2,3-epoxy-5-undecyn-4-ol | 219140-88-2

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: 2,3-epoxy-5-undecyn-4-ol
• 英文别名: 1-(3-Methyloxiran-2-yl)oct-2-yn-1-ol
• CAS: 219140-88-2
• 化学式: C₁₁H₁₈O₂
• 分子量: 182.263
• InChiKey: BDYWGAOWJJHENH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  13
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.82
• 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-5-undecyn-4-ol 在 mercury(II) oxide 硫酸 作用下， 以73%的产率得到1-(5-pentyl-2-furyl)ethan-1-ol
  参考文献：
  名称：

  Regiocontrolled synthesis of furans by a mercury(II) catalysed isomerisation of 1-alkynyl-2,3-epoxyalcohols

  摘要：

  2,3,5-三取代呋喃是通过 1-炔基-2,3-环氧醇与催化量的由 HgO 和稀硫酸制备的汞 (II) 反应形成的。

  DOI：

  10.1039/c39940001879
• 作为产物：
  描述：

  2-undecen-5-yn-4-ol 在 bis(acetylacetonate)oxovanadium 叔丁基过氧化氢 作用下， 以 苯 为溶剂， 生成 2,3-epoxy-5-undecyn-4-ol
  参考文献：
  名称：

  Regiocontrolled synthesis of furans by a mercury(II) catalysed isomerisation of 1-alkynyl-2,3-epoxyalcohols

  摘要：

  2,3,5-三取代呋喃是通过 1-炔基-2,3-环氧醇与催化量的由 HgO 和稀硫酸制备的汞 (II) 反应形成的。

  DOI：

  10.1039/c39940001879

文献信息

• Regiocontrolled synthesis of furans by a mercury(II) catalysed isomerisation of 1-alkynyl-2,3-epoxyalcohols
  作者：Charles M. Marson、Steven Harper、Roger Wrigglesworth

  DOI：10.1039/c39940001879

  日期：——

  2,3,5-Trisubstituted furans are formed by the reaction of 1-alkynyl-2,3-epoxyalcohols with a catalytic amount of mercury(II) prepared from HgO and dilute sulfuric acid.

  2,3,5-三取代呋喃是通过 1-炔基-2,3-环氧醇与催化量的由 HgO 和稀硫酸制备的汞 (II) 反应形成的。
• Marson Charles M., Harper Steven, Wrigglesworth Roger, J. Chem. Soc. Chem. Commun, (1994) N 16, S 1879-1880
  作者：Marson Charles M., Harper Steven, Wrigglesworth Roger

  DOI：——

  日期：——
• Synthesis of polysubstituted thiophenes by a catalytic cyclisation of functionalised episulfides
  作者：Charles M. Marson、Jonathan Campbell

  DOI：10.1016/s0040-4039(97)01819-4

  日期：1997.11

  Substituted thiophenes are formed by the reaction of 1-alkynyl-2,3-epithioalcohols with a catalytic amount of mercury(II) prepared from HgO and dilute sulfuric acid. (C) 1997 Elsevier Science Ltd.
• 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.