(E)-2-Trimethylsilanylmethyl-dec-2-enoic acid ethyl ester | 888020-89-1

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: (E)-2-Trimethylsilanylmethyl-dec-2-enoic acid ethyl ester
• 英文别名: ethyl 2-(trimethylsilylmethyl)dec-2-enoate
• CAS: 888020-89-1
• 化学式: C₁₆H₃₂O₂Si
• 分子量: 284.514
• InChiKey: RVWSJNSJFRUFFH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.17
• 重原子数：
  19.0
• 可旋转键数：
  10.0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.81
• 拓扑面积：
  26.3
• 氢给体数：
  0.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  (E)-2-Trimethylsilanylmethyl-dec-2-enoic acid ethyl ester 在 氢氧化钾 、 氯化亚砜 、 四丁基二氟三苯硅酸铵 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 乙醇 、 N,N-二甲基甲酰胺 为溶剂， 生成 (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：

  正辛醛 、 3-trimethylsilyl-2-diethylphosphonopropionic acid ethyl ester 在 sodium hydride 作用下， 以 乙二醇二甲醚 为溶剂， 以66%的产率得到(E)-2-Trimethylsilanylmethyl-dec-2-enoic acid ethyl 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

文献信息

• Design, synthesis, and biological activities of madindoline analogues
  作者：Daisuke Yamamoto、Toshiaki Sunazuka、Tomoyasu Hirose、Naoto Kojima、Eisuke Kaji、Satoshi Omura

  DOI：10.1016/j.bmcl.2006.01.107

  日期：2006.5

  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.