氨乙基次膦酸 | 74333-44-1

• 物质功能分类: 有机原料 - 有机膦化合物
• 分子结构分类: 有机化合物 - 有机磷化合物
• 中文名称: 氨乙基次膦酸
• 英文名称: (1-aminoethyl)phosphinic acid
• 英文别名: (R,S)-(1-(amino)ethyl)phosphinic acid；1-aminoethylphosphinic acid
• CAS: 74333-44-1
• 化学式: C₂H₈NO₂P
• 分子量: 109.065
• InChiKey: TVKUNRSARHGLNB-UHFFFAOYSA-N

物化性质

• 沸点：
  247.4±42.0 °C(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -3.8
• 重原子数：
  6
• 可旋转键数：
  1
• 环数：
  0.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  63.3
• 氢给体数：
  2
• 氢受体数：
  3

安全信息

• 储存条件：
  室温

反应信息

• 作为反应物：
  描述：

  氨乙基次膦酸 在 mercury dichloride 作用下， 以 水 为溶剂， 生成 DL-1-氨基乙基膦酸
  参考文献：
  名称：

  Baylis, E. Keith; Campbell, Colin D.; Dingwall, John G., Journal of the Chemical Society. Perkin transactions I, 1984, p. 2845 - 2853

  摘要：

  DOI：
• 作为产物：
  描述：

  乙醛肟 在 盐酸 、 次磷酸 作用下， 以 甲醇 为溶剂， 反应 17.0h， 以55%的产率得到氨乙基次膦酸
  参考文献：
  名称：

  Synthesis of alkyl hydrogen (1-aminoalkyl)phosphonates

  摘要：

  Addition of hypophosphorous acid to aldoximes affords (1-aminoalkyl)phosphinic acids which on treatment with bromine in alkanols are transformed into alkyl hydrogen (1-aminoalkyl)phosphonates.

  DOI：

  10.1016/j.mencom.2011.03.017

文献信息

• Application of in Situ Silylation for Improved, Convenient Preparation of Fluorenylmethoxycarbonyl (Fmoc)-Protected Phosphinate Amino Acids
  作者：Li、John K. Whitehead、Robert P. Hammer

  DOI：10.1021/jo070266p

  日期：2007.4.1

  A convenient and efficient method has been developed for the preparation of 9-fluorenylmethoxycarbonyl (Fmoc)-protected 1-aminoalkylphosphinic acids. Reproducible procedures for the synthesis and purification of free α-amino H-phosphinates are provided. Protection of free amino phosphinates as the N-Fmoc derivative was achieved by in situ trimethylsilylation of aminoalkylphosphinic acids, which then

  已经开发了一种方便且有效的方法来制备9-芴基甲氧基羰基（Fmoc）保护的1-氨基烷基次膦酸。提供了用于游离α-氨基H-次膦酸酯的合成和纯化的可再现程序。通过氨基烷基次膦酸的原位三甲基甲硅烷基化来保护游离氨基次膦酸酯作为N -Fmoc衍生物，然后将其与Fmoc-Cl反应，以简单的萃取分离后，就可以以优异的收率和高纯度提供相应的产物。讨论了甲硅烷基化的机理，并介绍了该方法在另一类氨基磷酸中的应用。
• (&agr;-aminophosphino) peptide derivatives, method for making same and therapeutic applications thereof
  申请人：Institut National de la Sante et de la Recherche Medicale (Inserm)

