1-[2-(1,3-dioxo-1,3-dihydroisoindol-2-yl)pent-4-enoyl]-5-methoxypyrrolidine-2-carboxylic acid methyl ester | 916049-20-2

• 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: 1-[2-(1,3-dioxo-1,3-dihydroisoindol-2-yl)pent-4-enoyl]-5-methoxypyrrolidine-2-carboxylic acid methyl ester
• CAS: 916049-20-2
• 化学式: C₂₀H₂₂N₂O₆
• 分子量: 386.404
• InChiKey: RPHSRQOUZRADRO-KSCSMHSMSA-N

物化性质

• 沸点：
  537.5±50.0 °C(Predicted)
• 密度：
  1.32±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.36
• 重原子数：
  28.0
• 可旋转键数：
  6.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  93.22
• 氢给体数：
  0.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  1-[2-(1,3-dioxo-1,3-dihydroisoindol-2-yl)pent-4-enoyl]-5-methoxypyrrolidine-2-carboxylic acid methyl ester 在 四氯化钛 作用下， 以 二氯甲烷 为溶剂， 反应 40.0h， 以64%的产率得到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 、 tetrabutylammonium tetrafluoroborate 、 sodium carbonate 、 三乙胺 作用下， 以 乙醚 、 水 为溶剂， 反应 14.0h， 生成 1-[2-(1,3-dioxo-1,3-dihydroisoindol-2-yl)pent-4-enoyl]-5-methoxypyrrolidine-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

文献信息

• Silyl-Substituted Amino Acids:  New Routes to the Construction of Selectively Functionalized Peptidomimetics
  作者：Haizhou Sun、Kevin D. Moeller

  DOI：10.1021/ol025776e

  日期：2002.5.1

  [reaction: see text]. Silylated amino acids have been incorporated into peptides and then converted into N-acyliminium ions with the use of an anodic oxidation reaction. The result is a method for selectively incorporating conformational constraints or external nucleophiles within the peptide.

  [反应：请参见文字]。甲硅烷基化的氨基酸已被掺入肽中，然后利用阳极氧化反应转化为N-酰基亚胺离子。结果是一种在肽内选择性掺入构象限制或外部亲核试剂的方法。