methyl (Z)-2-(9H-fluoren-9-ylmethoxycarbonylamino)but-2-enoate | 395063-30-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 芴
• 英文名称: methyl (Z)-2-(9H-fluoren-9-ylmethoxycarbonylamino)but-2-enoate
• CAS: 395063-30-6
• 化学式: C₂₀H₁₉NO₄
• 分子量: 337.375
• InChiKey: PZGSIAPPBBLNAV-ZUWFHJRGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  25
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  64.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  N-FMOC-蛋氨酸亚砜甲酯 以 2,4-二氯甲苯 为溶剂， 反应 2.0h， 以84%的产率得到[9-fluorenylmethoxycarbonyl]-2-vinylglycine methyl ester
  参考文献：
  名称：

  α-Amino-β-hydroxy-γ-lactam for Constraining Peptide Ser and Thr Residue Conformation

  摘要：

  alpha-Amino-beta-hydroxy-gamma-lactam 1 is a peptide mimic in which the Ser/Thr residue omega-, psi-, and chi-dihedral angle geometry all are constrained by the 5-membered lactam ring. Lactams 1 were made by employing N-(Fmoc)oxiranylglycine 3 as a bis-electrophile in TFE with cat. BzOH to sequentially alkylate and acylate a variety of amino acid derivatives in one pot. Solid-phase synthesis of beta-hydroxy-gamma-lactam 8, an analogue of the IL-1 modulator 101.10, was achieved using this method for studying Ser/Thr geometry.

  DOI：

  10.1021/ol1000582

文献信息

• α-Amino-β-hydroxy-γ-lactam for Constraining Peptide Ser and Thr Residue Conformation
  作者：Daniel J. St-Cyr、Andrew G. Jamieson、William D. Lubell

  DOI：10.1021/ol1000582

  日期：2010.4.16

  alpha-Amino-beta-hydroxy-gamma-lactam 1 is a peptide mimic in which the Ser/Thr residue omega-, psi-, and chi-dihedral angle geometry all are constrained by the 5-membered lactam ring. Lactams 1 were made by employing N-(Fmoc)oxiranylglycine 3 as a bis-electrophile in TFE with cat. BzOH to sequentially alkylate and acylate a variety of amino acid derivatives in one pot. Solid-phase synthesis of beta-hydroxy-gamma-lactam 8, an analogue of the IL-1 modulator 101.10, was achieved using this method for studying Ser/Thr geometry.