N-hydroxyethyl exo-2,3-dimethyl-7-oxabicyclo[2.2.1]heptane-2,3-dicarboximide

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 异吲哚及其衍生物
• 英文名称: N-hydroxyethyl exo-2,3-dimethyl-7-oxabicyclo[2.2.1]heptane-2,3-dicarboximide
• 英文别名: cantharimide D；(3aR,4S,7R,7aS)-2-(2-hydroxyethyl)-3a,7a-dimethyl-4,5,6,7-tetrahydro-4,7-epoxyisoindole-1,3-dione
• 化学式: C₁₂H₁₇NO₄
• 分子量: 239.271
• InChiKey: HWRPFCLFXMQUPU-IVQVNHIISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.5
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  66.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  1,2-二棕榈酰-sn-丙三醇 、 六乙基亚磷酸胺 、 N-hydroxyethyl exo-2,3-dimethyl-7-oxabicyclo[2.2.1]heptane-2,3-dicarboximide 在 碘 、 sulfur 作用下， 以 苯 为溶剂， 反应 6.5h， 以52.5%的产率得到[(2R)-3-[2-[(3aS,4R,7S,7aR)-3a,7a-dimethyl-1,3-dioxo-4,5,6,7-tetrahydro-4,7-epoxyisoindol-2-yl]ethoxy-(diethylamino)phosphinothioyl]oxy-2-hexadecanoyloxypropyl] hexadecanoate
  参考文献：
  名称：

  Synthesis of Glycerophospholipid Conjugates of Cantharidin and Its Analogues

  摘要：

  A series of glycerophospholipid conjugates of cantharidin and its analogues were synthesized in a one-pot reaction, using hexaehtyl phosphorus triamide, activated by a catalytic amount of iodine, as the phosphorylating reagent. The structures of the title compounds were confirmed by H-1 NMR, P-31 NMR, IR and elemental analysis.

  DOI：

  10.1080/00397910008087266
• 作为产物：
  描述：

  C.I.酸性橙108 、 cantharidin 以 乙醇 为溶剂， 反应 2.5h， 以80.1%的产率得到N-hydroxyethyl exo-2,3-dimethyl-7-oxabicyclo[2.2.1]heptane-2,3-dicarboximide
  参考文献：
  名称：

  Synthesis of Glycerophospholipid Conjugates of Cantharidin and Its Analogues

  摘要：

  A series of glycerophospholipid conjugates of cantharidin and its analogues were synthesized in a one-pot reaction, using hexaehtyl phosphorus triamide, activated by a catalytic amount of iodine, as the phosphorylating reagent. The structures of the title compounds were confirmed by H-1 NMR, P-31 NMR, IR and elemental analysis.

  DOI：

  10.1080/00397910008087266

文献信息

• Synthesis of Glycerophospholipid Conjugates of Cantharidin and Its Analogues
  作者：Zheng-Hong Zhou、Ru-Yu Chen

  DOI：10.1080/00397910008087266

  日期：2000.10

  A series of glycerophospholipid conjugates of cantharidin and its analogues were synthesized in a one-pot reaction, using hexaehtyl phosphorus triamide, activated by a catalytic amount of iodine, as the phosphorylating reagent. The structures of the title compounds were confirmed by H-1 NMR, P-31 NMR, IR and elemental analysis.