(S)-1-(Benzyloxycarbonylamino)-phenylmethanephosphonic acid | 71459-79-5

• 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: (S)-1-(Benzyloxycarbonylamino)-phenylmethanephosphonic acid
• 英文别名: (S)-1-benzyloxycarbonylamino-1-phenylmethylphosphonic acid；[(S)-phenyl(phenylmethoxycarbonylamino)methyl]phosphonic acid
• CAS: 71459-79-5
• 化学式: C₁₅H₁₆NO₅P
• 分子量: 321.269
• InChiKey: JYAHRYKTCFVWJU-AWEZNQCLSA-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：

  乙醇 、 (S)-1-(Benzyloxycarbonylamino)-phenylmethanephosphonic acid 在 氯化亚砜 作用下， 生成 (S)-Ethyl hydrogen 1-(benzyloxycarbonylamino)-phenylmethanephosphonate
  参考文献：
  名称：

  A Convenient Synthesis of Alkyl Hydrogen 1-(Benzyloxycarbonylamino)-alkanephosphonates

  摘要：

  DOI：

  10.1055/s-1986-31701
• 作为产物：
  描述：

  (S)-1-氨基苄基磷酸 以70%的产率得到(S)-1-(Benzyloxycarbonylamino)-phenylmethanephosphonic acid
  参考文献：
  名称：

  A Convenient Synthesis of Alkyl Hydrogen 1-(Benzyloxycarbonylamino)-alkanephosphonates

  摘要：

  DOI：

  10.1055/s-1986-31701

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。
• Direct Enantioselective Three-Component Kabachnik-Fields Reaction Catalyzed by Chiral Bis(imidazoline)-Zinc(II) Catalysts
  作者：Mutsuyo Ohara、Shuichi Nakamura、Norio Shibata

  DOI：10.1002/adsc.201100482

  日期：2011.12

  A direct three-component reaction of aldehydes, amines and diaryl phosphites was catalyzed by a zinc(II) complex of 1,3-bis(imidazolin-2-ly)pyridine (pybim) giving the corresponding α-aminophosphonates in good yield with good enantioselectivity. The reaction was applied to a wide variety of aromatic aldehydes to give products with excellent yields (up to 99%) and enantiomeric excesses (up to 93% ee)

  1,3-双（咪唑啉-2-ly）吡啶（pybim）的锌（II）络合物催化醛，胺和亚磷酸二芳酯的直接三组分反应，从而以高收率和良好收率得到相应的α-氨基膦酸酯对映选择性。反应可用于多种芳族醛，可制得具有极佳收率（最高达99％）和对映体过量（最高达ee 93％）的产物。
• Organocatalytic Enantioselective Hydrophosphonylation of Sulfonylimines having a Heteroarenesulfonyl Group as a Novel Stereocontroller
  作者：Shuichi Nakamura、Hiroki Nakashima、Akiko Yamamura、Norio Shibata、Takeshi Toru

  DOI：10.1002/adsc.200800134

  日期：2008.6.9

  Organocatalytic enantioselective hydrophosphonylation of imines having the a heteroarenesulfonyl group afforded the respective products with high enantioselectivity. Both enantiomers of α-amino phosphonates were obtained by using different Cinchona alkaloids with up to 98% ee.

  具有杂芳烃磺酰基的亚胺的有机催化对映选择性氢膦酰基化提供了具有高对映选择性的各个产物。通过使用具有高达98％ee的不同的Cinchona生物碱，可以得到两种α-氨基膦酸酯的对映体。
• 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.
• HOFFMANN M., SYNTHESIS,(1986) N 7, 557-559
  作者：HOFFMANN M.

  DOI：——

  日期：——