dichloroacetic acid 2,2-dimethyl-5-nitroso-[1,3]dioxan-5-yl ester | 1225446-62-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: dichloroacetic acid 2,2-dimethyl-5-nitroso-[1,3]dioxan-5-yl ester
• 英文别名: (2,2-Dimethyl-5-nitroso-1,3-dioxan-5-yl) 2,2-dichloroacetate；(2,2-dimethyl-5-nitroso-1,3-dioxan-5-yl) 2,2-dichloroacetate
• CAS: 1225446-62-7
• 化学式: C₈H₁₁Cl₂NO₅
• 分子量: 272.085
• InChiKey: ATKHABALQWOTAH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.88
• 拓扑面积：
  74.2
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  dichloroacetic acid 2,2-dimethyl-5-nitroso-[1,3]dioxan-5-yl ester 、 1,3-环己二烯 在 zinc trifluoromethanesulfonate 作用下， 以 甲苯 为溶剂， 反应 1.0h， 生成
  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：

  [bis-(2,2-dichloroacetyloxy)iodo]benzene 、 1,3-二噁烷-5-酮,2,2-二甲基-,肟 以 二氯甲烷 为溶剂， 反应 2.75h， 以52%的产率得到dichloroacetic acid 2,2-dimethyl-5-nitroso-[1,3]dioxan-5-yl ester
  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