Acetic acid 3-(2,3-dibromo-cyclohexyl)-1-methyl-2-oxo-1,2-dihydro-quinolin-4-yl ester | 211686-47-4

• 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: Acetic acid 3-(2,3-dibromo-cyclohexyl)-1-methyl-2-oxo-1,2-dihydro-quinolin-4-yl ester
• 英文别名: [3-(2,3-Dibromocyclohexyl)-1-methyl-2-oxoquinolin-4-yl] acetate
• CAS: 211686-47-4
• 化学式: C₁₈H₁₉Br₂NO₃
• 分子量: 457.162
• InChiKey: IFKMPRQDGMYPAY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  24
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  46.6
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  Acetic acid 3-(2,3-dibromo-cyclohexyl)-1-methyl-2-oxo-1,2-dihydro-quinolin-4-yl ester 在 氢氧化钾 作用下， 以 乙醇 为溶剂， 反应 2.0h， 以92%的产率得到17-Bromo-4-methyl-12-oxa-4-azatetracyclo[11.3.1.02,11.05,10]heptadeca-2(11),5,7,9-tetraen-3-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-cyclohex-2-enyloxy-1-methylquinolin-2(1H)-one 在 溴 作用下， 以 乙酸酐 、 溶剂黄146 、 氯苯 为溶剂， 反应 5.0h， 生成 Acetic acid 3-(2,3-dibromo-cyclohexyl)-1-methyl-2-oxo-1,2-dihydro-quinolin-4-yl ester
  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