isopropylidene derivative of 21,22-dihydroxyonnamide A₃ | 1079397-39-9

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: isopropylidene derivative of 21,22-dihydroxyonnamide A₃
• CAS: 1079397-39-9
• 化学式: C₄₂H₆₉N₅O₁₄
• 分子量: 868.035
• InChiKey: BSRUHJFCJQZVJO-FVUVETQBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  61.0
• 可旋转键数：
  20.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.76
• 拓扑面积：
  271.7
• 氢给体数：
  8.0
• 氢受体数：
  14.0

反应信息

• 作为产物：
  描述：

  21,22-dihydroxyonnamide A₃ 、 2,2-二甲氧基丙烷 在 4-甲基苯磺酸吡啶 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成 isopropylidene derivative of 21,22-dihydroxyonnamide A₃
  参考文献：
  名称：

  Structure elucidation of 21,22-dihydroxyonnamides A1–A4 from the marine sponge Theonella swinhoei: an empirical rule to assign the relative stereochemistry of linear 1,5-diols

  摘要：

  A polar cytotoxic fraction of the marine sponge Theonella swinhoei was analyzed to be a mixture of four isomeric compounds, 21,22-dihydroxyonnamides A(1), A(2), A(3), and A(4). They were separated after conversion to the isopropyridene derivatives. The structures of the 21S,22S- and 21R,22R-isomers were determined by comparison of their spectral data with those prepared from onnamide A by asymmetric dihydroxylation. During the analysis of NMR data of these derivatives, an empirical rule was implied to assign the relative stereochemistry of linear 1,5-diol. This rule was applied to assign the stereochemistry of the remaining congeners. (c) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2008.08.057