(2S,3S)-2-((R)-hydroxy(4-methylfuran-3-yl)methyl)-2,3-dimethylcyclohexanone | 1436393-43-9

• 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: (2S,3S)-2-((R)-hydroxy(4-methylfuran-3-yl)methyl)-2,3-dimethylcyclohexanone
• 英文别名: (2S,3S)-2-[(R)-hydroxy-(4-methylfuran-3-yl)methyl]-2,3-dimethylcyclohexan-1-one
• CAS: 1436393-43-9
• 化学式: C₁₄H₂₀O₃
• 分子量: 236.311
• InChiKey: ITDBATWFEFOSOF-ZLKJLUDKSA-N

物化性质

• 沸点：
  270.1±29.0 °C(predicted)
• 密度：
  1.089±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.64
• 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：

  (2S,3S)-2-((R)-hydroxy(4-methylfuran-3-yl)methyl)-2,3-dimethylcyclohexanone 在 tetrafluoroboric acid 、 三正丁基氢锡 、 1,1'-偶氮(氰基环己烷) 作用下， 以 四氢呋喃 、 二氯甲烷 、 水 、 甲苯 、 乙腈 为溶剂， 反应 10.0h， 生成 (2R,3S)-2,3-dimethyl-2-((4-methylfuran-3-yl)methyl)cyclohexanone 2,4,6-triisopropylbenzenesulfonylhydrazone
  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：

  2-(1-nitropropan-2-yl)-1,3-dioxolane 在 三乙烯二胺 、 盐酸 、 manganese(IV) oxide 、 水 、 barium(II) hydroxide 作用下， 以 乙二醇二甲醚 、 乙醚 、 二氯甲烷 、 丙酮 、 甲苯 为溶剂， 反应 79.5h， 生成 (2S,3S)-2-((R)-hydroxy(4-methylfuran-3-yl)methyl)-2,3-dimethylcyclohexanone
  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.