4-Cyclohex-2-en-1-yl-3-hydroxy-1-methylquinolin-2-one | 182890-79-5

• 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: 4-Cyclohex-2-en-1-yl-3-hydroxy-1-methylquinolin-2-one
• CAS: 182890-79-5
• 化学式: C₁₆H₁₇NO₂
• 分子量: 255.316
• InChiKey: IJZMNPMKYHYPSR-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：

  4-Cyclohex-2-en-1-yl-3-hydroxy-1-methylquinolin-2-one 在 palladium on activated charcoal 、 二苯醚 、 pyridinium hydrobromide perbromide 作用下， 以 二氯甲烷 为溶剂， 反应 3.5h， 生成 3-hydroxy-1-methyl-4-phenylquinolin-2(1H)-one
  参考文献：
  名称：

  Regioselective Synthesis of Polyheterocycles From 4-Cyclohex-2-ENYL-3-Hydroxy-1-Methylquinolin-2(1H)-One

  摘要：

  4-Cyclohex-2-enyl-3-hydrocy-1-methylquinolin-2(1H)-one (4) was prepared in 90% yield by the thermal [3,3]sigmatropic rearrangement of 3-cyclohex-2-enyloxy-1-methylquinolin-2(1H)-one (3) in refluxing chlorobenzene for 10 h. compound (4) was cyclised through a sequence of reactions viz. i) acetylation ii) addition of bromine and iii) treatment of the acetyl dibromo compound (6) with base to give a bicyclic product (7) in 90% yield. Treatment of compound 4 with pyridine hydrobromide perbromide in dichloromethane at 0-5 degrees C afforded a cyclic product 8 in excellent yield. Compound 4 when treated with cold cone. sulphuric acid at 0-5 degrees C furnished the bicyclic product 12 in 89% yield.

  DOI：

  10.1080/00397919608003824
• 作为产物：
  描述：

  3-羟基-1-甲基-2(1H)-喹啉酮 在 potassium carbonate 作用下， 以 氯苯 、 丙酮 为溶剂， 反应 19.0h， 生成 4-Cyclohex-2-en-1-yl-3-hydroxy-1-methylquinolin-2-one
  参考文献：
  名称：

  Regioselective Synthesis of Polyheterocycles From 4-Cyclohex-2-ENYL-3-Hydroxy-1-Methylquinolin-2(1H)-One

  摘要：

  4-Cyclohex-2-enyl-3-hydrocy-1-methylquinolin-2(1H)-one (4) was prepared in 90% yield by the thermal [3,3]sigmatropic rearrangement of 3-cyclohex-2-enyloxy-1-methylquinolin-2(1H)-one (3) in refluxing chlorobenzene for 10 h. compound (4) was cyclised through a sequence of reactions viz. i) acetylation ii) addition of bromine and iii) treatment of the acetyl dibromo compound (6) with base to give a bicyclic product (7) in 90% yield. Treatment of compound 4 with pyridine hydrobromide perbromide in dichloromethane at 0-5 degrees C afforded a cyclic product 8 in excellent yield. Compound 4 when treated with cold cone. sulphuric acid at 0-5 degrees C furnished the bicyclic product 12 in 89% yield.

  DOI：

  10.1080/00397919608003824

文献信息

• Regioselective Synthesis of Polyheterocycles From 4-Cyclohex-2-ENYL-3-Hydroxy-1-Methylquinolin-2(1H)-One
  作者：K. C. Majumdar、A. K. Kundu

  DOI：10.1080/00397919608003824

  日期：1996.11

  4-Cyclohex-2-enyl-3-hydrocy-1-methylquinolin-2(1H)-one (4) was prepared in 90% yield by the thermal [3,3]sigmatropic rearrangement of 3-cyclohex-2-enyloxy-1-methylquinolin-2(1H)-one (3) in refluxing chlorobenzene for 10 h. compound (4) was cyclised through a sequence of reactions viz. i) acetylation ii) addition of bromine and iii) treatment of the acetyl dibromo compound (6) with base to give a bicyclic product (7) in 90% yield. Treatment of compound 4 with pyridine hydrobromide perbromide in dichloromethane at 0-5 degrees C afforded a cyclic product 8 in excellent yield. Compound 4 when treated with cold cone. sulphuric acid at 0-5 degrees C furnished the bicyclic product 12 in 89% yield.