Dibenzyl (+/-)-<1-<(benzyloxycarbonyl)amino>-2-phenylethyl>phosphonate | 132035-93-9

• 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: Dibenzyl (+/-)-<1-<(benzyloxycarbonyl)amino>-2-phenylethyl>phosphonate
• 英文别名: benzyl N-[1-bis(phenylmethoxy)phosphoryl-2-phenylethyl]carbamate
• CAS: 132035-93-9
• 化学式: C₃₀H₃₀NO₅P
• 分子量: 515.546
• InChiKey: SMHXRJPBMMILHY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.8
• 重原子数：
  37
• 可旋转键数：
  13
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  73.9
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  Dibenzyl (+/-)-<1-<(benzyloxycarbonyl)amino>-2-phenylethyl>phosphonate 在 三乙烯二胺 作用下， 以 丙酮 、 甲苯 为溶剂， 反应 5.0h， 以83%的产率得到Benzyl (+/-)-<1-<(benzyloxycarbonyl)amino>-2-phenylethyl>phosphonic acid
  参考文献：
  名称：

  选择性裂解二苄基二对硝基苄基和二甲基 N 保护的氨基烷基膦酸酯中的一个酯基

  摘要：

  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。

  DOI：

  10.1080/10426509808545456
• 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 16.5h， 生成 Dibenzyl (+/-)-<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.
• 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。