1,3-bis(3-phenyl-4(5H)-oxoimidazo[1,5-a]quinoxalin-5-ylmethyl)benzene

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 1,3-bis(3-phenyl-4(5H)-oxoimidazo[1,5-a]quinoxalin-5-ylmethyl)benzene
• 英文别名: m-bis(3-phenylimidazo[1,5-a]quinoxalin-4(5H)-on-1-yl)benzene；m-bis(3-phenylimidazo[1,5-a]quinoxalin-4(5)-on-1-yl)benzene；1,3-bis(4(5H)-oxo-3-phenylimidazo[1,5-a]quinoxalin-1-yl)benzene；1-[3-(4-oxo-3-phenyl-5H-imidazo[1,5-a]quinoxalin-1-yl)phenyl]-3-phenyl-5H-imidazo[1,5-a]quinoxalin-4-one
• 化学式: C₃₈H₂₄N₆O₂
• 分子量: 596.648
• InChiKey: PCOBGRWGOORYFY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.6
• 重原子数：
  46
• 可旋转键数：
  4
• 环数：
  9.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  93.8
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  1,3-bis(3-phenyl-4(5H)-oxoimidazo[1,5-a]quinoxalin-5-ylmethyl)benzene 在 盐酸 、 potassium hydroxide 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 水 、 二甲基亚砜 为溶剂， 反应 132.0h， 生成 1,3-bis[5-(5-mercapto-3-oxapentyl)-4-oxo-3-phenylimidazo[1,5-a]quinoxalin-1-yl]benzene
  参考文献：
  名称：

  Macrocycles, derivatives of nitrogen-containing heterocycles 3. Synthesis of di(imidazo[1,5-a]quinoxalina)-2(1,3)-benzadithiacycloalkaphanes

  摘要：

  一种三步法构建二（咪唑[1,5-a]喹喔啉)-2（1,3）-苯-二硫-环烷烃的方法已被开发，具体包括在氨基酰基片段中引入不同长度和性质的卤烷基；将由此得到的双卤取代化合物转化为双硫醇；以及将后者与二硫化物偶联。

  DOI：

  10.1007/s11172-009-0201-5
• 作为产物：
  描述：

  间苯二甲胺 、 3-benzoylquinoxalin-2(1H)-one 以 二甲基亚砜 为溶剂， 反应 72.0h， 以97%的产率得到1,3-bis(3-phenyl-4(5H)-oxoimidazo[1,5-a]quinoxalin-5-ylmethyl)benzene
  参考文献：
  名称：

  Fused Polycyclic Nitrogen-Containing Heterocycles: IX. Oxidative Fusion of Imidazole Ring to 3-Benzoylquinoxalin-2-ones

  摘要：

  3-alpha-Chlorobenzyl- and 3-benzoylquinoxalin-2-ones react with benzylamine in DMSO to give intermediate 3-(alpha-benzyliminobenzylidene)quinoxalin-2-one which is capable of existing in several tautomeric forms. The subsequent oxidative cyclocondensation leads to imidazo[1,5-a]quinoxalin-4-one. This new procedure for building up iniidazo[1,5-a]quinoxalin-4-one system has been applied to the synthesis of various bis(irnidazo[1,5-a]quinoxalin-4-ones).

  DOI：

  10.1023/b:rujo.0000045201.90930.ff

文献信息

• Mamedov; Gubaidullin; Khafizova, Chemistry of Heterocyclic Compounds, 2014, vol. 50, # 2, p. 237 - 245
  作者：Mamedov、Gubaidullin、Khafizova、Samigullina、Bauer、Habicher

  DOI：——

  日期：——
• 4-Aza-2,3-dehydro-4-deoxypodophyllotoxins: simple aza-podophyllotoxin analogues possessing potent cytotoxicity
  作者：Yukio Hitotsuyanagi、Masamoto Fukuyo、Kyoko Tsuda、Masatsugu Kobayashi、Akira Ozeki、Hideji Itokawa、Koichi Takeya

  DOI：10.1016/s0960-894x(99)00693-9

  日期：2000.2

  4-Aza-2,3-dehydro-4-deoxypodophyllotoxin analogues 3a-n were synthesized through quinolines 2a-n. Comparison of their cytotoxicity against P-388 leukemia cells revealed that the steric effects of the ring B substituents on the activity are greater than the electronic effects, while the presence of a methoxy group on the ring E is not essential to exhibit potent cytotoxicity. Analogues 3a and 3b proved to be more than twice as cytotoxic as natural podophyllotoxin (1). (C) 2000 Elsevier Science Ltd. All rights reserved.
• Fused Polycyclic Nitrogen-Containing Heterocycles: IX. Oxidative Fusion of Imidazole Ring to 3-Benzoylquinoxalin-2-ones
  作者：V. A. Mamedov、A. A. Kalinin、E. A. Gorbunova、W. D. Habicher

  DOI：10.1023/b:rujo.0000045201.90930.ff

  日期：2004.7

  3-alpha-Chlorobenzyl- and 3-benzoylquinoxalin-2-ones react with benzylamine in DMSO to give intermediate 3-(alpha-benzyliminobenzylidene)quinoxalin-2-one which is capable of existing in several tautomeric forms. The subsequent oxidative cyclocondensation leads to imidazo[1,5-a]quinoxalin-4-one. This new procedure for building up iniidazo[1,5-a]quinoxalin-4-one system has been applied to the synthesis of various bis(irnidazo[1,5-a]quinoxalin-4-ones).
• Macrocycles, derivatives of nitrogen-containing heterocycles 3. Synthesis of di(imidazo[1,5-a]quinoxalina)-2(1,3)-benzadithiacycloalkaphanes
  作者：V. A. Mamedov、A. A. Kalinin、I. Kh. Rizvanov、I. Bauer、V. D. Habicher

  DOI：10.1007/s11172-009-0201-5

  日期：2009.7

  A three-step method for the construction of di(imidazo[1,5-a]quinoxalina)-2(1,3)-benza-dithiacycloalkaphanes has been developed, which includes introduction of a haloalkyl group of various length and nature into 1,3-bis(4(5H)-oxo-3-phenylimidazo[1,5-a]quinoxalin-1-yl)-benzene at the carbamoyl fragment, transformation of the bishalo-substituted compound thus obtained to bisthiol, and coupling of the latter to a disulfide.

  一种三步法构建二（咪唑[1,5-a]喹喔啉)-2（1,3）-苯-二硫-环烷烃的方法已被开发，具体包括在氨基酰基片段中引入不同长度和性质的卤烷基；将由此得到的双卤取代化合物转化为双硫醇；以及将后者与二硫化物偶联。