(4S,6R)-cis-4-(4-chlorophenyl)-6-(2-isopinocamphoxy)-5,6-dihydro-4H-1,2-oxazine-3-carbonitrile 2-oxide

• 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: (4S,6R)-cis-4-(4-chlorophenyl)-6-(2-isopinocamphoxy)-5,6-dihydro-4H-1,2-oxazine-3-carbonitrile 2-oxide
• 英文别名: [(4S,6R)-4-(4-chlorophenyl)-2-oxo-6-[[(1R,2R,3R,5S)-2,6,6-trimethyl-3-bicyclo[3.1.1]heptanyl]oxy]oxazinan-2-ium-3-ylidene]methylideneazanide
• 化学式: C₂₁H₂₅ClN₂O₃
• 分子量: 388.894
• InChiKey: YXFITPMRVSNLKS-NJZZVMOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.1
• 重原子数：
  27
• 可旋转键数：
  3
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  39.5
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  (-)-异松蒎醇 在 mercury(II) diacetate 作用下， 以 二甲基亚砜 为溶剂， 反应 5.5h， 生成 (4S,6R)-cis-4-(4-chlorophenyl)-6-(2-isopinocamphoxy)-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

文献信息

• [4 + 2] Cycloadditions of Nitroalkenes in Water. Highly Asymmetric Synthesis of Functionalized Nitronates
  作者：Francesco Fringuelli、Mizio Matteucci、Oriana Piermatti、Ferdinando Pizzo、Maria Cristina Burla

  DOI：10.1021/jo010182v

  日期：2001.6.1

  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.