(2RS,3aSR)-3,3a-dihydro-2-vinyl-2H-isoxazolo[2,3-a]pyridin-7(6H)-one

• 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: (2RS,3aSR)-3,3a-dihydro-2-vinyl-2H-isoxazolo[2,3-a]pyridin-7(6H)-one
• 英文别名: (2R,3aS)-2-ethenyl-2,3,3a,6-tetrahydro-[1,2]oxazolo[2,3-a]pyridin-7-one
• 化学式: C₉H₁₁NO₂
• 分子量: 165.192
• InChiKey: ROCBFZSQBWNPMA-SFYZADRCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  12
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.44
• 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：

  (2RS,3aSR)-3,3a-dihydro-2-vinyl-2H-isoxazolo[2,3-a]pyridin-7(6H)-one 、 烯丙基三甲基硅烷 在 RuCl2(1,3-dimesityl-imidazolidin-2-yl)(PCy3)(=CHPh) 作用下， 以 二氯甲烷 为溶剂， 以64%的产率得到(2SR,3aRS)-3,3a-dihydro-2-(3-(trimethylsilyl)prop-1-enyl)-2H-isoxazolo[2,3-a]pyridin-7(6H)-one
  参考文献：
  名称：

  Domino Metathesis of 3,6-Dihydro-1,2-oxazine:  Access to Isoxazolo[2,3-a]pyridin-7-ones

  摘要：

  Strained bicyclic 3,6-dihydro-1,2-oxazine is a reactive substrate in domino metathesis with an external alkene. This general transformation leads to isoxazolo[2,3-a]pyridin-7-one, a versatile scaffold combining chemical functions that could be selectively oxidized or reduced. The synthetic relevance of these domino metathesis products is demonstrated by a straightforward synthesis of a quinolizinone.

  DOI：

  10.1021/ol0702066
• 作为产物：
  描述：

  环戊二烯 、 alkaline earth salt of/the/ methylsulfuric acid 在 RuCl2(1,3-dimesityl-imidazolidin-2-yl)(PCy3)(=CHPh) 2,2-dimethyl-5-nitroso-1,3-dioxan-5-yl acetate 作用下， 以 二氯甲烷 、 水 为溶剂， 反应 25.83h， 生成 (2RS,3aSR)-3,3a-dihydro-2-vinyl-2H-isoxazolo[2,3-a]pyridin-7(6H)-one
  参考文献：
  名称：

  Domino Metathesis of 3,6-Dihydro-1,2-oxazine:  Access to Isoxazolo[2,3-a]pyridin-7-ones

  摘要：

  Strained bicyclic 3,6-dihydro-1,2-oxazine is a reactive substrate in domino metathesis with an external alkene. This general transformation leads to isoxazolo[2,3-a]pyridin-7-one, a versatile scaffold combining chemical functions that could be selectively oxidized or reduced. The synthetic relevance of these domino metathesis products is demonstrated by a straightforward synthesis of a quinolizinone.

  DOI：

  10.1021/ol0702066

文献信息

• Domino Metathesis of 3,6-Dihydro-1,2-oxazine:  Access to Isoxazolo[2,3-<i>a</i>]pyridin-7-ones
  作者：Géraldine Calvet、Nicolas Blanchard、Cyrille Kouklovsky

  DOI：10.1021/ol0702066

  日期：2007.4.1

  Strained bicyclic 3,6-dihydro-1,2-oxazine is a reactive substrate in domino metathesis with an external alkene. This general transformation leads to isoxazolo[2,3-a]pyridin-7-one, a versatile scaffold combining chemical functions that could be selectively oxidized or reduced. The synthetic relevance of these domino metathesis products is demonstrated by a straightforward synthesis of a quinolizinone.