dimethyl (2S,4S)-2,4-bis{(R)-[N-benzyl-N-((S)-1-phenylethyl)amino]phenylmethyl}glutarate | 950580-20-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: dimethyl (2S,4S)-2,4-bis{(R)-[N-benzyl-N-((S)-1-phenylethyl)amino]phenylmethyl}glutarate
• 英文别名: dimethyl (2S,4S)-2,4-bis[(R)-[benzyl-[(1S)-1-phenylethyl]amino]-phenylmethyl]pentanedioate
• CAS: 950580-20-8
• 化学式: C₅₁H₅₄N₂O₄
• 分子量: 759.001
• InChiKey: YTUBCZWBOOHVFI-ZCKDUDCGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  10.2
• 重原子数：
  57
• 可旋转键数：
  20
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  59.1
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  dimethyl (2S,4S)-2,4-bis{(R)-[N-benzyl-N-((S)-1-phenylethyl)amino]phenylmethyl}glutarate 在 ammonium cerium(IV) nitrate 作用下， 以 水 、 乙腈 为溶剂， 反应 7.0h， 以74%的产率得到dimethyl (2S,4S)-2,4-bis[(R)-phenyl-((S)-1-phenylethylamino)methyl]glutarate
  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：

  在 甲基磺酰氯 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 Petroleum ether 为溶剂， 反应 18.5h， 生成 dimethyl (2S,4S)-2,4-bis{(R)-[N-benzyl-N-((S)-1-phenylethyl)amino]phenylmethyl}glutarate
  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

文献信息

• First asymmetric synthesis of a C2-symmetric 2-endo,6-endo-disubstituted bispidine
  作者：Matthias Breuning、David Hein

  DOI：10.1016/j.tetasy.2007.06.010

  日期：2007.7

  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.