3-nitro-7,8-dimethoxy-2H-chromen-2-one | 1085451-92-8

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 香豆素及其衍生物
• 英文名称: 3-nitro-7,8-dimethoxy-2H-chromen-2-one
• 英文别名: 7,8-dimethoxy-3-nitro-2H-chromen-2-one；7,8-Dimethoxy-3-nitrochromen-2-one
• CAS: 1085451-92-8
• 化学式: C₁₁H₉NO₆
• 分子量: 251.196
• InChiKey: VMXBKEVPIJRBBQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  90.6
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  3-nitro-7,8-dimethoxy-2H-chromen-2-one 在 吡啶 、 2,4,6-三甲基吡啶 、 palladium 10% on activated carbon 、 氢气 、 N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate 作用下， 以 四氢呋喃 、 乙醇 、 N,N-二甲基甲酰胺 为溶剂， 23.0 ℃ 、172.37 kPa 条件下， 反应 0.41h， 生成 trichodermamide A
  参考文献：
  名称：

  Concise Total Synthesis of Trichodermamides A, B, and C Enabled by an Efficient Construction of the 1,2-Oxazadecaline Core

  摘要：

  We report herein a facile and efficient method of the construction of the cis-1,2-oxazadecaline system, distinctive of (pre)trichodermamides, aspergillazine A, gliovirin, and FA-2097. The formation of the 1,2-oxazadecaline core was accomplished by a 1,2-addition of an alpha C-lithiated O-silyl ethyl pyruvate oxime to benzoquinone, which is followed by an oxa-Michael ring-closure. The method was successfully applied to the concise total synthesis of trichodermamide A (in gram quantities) and trichodermamide B, as well as the first synthesis of trichodermamide C.

  DOI：

  10.1021/jacs.5b05205
• 作为产物：
  描述：

  2,3,4-三甲氧基苯甲醛 在 哌啶 、 aluminum (III) chloride 作用下， 以 苯 为溶剂， 反应 1.25h， 生成 3-nitro-7,8-dimethoxy-2H-chromen-2-one
  参考文献：
  名称：

  Concise Total Synthesis of Trichodermamides A, B, and C Enabled by an Efficient Construction of the 1,2-Oxazadecaline Core

  摘要：

  We report herein a facile and efficient method of the construction of the cis-1,2-oxazadecaline system, distinctive of (pre)trichodermamides, aspergillazine A, gliovirin, and FA-2097. The formation of the 1,2-oxazadecaline core was accomplished by a 1,2-addition of an alpha C-lithiated O-silyl ethyl pyruvate oxime to benzoquinone, which is followed by an oxa-Michael ring-closure. The method was successfully applied to the concise total synthesis of trichodermamide A (in gram quantities) and trichodermamide B, as well as the first synthesis of trichodermamide C.

  DOI：

  10.1021/jacs.5b05205

文献信息

• Wan, Xiaobo; Joullie, Madeleine M., Journal of the American Chemical Society, 2008, vol. 130, p. 17236 - 17237
  作者：Wan, Xiaobo、Joullie, Madeleine M.

  DOI：——

  日期：——