(1S,3R,5S)-tert-butyl 3-propyl-2-oxa-9-azabicyclo[3.3.1]nonane-9-carboxylate | 1201695-02-4

• 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: (1S,3R,5S)-tert-butyl 3-propyl-2-oxa-9-azabicyclo[3.3.1]nonane-9-carboxylate
• 英文别名: tert-butyl (1S,3R,5S)-3-propyl-2-oxa-9-azabicyclo[3.3.1]nonane-9-carboxylate
• CAS: 1201695-02-4
• 化学式: C₁₅H₂₇NO₃
• 分子量: 269.384
• InChiKey: IFYCPHSDUOKXQJ-XQQFMLRXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  19
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.93
• 拓扑面积：
  38.8
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (1S,3R,5S)-tert-butyl 3-propyl-2-oxa-9-azabicyclo[3.3.1]nonane-9-carboxylate 、 烯丙基三甲基硅烷 在 四氯化钛 作用下， 以 二氯甲烷 、 甲苯 为溶剂， 反应 1.0h， 生成 (2S,6S)-tert-butyl 2-allyl-6-((R)-2-hydroxypentyl)piperidine-1-carboxylate 、 (2R,6S)-tert-butyl 2-allyl-6-((R)-2-hydroxypentyl)piperidine-1-carboxylate
  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：

  tert-butyl (5S,7R)-1,1-diethoxy-7-hydroxydecan-5-ylcarbamate 在 4-甲基苯磺酸吡啶 作用下， 以 二氯甲烷 为溶剂， 反应 14.0h， 以69%的产率得到(1S,3R,5S)-tert-butyl 3-propyl-2-oxa-9-azabicyclo[3.3.1]nonane-9-carboxylate
  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.