methyl (5S,6R)-5,6-dimethyl-6-((4-methylfuran-3-yl)methyl)cyclohex-1-enecarboxylate | 1436393-61-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 杂芳族化合物
• 英文名称: methyl (5S,6R)-5,6-dimethyl-6-((4-methylfuran-3-yl)methyl)cyclohex-1-enecarboxylate
• 英文别名: methyl (5S,6R)-5,6-dimethyl-6-[(4-methylfuran-3-yl)methyl]cyclohexene-1-carboxylate
• CAS: 1436393-61-1
• 化学式: C₁₆H₂₂O₃
• 分子量: 262.349
• InChiKey: ZIGBPGANTPJPJA-BLLLJJGKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  19
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  39.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  (1R,2R,3S)-1-hydroxy-2,3-dimethyl-2-((4-methylfuran-3-yl)-methyl)cyclohexanecarbonitrile 在 吡啶 、 potassium hydroxide 、 三氯氧磷 作用下， 以 乙醚 、 丙酮 为溶剂， 反应 41.5h， 生成 methyl (5S,6R)-5,6-dimethyl-6-((4-methylfuran-3-yl)methyl)cyclohex-1-enecarboxylate
  参考文献：
  名称：

  An Enantioselective Approach to Furanoeremophilanes: (+)-9-Oxoeuryopsin

  摘要：

  An enantioselective total synthesis of the furanoeremophilane sesquiterpene (+)-9-oxoeuryopsin 1 is reported. The synthesis involves as a key step a copper(II) triflate catalyzed tandem asymmetric conjugate addition of AlMe3 to 2-methyl-2-cyclohexen-1-one with the Feringa (S,R,R)-phosphoramidite binaphthol ligand, followed by aldol condensation of the resulting aluminum enolate with 4-methyl-3-furaldehyde 4. This tandem transformation has not been previously reported with a 2-substituted-2-cyclohexen-1-one. Conventional functional group manipulations completed the synthesis.

  DOI：

  10.1021/jo400399q