(3R,6R,8aS)-6-ethyl-3-phenyl-6-vinyl-2,3,6,7,8,8a-hexahydro-5H-oxazolo[3,2-a]pyridin-5-one | 1275592-88-5

• 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: (3R,6R,8aS)-6-ethyl-3-phenyl-6-vinyl-2,3,6,7,8,8a-hexahydro-5H-oxazolo[3,2-a]pyridin-5-one
• 英文别名: (3R,6R,8aS)-6-ethenyl-6-ethyl-3-phenyl-3,7,8,8a-tetrahydro-2H-[1,3]oxazolo[3,2-a]pyridin-5-one
• CAS: 1275592-88-5
• 化学式: C₁₇H₂₁NO₂
• 分子量: 271.359
• InChiKey: SMDXREBJVLNYEK-YQQAZPJKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  20
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  29.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (3R,6R,8aS)-6-ethyl-3-phenyl-6-vinyl-2,3,6,7,8,8a-hexahydro-5H-oxazolo[3,2-a]pyridin-5-one 在 Hoveyda-Grubbs catalyst second generation 、 5% Pd(II)/C(eggshell) 、 氢气 、 palladium(II) hydroxide 、 sodium hydride 作用下， 以 1,4-二氧六环 、 丙醇 、 5,5-dimethyl-1,3-cyclohexadiene 、 乙醚 、 乙酸乙酯 、 oil 为溶剂， 140.0 ℃ 、101.33 kPa 条件下， 反应 41.5h， 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：

  [3R,6R,8aS]-6-allyl-6-ethyl-5-oxo-3-phenyl-2,3,6,7,8,8a-hexahydro-5H-oxazolo[3,2-a]pyridine 在 三丁基膦 、 双氧水 、 臭氧 作用下， 以 四氢呋喃 、 甲醇 、 水 为溶剂， 反应 12.25h， 生成 (3R,6R,8aS)-6-ethyl-3-phenyl-6-vinyl-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.