Benzyl (+/-)-<1-<(benzyloxycarbonyl)amino>-2-phenylethyl>phosphonic acid | 153465-23-7

• 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: Benzyl (+/-)-<1-<(benzyloxycarbonyl)amino>-2-phenylethyl>phosphonic acid
• 英文别名: Phenylmethoxy-[2-phenyl-1-(phenylmethoxycarbonylamino)ethyl]phosphinic acid
• CAS: 153465-23-7
• 化学式: C₂₃H₂₄NO₅P
• 分子量: 425.421
• InChiKey: OBSCACHFQWEUDY-UHFFFAOYSA-N

物化性质

• 密度：
  1.274±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  30
• 可旋转键数：
  10
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  84.9
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  Benzyl (+/-)-<1-<(benzyloxycarbonyl)amino>-2-phenylethyl>phosphonic acid 在 N,N'-二环己基碳二亚胺 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 生成 Benzyl <(R,S)-1-<(benzyloxycarbonyl)amino>-2-phenylethyl>pyrophosphonate
  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
• 作为产物：
  描述：

  (+/-)-<1-<(Benzyloxycarbonyl)amino>-2-phenylethyl>phosphonous acid benzyl ester 在 sodium periodate 作用下， 以 1,4-二氧六环 为溶剂， 反应 16.0h， 生成 Benzyl (+/-)-<1-<(benzyloxycarbonyl)amino>-2-phenylethyl>phosphonic acid
  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。
• Selective Cleavage of One Ester Group in Dibenzyl Di-P-Nitrobenzyl and Dimethyl N-Protected Aminoalkylphosphonates
  作者：Maria Hoffmann

  DOI：10.1080/10426509808545456

  日期：1998.2.1

  Benzyl, p-nitrobenzyl and methyl hydrogen N-protected aminoalkylphosphonates were efficiently prepared by selective cleavage of one ester group in the corresponding diesters using DABCO (1,4-diazabicyclo(2.2.2]octane).

  通过使用 DABCO（1,4-二氮杂双环（2.2.2）辛烷）选择性裂解相应二酯中的一个酯基团，有效地制备了苄基、对硝基苄基和甲基氢 N-保护的氨基烷基膦酸酯。
• A straightforward synthesis of α-amino phosphonate monoesters using BroP or TPyClU
  作者：Nathalie Galéotti、Jacques Coste、Philippe Bedos、Patrick Jouin

  DOI：10.1016/0040-4039(96)00742-3

  日期：1996.6

  Monoesters of N-protected α-amino phosphonic acid were prepared from phosphonic acid using BroP or TPyClU as activating agent. This reaction proceeds with good yield, even with hindered alcohols.

  使用BroP或TPyClU作为活化剂，由膦酸制备N-保护的α-氨基膦酸的单酯。即使受阻醇，该反应也以良好的收率进行。
• Solid phase synthesis of phosphonopeptides
  作者：Jean-Marc Campagne、Jacques Coste、Patrick Jouin

  DOI：10.1016/0040-4039(95)00224-z

  日期：1995.3

  A solid phase synthesis of a phosphonopeptide is described, in which a type 1 aminophosphonate with a free phosphonic acid was coupled just like an amino acid, using BOP as reagent.

  描述了膦酰基肽的固相合成，其中使用BOP作为试剂，将1型氨基膦酸酯与游离膦酸像氨基酸一样偶联。