mercedes T. Grande、J.Carlos Menéndez、Carmen Avendaño

  DOI：10.1016/s0040-4020(01)85276-5

  日期：1994.1

  Diels-Alder reactions of 2,5,8(1H)-quinolinetriones were completely regioselective for all the unsymmetrical dienes tested, except in the case of isoprene. This corresponds to a level of regioselectivity higher than the one found by previous workers for 5,8-quinolinequinone.