4(RS)-1-(p-methoxybenzyl)-4-methoxycarbonyl-4-methyl-2-azetidinone | 1013038-76-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 内酰胺类
• 英文名称: 4(RS)-1-(p-methoxybenzyl)-4-methoxycarbonyl-4-methyl-2-azetidinone
• 英文别名: Methyl 1-[(4-methoxyphenyl)methyl]-2-methyl-4-oxoazetidine-2-carboxylate
• CAS: 1013038-76-0
• 化学式: C₁₄H₁₇NO₄
• 分子量: 263.293
• InChiKey: LJALZBNXKPBITM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  19
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  55.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  4(RS)-1-(p-methoxybenzyl)-4-methoxycarbonyl-4-methyl-2-azetidinone 在 三(三苯基膦)羰基氢化铑 二苯基硅烷 作用下， 以 四氢呋喃 为溶剂， 反应 24.0h， 以63%的产率得到Methyl 1-[(4-methoxyphenyl)methyl]-2-methylazetidine-2-carboxylate
  参考文献：
  名称：

  Azetidine-Derived Amino Acids versus Proline Derivatives. Alternative Trends in Reverse Turn Induction

  摘要：

  [Graphics]The influence of 2-alkyl-2-carboxyazetidines (Aze) on the 3D structure of model tetrapeptides (RCO)-C-2-2-R(1)Aze-L-Ala-NHMe has been analyzed by molecular modeling, H-1 NMR, and FT-IR studies. The conformational constraints introduced by the four-membered ring resulted in an effective way to stabilize gamma-turn-like conformations in these short peptides. The conformational preferences of these Aze-containing peptides have been compared to those of the corresponding peptide analogues containing Pro or a-MePro in the place of 2-alkyl-Aze residue. In the model studied, both Pro and Aze derivatives are able to induce reverse turns, but the nature of the turn is different as a function of the ring size. While the five-membered ring of Pro tends to induce beta-turns, as previously suggested by different authors, the four-membered ring of Aze residues forces the peptide to preferentially adopt gamma-turn conformations. In both cases, the presence of an alkyl group at the alpha-position of Pro or the azetidine-2-carboxylate ring enhances significantly the turn-inducing ability. These results might open the opportunity of using 2-alkyl-Aze residues as versatile tools in defining the role of gamma-turn structures within the bioactive conformation of selected peptides, and represent an alternative to Pro derivatives as turn inducers.

  DOI：

  10.1021/jo701746w
• 作为产物：
  描述：

  N-(p-methoxybenzyl)-N-chloroacetyl-L-Ala-OMe 在 caesium carbonate 作用下， 以 乙腈 为溶剂， 反应 120.0h， 以57%的产率得到4(RS)-1-(p-methoxybenzyl)-4-methoxycarbonyl-4-methyl-2-azetidinone
  参考文献：
  名称：

  Azetidine-Derived Amino Acids versus Proline Derivatives. Alternative Trends in Reverse Turn Induction

  摘要：

  [Graphics]The influence of 2-alkyl-2-carboxyazetidines (Aze) on the 3D structure of model tetrapeptides (RCO)-C-2-2-R(1)Aze-L-Ala-NHMe has been analyzed by molecular modeling, H-1 NMR, and FT-IR studies. The conformational constraints introduced by the four-membered ring resulted in an effective way to stabilize gamma-turn-like conformations in these short peptides. The conformational preferences of these Aze-containing peptides have been compared to those of the corresponding peptide analogues containing Pro or a-MePro in the place of 2-alkyl-Aze residue. In the model studied, both Pro and Aze derivatives are able to induce reverse turns, but the nature of the turn is different as a function of the ring size. While the five-membered ring of Pro tends to induce beta-turns, as previously suggested by different authors, the four-membered ring of Aze residues forces the peptide to preferentially adopt gamma-turn conformations. In both cases, the presence of an alkyl group at the alpha-position of Pro or the azetidine-2-carboxylate ring enhances significantly the turn-inducing ability. These results might open the opportunity of using 2-alkyl-Aze residues as versatile tools in defining the role of gamma-turn structures within the bioactive conformation of selected peptides, and represent an alternative to Pro derivatives as turn inducers.

  DOI：

  10.1021/jo701746w

文献信息

• Azetidine-Derived Amino Acids versus Proline Derivatives. Alternative Trends in Reverse Turn Induction
  作者：José Luis Baeza、Guillermo Gerona-Navarro、Jesús Pérez de Vega、M. Teresa García-López、Rosario González-Muñiz、Mercedes Martín-Martínez

  DOI：10.1021/jo701746w

  日期：2008.3.1

  [Graphics]The influence of 2-alkyl-2-carboxyazetidines (Aze) on the 3D structure of model tetrapeptides (RCO)-C-2-2-R(1)Aze-L-Ala-NHMe has been analyzed by molecular modeling, H-1 NMR, and FT-IR studies. The conformational constraints introduced by the four-membered ring resulted in an effective way to stabilize gamma-turn-like conformations in these short peptides. The conformational preferences of these Aze-containing peptides have been compared to those of the corresponding peptide analogues containing Pro or a-MePro in the place of 2-alkyl-Aze residue. In the model studied, both Pro and Aze derivatives are able to induce reverse turns, but the nature of the turn is different as a function of the ring size. While the five-membered ring of Pro tends to induce beta-turns, as previously suggested by different authors, the four-membered ring of Aze residues forces the peptide to preferentially adopt gamma-turn conformations. In both cases, the presence of an alkyl group at the alpha-position of Pro or the azetidine-2-carboxylate ring enhances significantly the turn-inducing ability. These results might open the opportunity of using 2-alkyl-Aze residues as versatile tools in defining the role of gamma-turn structures within the bioactive conformation of selected peptides, and represent an alternative to Pro derivatives as turn inducers.