2,3-epoxy-4-methyl-5-nonyn-4-ol | 219140-90-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2,3-epoxy-4-methyl-5-nonyn-4-ol
• 英文别名: 2-(3-Methyloxiran-2-yl)hept-3-yn-2-ol
• CAS: 219140-90-6
• 化学式: C₁₀H₁₆O₂
• 分子量: 168.236
• InChiKey: FLQDHMQWAOGQPJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  12
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  32.8
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2,3-epoxy-4-methyl-5-nonyn-4-ol 在 硫酸 、 mercury(II) oxide 作用下， 以 水 、 丙酮 为溶剂， 反应 0.25h， 以72%的产率得到1,1-bis<(3-methyl-5-n-propyl)-2-furyl>ethane
  参考文献：
  名称：

  Catalytic Isomerization of 1-Alkynyl-2,3-epoxy Alcohols to Substituted Furans:  Succinct Routes to Furanoid Fatty Acids and Difurylmethanes

  摘要：

  A versatile procedure for the preparation of synthetically valuable 2,5-disubstituted and 2,3,5-trisubstituted furans via mercury(II)-mediated isomerization of 1-alkynyl-2,3-epoxy alcohols is described. Mercury(II)-catalyzed isomerization of alkynyl epoxides 3a-k derived from cyclic Phi-alkynyl allylic alcohols furnishes 2,3,5-substituted furans bearing an aldehyde or keto group on the C-2 side chain. The reaction is used in a succinct and efficient synthesis of the furanoid fatty acid F-5. In contrast, the mercury(II)-catalyzed reaction of a series of alkynyl epoxides 3m-p lacking ring fusion affords difurylmethanes 5, presumably by the dimerization of intermediate 2-(alpha-hydroxyalkyl)furans 4.

  DOI：

  10.1021/jo980856a
• 作为产物：
  描述：

  戊-3-烯-2-酮 在 叔丁基过氧化氢 、 正丁基锂 、 bis(acetylacetonate)oxovanadium 作用下， 以 水 、 苯 为溶剂， 反应 7.5h， 生成 2,3-epoxy-4-methyl-5-nonyn-4-ol
  参考文献：
  名称：

  Catalytic Isomerization of 1-Alkynyl-2,3-epoxy Alcohols to Substituted Furans:  Succinct Routes to Furanoid Fatty Acids and Difurylmethanes

  摘要：

  A versatile procedure for the preparation of synthetically valuable 2,5-disubstituted and 2,3,5-trisubstituted furans via mercury(II)-mediated isomerization of 1-alkynyl-2,3-epoxy alcohols is described. Mercury(II)-catalyzed isomerization of alkynyl epoxides 3a-k derived from cyclic Phi-alkynyl allylic alcohols furnishes 2,3,5-substituted furans bearing an aldehyde or keto group on the C-2 side chain. The reaction is used in a succinct and efficient synthesis of the furanoid fatty acid F-5. In contrast, the mercury(II)-catalyzed reaction of a series of alkynyl epoxides 3m-p lacking ring fusion affords difurylmethanes 5, presumably by the dimerization of intermediate 2-(alpha-hydroxyalkyl)furans 4.

  DOI：

  10.1021/jo980856a

文献信息

• Catalytic Isomerization of 1-Alkynyl-2,3-epoxy Alcohols to Substituted Furans:  Succinct Routes to Furanoid Fatty Acids and Difurylmethanes
  作者：Charles M. Marson、Steven Harper

  DOI：10.1021/jo980856a

  日期：1998.12.1

  A versatile procedure for the preparation of synthetically valuable 2,5-disubstituted and 2,3,5-trisubstituted furans via mercury(II)-mediated isomerization of 1-alkynyl-2,3-epoxy alcohols is described. Mercury(II)-catalyzed isomerization of alkynyl epoxides 3a-k derived from cyclic Phi-alkynyl allylic alcohols furnishes 2,3,5-substituted furans bearing an aldehyde or keto group on the C-2 side chain. The reaction is used in a succinct and efficient synthesis of the furanoid fatty acid F-5. In contrast, the mercury(II)-catalyzed reaction of a series of alkynyl epoxides 3m-p lacking ring fusion affords difurylmethanes 5, presumably by the dimerization of intermediate 2-(alpha-hydroxyalkyl)furans 4.