(R)-1-benzyloxycarbonylamino-1-phenylmethylphosphonic acid | 615264-92-1

• 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: (R)-1-benzyloxycarbonylamino-1-phenylmethylphosphonic acid
• 英文别名: [(R)-phenyl(phenylmethoxycarbonylamino)methyl]phosphonic acid
• CAS: 615264-92-1
• 化学式: C₁₅H₁₆NO₅P
• 分子量: 321.269
• InChiKey: JYAHRYKTCFVWJU-CQSZACIVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  22
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.13
• 拓扑面积：
  95.9
• 氢给体数：
  3
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  三甲基硅烷化重氮甲烷 、 (R)-1-benzyloxycarbonylamino-1-phenylmethylphosphonic acid 在 三甲基硅烷化重氮甲烷 作用下， 以 正己烷 、 二氯甲烷 为溶剂， 反应 0.5h， 以0.0079 g的产率得到dimethyl ((R)-(+)-(benzyloxycarbonylamino)(phenyl)methyl)phosphonate
  参考文献：
  名称：

  Thiourea-Catalyzed Enantioselective Hydrophosphonylation of Imines:  Practical Access to Enantiomerically Enriched α-Amino Phosphonic Acids

  摘要：

  Chiral thiourea 1b catalyzes the highly enantioselective hydrophosphonylation of a wide range of N-benzyl imines. The hydrophosphonylation products are readily deprotected by hydrogenolysis, providing access to free alpha-amino phosphonic acids in highly enantioenriched form.

  DOI：

  10.1021/ja0494398
• 作为产物：
  描述：

  (E)-N-benzylidenebenzylamine 在 palladium on activated charcoal 氢气 、 三乙胺 、 (R,r)-八氢-苯并咪唑-2-硫酮 作用下， 以 1,4-二氧六环 、 甲醇 、 乙醚 、 水 为溶剂， 反应 112.0h， 生成 (R)-1-benzyloxycarbonylamino-1-phenylmethylphosphonic acid
  参考文献：
  名称：

  Thiourea-Catalyzed Enantioselective Hydrophosphonylation of Imines:  Practical Access to Enantiomerically Enriched α-Amino Phosphonic Acids

  摘要：

  Chiral thiourea 1b catalyzes the highly enantioselective hydrophosphonylation of a wide range of N-benzyl imines. The hydrophosphonylation products are readily deprotected by hydrogenolysis, providing access to free alpha-amino phosphonic acids in highly enantioenriched form.

  DOI：

  10.1021/ja0494398

文献信息

• Straightforward Synthesis of Depsiphosphonopeptides via Mannich-Type Multicomponent Condensation
  作者：Jiaxi Xu、Yuanhe Gao

  DOI：10.1055/s-2006-926324

  日期：——

  A straightforward method for the synthesis of depsiphosphonopeptides via a Mannich-type multicomponent condensation of simple starting materials, such as benzyl carbamate, aldehydes, and 1-carbethoxyalkyl phosphorodichloridites, was developed. Compared to previous methods, our strategy provides a more efficient, convenient, and practical route for the preparation of depsiphosphonopeptides under mild reaction conditions with good yields. Such a strategy avoids the initial synthesis of 1-aminoalkyl­phosphonic acid or 1-aminoalkylphosphonous acid derivatives as starting materials.

  开发了一种通过Mannich型多组分缩合反应，利用简单的起始材料（如苄基氨基甲酸酯、醛和1-羧乙基磷酸二氯酯）合成depsiphosphonopeptides的直接方法。与以前的方法相比，我们的策略在温和的反应条件下提供了一条更加高效、方便和实用的路线，且产率良好。该策略避免了将1-氨基烷基磷酸或1-氨基烷基磷酸酯衍生物作为起始材料的初步合成。
• High-performance liquid chromatographic enantiomer separation and determination of absolute configurations of phosphinic acid analogues of dipeptides and their α-aminophosphinic acid precursors
  作者：Michael Lämmerhofer、Dieter Hebenstreit、Elena Gavioli、Wolfgang Lindner、Artur Mucha、Paweł Kafarski、Piotr Wieczorek

  DOI：10.1016/s0957-4166(03)00537-8

  日期：2003.9

  The enantiomers of N-benzyloxycarbonyl-phospinic pseudodipeptides and their N-benzyloxycarbonyl-alpha-aminophosphinic acid precursors as well as various other structural analogues were separated oil a set of cinchona alkaloid-derived chiral anion-exchangers by HPLC in the reversed-phase mode. Semi-preparative scale chromatography provided single enantiomers in 100 mg quantities. The configurations of the enantiomers were assigned indirectly by enantioselective chromatography on the basis of the elution order and was confirmed by enantiomeric reference compounds. (C) 2003 Elsevier Ltd. All rights reserved.
• Thiourea-Catalyzed Enantioselective Hydrophosphonylation of Imines:  Practical Access to Enantiomerically Enriched α-Amino Phosphonic Acids
  作者：Guy D. Joly、Eric N. Jacobsen

  DOI：10.1021/ja0494398

  日期：2004.4.1

  Chiral thiourea 1b catalyzes the highly enantioselective hydrophosphonylation of a wide range of N-benzyl imines. The hydrophosphonylation products are readily deprotected by hydrogenolysis, providing access to free alpha-amino phosphonic acids in highly enantioenriched form.