dimethyl (4-(((2S,5R)-5-isopropyl-3,6-dimethoxy-2,5-dihydropyrazin-2-yl)methyl)benzyl)phosphonate | 140866-79-1

• 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: dimethyl (4-(((2S,5R)-5-isopropyl-3,6-dimethoxy-2,5-dihydropyrazin-2-yl)methyl)benzyl)phosphonate
• CAS: 140866-79-1
• 化学式: C₁₉H₂₉N₂O₅P
• 分子量: 396.423
• InChiKey: MAGJHHPFUWFREL-DLBZAZTESA-N

物化性质

• 沸点：
  505.3±50.0 °C(Predicted)
• 密度：
  1.20±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.71
• 重原子数：
  27.0
• 可旋转键数：
  7.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.58
• 拓扑面积：
  78.71
• 氢给体数：
  0.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  dimethyl (4-(((2S,5R)-5-isopropyl-3,6-dimethoxy-2,5-dihydropyrazin-2-yl)methyl)benzyl)phosphonate 在 N-甲基吗啉 、 盐酸 、 sodium hydroxide 、 1-羟基苯并三唑 、 三乙胺 、 N,N'-二环己基碳二亚胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 21.0h， 生成 L-Leucine,N-[4-[(dimethoxyphosphinyl)methyl]-N-[(1,1-dimethylethoxy)carbonyl]-L-phenylalanyl]-, methyl ester
  参考文献：
  名称：

  Preparation of an angiotensin i analog containing a p-phosphonomethyl-l-phenylalanine residue via asymmetric synthesis of t-boc-p- dimethylphosphonomethyl-l-phenylalanine

  摘要：

  t-BOC-p-Dimethylphosphonomethyl-L-phenylalanine has been prepared and incorporated into a peptide sequence corresponding to angiotensin I. Demethylation of the dimethylphosphonomethyl moiety then yielded a peptide containing a p-phosphonomethyl-L-phenylalanine residue.

  DOI：

  10.1016/s0040-4039(00)91893-8
• 作为产物：
  描述：

  (R)-2,5-二氢-3,6-二甲氧基-2-异丙基吡嗪 在 正丁基锂 作用下， 生成 dimethyl (4-(((2S,5R)-5-isopropyl-3,6-dimethoxy-2,5-dihydropyrazin-2-yl)methyl)benzyl)phosphonate
  参考文献：
  名称：

  Preparation of an angiotensin i analog containing a p-phosphonomethyl-l-phenylalanine residue via asymmetric synthesis of t-boc-p- dimethylphosphonomethyl-l-phenylalanine

  摘要：

  t-BOC-p-Dimethylphosphonomethyl-L-phenylalanine has been prepared and incorporated into a peptide sequence corresponding to angiotensin I. Demethylation of the dimethylphosphonomethyl moiety then yielded a peptide containing a p-phosphonomethyl-L-phenylalanine residue.

  DOI：

  10.1016/s0040-4039(00)91893-8

文献信息

• Synthesis of p-Phosphonomethyl-L-phenylalanine using Camphor Sultam or D-Valine as Chiral Auxiliaries and its Incorporation into Integrin Sequences.
  作者：Elisabeth Larsson、Björn Lüning、Klaus Bechgaard、Jon Songstad、Markku Leskelä、Mika Polamo、Muhammed Nour Homsi、Frank K. H. Kuske、Monika Haugg、Nathalie Trabesinger-Rüf、Elmar G. Weinhold

  DOI：10.3891/acta.chem.scand.50-0054

  日期：——

  The synthesis of N-Boc-p-phosphonomethyl-L-phenylalanine with two different chiral auxiliaries, camphor sultam or D-valine is described. The preparations have essentially identical properties and have been used to incorporate the amino acid into two integrin peptides as non-hydrolyzable isosteres of phosphotyrosine.