2-methyl-5-phenoxy-3-phenylpent-4-yne-2,3-diol | 1448620-95-8

• 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: 2-methyl-5-phenoxy-3-phenylpent-4-yne-2,3-diol
• 英文别名: 2-Methyl-5-phenoxy-3-phenylpent-4-yne-2,3-diol
• CAS: 1448620-95-8
• 化学式: C₁₈H₁₈O₃
• 分子量: 282.339
• InChiKey: OUPNQCUYSFOEOH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  21
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  49.7
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-methyl-5-phenoxy-3-phenylpent-4-yne-2,3-diol 在 silver trifluoromethanesulfonate 作用下， 以 甲苯 为溶剂， 反应 0.5h， 以93%的产率得到5,5-Dimethyl-4-phenyl-2(5H)-furanone
  参考文献：
  名称：

  Efficient Intramolecular Cyclizations of Phenoxyethynyl Diols into Multisubstituted α,β-Unsaturated Lactones

  摘要：

  AgOTf-catalyzed intramolecular cyclization of phenoxyethynyl diols proceeded under mild conditions to afford the multisubstituted alpha,beta-unsaturated-gamma-lactones in 55-98% yields. This method was also applicable to the synthesis of alpha,beta-unsaturated-delta-lactones. A similar cyclization proceeded when AgOTf was replaced with a stoichiometric amount of N-bromosuccinimide to furnish the a-bromo-substituted alpha,beta-unsaturated lactones.

  DOI：

  10.1021/ol401824v
• 作为产物：
  描述：

  1,2-dichlorovinyl phenyl ether 、 2-羟基-2-甲基-1-苯基-1-丙酮 在 正丁基锂 作用下， 以 乙醚 、 正己烷 为溶剂， 反应 2.0h， 以93%的产率得到2-methyl-5-phenoxy-3-phenylpent-4-yne-2,3-diol
  参考文献：
  名称：

  Efficient Intramolecular Cyclizations of Phenoxyethynyl Diols into Multisubstituted α,β-Unsaturated Lactones

  摘要：

  AgOTf-catalyzed intramolecular cyclization of phenoxyethynyl diols proceeded under mild conditions to afford the multisubstituted alpha,beta-unsaturated-gamma-lactones in 55-98% yields. This method was also applicable to the synthesis of alpha,beta-unsaturated-delta-lactones. A similar cyclization proceeded when AgOTf was replaced with a stoichiometric amount of N-bromosuccinimide to furnish the a-bromo-substituted alpha,beta-unsaturated lactones.

  DOI：

  10.1021/ol401824v

文献信息

• Efficient Intramolecular Cyclizations of Phenoxyethynyl Diols into Multisubstituted α,β-Unsaturated Lactones
  作者：Masahiro Egi、Yuya Ota、Yuka Nishimura、Kaori Shimizu、Kenji Azechi、Shuji Akai

  DOI：10.1021/ol401824v

  日期：2013.8.16

  AgOTf-catalyzed intramolecular cyclization of phenoxyethynyl diols proceeded under mild conditions to afford the multisubstituted alpha,beta-unsaturated-gamma-lactones in 55-98% yields. This method was also applicable to the synthesis of alpha,beta-unsaturated-delta-lactones. A similar cyclization proceeded when AgOTf was replaced with a stoichiometric amount of N-bromosuccinimide to furnish the a-bromo-substituted alpha,beta-unsaturated lactones.