4-[(2-Bromo-4-methylphenyl)sulfanylmethyl]-1-methylquinolin-2-one | 944048-37-7

• 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: 4-[(2-Bromo-4-methylphenyl)sulfanylmethyl]-1-methylquinolin-2-one
• 英文别名: 4-[(2-bromo-4-methylphenyl)sulfanylmethyl]-1-methylquinolin-2-one
• CAS: 944048-37-7
• 化学式: C₁₈H₁₆BrNOS
• 分子量: 374.301
• InChiKey: NUODDGJDKNRTHN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  22
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  45.6
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  4-[(2-Bromo-4-methylphenyl)sulfanylmethyl]-1-methylquinolin-2-one 在 偶氮二异丁腈 、 三正丁基氢锡 作用下， 以 甲苯 为溶剂， 反应 1.0h， 以90%的产率得到
  参考文献：
  名称：

  Regioselective Synthesis of 2H‐Benzothiopyrano[3,2‐c]quinolin‐7(8H)‐ones by Tri‐n‐butyltinhydride–Mediated Radical Cyclization

  摘要：

  A number of hitherto unreported2H-benzothiopyrano[3,2-c]quinolin-7(8H)-ones have been regioselectively synthesized in 90-96% yield by tri-n-butyltinhydride-AIBN-mediated radical cyclization from 4-(20-bromothioarylmethyl)1-methylquinolin- 2(1H)-ones and their corresponding sulfones. 4-(20-Bromothioarylmethyl) quinolin-2(1H)-ones were in turn prepared from 4-bromomethylquinolin2(1H)-one and o-bromothiophenols by refluxing in acetone in the presence of anhydrous K2CO3. These were converted to the corresponding sulfones by oxidation with two equivalents of m-CPBA in refluxing dichloromethane for 1 h.

  DOI：

  10.1080/00397910701266182
• 作为产物：
  描述：

  4-(溴甲基)-1-甲基-2(1H)-喹啉酮 、 2-溴-4-甲基苯并硫醇 在 potassium carbonate 、 sodium iodide 作用下， 以 丙酮 为溶剂， 反应 8.0h， 以94%的产率得到4-[(2-Bromo-4-methylphenyl)sulfanylmethyl]-1-methylquinolin-2-one
  参考文献：
  名称：

  Regioselective Synthesis of 2H‐Benzothiopyrano[3,2‐c]quinolin‐7(8H)‐ones by Tri‐n‐butyltinhydride–Mediated Radical Cyclization

  摘要：

  A number of hitherto unreported2H-benzothiopyrano[3,2-c]quinolin-7(8H)-ones have been regioselectively synthesized in 90-96% yield by tri-n-butyltinhydride-AIBN-mediated radical cyclization from 4-(20-bromothioarylmethyl)1-methylquinolin- 2(1H)-ones and their corresponding sulfones. 4-(20-Bromothioarylmethyl) quinolin-2(1H)-ones were in turn prepared from 4-bromomethylquinolin2(1H)-one and o-bromothiophenols by refluxing in acetone in the presence of anhydrous K2CO3. These were converted to the corresponding sulfones by oxidation with two equivalents of m-CPBA in refluxing dichloromethane for 1 h.

  DOI：

  10.1080/00397910701266182

文献信息

• Regioselective Synthesis of <i>2H‐</i>Benzothiopyrano[3,2‐<i>c</i>]quinolin‐7(8<i>H</i>)‐ones by Tri‐<i>n</i>‐butyltinhydride–Mediated Radical Cyclization
  作者：K. C. Majumdar、N. Kundu

  DOI：10.1080/00397910701266182

  日期：2007.5.1

  A number of hitherto unreported2H-benzothiopyrano[3,2-c]quinolin-7(8H)-ones have been regioselectively synthesized in 90-96% yield by tri-n-butyltinhydride-AIBN-mediated radical cyclization from 4-(20-bromothioarylmethyl)1-methylquinolin- 2(1H)-ones and their corresponding sulfones. 4-(20-Bromothioarylmethyl) quinolin-2(1H)-ones were in turn prepared from 4-bromomethylquinolin2(1H)-one and o-bromothiophenols by refluxing in acetone in the presence of anhydrous K2CO3. These were converted to the corresponding sulfones by oxidation with two equivalents of m-CPBA in refluxing dichloromethane for 1 h.