3-cyclohex-2-enyl-4-hydroxy-1-methylquinolin-2(1H)-one | 211686-40-7

• 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: 3-cyclohex-2-enyl-4-hydroxy-1-methylquinolin-2(1H)-one
• 英文别名: 3-(Cyclohex-2-en-1-yl)-4-hydroxy-1-methylquinolin-2(1H)-one；3-cyclohex-2-en-1-yl-4-hydroxy-1-methylquinolin-2-one
• CAS: 211686-40-7
• 化学式: C₁₆H₁₇NO₂
• 分子量: 255.316
• InChiKey: WNQUHJQYZORFJE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  19
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  40.5
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  3-cyclohex-2-enyl-4-hydroxy-1-methylquinolin-2(1H)-one 在 硫酸 作用下， 反应 2.0h， 以90%的产率得到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 以 氯苯 为溶剂， 以90%的产率得到3-cyclohex-2-enyl-4-hydroxy-1-methylquinolin-2(1H)-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

• Solid‐State Regioselective Cyclization Initiated by the Electrophilic Attack on the Double Bond by N‐Bromosuccinimide on Montmorillonite K‐10 Clay Support under Microwave Irradiation
  作者：K. C. Majumdar、H. Rahaman、B. Roy

  DOI：10.1080/00397910701228992

  日期：2007.5

  3-AllyI-4-hydroxy-coumarins and pyrones were regioselectively cyclized with N-bromosuccinimide (NBS) on solid phase under microwave irradiation in excellent yield. NBS on montmorillonite K-10 clay under microwave irradiation for expeditious solvent-free regioselective cyclization has been used for the first time.