(1S)-(-)-10-(N,N-dicyclohexylsulfonamide) isoborneyl vinyl ether | 351464-38-5

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: (1S)-(-)-10-(N,N-dicyclohexylsulfonamide) isoborneyl vinyl ether
• 英文别名: N,N-dicyclohexyl-1-[(1S,2R,4R)-2-ethenoxy-7,7-dimethyl-1-bicyclo[2.2.1]heptanyl]methanesulfonamide
• CAS: 351464-38-5
• 化学式: C₂₄H₄₁NO₃S
• 分子量: 423.66
• InChiKey: CQQOLIAAAVCOGM-ZFJSRUIDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.2
• 重原子数：
  29
• 可旋转键数：
  7
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.92
• 拓扑面积：
  55
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (E)-1-cyano-2-(4'-methoxyphenyl)-1-nitroethene 、 (1S)-(-)-10-(N,N-dicyclohexylsulfonamide) isoborneyl vinyl ether 以 水 为溶剂， 反应 1.0h， 以80%的产率得到(4R,6S)-cis-6-[(1S)-10-(N,N-dicyclohexylsulfonamide)isoborneyl]-4-(4-methoxyphenyl)-5,6-dihydro-4H-1,2-oxazine-3-carbonitrile 2-oxide
  参考文献：
  名称：

  [4 + 2] Cycloadditions of Nitroalkenes in Water. Highly Asymmetric Synthesis of Functionalized Nitronates

  摘要：

  The [4 + 2] cycloadditions of (E)-2-aryl-1-cyano-1-nitroalkenes 1 with achiral and enantiopure vinyl ethers 2 and 3 carried out in sole water are reported. These reactions occur in a heterogeneous phase under mild conditions and are fast and highly stereoselective. By using(-)-N,N-dicyclohexyl-(1S)-isoborneol-10-sulfonamide as achiral auxiliary, the cycloadditions are totally asymmetric. The face selectivity is discussed in terms of the shape of the chiral auxiliary and the reactive conformation of vinyl ether.

  DOI：

  10.1021/jo010182v
• 作为产物：
  描述：

  乙烯基正丁醚 、 (-)-10-dicyclohexylsulfamoyl-D-isoborneol 在 mercury(II) diacetate 作用下， 反应 15.0h， 以80%的产率得到(1S)-(-)-10-(N,N-dicyclohexylsulfonamide) isoborneyl vinyl ether
  参考文献：
  名称：

  [4 + 2] Cycloadditions of Nitroalkenes in Water. Highly Asymmetric Synthesis of Functionalized Nitronates

  摘要：

  The [4 + 2] cycloadditions of (E)-2-aryl-1-cyano-1-nitroalkenes 1 with achiral and enantiopure vinyl ethers 2 and 3 carried out in sole water are reported. These reactions occur in a heterogeneous phase under mild conditions and are fast and highly stereoselective. By using(-)-N,N-dicyclohexyl-(1S)-isoborneol-10-sulfonamide as achiral auxiliary, the cycloadditions are totally asymmetric. The face selectivity is discussed in terms of the shape of the chiral auxiliary and the reactive conformation of vinyl ether.

  DOI：

  10.1021/jo010182v