(2R,3S,4S)-2,3-Epoxy-4-hydroxy-6-(3-methylbut-3-en-1-ynyl)-5-cyclohexen-1-one | 125555-67-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (2R,3S,4S)-2,3-Epoxy-4-hydroxy-6-(3-methylbut-3-en-1-ynyl)-5-cyclohexen-1-one
• 英文别名: (+)-Harveynone；(1R,5S,6R)-5-hydroxy-3-(3-methylbut-3-en-1-ynyl)-7-oxabicyclo[4.1.0]hept-3-en-2-one
• CAS: 125555-67-1；142435-66-3
• 化学式: C₁₁H₁₀O₃
• 分子量: 190.199
• InChiKey: PQAVKHOYIGJVBH-GDPRMGEGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  49.8
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  (3aR,7R,7aS)-7-hydroxy-2,2-dimethyltetrahydrobenzo[d][1,3]dioxol-5(6H)-one 在 bis-triphenylphosphine-palladium(II) chloride 吡啶 、 咪唑 、 4-二甲氨基吡啶 、 sodium hydroxide 、 copper(l) iodide 、 氢氟酸 、 碘 作用下， 以 四氢呋喃 、 四氯化碳 、 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 反应 28.0h， 生成 (2R,3S,4S)-2,3-Epoxy-4-hydroxy-6-(3-methylbut-3-en-1-ynyl)-5-cyclohexen-1-one
  参考文献：
  名称：

  The First Synthesis of (−)-Asperpentyn and Efficient Syntheses of (+)-Harveynone, (+)-Epiepoformin and (−)-Theobroxide

  摘要：

  A generally applicable strategy for the synthesis of a range of polyoxygenated cyclohexane natural products has been developed. The enantioselective syntheses of (-)-theobroxide, a polyoxygenated cyclohexane natural compound with potent growth inducing properties in potato microtubers has been achieved via a 1,2 O-silyl migration between trans-hydroxyl groups and a remote hydroxyl directed epoxidation of an enone derived from quinic acid. A thus derived alpha -iodoenone was subjected to Stille coupling with tetramethylstannane to afford the first title compound. A similar strategy enabled a route to the complete asymmetric synthesis of the acetylenic phytotoxin (+)-harveynone. By selective reduction of (-)-theobroxide, (+)-epiepoformin was also prepared in enantiopure form and similarly, stereoselective reduction of (+)-harveynone completed the first enantioselective synthesis of (-)-asperpentyn, another natural compound with antimicrobial activity.

  DOI：

  10.1002/1521-3765(20001103)6:21<3991::aid-chem3991>3.3.co;2-m

文献信息

• Enantioselective syntheses of bioactive epoxyquinone natural products (+)-harveynone and (−)-asperpentyn
  作者：Goverdhan Mehta、Subhrangsu Roy、Subhas Chandra Pan

  DOI：10.1016/j.tetlet.2012.05.115

  日期：2012.8

  Stereo- and enantioselective syntheses of (+)-harveynone and (−)-asperpentyn are reported.

  报告了（+）-harveynone和（-）-asperpentyn的立体和对映选择性合成。
• Sonogashira Coupling of 2-Iodo-2-cycloalkenones:  Synthesis of (+)- and (−)-Harveynone and (−)-Tricholomenyn A
  作者：Michael W. Miller、Carl R. Johnson

  DOI：10.1021/jo962295y

  日期：1997.3.1
• Absolute Configuration of (+)-PT-Toxin: Enantiodivergent Synthesis of (+)- and (-)-PT-Toxins
  作者：Kunio Ogasawara、Takashi Kamikubo

  DOI：10.3987/com-97-s(n)5

  日期：——
• The First Synthesis of (−)-Asperpentyn and Efficient Syntheses of (+)-Harveynone, (+)-Epiepoformin and (−)-Theobroxide
  作者：M. Teresa Barros、Christopher D. Maycock、M. Rita Ventura

  DOI：10.1002/1521-3765(20001103)6:21<3991::aid-chem3991>3.3.co;2-m

  日期：2000.11.3

  A generally applicable strategy for the synthesis of a range of polyoxygenated cyclohexane natural products has been developed. The enantioselective syntheses of (-)-theobroxide, a polyoxygenated cyclohexane natural compound with potent growth inducing properties in potato microtubers has been achieved via a 1,2 O-silyl migration between trans-hydroxyl groups and a remote hydroxyl directed epoxidation of an enone derived from quinic acid. A thus derived alpha -iodoenone was subjected to Stille coupling with tetramethylstannane to afford the first title compound. A similar strategy enabled a route to the complete asymmetric synthesis of the acetylenic phytotoxin (+)-harveynone. By selective reduction of (-)-theobroxide, (+)-epiepoformin was also prepared in enantiopure form and similarly, stereoselective reduction of (+)-harveynone completed the first enantioselective synthesis of (-)-asperpentyn, another natural compound with antimicrobial activity.