1-(allyloxy)-2-propylpiperidine | 1108621-30-2

• 分子结构分类: 有机化合物 - 生物碱及其衍生物
• 英文名称: 1-(allyloxy)-2-propylpiperidine
• 英文别名: 1-Prop-2-enoxy-2-propylpiperidine；1-prop-2-enoxy-2-propylpiperidine
• CAS: 1108621-30-2
• 化学式: C₁₁H₂₁NO
• 分子量: 183.294
• InChiKey: UCEVRSHJRAGZHM-UHFFFAOYSA-N

物化性质

• 沸点：
  232.1±33.0 °C(Predicted)
• 密度：
  0.91±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  13
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.82
• 拓扑面积：
  12.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1-(allyloxy)-2-propylpiperidine 在 溶剂黄146 、 锌 作用下， 反应 4.0h， 生成 2-丙基哌啶
  参考文献：
  名称：

  Bourgeois, Joffre; Dion, Isabelle; Cebrowski, Pamela H., Journal of the American Chemical Society, 2009, vol. 131, p. 874 - 875

  摘要：

  DOI：
• 作为产物：
  描述：

  5-辛烯-1-醇 在 potassium carbonate 、 三苯基膦 、 三氟乙酸 、 DIAD 作用下， 以 四氢呋喃 、 二氯甲烷 、 苯 为溶剂， 反应 21.5h， 生成 1-(allyloxy)-2-propylpiperidine
  参考文献：
  名称：

  Studies on Difficult Intramolecular Hydroaminations in the Context of Four Syntheses of Alkaloid Natural Products

  摘要：

  Examples of intramolecular alkene hydroaminations forming six-membered ring systems are rare, especially for systems in which the double bond is disubstituted. Such cyclizations have important synthetic relevance. Herein we report a systematic study of these cyclizations using recently developed Cope-type hydroamination methodologies. Difficult intramolecular alkene hydroaminations were used as key steps in syntheses of 2-epi-pumiliotoxin C, coniine, N-norreticuline and desbromoarborescidine A. This effort required the development of optimized hydroamination conditions to improve the efficiency of the cyclizations. Collectively, our results show that Cope-type cyclizations can be achieved on a variety of challenging substrates and proceed under similar conditions for both N-H and N-substituted hydroxylamines.

  DOI：

  10.1021/jo4023149

文献信息

• Bourgeois, Joffre; Dion, Isabelle; Cebrowski, Pamela H., Journal of the American Chemical Society, 2009, vol. 131, p. 874 - 875
  作者：Bourgeois, Joffre、Dion, Isabelle、Cebrowski, Pamela H.、Loiseau, Francis、Bedard, Anne-Catherine、Beauchemin, Andre M.

  DOI：——

  日期：——
• Studies on Difficult Intramolecular Hydroaminations in the Context of Four Syntheses of Alkaloid Natural Products
  作者：Isabelle Dion、Jean-François Vincent-Rocan、Lei Zhang、Pamela H. Cebrowski、Marie-Eve Lebrun、Jennifer Y. Pfeiffer、Anne-Catherine Bédard、André M. Beauchemin

  DOI：10.1021/jo4023149

  日期：2013.12.20

  Examples of intramolecular alkene hydroaminations forming six-membered ring systems are rare, especially for systems in which the double bond is disubstituted. Such cyclizations have important synthetic relevance. Herein we report a systematic study of these cyclizations using recently developed Cope-type hydroamination methodologies. Difficult intramolecular alkene hydroaminations were used as key steps in syntheses of 2-epi-pumiliotoxin C, coniine, N-norreticuline and desbromoarborescidine A. This effort required the development of optimized hydroamination conditions to improve the efficiency of the cyclizations. Collectively, our results show that Cope-type cyclizations can be achieved on a variety of challenging substrates and proceed under similar conditions for both N-H and N-substituted hydroxylamines.