[3-(2-(3-(2-ethoxy-2-oxoethylamino)prop-1-ynyl)phenyl)prop-2-ynyl]-L-valine ethyl ester | 1245504-16-8

• 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: [3-(2-(3-(2-ethoxy-2-oxoethylamino)prop-1-ynyl)phenyl)prop-2-ynyl]-L-valine ethyl ester
• 英文别名: ethyl (2S)-2-[3-[2-[3-[(2-ethoxy-2-oxoethyl)amino]prop-1-ynyl]phenyl]prop-2-ynylamino]-3-methylbutanoate
• CAS: 1245504-16-8
• 化学式: C₂₃H₃₀N₂O₄
• 分子量: 398.502
• InChiKey: TUJUFLGPGIMXKU-QFIPXVFZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  29
• 可旋转键数：
  13
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.48
• 拓扑面积：
  76.7
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  (2-nitrobenzensulfonyl)[3-(2-(3-(N-(2-ethoxy-2-oxoethyl)-2-nitrophenylsulfonamido)prop-1-ynyl)phenyl)prop-2-ynyl]-L-valine 在 potassium carbonate 、 苯硫酚 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 1.0h， 以67%的产率得到[3-(2-(3-(2-ethoxy-2-oxoethylamino)prop-1-ynyl)phenyl)prop-2-ynyl]-L-valine ethyl ester
  参考文献：
  名称：

  Bergman Cyclization of Acyclic Amino Acid Derived Enediynes Leads to the Formation of 2,3-Dihydrobenzo[f]isoindoles

  摘要：

  Enediyne-peptide conjugates are recently recognized as useful tools in targeting various proteins, while the mechanism underlying the observed activity remains somewhat unclear. Addressing these issues, we have prepared acyclic amino acid derived enediynes and disclosed a novel thermally induced cyclization-elimination pathway. Initial formation of 1,4-benzene diradical and H-atom abstraction from an external donor is followed by S(N)2 substitution leading to 2,3-dihydrobenzo-[f]isoindoles. The proposed mechanism is supported by experimental and computational data. Additionally, we showed that amino acid side chains, although placed three bonds away from acetylene terminuses, have an appreciable influence on the reactivity of studied enediynes. These results demonstrate that amino acid or peptide parts of enediyne-peptide conjugates cannot be considered as recognition elements exclusively but may also participate in various reactions through amine functionality.

  DOI：

  10.1021/jo101302n