(R,S)-2-((1'-(N-benzyloxycarbonyl)amino-2'-phenylethyl)-hydroxyphosphinyl)methyl-prop-2-enoic acid, ethyl ester | 332113-61-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (R,S)-2-((1'-(N-benzyloxycarbonyl)amino-2'-phenylethyl)-hydroxyphosphinyl)methyl-prop-2-enoic acid, ethyl ester
• 英文别名: 2-Ethoxycarbonylprop-2-enyl-[2-phenyl-1-(phenylmethoxycarbonylamino)ethyl]phosphinic acid；2-ethoxycarbonylprop-2-enyl-[2-phenyl-1-(phenylmethoxycarbonylamino)ethyl]phosphinic acid
• CAS: 332113-61-8
• 化学式: C₂₂H₂₆NO₆P
• 分子量: 431.425
• InChiKey: QBJHGLUHORTGOQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  30
• 可旋转键数：
  12
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  102
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  丙二酸二乙酯钠盐 、 (R,S)-2-((1'-(N-benzyloxycarbonyl)amino-2'-phenylethyl)-hydroxyphosphinyl)methyl-prop-2-enoic acid, ethyl ester 以 乙醇 为溶剂， 反应 12.0h， 以87%的产率得到[5-Ethoxy-2,4-bis(ethoxycarbonyl)-5-oxopentyl]-[2-phenyl-1-(phenylmethoxycarbonylamino)ethyl]phosphinic acid
  参考文献：
  名称：

  Convenient Synthesis and Diversification of Dehydroalaninyl Phosphinic Peptide Analogues

  摘要：

  [GRAPHICS]Dehydroalaninyl phosphinic dipeptide analogues were synthesized, via an efficient tandem Arbuzov addition/allylic rearrangement, in high yields. The susceptibility of the conjugate system to 1,4 nucleophilic additions was investigated, C-Elongation of the dipeptides was performed, and the efficiency of 1,4 addition to the resulting arcylamidic moiety was evaluated, Derivatization of such phosphinic templates is a powerful approach for rapid access to large number of phosphinic pseudopeptides bearing various side chains in the P-1' position.

  DOI：

  10.1021/ol0069103
• 作为产物：
  描述：

  [2-phenyl-1-[[(phenylmethoxy)carbonyl]amino]ethyl]phosphinic acid 在 N,N-二异丙基乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 27.0h， 生成 (R,S)-2-((1'-(N-benzyloxycarbonyl)amino-2'-phenylethyl)-hydroxyphosphinyl)methyl-prop-2-enoic acid, ethyl ester
  参考文献：
  名称：

  Convenient Synthesis and Diversification of Dehydroalaninyl Phosphinic Peptide Analogues

  摘要：

  [GRAPHICS]Dehydroalaninyl phosphinic dipeptide analogues were synthesized, via an efficient tandem Arbuzov addition/allylic rearrangement, in high yields. The susceptibility of the conjugate system to 1,4 nucleophilic additions was investigated, C-Elongation of the dipeptides was performed, and the efficiency of 1,4 addition to the resulting arcylamidic moiety was evaluated, Derivatization of such phosphinic templates is a powerful approach for rapid access to large number of phosphinic pseudopeptides bearing various side chains in the P-1' position.

  DOI：

  10.1021/ol0069103