(7S*,12bS*,12cS*,4aS*)-4a-morpholino-11-nitro-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*)-4a-morpholino-11-nitro-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)-4a-morpholin-4-yl-11-nitro-6-oxido-7-(trifluoromethyl)-2,3,4,7,12b,12c-hexahydro-1H-chromeno[3,4-c][1,2]benzoxazin-6-ium
• 化学式: C₂₀H₂₂F₃N₃O₆
• 分子量: 457.406
• InChiKey: VYMGBBWZANNTNM-FXECBMLZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  32
• 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：
  106
• 氢给体数：
  0
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  (7S*,12bS*,12cS*,4aS*)-4a-morpholino-11-nitro-7-(trifluoromethyl)-2,3,4,4a,12b,12c-hexahydro-1H,7H-chromeno[3,4-c][1,2]benzoxazin-6-oxide 在 盐酸 作用下， 以 乙醇 、 水 为溶剂， 反应 3.0h， 以54%的产率得到(2R*)-(2S*,3R*,4S*)-2-[3,6-dinitro-2-(trifluoromethyl)-3,4-dihydro-2H-chromen-4-yl]cyclohexanone
  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
• 作为产物：
  描述：

  3,6-Dinitro-2-trifluoromethyl-2H-chromene 、 1-吗啉基-1-环己烯 以 乙腈 为溶剂， 反应 0.5h， 以54%的产率得到(7S*,12bS*,12cS*,4aS*)-4a-morpholino-11-nitro-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