Isopropyl benzyl <(R,S)-1-<(benzyloxycarbonyl)amino>-2-phenylethyl>phosphonate

• 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: Isopropyl benzyl <(R,S)-1-<(benzyloxycarbonyl)amino>-2-phenylethyl>phosphonate
• 英文别名: benzyl N-[2-phenyl-1-[phenylmethoxy(propan-2-yloxy)phosphoryl]ethyl]carbamate
• 化学式: C₂₆H₃₀NO₅P
• 分子量: 467.502
• InChiKey: KOJSVYIOBJQUBZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.1
• 重原子数：
  33
• 可旋转键数：
  12
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  73.9
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  (+/-)-<1-<(Benzyloxycarbonyl)amino>-2-phenylethyl>phosphonous acid benzyl ester 在 sodium periodate 、 (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate 、 N,N-二异丙基乙胺 作用下， 以 1,4-二氧六环 、 N,N-二甲基甲酰胺 为溶剂， 反应 17.5h， 生成 Isopropyl benzyl <(R,S)-1-<(benzyloxycarbonyl)amino>-2-phenylethyl>phosphonate
  参考文献：
  名称：

  (1H-Benzotriazol-1-yloxy)tris(dimethylamino)phosphonium Hexafluorophosphate- and (1H-Benzotriazol-1-yloxy)tripyrrolidinophosphonium Hexafluorophosphate-Mediated Activation of Monophosphonate Esters: Synthesis of Mixed Phosphonate Diesters, the Reactivity of the Benzotriazolyl Phosphonic Esters vs the Reactivity of the Benzotriazolyl Carboxylic Esters

  摘要：

  A general method for synthesizing mixed phosphonate diesters from monoesters using (1H-benzotriazol-1-yloxy)tris(dimethylamino) hexafluorophosphate or (1H-benzotriazol-1-yloxy)tripyrrolidinophosphonium hexafluorophosphate reagents is described. The reaction proceeded through a benzotriazolyl ester as shown by comparison with other reagents such as DCC, DCC/DMAP, DCC/1-hydroxybenzotriazole, bromotris(dimethylamino)phosphonium hexafluorophosphate, or O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate and by P-31 NMR analysis. This benzotriazolyl phosphonic ester intermediate was more reactive toward alcohols than toward amines, contrary to its carboxylic analogue.

  DOI：

  10.1021/jo00121a045

文献信息

• Synthesis of mixed phosphonate diester analogues of dipeptides using BOP or PyBOP reagents
  作者：Jean-Marc Campagne、Jacques Coste、Patrick Jouin

  DOI：10.1016/s0040-4039(00)61690-8

  日期：1993.10

  Mixed phosphonate diesters of a N-protected α-amino phosphonic acid are prepared from phosphonate monoesters using BOP or PyBOP as activating agent. This reaction proceeds without racemisation.

  使用BOP或PyBOP作为活化剂，由膦酸酯单酯制备N-保护的α-氨基膦酸的混合膦酸酯二酯。该反应在没有外消旋的情况下进行。
• (1H-Benzotriazol-1-yloxy)tris(dimethylamino)phosphonium Hexafluorophosphate- and (1H-Benzotriazol-1-yloxy)tripyrrolidinophosphonium Hexafluorophosphate-Mediated Activation of Monophosphonate Esters: Synthesis of Mixed Phosphonate Diesters, the Reactivity of the Benzotriazolyl Phosphonic Esters vs the Reactivity of the Benzotriazolyl Carboxylic Esters
  作者：Jean-Marc Campagne、Jacques Coste、Patrick Jouin

  DOI：10.1021/jo00121a045

  日期：1995.8

  A general method for synthesizing mixed phosphonate diesters from monoesters using (1H-benzotriazol-1-yloxy)tris(dimethylamino) hexafluorophosphate or (1H-benzotriazol-1-yloxy)tripyrrolidinophosphonium hexafluorophosphate reagents is described. The reaction proceeded through a benzotriazolyl ester as shown by comparison with other reagents such as DCC, DCC/DMAP, DCC/1-hydroxybenzotriazole, bromotris(dimethylamino)phosphonium hexafluorophosphate, or O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate and by P-31 NMR analysis. This benzotriazolyl phosphonic ester intermediate was more reactive toward alcohols than toward amines, contrary to its carboxylic analogue.