(1R,2S,5R)-2-(4-(tert-butyldimethylsilyloxy)butyl)-7-methyl-9-oxa-3,7-diazabicyclo[3.3.1]nonane | 1075213-38-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 恶嗪烷类
• 英文名称: (1R,2S,5R)-2-(4-(tert-butyldimethylsilyloxy)butyl)-7-methyl-9-oxa-3,7-diazabicyclo[3.3.1]nonane
• CAS: 1075213-38-5
• 化学式: C₁₇H₃₆N₂O₂Si
• 分子量: 328.571
• InChiKey: BSQACHAUTHKCCN-OWCLPIDISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.85
• 重原子数：
  22.0
• 可旋转键数：
  6.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  33.73
• 氢给体数：
  1.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  (1R,2S,5R)-2-(4-(tert-butyldimethylsilyloxy)butyl)-7-methyl-9-oxa-3,7-diazabicyclo[3.3.1]nonane 在 四丁基氟化铵 作用下， 以 四氢呋喃 为溶剂， 反应 36.0h， 以84%的产率得到(1R,2S,5R)-2-(4-hydroxybutyl)-7-methyl-9-oxa-3,7-diazabicyclo[3.3.1]nonane
  参考文献：
  名称：

  Enantioselective total synthesis of the tricyclic 9-oxabispidine (1R,2S,9S)-11-methyl-13-oxa-7,11-diazatricyclo[7.3.1.02,7]tridecane

  摘要：

  The enantiomerically pure tricyclic 9-oxabispidine (1R,2S,9S)-11-methyl-13-oxa-7,11-diazatricyclo[7.3.1.0(2.7) ]tridecane, a potential substitute for (+)-sparteine in asymmetric synthesis, was prepared in 7 steps and in 11% overall yield from a chiral epoxy alcohol and (S)-epichlorohydrin. The key intermediate was a bicyclic 9-oxabispidine with an appropriately functionalized, endo-oriented side chain. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2008.08.002
• 作为产物：
  描述：

  (1R,2S,5S)-3-benzyl-2-(4-(tert-butyldimethylsilyloxy)butyl)-7-methyl-9-oxa-3,7-diazabicyclo[3.3.1]nonane 在 palladium dihydroxide 氢气 作用下， 以 乙酸乙酯 为溶剂， 20.0 ℃ 、100.0 kPa 条件下， 反应 5.0h， 以99%的产率得到(1R,2S,5R)-2-(4-(tert-butyldimethylsilyloxy)butyl)-7-methyl-9-oxa-3,7-diazabicyclo[3.3.1]nonane
  参考文献：
  名称：

  Enantioselective total synthesis of the tricyclic 9-oxabispidine (1R,2S,9S)-11-methyl-13-oxa-7,11-diazatricyclo[7.3.1.02,7]tridecane

  摘要：

  The enantiomerically pure tricyclic 9-oxabispidine (1R,2S,9S)-11-methyl-13-oxa-7,11-diazatricyclo[7.3.1.0(2.7) ]tridecane, a potential substitute for (+)-sparteine in asymmetric synthesis, was prepared in 7 steps and in 11% overall yield from a chiral epoxy alcohol and (S)-epichlorohydrin. The key intermediate was a bicyclic 9-oxabispidine with an appropriately functionalized, endo-oriented side chain. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2008.08.002