5-(cyclohex-2-enyl)-6-hydroxy-1-methylquinolin-2(1H)-one | 310889-00-0

• 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: 5-(cyclohex-2-enyl)-6-hydroxy-1-methylquinolin-2(1H)-one
• 英文别名: 5-Cyclohex-2-en-1-yl-6-hydroxy-1-methylquinolin-2-one
• CAS: 310889-00-0
• 化学式: C₁₆H₁₇NO₂
• 分子量: 255.316
• InChiKey: XHXLTMWAUYUOLM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 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：

  5-(cyclohex-2-enyl)-6-hydroxy-1-methylquinolin-2(1H)-one 在 氢氧化钾 、 溴 、 sodium acetate 作用下， 以 乙醇 、 溶剂黄146 为溶剂， 反应 8.0h， 生成 (1S,13S)-17-bromo-7-methyl-12-oxa-7-azatetracyclo[11.3.1.02,11.03,8]heptadeca-2(11),3(8),4,9-tetraen-6-one
  参考文献：
  名称：

  Studies in [3, 3] Sigmatropic Rearrangement: Regioselective Cyclization of 5-(Cyclohex-2-Enyl)-6-Hydroxy-1-Methylquinolin-2(1H)-One

  摘要：

  Thermal [3,3] sigmatropic rearrangement of 6-cydohex-2-enyloxy-1-methylquinolin-2(1H)-one (3) afforded 5-cyclohex-2-enyl-6-hydroxy-1-methylquinolin-2(1H)-one (4) in 86% yield. Compound 4 on treatment with pyridine hydrotribromide in CH2Cl2 gave exclusively non-bridged product 6 (85%) whereas compound 4 by a different route viz., acetylation followed by bromine addition and cyclization gave the bicyclic product 7 (80%). Compound 4 also furnished a bicyclic product 11 (80%) on treatment with cone. H2SO4.

  DOI：

  10.1080/00397910008087028
• 作为产物：
  描述：

  6-hydroxy-1-methyl-2-quinolinone 在 potassium carbonate 作用下， 以 丙酮 为溶剂， 反应 26.0h， 生成 5-(cyclohex-2-enyl)-6-hydroxy-1-methylquinolin-2(1H)-one
  参考文献：
  名称：

  Studies in [3, 3] Sigmatropic Rearrangement: Regioselective Cyclization of 5-(Cyclohex-2-Enyl)-6-Hydroxy-1-Methylquinolin-2(1H)-One

  摘要：

  Thermal [3,3] sigmatropic rearrangement of 6-cydohex-2-enyloxy-1-methylquinolin-2(1H)-one (3) afforded 5-cyclohex-2-enyl-6-hydroxy-1-methylquinolin-2(1H)-one (4) in 86% yield. Compound 4 on treatment with pyridine hydrotribromide in CH2Cl2 gave exclusively non-bridged product 6 (85%) whereas compound 4 by a different route viz., acetylation followed by bromine addition and cyclization gave the bicyclic product 7 (80%). Compound 4 also furnished a bicyclic product 11 (80%) on treatment with cone. H2SO4.

  DOI：

  10.1080/00397910008087028

文献信息

• Studies in [3, 3] Sigmatropic Rearrangement: Regioselective Cyclization of 5-(Cyclohex-2-Enyl)-6-Hydroxy-1-Methylquinolin-2(1H)-One
  作者：K. C. Majumdar、P. Biswas、S. K. Ghosh

  DOI：10.1080/00397910008087028

  日期：2000.11

  Thermal [3,3] sigmatropic rearrangement of 6-cydohex-2-enyloxy-1-methylquinolin-2(1H)-one (3) afforded 5-cyclohex-2-enyl-6-hydroxy-1-methylquinolin-2(1H)-one (4) in 86% yield. Compound 4 on treatment with pyridine hydrotribromide in CH2Cl2 gave exclusively non-bridged product 6 (85%) whereas compound 4 by a different route viz., acetylation followed by bromine addition and cyclization gave the bicyclic product 7 (80%). Compound 4 also furnished a bicyclic product 11 (80%) on treatment with cone. H2SO4.