(2S,4S)-2,4-bis[(R)-phenyl-((S)-1-phenylethylamino)methyl]pentane-1,5-diol | 950580-23-1

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: (2S,4S)-2,4-bis[(R)-phenyl-((S)-1-phenylethylamino)methyl]pentane-1,5-diol
• 英文别名: (2S,4S)-2,4-bis[(R)-phenyl-[[(1S)-1-phenylethyl]amino]methyl]pentane-1,5-diol
• CAS: 950580-23-1
• 化学式: C₃₅H₄₂N₂O₂
• 分子量: 522.731
• InChiKey: ISLWSNYZZFNMAP-NJQHDRMHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.7
• 重原子数：
  39
• 可旋转键数：
  14
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  64.5
• 氢给体数：
  4
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (2S,4S)-2,4-bis[(R)-phenyl-((S)-1-phenylethylamino)methyl]pentane-1,5-diol 在 甲基磺酰氯 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 22.0h， 以73%的产率得到(1R,2R,5R,6R)-2,6-diphenyl-3,7-bis((S)-1-phenylethyl)-3,7-diazabicyclo[3.3.1]nonane
  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 lithium aluminium tetrahydride 、 ammonium cerium(IV) nitrate 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 水 、 乙腈 、 Petroleum ether 为溶剂， 反应 7.0h， 生成 (2S,4S)-2,4-bis[(R)-phenyl-((S)-1-phenylethylamino)methyl]pentane-1,5-diol
  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