syn-3-(1,2-Epoxycyclohexyl)-1-phenyl-1-butyn-3-ol

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 氧杂环己烷
• 英文名称: syn-3-(1,2-Epoxycyclohexyl)-1-phenyl-1-butyn-3-ol
• 英文别名: (2S)-2-[(1R,6S)-7-oxabicyclo[4.1.0]heptan-1-yl]-4-phenylbut-3-yn-2-ol
• 化学式: C₁₆H₁₈O₂
• 分子量: 242.318
• InChiKey: CWOJQYLDAWKVSK-HRCADAONSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.5
• 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：

  syn-3-(1,2-Epoxycyclohexyl)-1-phenyl-1-butyn-3-ol 在 mercury(II) oxide 硫酸 作用下， 以81%的产率得到4-<(3-methyl-5-phenyl)-2-furyl>pentanal
  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：

  3-(1-Cyclohexenyl)-1-phenyl-1-butyn-3-ol 在 bis(acetylacetonate)oxovanadium 叔丁基过氧化氢 作用下， 以 苯 为溶剂， 生成 syn-3-(1,2-Epoxycyclohexyl)-1-phenyl-1-butyn-3-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

• Stereoselective construction of quaternary centers at ambient temperature by the highly stereocontrolled migration of groups containing sp-, sp2-, and sp3-hybridized carbon atoms
  作者：Charles M. Marson、Andrew J. Walker、Jane Pickering、Adrian D. Hobson、Roger Wrigglesworth、Simon J. Edge

  DOI：10.1021/jo00074a019

  日期：1993.10

  A very highly diastereoselective semipinacol rearrangement of 2,3-epoxy alcohols mediated by tin(IV) chloride at ambient temperatures is shown to be applicable to a wide variety of migrating groups including methyl, tert-butyl, cyclopropyl, vinyl, alkynyl, phenyl, and 2-furyl. A synthetically valuable feature is that a mixture of syn- and anti-epoxy alcohols affords only a single diastereoisomerically pure beta-hydroxy ketone. Additional advantages of the reaction include the presence in the product of two adjacent stereocenters and the efficient creation of a new quaternary center, valuable features in the synthesis of a variety of natural products.
• 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。
• 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.