(5S,6S,9S)-5-(2-hydroxyethyl)-6-vinylhexahydrooxazolo[3,4-a]pyridin-3-one | 460054-18-6

• 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-hydroxyethyl)-6-vinylhexahydrooxazolo[3,4-a]pyridin-3-one
• 英文别名: (5S,6S,8aS)-6-ethenyl-5-(2-hydroxyethyl)-1,5,6,7,8,8a-hexahydro-[1,3]oxazolo[3,4-a]pyridin-3-one
• CAS: 460054-18-6
• 化学式: C₁₁H₁₇NO₃
• 分子量: 211.261
• InChiKey: OCDOGGQEWBPIFZ-UTLUCORTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  15
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.73
• 拓扑面积：
  49.8
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (5S,6S,9S)-5-(2-hydroxyethyl)-6-vinylhexahydrooxazolo[3,4-a]pyridin-3-one 在 草酰氯 、 sodium acetate 、 二甲基亚砜 、 三乙胺 、 pyridinium chlorochromate 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 19.0h， 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
• 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 四丁基氟化铵 、 silver benzoate 、 sodium hydride 、 三乙基硼氢化锂 、 三乙胺 作用下， 以 四氢呋喃 、 乙醚 为溶剂， 反应 27.0h， 生成 (5S,6S,9S)-5-(2-hydroxyethyl)-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