10-Bromo-5-methyl-6b,7,8,9,10,10a-hexahydro-5H-11-oxa-5-aza-benzo[a]fluoren-6-one | 211686-42-9

• 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: 10-Bromo-5-methyl-6b,7,8,9,10,10a-hexahydro-5H-11-oxa-5-aza-benzo[a]fluoren-6-one
• 英文别名: 10-Bromo-5-methyl-6b,7,8,9,10,10a-hexahydro-[1]benzofuro[3,2-c]quinolin-6-one
• CAS: 211686-42-9
• 化学式: C₁₆H₁₆BrNO₂
• 分子量: 334.213
• InChiKey: CEWMZFQKBHVEGH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  20
• 可旋转键数：
  0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  29.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  10-Bromo-5-methyl-6b,7,8,9,10,10a-hexahydro-5H-11-oxa-5-aza-benzo[a]fluoren-6-one 在 palladium on activated charcoal 氢氧化钾 作用下， 以 二苯醚 、 乙醇 为溶剂， 反应 1.5h， 生成 5-methylbenzofuro[3,2-c]quinolin-6(5H)-one
  参考文献：
  名称：

  Regioselective Synthesis of Heterocycles from 3-Cyclohex-2-enyl-4-hydroxy-1-methylquinolin-2-(1H)-one

  摘要：

  3-Cyclohex-2-enyl-4-hydroxy-1-methylquinolin-2(1H)-one (5) reacts with pyridine hydrotribromide in CH2Cl2 at 0-5 degrees C for 0.75h to give a furo fused heterocycle 6 in 96% yield. Product 6 on treatment with KOH-EtOH eliminates HBr to give compound 8 which on treatement with Pd-C in refluxing diphenyl ether for 0.5 h furnishes benzofuro[3,2-c]quinolone 9 in 90% yield. Substrate 5 on sequential treatment with Ac2O-AcONa and Br-2/AcOH followed by KOH-EtOH, however produces bicyclic product 7 in excllent overall yield. Substrate 5 reacts with 1 equivalent of m-chloroperbenzoic acid in refluxing benzene to furnish bicyclic heterocycle 12 in 80% yield and with cold cone. H2SO4 at 0-5 degrees C for 2h generates the bicyclic heterocycle 14 in 90% yield.

  DOI：

  10.1080/00397919808004868
• 作为产物：
  描述：

  4-羟基-N-甲基-2-喹啉 在 四丁基溴化铵 sodium hydroxide 、 hexamethylene tetramine hydrobromide perbromide 作用下， 以 二氯甲烷 、 氯苯 为溶剂， 反应 1.33h， 生成 10-Bromo-5-methyl-6b,7,8,9,10,10a-hexahydro-5H-11-oxa-5-aza-benzo[a]fluoren-6-one
  参考文献：
  名称：

  Regioselective Synthesis of Heterocycles from 3-Cyclohex-2-enyl-4-hydroxy-1-methylquinolin-2-(1H)-one

  摘要：

  3-Cyclohex-2-enyl-4-hydroxy-1-methylquinolin-2(1H)-one (5) reacts with pyridine hydrotribromide in CH2Cl2 at 0-5 degrees C for 0.75h to give a furo fused heterocycle 6 in 96% yield. Product 6 on treatment with KOH-EtOH eliminates HBr to give compound 8 which on treatement with Pd-C in refluxing diphenyl ether for 0.5 h furnishes benzofuro[3,2-c]quinolone 9 in 90% yield. Substrate 5 on sequential treatment with Ac2O-AcONa and Br-2/AcOH followed by KOH-EtOH, however produces bicyclic product 7 in excllent overall yield. Substrate 5 reacts with 1 equivalent of m-chloroperbenzoic acid in refluxing benzene to furnish bicyclic heterocycle 12 in 80% yield and with cold cone. H2SO4 at 0-5 degrees C for 2h generates the bicyclic heterocycle 14 in 90% yield.

  DOI：

  10.1080/00397919808004868

文献信息

• Regioselective Synthesis of Heterocycles from 3-Cyclohex-2-enyl-4-hydroxy-1-methylquinolin-2-(1<i>H</i>)-one
  作者：K. C. Majumdar、T. Bhattacharyya

  DOI：10.1080/00397919808004868

  日期：1998.8

  3-Cyclohex-2-enyl-4-hydroxy-1-methylquinolin-2(1H)-one (5) reacts with pyridine hydrotribromide in CH2Cl2 at 0-5 degrees C for 0.75h to give a furo fused heterocycle 6 in 96% yield. Product 6 on treatment with KOH-EtOH eliminates HBr to give compound 8 which on treatement with Pd-C in refluxing diphenyl ether for 0.5 h furnishes benzofuro[3,2-c]quinolone 9 in 90% yield. Substrate 5 on sequential treatment with Ac2O-AcONa and Br-2/AcOH followed by KOH-EtOH, however produces bicyclic product 7 in excllent overall yield. Substrate 5 reacts with 1 equivalent of m-chloroperbenzoic acid in refluxing benzene to furnish bicyclic heterocycle 12 in 80% yield and with cold cone. H2SO4 at 0-5 degrees C for 2h generates the bicyclic heterocycle 14 in 90% yield.