1-(3-oxa-2-aza-bicyclo[2.2.1]hept-5-en-2-yl)but-3-en-1-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: 1-(3-oxa-2-aza-bicyclo[2.2.1]hept-5-en-2-yl)but-3-en-1-one
• 英文别名: 2-[3-butenoyl]-2-aza-3-oxabicyclo[2,2,1]-5-heptene；1-[(1R,4S)-2-oxa-3-azabicyclo[2.2.1]hept-5-en-3-yl]but-3-en-1-one
• 化学式: C₉H₁₁NO₂
• 分子量: 165.192
• InChiKey: MEOZYSGOIQSOPQ-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：
  2
• 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：

  1-(3-oxa-2-aza-bicyclo[2.2.1]hept-5-en-2-yl)but-3-en-1-one 在 RuCl2(1,3-dimesityl-imidazolidin-2-yl)(PCy3)(=CHPh) 咪唑 、 4-二甲氨基吡啶 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 15.83h， 生成 (2RS,3aSR)-3,3a-dihydro-2-((E)-4-[tert-butyl(diphenyl)silyloxy]-but-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 、 3-butenohydroxamic acid 在 草酰氯 、 二甲基亚砜 、 三乙胺 作用下， 以 二氯甲烷 、 二甲基亚砜 为溶剂， 反应 3.5h， 以80%的产率得到1-(3-oxa-2-aza-bicyclo[2.2.1]hept-5-en-2-yl)but-3-en-1-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

• Stereodivergent Synthesis of Piperidine Alkaloids by Ring-Rearrangement Metathesis/Reductive Lactam Alkylation of Nitroso Diels-Alder Cycloadducts
  作者：Guillaume Vincent、Delphine Karila、Georges Khalil、Pierre Sancibrao、Didier Gori、Cyrille Kouklovsky

  DOI：10.1002/chem.201300836

  日期：2013.7.8

  stereoselective synthesis of 2‐(2‐hydroxyalkyl)piperidine alkaloids by ring‐rearrangement metathesis of nitroso Diels–Alder cycloadducts is reported. The approach is illustrated by the formal synthesis of porantheridine and the total synthesis of andrachcinidine through a diastereodivergent allylation of an N‐alkoxy bicyclic lactam. The asymmetric synthesis of the latter alkaloid provides new insights into the configurational

  报道了通过亚硝基Diels-Alder环加成物的环重整易位立体选择性合成2-（2-羟烷基）哌啶生物碱的一般方法。通过N-烷氧基双环内酰胺的非对映异构烯丙基化的形式，通过正式合成Porantheridine和通过Andrachcinidine进行总合成，可以说明这种方法。后一种生物碱的不对称合成为氯亚硝基试剂和环戊二烯之间环加合物的构型稳定性提供了新的见解。
• 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.