N-((1R,9R,10R,11R)-9-Hydroxy-6-methoxy-9-methyl-2,13-dioxa-tricyclo[8.2.1.0^3,8]trideca-3(8),4,6-trien-11-yl)-N-methyl-acetamide | 131636-99-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: N-((1R,9R,10R,11R)-9-Hydroxy-6-methoxy-9-methyl-2,13-dioxa-tricyclo[8.2.1.0^3,8]trideca-3(8),4,6-trien-11-yl)-N-methyl-acetamide
• 英文别名: N-[(1R,9R,10R,11R)-9-hydroxy-6-methoxy-9-methyl-2,13-dioxatricyclo[8.2.1.03,8]trideca-3(8),4,6-trien-11-yl]-N-methylacetamide
• CAS: 131636-99-2
• 化学式: C₁₆H₂₁NO₅
• 分子量: 307.346
• InChiKey: RQVZSUSDOGCZLD-SLBVQIDZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  22
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  68.2
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  (R)-3-[(2R,4R,5R)-5-(2,5-Bis-benzyloxy-phenyl)-5-methyl-2-phenyl-[1,3]dioxolan-4-yl]-2-methyl-5-trimethylsilanyl-isoxazolidine 在 palladium dihydroxide 氢气 、 碳酸氢钠 、 potassium carbonate 作用下， 以 四氢呋喃 、 溶剂黄146 、 丙酮 为溶剂， 反应 7.25h， 生成 N-((1R,9R,10R,11R)-9-Hydroxy-6-methoxy-9-methyl-2,13-dioxa-tricyclo[8.2.1.0^3,8]trideca-3(8),4,6-trien-11-yl)-N-methyl-acetamide
  参考文献：
  名称：

  A nitrone-based cycloaddition approach to the synthesis of the glycosyl system of nogalomycin, menogaril, and their congeners

  摘要：

  A series of model systems for the benzoxocin portion of nogalomycin was synthesized by cycloaddition of nitrone 8 with assorted dipolarophiles. Cycloaddition between nitrone 8 and vinyltrimethylsilane afforded isoxazolidines which were fragmented to produce either benzoxocins 21 and 23 or tricyclic isomer 27. Tricyclic systems 23 and 27 were produced also from the adduct of nitrone 8 and allyltrimethylsilane following fragmentation and oxidative cleavage of the resulting homoallylic amine derivative. Dipolar cycloaddition between nitrone 8 and vinylene carbonate yielded two diastereomeric isoxazolidines 40 and 41, both of which had the intact carbon skeleton of the glycosyl region of nogalomycin but which bore the incorrect relative configuration for transformation to menogaril analogue 5.

  DOI：

  10.1021/jo00004a008

文献信息

• DESHONG, PHILIP;LI, WEI;KENNINGTON, JOHN W. (JR);AMMON, HERMAN L.;LEGINUS+, J. ORG. CHEM., 56,(1991) N, C. 1364-1373
  作者：DESHONG, PHILIP、LI, WEI、KENNINGTON, JOHN W. (JR)、AMMON, HERMAN L.、LEGINUS+

  DOI：——

  日期：——