2-(Diphenylphosphorylamino)-3-phenylpropanoic acid | 62056-93-3

• 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: 2-(Diphenylphosphorylamino)-3-phenylpropanoic acid
• CAS: 62056-93-3
• 化学式: C₂₁H₂₀NO₃P
• 分子量: 365.368
• InChiKey: CFEYLTCTDDDYDN-UHFFFAOYSA-N

物化性质

• 沸点：
  552.4±60.0 °C(Predicted)
• 密度：
  1.27±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  26
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  66.4
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-(Diphenylphosphorylamino)-3-phenylpropanoic acid 、 碘甲烷 生成 2-[diphenylphosphoryl(methyl)amino]-3-phenylpropanoic acid
  参考文献：
  名称：

  Diphenylphosphinamides: Synthesis of secondary amines and N-methylaminoacid derivatives

  摘要：

  DOI：

  10.1016/s0040-4039(00)92561-9
• 作为产物：
  描述：

  (S)-N-diphenylphosphinyl-phenylalanine methyl ester 在 lithium hydroxide monohydrate 、 盐酸 作用下， 以 甲醇 、 水 为溶剂， 以95%的产率得到2-(Diphenylphosphorylamino)-3-phenylpropanoic acid
  参考文献：
  名称：

  Group-Assisted Purification (GAP) for Protection of Amino Acids Using N-Phosphonyl Functional Groups

  摘要：

  Various phosphonyl halides have been synthesized and utilized as protection groups for amino acids. The protection synthesis was performed via GAP (Group-Assisted Purification) procedure under convenient conditions without the use of column chromatography and recrystallization. The synthesis can be carried out on applicational scales with excellent yields (82% - 98%). The phosphonyl protection of amino acids would provide a new greener tool for GAP peptide synthesis.

  DOI：

  10.3987/com-14-s(k)25

文献信息

• A new reagent for the mediation of amide bond formation in peptide synthesis.
  作者：Robert Ramage、Christopher P. Ashton、David Hopton、Maxwell J. Parrott

  DOI：10.1016/s0040-4039(01)81530-6

  日期：——
• Diphenylphosphinamides: Synthesis of secondary amines and N-methylaminoacid derivatives
  作者：S. Coulton、G.A. Moore、R. Ramage

  DOI：10.1016/s0040-4039(00)92561-9

  日期：1976.10
• Group-Assisted Purification (GAP) for Protection of Amino Acids Using N-Phosphonyl Functional Groups
  作者：Guigen Li、Guanghui An、Cole Seifert、Hao Sun、Yi Pan

  DOI：10.3987/com-14-s(k)25

  日期：——

  Various phosphonyl halides have been synthesized and utilized as protection groups for amino acids. The protection synthesis was performed via GAP (Group-Assisted Purification) procedure under convenient conditions without the use of column chromatography and recrystallization. The synthesis can be carried out on applicational scales with excellent yields (82% - 98%). The phosphonyl protection of amino acids would provide a new greener tool for GAP peptide synthesis.