(R)-2-{(4aR,12aS)-7-(2-tert-butyldiphenylsilyloxyethyl)-4a-ethyl-1,2,3,4,4a,5,6,12a-octahydroindolo[1,2-a][1,8]naphthyridin-1-yl}-2-phenylethanol | 1275592-91-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氮杂萘
• 英文名称: (R)-2-{(4aR,12aS)-7-(2-tert-butyldiphenylsilyloxyethyl)-4a-ethyl-1,2,3,4,4a,5,6,12a-octahydroindolo[1,2-a][1,8]naphthyridin-1-yl}-2-phenylethanol
• 英文别名: (2R)-2-[(4aR,12aS)-7-[2-[tert-butyl(diphenyl)silyl]oxyethyl]-4a-ethyl-2,3,4,5,6,12a-hexahydroindolo[1,2-a][1,8]naphthyridin-1-yl]-2-phenylethanol
• CAS: 1275592-91-0
• 化学式: C₄₃H₅₂N₂O₂Si
• 分子量: 656.984
• InChiKey: BFQZILZNFPIVRT-DMRUGVJZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.43
• 重原子数：
  48
• 可旋转键数：
  11
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  37.6
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (R)-2-{(4aR,12aS)-7-(2-tert-butyldiphenylsilyloxyethyl)-4a-ethyl-1,2,3,4,4a,5,6,12a-octahydroindolo[1,2-a][1,8]naphthyridin-1-yl}-2-phenylethanol 在 氢气 、 palladium(II) hydroxide 作用下， 以 1,4-二氧六环 、 丙醇 为溶剂， 20.0 ℃ 、101.33 kPa 条件下， 反应 11.0h， 生成
  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) 、 四丁基氯化铵 、 氢气 、 sodium hydride 作用下， 以 5,5-dimethyl-1,3-cyclohexadiene 、 乙醚 、 乙酸乙酯 、 N,N-二甲基甲酰胺 、 oil 为溶剂， 140.0 ℃ 、101.33 kPa 条件下， 反应 32.5h， 生成 (R)-2-{(4aR,12aS)-7-(2-tert-butyldiphenylsilyloxyethyl)-4a-ethyl-1,2,3,4,4a,5,6,12a-octahydroindolo[1,2-a][1,8]naphthyridin-1-yl}-2-phenylethanol
  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.