1-benzyl-3-ethyl-3-{2-[3-(2-tert-butyldiphenylsiloxyethyl)-1H-indol-2-yl]ethyl}piperidin-2-one | 1275592-84-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 哌啶类
• 英文名称: 1-benzyl-3-ethyl-3-{2-[3-(2-tert-butyldiphenylsiloxyethyl)-1H-indol-2-yl]ethyl}piperidin-2-one
• 英文别名: 1-benzyl-3-[2-[3-[2-[tert-butyl(diphenyl)silyl]oxyethyl]-1H-indol-2-yl]ethyl]-3-ethylpiperidin-2-one
• CAS: 1275592-84-1
• 化学式: C₄₂H₅₀N₂O₂Si
• 分子量: 642.957
• InChiKey: ZNHZCPIORCSTPT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.44
• 重原子数：
  47
• 可旋转键数：
  13
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  45.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1-benzyl-3-ethyl-3-{2-[3-(2-tert-butyldiphenylsiloxyethyl)-1H-indol-2-yl]ethyl}piperidin-2-one 在 二异丁基氢化铝 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 以87%的产率得到(4aRS,12aSR)-1-benzyl-7-(2-tert-butyldiphenylsilyloxyethyl)-4a-ethyl-1,2,3,4,4a,5,6,12a-octahydroindolo[1,2-a][1,8]naphthyridine
  参考文献：
  名称：

  Total Syntheses of (−)- and (+)-Goniomitine

  摘要：

  The Stille coupling reaction of 3-(benzyloxymethyl)-1-(tert-butyldiphenylsiloxy)ethyl-1-(tributylstannyl)allene with N-(tert-butoxycarbonyl)-2-iodoaniline directly produced the corresponding 2-vinylindole derivative, which was Independently transformed into natural (-)-goniomitine and unnatural (+)-goniomitine via the cross-metathesis with chiral oxazolopiperidone lactams. The antiproliferative activity of the synthesized natural (-)-goniomitine in Mock and MDCK/MDR1 cells showed them to be more potent to retard cell growth than unnatural (+)-goniomitine.

  DOI：

  10.1021/ol200320z
• 作为产物：
  描述：

  N-Boc-2-碘苯胺 在 tris-(dibenzylideneacetone)dipalladium(0) 、 copper(l) iodide 、 Hoveyda-Grubbs catalyst second generation 、 三(2-呋喃基)膦 、 5% Pd(II)/C(eggshell) 、 氢气 、 potassium carbonate 作用下， 以 乙醇 、 乙酸乙酯 、 N,N-二甲基甲酰胺 为溶剂， 20.0~140.0 ℃ 、101.33 kPa 条件下， 反应 46.0h， 生成 1-benzyl-3-ethyl-3-{2-[3-(2-tert-butyldiphenylsiloxyethyl)-1H-indol-2-yl]ethyl}piperidin-2-one
  参考文献：
  名称：

  Total Syntheses of (−)- and (+)-Goniomitine

  摘要：

  The Stille coupling reaction of 3-(benzyloxymethyl)-1-(tert-butyldiphenylsiloxy)ethyl-1-(tributylstannyl)allene with N-(tert-butoxycarbonyl)-2-iodoaniline directly produced the corresponding 2-vinylindole derivative, which was Independently transformed into natural (-)-goniomitine and unnatural (+)-goniomitine via the cross-metathesis with chiral oxazolopiperidone lactams. The antiproliferative activity of the synthesized natural (-)-goniomitine in Mock and MDCK/MDR1 cells showed them to be more potent to retard cell growth than unnatural (+)-goniomitine.

  DOI：

  10.1021/ol200320z

文献信息

• Total Syntheses of (−)- and (+)-Goniomitine
  作者：Masaya Mizutani、Fuyuhiko Inagaki、Takeo Nakanishi、Chihiro Yanagihara、Ikumi Tamai、Chisato Mukai

  DOI：10.1021/ol200320z

  日期：2011.4.1

  The Stille coupling reaction of 3-(benzyloxymethyl)-1-(tert-butyldiphenylsiloxy)ethyl-1-(tributylstannyl)allene with N-(tert-butoxycarbonyl)-2-iodoaniline directly produced the corresponding 2-vinylindole derivative, which was Independently transformed into natural (-)-goniomitine and unnatural (+)-goniomitine via the cross-metathesis with chiral oxazolopiperidone lactams. The antiproliferative activity of the synthesized natural (-)-goniomitine in Mock and MDCK/MDR1 cells showed them to be more potent to retard cell growth than unnatural (+)-goniomitine.