5,13-dihydro-11H-isoquino[3,2-b]quinazolin-11-one | 25113-70-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 异喹啉及其衍生物
• 英文名称: 5,13-dihydro-11H-isoquino[3,2-b]quinazolin-11-one
• 英文别名: 5H-isoquinolino[3,2-b]quinazolin-11(13H)-one；5,13-dihydro-isoquino[3,2-b]quinazolin-11-one；11-Oxo-5,13-dihydro-11H-isochino<3,2-b>chinazolin；5,13-dihydroisoquinolino[3,2-b]quinazolin-11-one
• CAS: 25113-70-6
• 化学式: C₁₆H₁₂N₂O
• 分子量: 248.284
• InChiKey: DDHOFRIITBWZRK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  19
• 可旋转键数：
  0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  32.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  5,13-dihydro-11H-isoquino[3,2-b]quinazolin-11-one 在 碘 、 sulfur 作用下， 以 邻二氯苯 为溶剂， 以76%的产率得到dibenzo[b,f][1,8]naphthyridin-5(6H)-one
  参考文献：
  名称：

  Condensed isoquinolines 27*. Synthesis and oxidation reactions of 5,13-dihydro-11H-isoquino[3,2-b]quinazolin-11-one

  摘要：

  Condensation of 2-(cyanomethyl)benzoic acid with 2-aminobenzylamine gave 6,11-dihydro-13H-isoquino[3,2-b]quinazolin-11-one. Its oxidation in nitrobenzene led to the formation of 5,13,5',13'-hexahydro[6,6']bi[isoquino[3,2-b]quinazoline]-11,11'-dione, but in dichlorobenzene in the presence of elemental sulfur and iodine it gave the rearrangement product 6H-dibenzo[b,f][1,8]naphthyridin-5-one.

  DOI：

  10.1007/s10593-008-0024-6
• 作为产物：
  描述：

  methyl 2-(2-(2-((tert-butoxycarbonylamino)methyl)-phenylamino)-2-oxoethyl)benzoate 在 三氟乙酸 、 碳酸氢钠 作用下， 以 二氯甲烷 、 水 为溶剂， 反应 5.0h， 以87%的产率得到5,13-dihydro-11H-isoquino[3,2-b]quinazolin-11-one
  参考文献：
  名称：

  简便的方法来处理1,3-二氮杂杂环的各种范围：角度/线性选择性范式和显着的分子内甲基迁移

  摘要：

  从环状酸酐和2-氨基苄基氨基甲酸叔丁酯开始，已经通过相应的酰亚胺/苯胺的分子内环化描述了简单而有效的合成方法，该方法可简单有效地合成各种范围的动力学控制的角和热力学控制的线性三环和四环1，3-二氮杂杂环。酸酯。还描述了酰亚胺稳定性对角/线性产物选择性的影响。通过在甲醇或甲醇和乙酸的混合物中回流，将动力学控制的角产物成功转化为相应的热力学控制的线性产物。还描述了有趣的原位1,2-分子内甲基迁移。

  DOI：

  10.1016/j.tet.2009.04.088

文献信息

• Condensed isoquinolines 33*. Synthesis of 1′-R-spiro-[7H,8H-2a,7a-diazacyclopenta-[fg]naphthacene-2,4′-(1′H)-pyridine]-1,8(2H)-diones
  作者：L. M. Potikha、R. M. Gutsul、V. A. Kovtunenko

  DOI：10.1007/s10593-009-0223-9

  日期：2009.1

  Heating 5,13-dihydro-11H-isoquino[3,2-b]quinazolin-11-one with isonicotinoyl chloride in pyridine gives 6-isonicotinoyl-5,13-dihydro-11H-isoquino[3,2-b]quinazolin-11-one. The 1-alkyl-4[(11-oxo-5,13-dihydro-11H-isoquino[3,2-b]quinazolin-6-yl)carbonyl]pyridinium iodides obtained by alkylation of 6-isonicotinoyl-5,13-dihydro-11H-isoquino[3,2-b]quinazolin-11-one using alkyl iodides in the presence of NaH are converted to 1'-R-spiro[7H,8H-2a,7a-diazacyclopenta[fg]naphthacene-2,4'(1'H)-pyridine]-1,8(2H)-diones. The chemical and spectroscopic properties of the spiro compounds obtained were studied.
• Condensed isoquinolines 30. Acylation and alkylation of 5,13-dihydro-11H-isoquino-[3,2-b]quinazolin-11-one
  作者：L. M. Potikha、R. M. Gutsul、V. A. Kovtunenko、G. G. Dubinina、A. A. Tolmachev

  DOI：10.1007/s10593-008-0078-5

  日期：2008.5

  It was shown that 6-acyl-5,13-dihydro-11H-isoquino[3,2-b]quinazolin-11-ones are formed when 5,13-dihydro- 11H-isoquino[3,2-b]quinazolin-11-one is heated with the chlorides and anhydrides of carboxylic acids in the presence of bases (pyridine, NaOAc) while 5-acyl-5,13-dihydro-11H-isoquino[ 3,2-b]quinazolin-11-ones are formed in the presence of NaH. In the presence of NaH 6-acyl-5,13- dihydro-11H-isoquino[3,2-b]quinazolin-11-ones form the products from acylation and alkylation at position 5. The action of heat on 5,13-dihydro-11H-isoquino[3,2-b]quinazolin-11-one in oxalyl chloride leads to 7H,8H-2a, 7a-diazacyclopenta[fg]naphthacene-1,2,8-trione.
• Condensed isoquinolines 27*. Synthesis and oxidation reactions of 5,13-dihydro-11H-isoquino[3,2-b]quinazolin-11-one
  作者：L. M. Potikha、R. M. Gutsul、A. V. Turov、V. A. Kovtunenko

  DOI：10.1007/s10593-008-0024-6

  日期：2008.2

  Condensation of 2-(cyanomethyl)benzoic acid with 2-aminobenzylamine gave 6,11-dihydro-13H-isoquino[3,2-b]quinazolin-11-one. Its oxidation in nitrobenzene led to the formation of 5,13,5',13'-hexahydro[6,6']bi[isoquino[3,2-b]quinazoline]-11,11'-dione, but in dichlorobenzene in the presence of elemental sulfur and iodine it gave the rearrangement product 6H-dibenzo[b,f][1,8]naphthyridin-5-one.
• Facile approach to diverse range of 1,3-diaza-heterocycles: angular/linear selectivity paradigm and a remarkable intramolecular methyl migration
  作者：Umesh A. Kshirsagar、Narshinha P. Argade

  DOI：10.1016/j.tet.2009.04.088

  日期：2009.7

  diverse range of kinetically controlled angular and thermodynamically controlled linear tricyclic and tetracyclic 1,3-diaza-heterocycles have been described via the intramolecular cyclizations of the corresponding imides/anilic acid esters. The effect of imide stability on the angular/linear product selectivity has also been described. The kinetically controlled angular products were successfully transformed

  从环状酸酐和2-氨基苄基氨基甲酸叔丁酯开始，已经通过相应的酰亚胺/苯胺的分子内环化描述了简单而有效的合成方法，该方法可简单有效地合成各种范围的动力学控制的角和热力学控制的线性三环和四环1，3-二氮杂杂环。酸酯。还描述了酰亚胺稳定性对角/线性产物选择性的影响。通过在甲醇或甲醇和乙酸的混合物中回流，将动力学控制的角产物成功转化为相应的热力学控制的线性产物。还描述了有趣的原位1,2-分子内甲基迁移。