(3R,6S,8aS)-6-{2-[3-(2-tert-butyldiphenylsilyloxyethyl)-1H-indol-2-yl]ethyl}-6-ethyl-3-phenyl-2,3,6,7,8,8a-hexahydro-5H-oxazolo[3,2-a]pyridin-5-one | 1275592-90-9

• 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: (3R,6S,8aS)-6-{2-[3-(2-tert-butyldiphenylsilyloxyethyl)-1H-indol-2-yl]ethyl}-6-ethyl-3-phenyl-2,3,6,7,8,8a-hexahydro-5H-oxazolo[3,2-a]pyridin-5-one
• 英文别名: (3R,6S,8aS)-6-[2-[3-[2-[tert-butyl(diphenyl)silyl]oxyethyl]-1H-indol-2-yl]ethyl]-6-ethyl-3-phenyl-3,7,8,8a-tetrahydro-2H-[1,3]oxazolo[3,2-a]pyridin-5-one
• CAS: 1275592-90-9
• 化学式: C₄₃H₅₀N₂O₃Si
• 分子量: 670.967
• InChiKey: YMALGSCODAGYLA-RNMNAOLMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.34
• 重原子数：
  49
• 可旋转键数：
  12
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.37
• 拓扑面积：
  54.6
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (3R,6S,8aS)-6-{2-[3-(2-tert-butyldiphenylsilyloxyethyl)-1H-indol-2-yl]ethyl}-6-ethyl-3-phenyl-2,3,6,7,8,8a-hexahydro-5H-oxazolo[3,2-a]pyridin-5-one 在 氢气 、 palladium(II) hydroxide 、 sodium hydride 作用下， 以 1,4-二氧六环 、 丙醇 、 乙醚 、 oil 为溶剂， 20.0 ℃ 、101.33 kPa 条件下， 反应 11.5h， 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 作用下， 以 5,5-dimethyl-1,3-cyclohexadiene 、 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 32.0h， 生成 (3R,6S,8aS)-6-{2-[3-(2-tert-butyldiphenylsilyloxyethyl)-1H-indol-2-yl]ethyl}-6-ethyl-3-phenyl-2,3,6,7,8,8a-hexahydro-5H-oxazolo[3,2-a]pyridin-5-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.