tert-butyl (S,E)-2-((2-(isopropylcarbamoyl)-2-methylhydrazineylidene)methyl)pyrrolidine-1-carboxylate | 156574-92-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯烷类
• 英文名称: tert-butyl (S,E)-2-((2-(isopropylcarbamoyl)-2-methylhydrazineylidene)methyl)pyrrolidine-1-carboxylate
• CAS: 156574-92-4
• 化学式: C₁₅H₂₈N₄O₃
• 分子量: 312.412
• InChiKey: YMKGTVFQHXOEID-SEJMYLSOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.42
• 重原子数：
  22.0
• 可旋转键数：
  3.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  74.24
• 氢给体数：
  1.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  tert-butyl (S,E)-2-((2-(isopropylcarbamoyl)-2-methylhydrazineylidene)methyl)pyrrolidine-1-carboxylate 在 N,N-二异丙基乙胺 、 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 反应 0.25h， 生成 Piv-Proψ(CH=N)AzAla-NH-iPr
  参考文献：
  名称：

  The semicarbazone peptidomimetic group in imino aza peptides

  摘要：

  The semicarbazone moiety (C-CH=N-NR-CO-NH-C), either obtained by coupling a peptide aldehyde with a semicarbazide, or by action of an alkylisocyanate on a peptide hydrazone, is a dipeptide isostere. The structure of four imino aza dipeptides, analogues of the Pro-Gly, Pro-Ala and Pro-Phe dipeptides, has been studied in solution by H-1-NMR and IR spectroscopy, and in the solid state by X-ray diffraction.

  DOI：

  10.1016/s0040-4039(00)73078-4
• 作为产物：
  描述：

  (S)-(S)-1-(tert-butoxycarbonyl)pyrrolidine-2-carboxylic (isobutyl carbonic) anhydride 在 N-甲基吗啉 、 lithium aluminium tetrahydride 、 sodium acetate 作用下， 以 四氢呋喃 、 乙醇 为溶剂， 生成 tert-butyl (S,E)-2-((2-(isopropylcarbamoyl)-2-methylhydrazineylidene)methyl)pyrrolidine-1-carboxylate
  参考文献：
  名称：

  The semicarbazone peptidomimetic group in imino aza peptides

  摘要：

  The semicarbazone moiety (C-CH=N-NR-CO-NH-C), either obtained by coupling a peptide aldehyde with a semicarbazide, or by action of an alkylisocyanate on a peptide hydrazone, is a dipeptide isostere. The structure of four imino aza dipeptides, analogues of the Pro-Gly, Pro-Ala and Pro-Phe dipeptides, has been studied in solution by H-1-NMR and IR spectroscopy, and in the solid state by X-ray diffraction.

  DOI：

  10.1016/s0040-4039(00)73078-4

文献信息

• Structural Comparison of Homologous Reduced Peptide, Reduced Azapeptide, Iminoazapeptide, and Methyleneoxypeptide Analogues
  作者：R. Vanderesse、V. Grand、D. Limal、A. Vicherat、M. Marraud、C. Didierjean、A. Aubry

  DOI：10.1021/ja980937o

  日期：1998.9.1

  The homologous RCO-Pro-Xaa-NHR' model pseudodipeptides containing the reduced peptide ((CCH2NHCalpha)-C-alpha), reduced azapeptide ((CCH2NHNalpha)-C-alpha), methyleneoxy ((CCH2OCalpha)-C-alpha), and iminoazapeptide ((CCH)-C-alpha=NNalpha) surrogate of the middle amide group have been prepared. Their structural analysis has been carried out in solution by H-1 NMR and IR spectroscopy and in the solid state by X-ray diffraction. The last three fragments, not protonated in the pH range 2-12, and the reduced fragment in its neutral amine form induce quite similar molecular structures characterized by a hydrogen bond between NHR' and the N/O atom replacing the amide NH group and closing a five-membered cycle. The neutral amine or protonated ammonium state of the reduced amide fragment, with a pK(a) value of about 7, depends on the environment. Protonation induces a conformational transition due to the strong proton donating properties of the ammonium group which interacts with the RCO carbonyl.
• The non protonable reduced aza-peptide fragment
  作者：Régis Vanderesse、Laurent David、Vincent Grand、Michel Marraud、Jean Paul Mangeot、André Aubry

  DOI：10.1016/s0040-4039(97)00410-3

  日期：1997.4

  The reduced aza-peptide fragment (C-alpha-CH2-NH-N(alpha)R-CO-NH-C-alpha) is obtained by reduction of the semicarbazone moiety (C-alpha-CH=N-N(alpha)R-CO-NH-C-alpha) in an imino aza-peptide. It differs from the aminomethylene link (C-alpha-CH2-NH-C(alpha)HR-CO-NH-C-alpha) found in the reduced peptides by the absence of protonation in water in the 2-12 pH range. The reduced aza-analogue of the Pro-Ala dipeptide has been studied in solution by H-1-NMR and IR spectroscopy, and in the solid state by X-ray diffraction. Its structure is quite similar to that of the neutral reduced dipeptide analogue in solution. (C) 1997 Elsevier Science Ltd.