(Z)-(S)-2-[(3aR,8aS)-3a-(tert-Butyl-dimethyl-silanyloxy)-2,3,3a,8a-tetrahydro-furo[2,3-b]indol-8-ylmethyl]-2-methyl-3-oxo-4-trimethylsilanylmethyl-dodec-4-enoic acid methyl ester | 888021-07-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 英文名称: (Z)-(S)-2-[(3aR,8aS)-3a-(tert-Butyl-dimethyl-silanyloxy)-2,3,3a,8a-tetrahydro-furo[2,3-b]indol-8-ylmethyl]-2-methyl-3-oxo-4-trimethylsilanylmethyl-dodec-4-enoic acid methyl ester
• CAS: 888021-07-6
• 化学式: C₃₅H₅₉NO₅Si₂
• 分子量: 630.028
• InChiKey: IHTRZRUHOUINLS-LGJQJDQBSA-N

物化性质

• 沸点：
  642.0±55.0 °C(predicted)
• 密度：
  1.03±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  8.84
• 重原子数：
  43.0
• 可旋转键数：
  15.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  65.07
• 氢给体数：
  0.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  (Z)-(S)-2-[(3aR,8aS)-3a-(tert-Butyl-dimethyl-silanyloxy)-2,3,3a,8a-tetrahydro-furo[2,3-b]indol-8-ylmethyl]-2-methyl-3-oxo-4-trimethylsilanylmethyl-dodec-4-enoic acid methyl ester 在 四丁基二氟三苯硅酸铵 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以54%的产率得到(S)-4-Heptyl-2-((3aR,8aS)-3a-hydroxy-2,3,3a,8a-tetrahydro-furo[2,3-b]indol-8-ylmethyl)-2,5-dimethyl-cyclopent-4-ene-1,3-dione
  参考文献：
  名称：

  Design, synthesis, and biological activities of madindoline analogues

  摘要：

  A research program is under way to develop a series of madindoline-based inhibitors targeting interleukin 6. Such inhibitors will have potential use in fighting a variety of diseases for which no effective therapeutic drugs currently exist. Madindoline is no longer available from natural Sources. Consequently, we have developed a purely synthetic route to ensure a supply of the compound. The synthesis of a range of analogues is described, all of which were evaluated for their inhibitory activity against the growth of IL-6-dependent 7TDI cells. From these assays, several synthetic madindoline analogues were identified as highly promising candidates for further development. (C) 2006 Published by Elsevier Ltd.

  DOI：

  10.1016/j.bmcl.2006.01.107
• 作为产物：
  描述：

  (E)-2-Trimethylsilanylmethyl-dec-2-enoic acid ethyl ester 在 氢氧化钾 、 氯化亚砜 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 乙醇 为溶剂， 生成 (Z)-(S)-2-[(3aR,8aS)-3a-(tert-Butyl-dimethyl-silanyloxy)-2,3,3a,8a-tetrahydro-furo[2,3-b]indol-8-ylmethyl]-2-methyl-3-oxo-4-trimethylsilanylmethyl-dodec-4-enoic acid methyl ester
  参考文献：
  名称：

  Design, synthesis, and biological activities of madindoline analogues

  摘要：

  A research program is under way to develop a series of madindoline-based inhibitors targeting interleukin 6. Such inhibitors will have potential use in fighting a variety of diseases for which no effective therapeutic drugs currently exist. Madindoline is no longer available from natural Sources. Consequently, we have developed a purely synthetic route to ensure a supply of the compound. The synthesis of a range of analogues is described, all of which were evaluated for their inhibitory activity against the growth of IL-6-dependent 7TDI cells. From these assays, several synthetic madindoline analogues were identified as highly promising candidates for further development. (C) 2006 Published by Elsevier Ltd.

  DOI：

  10.1016/j.bmcl.2006.01.107