  公开号：US06518260B1

  公开（公告）日：2003-02-11

  The invention concerns compounds derived from (&agr;-aminophosphino) peptides, of general formula (I), in which R1 and R2 each represents a hydrogen atom or taken together form an imine with the adjacent nitrogen atom; R3 represents an alkyl group, an alkenyl group, a phenyl group, a benzyl group, all these groups capable of being substituted or not, a hydrogen atom, a cycloalkyl group, a cycloalkylmethyl group or finally, a methyl group substituted by a heterocyclic, aromatic or saturated group; R4 represents a phenyl group, a benzyl group, these groups capable of being substituted or not, a hydrogen atom, an alkyl group, analkenyl group or a cycloalkyl group; R5 represents an alkyl group, an alkenyl group, a phenyl group, a benzyl group, all these groups capable of being substituted or not, a hydrogen atom, a cycloalkyl, cycloalkylmethyl group or finally a methyl group substituted by a heterocyclic, aromatic or saturated group; R6, R7 and R8 can in particular represent a hydrogen atom, an alkyl group, a phenyl group substituted or not . . . n is equal to 0 or 1, in the form of enantiomers, diastereoisomers or racemic mixtures, their salts, their method of preparation and their therapeutic applications.

  该发明涉及从(&agr;-氨基膦)肽衍生的化合物，其一般式为(I)，其中R1和R2分别表示氢原子或与相邻氮原子形成亚胺；R3表示烷基、烯基、苯基、苄基，所有这些基团均可被取代或不取代，氢原子、环烷基、环烷基甲基基团或最后，被杂环、芳香或饱和基团取代的甲基基团；R4表示苯基、苄基，这些基团可被取代或不取代，氢原子、烷基、烯基或环烷基；R5表示烷基、烯基、苯基、苄基，所有这些基团均可被取代或不取代，氢原子、环烷基、环烷基甲基基团或最后，被杂环、芳香或饱和基团取代的甲基基团；R6、R7和R8可以特别表示氢原子、烷基、苯基取代或不取代... n等于0或1，以对映异构体、非对映异构体或混合物的形式存在，它们的盐、制备方法和治疗应用。
• AMINOPHOSPHINIC DERIVATIVES THAT CAN BE USED IN THE TREATMENT OF PAIN
  申请人：Roques Bernard

  公开号：US20110124601A1

  公开（公告）日：2011-05-26

  The present invention relates to a compound of the following general formula (I): R 1 —NH—CH(R 2 )—P(═O)(OR 3 )—CH 2 —C(R 4 )(R 5 )—CONH—CH(R 6 )—COOR 7 (I) or a pharmaceutically acceptable salt of the latter, an isomer or a mixture of isomers in any proportions, especially a mixture of enantiomers, and in particular a racemic mixture, for which R 1 represents a —C(═O)—O—C(R 8 )(R 9 )—OC(═O)—R 10 group; R 2 represents an optionally substituted hydrocarbon-based chain, an aryl or heteroaryl group or a methylene group substituted by a heterocycle; R 3 represents a hydrogen atom or a —C(R 12 )(R 13 )—OC(═O)—R 14 group; R 4 and R 5 form, together with the carbon that bears them, a saturated hydrocarbon-based ring or an optionally substituted piperidine ring or R 4 represents a hydrogen atom and R 5 represents a phenyl or a benzyl that is optionally substituted, a heteroaromatic ring or a methylene group substituted by a heterocycle; R 6 represents an optionally substituted hydrocarbon-based chain or a phenyl or a benzyl that is optionally substituted; and R 7 represents a hydrogen atom or a benzyl, alkyl, heteroaryl, alkylheteroaryl, —CHMe—COOR 18 , —CHR 19 —OC(═O)OR 20 and —CHR 19 —OC(═O)OR 20 group. The present invention also relates to the use of these compounds as a medicinal product, and in particular for the treatment of pain, more advantageously neuropathic and neuroinflammatory pain, to their method of synthesis and also to the compositions containing them.

