1-acetoxy-1,2-epoxytetralin | 428862-55-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 四氢化萘
• 英文名称: 1-acetoxy-1,2-epoxytetralin
• 英文别名: 2,3-dihydro-1aH-naphtho[1,2-b]oxiren-7b-yl acetate
• CAS: 428862-55-9；773893-24-6；773893-26-8
• 化学式: C₁₂H₁₂O₃
• 分子量: 204.225
• InChiKey: HLWVZCJCIGSBKK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  38.8
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1-acetoxy-1,2-epoxytetralin 在 potassium carbonate 作用下， 以 甲醇 为溶剂， 反应 0.17h， 以86%的产率得到2-hydroxy-1-tetralone
  参考文献：
  名称：

  Synthesis of Racemic and Enantiomerically Enriched a-Oxyfunctionalized Benzocyclanones and Chromanones by Dimethyldioxirane and Dimethyldioxirane/Mn(III) salen System

  摘要：

  Enolacetates of benzocyclanones and chromanones were synthesized and treated with dimethyldioxirane and the asymmetric oxidizing system dimethyldioxirane/chiral, non-racemic Mn(III) salen complex/axial ligand. The latter reagent resulted in the corresponding enantiomerically enriched cyclic alpha-hydroxy ketones and their acetates in moderate-to-good yields and modest enantioselectivity under mild and neutral conditions from tetralone and chromanone. On the contrary, flavanone provided poor yields due to the competitive C-H insertion at position 2. The use of R,R-Mn(III)salen catalyst induced an S absolute configuration at the position alpha in the whole series.

  DOI：

  10.1007/s00706-004-0159-9
• 作为产物：
  描述：

  3,4-dihydronaphthalen-1-yl acetate 在 二甲基二环氧乙烷 、 potassium carbonate 作用下， 以 丙酮 为溶剂， 反应 2.0h， 以84%的产率得到1-acetoxy-1,2-epoxytetralin
  参考文献：
  名称：

  Synthesis of Racemic and Enantiomerically Enriched a-Oxyfunctionalized Benzocyclanones and Chromanones by Dimethyldioxirane and Dimethyldioxirane/Mn(III) salen System

  摘要：

  Enolacetates of benzocyclanones and chromanones were synthesized and treated with dimethyldioxirane and the asymmetric oxidizing system dimethyldioxirane/chiral, non-racemic Mn(III) salen complex/axial ligand. The latter reagent resulted in the corresponding enantiomerically enriched cyclic alpha-hydroxy ketones and their acetates in moderate-to-good yields and modest enantioselectivity under mild and neutral conditions from tetralone and chromanone. On the contrary, flavanone provided poor yields due to the competitive C-H insertion at position 2. The use of R,R-Mn(III)salen catalyst induced an S absolute configuration at the position alpha in the whole series.

  DOI：

  10.1007/s00706-004-0159-9