(1S,4R,5S,8R)-4,8-diphenyl-3,7-bis((S)-1-phenylethyl)-3,7-diazabicyclo[3.3.1]nonane-2,6-dione | 950580-25-3

• 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,4R,5S,8R)-4,8-diphenyl-3,7-bis((S)-1-phenylethyl)-3,7-diazabicyclo[3.3.1]nonane-2,6-dione
• CAS: 950580-25-3
• 化学式: C₃₅H₃₄N₂O₂
• 分子量: 514.667
• InChiKey: ZOIMYQWCEIJDMU-WBVMMGACSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.3
• 重原子数：
  39.0
• 可旋转键数：
  6.0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.26
• 拓扑面积：
  40.62
• 氢给体数：
  0.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  (1S,4R,5S,8R)-4,8-diphenyl-3,7-bis((S)-1-phenylethyl)-3,7-diazabicyclo[3.3.1]nonane-2,6-dione 在 lithium aluminium tetrahydride 、 Adam’s catalyst 、 氢气 作用下， 以 四氢呋喃 、 乙醇 为溶剂， -78.0~65.0 ℃ 、400.01 kPa 条件下， 反应 9.0h， 生成 (2R,4R)-2,4-dibenzyl-N,N'-bis((S)-1-phenylethyl)-pentane-1,5-diamine
  参考文献：
  名称：

  First asymmetric synthesis of a C2-symmetric 2-endo,6-endo-disubstituted bispidine

  摘要：

  The enantioselective synthesis of a Q-symmetric 2-endo,6-endo-disubstituted bispidine (3,7-diazabicyclo[3.3.1]nonane) has been accomplished for the first time. The key step was a Michael addition of the protected beta-amino ester methyl (R)-3-{N-benzyl-N[(S)-1-phenylethyl]amino}-3-phenylpropionate to its alpha-methylene derivative delivering an anti,anti-configured alpha,alpha'-methylene-bridged bis(beta-amino ester) as the major diastereomer. Deprotection, reduction and cyclisation furnished (1R,2R,5R,6R)-2,6-diphenyl-3,7-bis(S)-1-phenylethyl)-3,7-diazabicyclo[3.3.1]nonane in six steps and 15% overall yield. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2007.06.010
• 作为产物：
  描述：

  methyl 2-{(S)-[N-benzyl-N-((S)-1-phenylethyl)amino]phenylmethyl}acrylate 在 ammonium cerium(IV) nitrate 、 甲基溴化镁 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 乙醚 、 水 、 乙腈 、 Petroleum ether 为溶剂， 反应 25.0h， 生成 (1S,4R,5S,8R)-4,8-diphenyl-3,7-bis((S)-1-phenylethyl)-3,7-diazabicyclo[3.3.1]nonane-2,6-dione
  参考文献：
  名称：

  First asymmetric synthesis of a C2-symmetric 2-endo,6-endo-disubstituted bispidine

  摘要：

  The enantioselective synthesis of a Q-symmetric 2-endo,6-endo-disubstituted bispidine (3,7-diazabicyclo[3.3.1]nonane) has been accomplished for the first time. The key step was a Michael addition of the protected beta-amino ester methyl (R)-3-{N-benzyl-N[(S)-1-phenylethyl]amino}-3-phenylpropionate to its alpha-methylene derivative delivering an anti,anti-configured alpha,alpha'-methylene-bridged bis(beta-amino ester) as the major diastereomer. Deprotection, reduction and cyclisation furnished (1R,2R,5R,6R)-2,6-diphenyl-3,7-bis(S)-1-phenylethyl)-3,7-diazabicyclo[3.3.1]nonane in six steps and 15% overall yield. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2007.06.010