(6R)-benzyl 2-oxo-6-((S)-5-oxo-2,5-dihydrofuran-2-yl)cyclohexanecarboxylate | 1425313-50-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (6R)-benzyl 2-oxo-6-((S)-5-oxo-2,5-dihydrofuran-2-yl)cyclohexanecarboxylate
• 英文别名: benzyl (6R)-2-oxo-6-[(2S)-5-oxo-2H-furan-2-yl]cyclohexane-1-carboxylate
• CAS: 1425313-50-3
• 化学式: C₁₈H₁₈O₅
• 分子量: 314.338
• InChiKey: GHQFMQCTMNLNRT-JENVPCQVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  23
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.39
• 拓扑面积：
  69.7
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (6R)-benzyl 2-oxo-6-((S)-5-oxo-2,5-dihydrofuran-2-yl)cyclohexanecarboxylate 、 氯磷酸二苯酯 在 sodium hydride 作用下， 以 四氢呋喃 为溶剂， 反应 0.5h， 生成 (R)-benzyl 2-((diphenoxyphosphoryl)oxy)-6-((S)-5-oxo-2,5-dihydrofuran-2-yl)cyclohex-1-enecarboxylate
  参考文献：
  名称：

  Catalytic Enantioselective Vinylogous Mukaiyama–Michael Addition of 2-Silyloxyfurans to Cyclic Unsaturated Oxo Esters

  摘要：

  The copper-catalyzed asymmetric addition of 2-silyloxyfurans to cyclic unsaturated oxo esters is reported. The reaction proceeds with excellent diastereocontrol (usually dr 99:1) and modest to high enantioselectivity, depending on the nature of the ester group and the substitution of the cyclic oxo ester. We have shown that these substrates can be transformed into a variety of building blocks bearing a gamma-butenolide or gamma-lactone connected to a cycloalkane or cycoalkene moiety.

  DOI：

  10.1021/jo3020648
• 作为产物：
  描述：

  benzyl 6-oxocyclohex-1-enecarboxylate 在 copper(II) bis(trifluoromethanesulfonate) 、 (4R,4’R)-2,2’-(propane-2,2-diyl)bis(4-benzyl-4,5-dihydrooxazole) 作用下， 以 四氢呋喃 、 甲苯 为溶剂， 反应 1.0h， 以57%的产率得到(6R)-benzyl 2-oxo-6-((S)-5-oxo-2,5-dihydrofuran-2-yl)cyclohexanecarboxylate
  参考文献：
  名称：

  Catalytic Enantioselective Vinylogous Mukaiyama–Michael Addition of 2-Silyloxyfurans to Cyclic Unsaturated Oxo Esters

  摘要：

  The copper-catalyzed asymmetric addition of 2-silyloxyfurans to cyclic unsaturated oxo esters is reported. The reaction proceeds with excellent diastereocontrol (usually dr 99:1) and modest to high enantioselectivity, depending on the nature of the ester group and the substitution of the cyclic oxo ester. We have shown that these substrates can be transformed into a variety of building blocks bearing a gamma-butenolide or gamma-lactone connected to a cycloalkane or cycoalkene moiety.

  DOI：

  10.1021/jo3020648

文献信息

• Catalytic Enantioselective Vinylogous Mukaiyama–Michael Addition of 2-Silyloxyfurans to Cyclic Unsaturated Oxo Esters
  作者：Xavier Jusseau、Pascal Retailleau、Laurent Chabaud、Catherine Guillou

  DOI：10.1021/jo3020648

  日期：2013.3.15

  The copper-catalyzed asymmetric addition of 2-silyloxyfurans to cyclic unsaturated oxo esters is reported. The reaction proceeds with excellent diastereocontrol (usually dr 99:1) and modest to high enantioselectivity, depending on the nature of the ester group and the substitution of the cyclic oxo ester. We have shown that these substrates can be transformed into a variety of building blocks bearing a gamma-butenolide or gamma-lactone connected to a cycloalkane or cycoalkene moiety.