(5S,6S,9S)-(+)-5-(2-oxobut-3-enyl)-6-vinylhexahydrooxazolo[3,4-a]pyridin-3-one | 460054-19-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑烷类
• 英文名称: (5S,6S,9S)-(+)-5-(2-oxobut-3-enyl)-6-vinylhexahydrooxazolo[3,4-a]pyridin-3-one
• 英文别名: (5S,6S,8aS)-6-ethenyl-5-(2-oxobut-3-enyl)-1,5,6,7,8,8a-hexahydro-[1,3]oxazolo[3,4-a]pyridin-3-one
• CAS: 460054-19-7
• 化学式: C₁₃H₁₇NO₃
• 分子量: 235.283
• InChiKey: LBGYGURHMRRPRH-SCVCMEIPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  17
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.54
• 拓扑面积：
  46.6
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (5S,6S,9S)-(+)-5-(2-oxobut-3-enyl)-6-vinylhexahydrooxazolo[3,4-a]pyridin-3-one 在 Grubbs catalyst first generation 作用下， 以 二氯甲烷 为溶剂， 反应 15.0h， 以96%的产率得到(3aS,5aS,9aS)-(-)-3a,4,5,5a,9,9a-hexahydro-3H-oxazolo[3,4-a]quinoline-1,8-dione
  参考文献：
  名称：

  Stereodivergent Process for the Synthesis of the Decahydroquinoline Type of Dendrobatid Alkaloids

  摘要：

  A flexible and stereodivergent synthesis of the cis- and trans-fused 2,5-disubstituted octahydroquinolinone ring systems bearing all four stereogenic centers for the synthesis of the decahydroquinoline type of dendrobatid alkaloids has been achieved. The strategy involves stereoselective and stereodivergent construction of 2,3,6-trisubstituted piperidine ring systems using the Michael type of conjugate addition reaction to the enaminoesters 1 and 3, the intramolecular aldol type of cyclization reaction of keto aldehydes 11 and 12, and ring-closing metathesis of 21 as key steps.

  DOI：

  10.1021/jo025929b
• 作为产物：
  描述：

  2-O-ethoxycarbonyl 1-O-methyl (2R,3S,6S)-6-[[tert-butyl(diphenyl)silyl]oxymethyl]-3-ethenylpiperidine-1,2-dicarboxylate 在 草酰氯 、 四丁基氟化铵 、 sodium acetate 、 silver benzoate 、 sodium hydride 、 三乙基硼氢化锂 、 二甲基亚砜 、 三乙胺 、 pyridinium chlorochromate 作用下， 以 四氢呋喃 、 乙醚 、 二氯甲烷 为溶剂， 反应 46.0h， 生成 (5S,6S,9S)-(+)-5-(2-oxobut-3-enyl)-6-vinylhexahydrooxazolo[3,4-a]pyridin-3-one
  参考文献：
  名称：

  Stereodivergent Process for the Synthesis of the Decahydroquinoline Type of Dendrobatid Alkaloids

  摘要：

  A flexible and stereodivergent synthesis of the cis- and trans-fused 2,5-disubstituted octahydroquinolinone ring systems bearing all four stereogenic centers for the synthesis of the decahydroquinoline type of dendrobatid alkaloids has been achieved. The strategy involves stereoselective and stereodivergent construction of 2,3,6-trisubstituted piperidine ring systems using the Michael type of conjugate addition reaction to the enaminoesters 1 and 3, the intramolecular aldol type of cyclization reaction of keto aldehydes 11 and 12, and ring-closing metathesis of 21 as key steps.

  DOI：

  10.1021/jo025929b

文献信息

• Stereodivergent Process for the Synthesis of the Decahydroquinoline Type of Dendrobatid Alkaloids
  作者：Naoki Toyooka、Maiko Okumura、Hideo Nemoto

  DOI：10.1021/jo025929b

  日期：2002.8.1

  A flexible and stereodivergent synthesis of the cis- and trans-fused 2,5-disubstituted octahydroquinolinone ring systems bearing all four stereogenic centers for the synthesis of the decahydroquinoline type of dendrobatid alkaloids has been achieved. The strategy involves stereoselective and stereodivergent construction of 2,3,6-trisubstituted piperidine ring systems using the Michael type of conjugate addition reaction to the enaminoesters 1 and 3, the intramolecular aldol type of cyclization reaction of keto aldehydes 11 and 12, and ring-closing metathesis of 21 as key steps.