(E)-1,2-bis(5-acetoxy-2,2-dimethyl-1,3-dioxan-5-yl)diazene 1,2-dioxide | 1225446-67-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (E)-1,2-bis(5-acetoxy-2,2-dimethyl-1,3-dioxan-5-yl)diazene 1,2-dioxide
• CAS: 1225446-67-2
• 化学式: C₁₆H₂₆N₂O₁₀
• 分子量: 406.39
• InChiKey: GQCYQNYYUUDOJQ-ISLYRVAYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.54
• 重原子数：
  28.0
• 可旋转键数：
  4.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.88
• 拓扑面积：
  141.66
• 氢给体数：
  0.0
• 氢受体数：
  10.0

反应信息

• 作为反应物：
  描述：

  (E)-1,2-bis(5-acetoxy-2,2-dimethyl-1,3-dioxan-5-yl)diazene 1,2-dioxide 以 二氯甲烷 为溶剂， 生成 2,2-dimethyl-5-nitroso-1,3-dioxan-5-yl acetate
  参考文献：
  名称：

  α-Acyloxynitroso dienophiles in [4+2] hetero Diels–Alder cycloadditions: mechanistic insights

  摘要：

  alpha-Acyloxynitroso derivatives are a class of heterodienophiles leading to valuable 3,6-dihydro-1,2-oxazines or the corresponding aminoalcohols in good yields. The discovery that a beta-oxygenated moiety led to a domino [4+2] cycloaddition/sigma(N-O) bond cleavage in the presence of a catalytic amount of Lewis acid was investigated in detail, through kinetic profiling of the reaction both in the absence and presence of a promoter. These studies showed that the role of the Lewis acid was to accelerate the sigma(N-O) bond cleavage thereby promoting a highly reproducible sequence. In addition, our preliminary results on an asymmetric version of this domino sequence are reported. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2010.02.065
• 作为产物：
  描述：

  2,2-dimethyl-5-nitroso-1,3-dioxan-5-yl acetate 生成 (E)-1,2-bis(5-acetoxy-2,2-dimethyl-1,3-dioxan-5-yl)diazene 1,2-dioxide
  参考文献：
  名称：

  α-Acyloxynitroso dienophiles in [4+2] hetero Diels–Alder cycloadditions: mechanistic insights

  摘要：

  alpha-Acyloxynitroso derivatives are a class of heterodienophiles leading to valuable 3,6-dihydro-1,2-oxazines or the corresponding aminoalcohols in good yields. The discovery that a beta-oxygenated moiety led to a domino [4+2] cycloaddition/sigma(N-O) bond cleavage in the presence of a catalytic amount of Lewis acid was investigated in detail, through kinetic profiling of the reaction both in the absence and presence of a promoter. These studies showed that the role of the Lewis acid was to accelerate the sigma(N-O) bond cleavage thereby promoting a highly reproducible sequence. In addition, our preliminary results on an asymmetric version of this domino sequence are reported. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2010.02.065