(1R,2S,4S)-1-((N,N-dicyclohexylsulfamoyl)methyl)-7,7-dimethylbicyclo[2.2.1]heptan-2-yl (S)-1-(4-methoxybenzyl)-2-methylazetidine-2-carboxylate | 942203-05-6

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: (1R,2S,4S)-1-((N,N-dicyclohexylsulfamoyl)methyl)-7,7-dimethylbicyclo[2.2.1]heptan-2-yl (S)-1-(4-methoxybenzyl)-2-methylazetidine-2-carboxylate
• CAS: 942203-05-6
• 化学式: C₃₅H₅₄N₂O₅S
• 分子量: 614.89
• InChiKey: BLDUBRDWPSEZTJ-AHRJLOSMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.69
• 重原子数：
  43.0
• 可旋转键数：
  10.0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  76.15
• 氢给体数：
  0.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  (1R,2S,4S)-1-((N,N-dicyclohexylsulfamoyl)methyl)-7,7-dimethylbicyclo[2.2.1]heptan-2-yl (S)-1-(4-methoxybenzyl)-2-methylazetidine-2-carboxylate 在 palladium on activated charcoal palladium dihydroxide 、 sodium hydroxide 、 氢气 、 (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate 作用下， 生成 (2S)-1-acetyl-2-methyl-N-[(2S)-1-(methylamino)-1-oxopropan-2-yl]azetidine-2-carboxamide
  参考文献：
  名称：

  2-Alkyl-2-carboxy-azetidines as scaffolds for the induction of γ-turns

  摘要：

  To investigate the ability of 2-alkyl-2-carboxy-azetidines (Azx) to induce reverse turns when incorporated into peptides, RCO-Azx-L-A1a-NHMe dipeptide derivatives were selected as simplified tetrapeptide models, in which the azetidine residue is incorporated at the i + 1 position. Molecular modelling, H-1 NMR and FTIR studies showed the high tendency of the model tetrapeptides to adopt gamma-turn conformations, indicating that these azetidine-containing amino acids could serve as general gamma-turn promoters. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2007.03.126
• 作为产物：
  描述：

  [(1R,2S,4S)-1-(dicyclohexylsulfamoylmethyl)-7,7-dimethyl-2-bicyclo[2.2.1]heptanyl] (2S)-1-[(4-methoxyphenyl)methyl]-2-methyl-4-oxoazetidine-2-carboxylate 在 三(三苯基膦)羰基氢化铑 、 二苯基硅烷 作用下， 以42%的产率得到(1R,2S,4S)-1-((N,N-dicyclohexylsulfamoyl)methyl)-7,7-dimethylbicyclo[2.2.1]heptan-2-yl (S)-1-(4-methoxybenzyl)-2-methylazetidine-2-carboxylate
  参考文献：
  名称：

  2-Alkyl-2-carboxy-azetidines as scaffolds for the induction of γ-turns

  摘要：

  To investigate the ability of 2-alkyl-2-carboxy-azetidines (Azx) to induce reverse turns when incorporated into peptides, RCO-Azx-L-A1a-NHMe dipeptide derivatives were selected as simplified tetrapeptide models, in which the azetidine residue is incorporated at the i + 1 position. Molecular modelling, H-1 NMR and FTIR studies showed the high tendency of the model tetrapeptides to adopt gamma-turn conformations, indicating that these azetidine-containing amino acids could serve as general gamma-turn promoters. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2007.03.126