(3R,4aS,8S)-8-allyl-3-propylhexahydropyrido[1,2-c][1,3]oxazin-1(3H)-one | 1201695-20-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 哌啶类
• 英文名称: (3R,4aS,8S)-8-allyl-3-propylhexahydropyrido[1,2-c][1,3]oxazin-1(3H)-one
• 英文别名: (3R,4aS,8S)-8-prop-2-enyl-3-propyl-4,4a,5,6,7,8-hexahydro-3H-pyrido[1,2-c][1,3]oxazin-1-one
• CAS: 1201695-20-6
• 化学式: C₁₄H₂₃NO₂
• 分子量: 237.342
• InChiKey: XSKUXICUYJUVFS-FRRDWIJNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  17
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.79
• 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：

  3-戊烯-2-酮 、 (3R,4aS,8S)-8-allyl-3-propylhexahydropyrido[1,2-c][1,3]oxazin-1(3H)-one 在 RuCl2(1,3-dimesityl-imidazolidin-2-yl)(PCy3)(=CHPh) 作用下， 生成 (3R,4aS,8S)-hexahydro-8-((E)-4-oxopent-2-enyl)-3-propylpyrido[1,2-c][1,3]oxazin-1(3H)-one
  参考文献：
  名称：

  A Formal Synthesis of Porantheridine and an Epimer

  摘要：

  A formal synthesis of porantheridine and a synthesis of its C6-epimer have been completed, employing silver-catalyzed allene cyclization to form a common cis-isoxazolidine intermediate and related N-acyl iminium ion intermediates for side-chain introduction. The stereochemistry of this step can be controlled by choice of the N-protection method.

  DOI：

  10.1021/jo9021925
• 作为产物：
  描述：

  (6S)-tert-butyl 2-allyl-6-((R)-2-hydroxypentyl)piperidine-1-carboxylate 在 potassium tert-butylate 作用下， 以 四氢呋喃 为溶剂， 以90%的产率得到(3R,4aS,8R)-8-allyl-3-propylhexahydropyrido[1,2-c][1,3]oxazin-1(3H)-one
  参考文献：
  名称：

  A Formal Synthesis of Porantheridine and an Epimer

  摘要：

  A formal synthesis of porantheridine and a synthesis of its C6-epimer have been completed, employing silver-catalyzed allene cyclization to form a common cis-isoxazolidine intermediate and related N-acyl iminium ion intermediates for side-chain introduction. The stereochemistry of this step can be controlled by choice of the N-protection method.

  DOI：

  10.1021/jo9021925

文献信息

• A Formal Synthesis of Porantheridine and an Epimer
  作者：Roderick W. Bates、Yongna Lu

  DOI：10.1021/jo9021925

  日期：2009.12.18

  A formal synthesis of porantheridine and a synthesis of its C6-epimer have been completed, employing silver-catalyzed allene cyclization to form a common cis-isoxazolidine intermediate and related N-acyl iminium ion intermediates for side-chain introduction. The stereochemistry of this step can be controlled by choice of the N-protection method.