  本发明涉及以下通式（I）的化合物：R1—NH—CH（R2）—P（═O）（OR3）—CH2—C（R4）（R5）—CONH—CH（R6）—COOR7或其药学上可接受的盐、异构体或任意比例的异构体混合物，特别是对映体混合物，尤其是外消旋混合物，其中R1代表—C（═O）—O—C（R8）（R9）—OC（═O）—R10基团；R2代表可选取代的碳氢链、芳基或杂环芳基基团或被杂环取代的亚甲基基团；R3代表氢原子或—C（R12）（R13）—OC（═O）—R14基团；R4和R5与承载它们的碳原子一起形成饱和碳氢基环或可选取代的哌啶环或R4代表氢原子，R5代表可选取代的苯基或苄基、杂环芳基环或被杂环取代的亚甲基基团；R6代表可选取代的碳氢链或可选取代的苯基或苄基；R7代表氢原子或苄基、烷基、杂环芳基、烷基杂环芳基、—CHMe—COOR18、—CHR19—OC（═O）OR20和—CHR19—OC（═O）OR20基团。本发明还涉及这些化合物作为药物的用途，特别是用于疼痛治疗，更有利的是神经病理性和神经炎性疼痛的治疗，以及它们的合成方法和含有它们的组合物。
• (&agr;-aminophosphino) peptides derivative and compositions containing same
  申请人：Institut National de la Sante et de la Recherche Medicale (Inserm)

  公开号：US06391866B1

  公开（公告）日：2002-05-21

  The invention concerns (&agr;-aminophosphino) peptide derivative compounds of general formula (I) wherein: R1 and R2 represent each a hydrogen atom or together form an imine with the adjacent nitrogen atom; R3 represents an alkyl group, an alkenyl group, a phenyl group, a benzyl group, all said groups capable of being substituted or not, a hydrogen atom, a cycloalkyl group, a cycloalkylmethyl group or finally a methyl group substituted by an aromatic or saturated heterocyclic group; R4 represents a CH(X)—(O)—C(O)—Y group or a CH2CH2—S—C(O)—W group; R5 represents an alkyl group, an alkenyl group, a phenyl group, a benzyl group, all said groups capable of being substituted or not, a hydrogen atom, a cycloalkyl group, a cycloalkylmethyl group or finally a methyl group substituted by an aromatic or unsaturated heterocyclic group; R6 and R7 can in particular represent a hydrogen atom, an alkyl group, a phenyl group substituted or not; R8 represents an alkyl, alkenyl, phenyl or benzyl group; n=0 or 1, in the form of enantiomers, diastereoisomers or racemic mixtures, their salts, the method for preparing them and their therapeutic applications.

  该发明涉及一般式（I）的（α-氨基膦）肽衍生物化合物，其中：R1和R2分别表示氢原子或与相邻氮原子形成亚胺；R3表示烷基、烯基、苯基、苄基，所有这些基团都可以被取代或不取代，氢原子、环烷基、环烷基甲基基团或最终被芳香族或饱和杂环基团取代的甲基基团；R4表示CH(X)—(O)—C(O)—Y基团或CH2CH2—S—C(O)—W基团；R5表示烷基、烯基、苯基、苄基，所有这些基团都可以被取代或不取代，氢原子、环烷基、环烷基甲基基团或最终被芳香族或不饱和杂环基团取代的甲基基团；R6和R7特别表示氢原子、烷基、苯基，可取代或不取代；R8表示烷基、烯基、苯基或苄基；n=0或1，以对映体、非对映异构体或混合物形式存在，它们的盐、制备方法及其治疗应用。
• Synthesis of phosphinic and phosphoric analogs of aspartic acid
  作者：A. R. Khomutov、T. I. Oslpova、E. N. Khurs、K. V. Alferov、R. M. Khomutov

  DOI：10.1007/bf01457787

  日期：1996.8

  Approaches to the synthesis of 1-amino- and 2-amino-2-carboxyethylphosphinic and-phosphoric acids have been studied. A convenient method for the preparation of phosphinic acids is the reactions of ethyl diethoxymethylphosphonite with ethyl acetamidomethylenemalonate and ethyl 2-acetamidoacrylate.

  已经研究了合成 1-氨基和 2-氨基-2-羧乙基次膦酸和磷酸的方法。制备次膦酸的一种方便的方法是二乙氧基甲基亚膦酸乙酯与乙酰胺基亚甲基丙二酸乙酯和2-乙酰胺基丙烯酸乙酯的反应。