(5S,6R)-5,6-dimethyl-6-((4-methylfuran-3-yl)methyl)cyclohex-1-enecarboxylic acid | 1436393-60-0

• 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-enecarboxylic acid
• 英文别名: (5S,6R)-5,6-dimethyl-6-[(4-methylfuran-3-yl)methyl]cyclohexene-1-carboxylic acid
• CAS: 1436393-60-0
• 化学式: C₁₅H₂₀O₃
• 分子量: 248.322
• InChiKey: PJIBIGKMSYPITK-XHDPSFHLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  50.4
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (5S,6R)-5,6-dimethyl-6-((4-methylfuran-3-yl)methyl)cyclohex-1-enecarboxylic acid 在 五氯化磷 、 四氯化锡 作用下， 以 苯 为溶剂， 反应 1.92h， 以59%的产率得到(+)-9-oxoeuryopsin
  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：

  (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， 反应 40.5h， 生成 (5S,6R)-5,6-dimethyl-6-((4-methylfuran-3-yl)methyl)cyclohex-1-enecarboxylic acid
  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.