5-(dimethylphenylsilyl)-1-[2-(1,3-dioxo-1,3-dihydroisoindol-2-yl)pent-4-enoyl]pyrrolidine-2-carboxylic acid methyl ester | 916049-29-1

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: 5-(dimethylphenylsilyl)-1-[2-(1,3-dioxo-1,3-dihydroisoindol-2-yl)pent-4-enoyl]pyrrolidine-2-carboxylic acid methyl ester
• CAS: 916049-29-1
• 化学式: C₂₇H₃₀N₂O₅Si
• 分子量: 490.631
• InChiKey: DDMKYLGHEYTDQN-OJSMNCEXSA-N

物化性质

• 沸点：
  614.4±55.0 °C(Predicted)
• 密度：
  1.24±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.91
• 重原子数：
  35.0
• 可旋转键数：
  7.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  83.99
• 氢给体数：
  0.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  5-(dimethylphenylsilyl)-1-[2-(1,3-dioxo-1,3-dihydroisoindol-2-yl)pent-4-enoyl]pyrrolidine-2-carboxylic acid methyl ester 在 tetrabutylammonium tetrafluoroborate 、 四氯化钛 作用下， 以 二氯甲烷 为溶剂， 反应 40.0h， 生成 8-chloro-6-(1,3-dioxo-1,3-dihydroisoindol-2-yl)-5-oxooctahydropyrrolo[1,2-a]azepine-3-carboxylic acid methyl ester
  参考文献：
  名称：

  Building Functionalized Peptidomimetics:  Use of Electroauxiliaries for Introducing N-Acyliminium Ions into Peptides

  摘要：

  A series of silyl-substituted amino acids have been synthesized, inserted into peptides, and then employed as precursors for oxidatively generating reactive N-acyliminium ions. Both electrochemical and chemical oxidation procedures have been employed. N-Acyliminium ion generation in a solid-phase substrate as well as application to a small library of functionalized dipeptides has been demonstrated. Limitations in terms of how electron-rich the silyl groups can be as well as the compatibility of multiple silyl groups within a longer peptide are defined.

  DOI：

  10.1021/ja064737l
• 作为产物：
  描述：

  (S)-(-)-2-氨基-4-戊烯酸 在 五氯化磷 、 sodium carbonate 、 三乙胺 作用下， 以 乙醚 、 水 为溶剂， 反应 14.0h， 生成 5-(dimethylphenylsilyl)-1-[2-(1,3-dioxo-1,3-dihydroisoindol-2-yl)pent-4-enoyl]pyrrolidine-2-carboxylic acid methyl ester
  参考文献：
  名称：

  Building Functionalized Peptidomimetics:  Use of Electroauxiliaries for Introducing N-Acyliminium Ions into Peptides

  摘要：

  A series of silyl-substituted amino acids have been synthesized, inserted into peptides, and then employed as precursors for oxidatively generating reactive N-acyliminium ions. Both electrochemical and chemical oxidation procedures have been employed. N-Acyliminium ion generation in a solid-phase substrate as well as application to a small library of functionalized dipeptides has been demonstrated. Limitations in terms of how electron-rich the silyl groups can be as well as the compatibility of multiple silyl groups within a longer peptide are defined.

  DOI：

  10.1021/ja064737l