(7S*,12bS*,12cS*,4aS*)-11-bromo-4a-morpholino-7-(trifluoromethyl)-2,3,4,4a,12b,12c-hexahydro-1H,7H-chromeno[3,4-c][1,2]benzoxazin-6-oxide

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并吡喃
• 英文名称: (7S*,12bS*,12cS*,4aS*)-11-bromo-4a-morpholino-7-(trifluoromethyl)-2,3,4,4a,12b,12c-hexahydro-1H,7H-chromeno[3,4-c][1,2]benzoxazin-6-oxide
• 英文别名: (4aS,7S,12bS,12cS)-11-bromo-4a-morpholin-4-yl-6-oxido-7-(trifluoromethyl)-2,3,4,7,12b,12c-hexahydro-1H-chromeno[3,4-c][1,2]benzoxazin-6-ium
• 化学式: C₂₀H₂₂BrF₃N₂O₄
• 分子量: 491.305
• InChiKey: KQCUOHKPSZOPLU-FXECBMLZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  30
• 可旋转键数：
  1
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.65
• 拓扑面积：
  59.7
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为产物：
  描述：

  6-bromo-3-nitro-2-(trifluoromethyl)-2H-chromene 、 1-吗啉基-1-环己烯 以 乙腈 为溶剂， 反应 0.5h， 以59%的产率得到(7S*,12bS*,12cS*,4aS*)-11-bromo-4a-morpholino-7-(trifluoromethyl)-2,3,4,4a,12b,12c-hexahydro-1H,7H-chromeno[3,4-c][1,2]benzoxazin-6-oxide
  参考文献：
  名称：

  Synthesis of chromeno[3,4-c][1,2]oxazine-N-oxides via formal [4+2] cycloaddition of 3-nitro-2-trihalomethyl-2H-chromenes with cyclohexanone and pinacolone enamines

  摘要：

  3-Nitro-2-trichloro(trifluoro)methyl-2H-chromenes undergo a formal [4+2] cycloaddition reaction to cyclohexanone and pinacolone enamines, producing chromeno[3,4-c][1,2]benzoxazin-6-oxides with high diastereoselectivity and in good yields. In addition, some novel 2,3,4-trisubstituted chromanes were obtained. The stereochemistry of the products was established based on a 2D NOESY experiment and an X-ray diffraction study. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2014.05.100