(5S,6R)-5,6-dimethyl-6-((4-methylfuran-3-yl)methyl)cyclohex-1-enecarbonitrile | 1436393-59-7

• 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: (5S,6R)-5,6-dimethyl-6-((4-methylfuran-3-yl)methyl)cyclohex-1-enecarbonitrile
• 英文别名: (5S,6R)-5,6-dimethyl-6-[(4-methylfuran-3-yl)methyl]cyclohexene-1-carbonitrile
• CAS: 1436393-59-7
• 化学式: C₁₅H₁₉NO
• 分子量: 229.322
• InChiKey: NHFLXYIVTQZQFY-SWLSCSKDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  36.9
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (5S,6R)-5,6-dimethyl-6-((4-methylfuran-3-yl)methyl)cyclohex-1-enecarbonitrile 在 potassium hydroxide 作用下， 以 乙醚 、 丙酮 为溶剂， 反应 25.0h， 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
• 作为产物：
  描述：

  (2R,3S)-1-hydroxy-2,3-dimethyl-2-((4-methylfuran-3-yl)methyl)cyclohexanecarbonitrile trimethylsilyl ether 在 吡啶 、 盐酸 、 水 、 三氯氧磷 作用下， 以 四氢呋喃 为溶剂， 反应 35.5h， 生成 (5S,6R)-5,6-dimethyl-6-((4-methylfuran-3-yl)methyl)cyclohex-1-enecarbonitrile
  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

文献信息

• An Enantioselective Approach to Furanoeremophilanes: (+)-9-Oxoeuryopsin
  作者：Ana L. Silva、Rubén A. Toscano、Luis A. Maldonado

  DOI：10.1021/jo400399q

  日期：2013.6.7

  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.