4-Bromo-1-(4-nitrophenyl)but-3-yn-1-ol | 1356451-43-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 4-Bromo-1-(4-nitrophenyl)but-3-yn-1-ol
• CAS: 1356451-43-8
• 化学式: C₁₀H₈BrNO₃
• 分子量: 270.082
• InChiKey: CUPWPYDNHNXYLO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  66
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  4-Bromo-1-(4-nitrophenyl)but-3-yn-1-ol 在 gold(III) chloride 、 水 作用下， 以 甲苯 为溶剂， 反应 6.0h， 以75%的产率得到5-(4-nitrophenyl)-dihydro-2(3H)-furanone
  参考文献：
  名称：

  A New Synthesis of γ-Butyrolactones via AuCl₃- or Hg(II)-Catalyzed Intramolecular Hydroalkoxylation of 4-Bromo-3-yn-1-ols

  摘要：

  An efficient conversion of 4-bromo-3-yn-1-ols to gamma-butyrolactones via AuCl3-catalyzed electrophilic cyclization (hydroxyl-assisted regioselective hydration) in wet toluene is described. Various secondary and tertiary alcohols including benzylic systems were found to be equally reactive with moderate to excellent yields obtained in all cases.

  DOI：

  10.1021/ol2033493
• 作为产物：
  描述：

  1-(4-Nitrophenyl)-3-butyn-1-ol 在 N-溴代丁二酰亚胺(NBS) 、 silver nitrate 作用下， 以 丙酮 为溶剂， 生成 4-Bromo-1-(4-nitrophenyl)but-3-yn-1-ol
  参考文献：
  名称：

  A New Synthesis of γ-Butyrolactones via AuCl₃- or Hg(II)-Catalyzed Intramolecular Hydroalkoxylation of 4-Bromo-3-yn-1-ols

  摘要：

  An efficient conversion of 4-bromo-3-yn-1-ols to gamma-butyrolactones via AuCl3-catalyzed electrophilic cyclization (hydroxyl-assisted regioselective hydration) in wet toluene is described. Various secondary and tertiary alcohols including benzylic systems were found to be equally reactive with moderate to excellent yields obtained in all cases.

  DOI：

  10.1021/ol2033493

文献信息

• A New Synthesis of γ-Butyrolactones via AuCl₃- or Hg(II)-Catalyzed Intramolecular Hydroalkoxylation of 4-Bromo-3-yn-1-ols
  作者：Maddi Sridhar Reddy、Yalla Kiran Kumar、Nuligonda Thirupathi

  DOI：10.1021/ol2033493

  日期：2012.2.3

  An efficient conversion of 4-bromo-3-yn-1-ols to gamma-butyrolactones via AuCl3-catalyzed electrophilic cyclization (hydroxyl-assisted regioselective hydration) in wet toluene is described. Various secondary and tertiary alcohols including benzylic systems were found to be equally reactive with moderate to excellent yields obtained in all cases.