4-methyl-3-pentenylphosphonic acid | 387335-67-3

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 有机膦酸及其衍生物
• 英文名称: 4-methyl-3-pentenylphosphonic acid
• 英文别名: 5-phosphono-2-methylpent-2-ene；1-(4-methyl-3-pentenyl)phosphonic acid；4-Methylpent-3-enylphosphonic acid
• CAS: 387335-67-3
• 化学式: C₆H₁₃O₃P
• 分子量: 164.141
• InChiKey: XZRUDDFTZNELMF-UHFFFAOYSA-N

物化性质

• 沸点：
  302.0±35.0 °C(Predicted)
• 密度：
  1.171±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.4
• 重原子数：
  10
• 可旋转键数：
  3
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  57.5
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  氯磷酸二苯酯 、 4-methyl-3-pentenylphosphonic acid 在 三正丁胺 作用下， 以 甲醇 、 四氢呋喃 为溶剂， 反应 2.5h， 生成
  参考文献：
  名称：

  Synthesis of Prenyl Pyrophosphonates as New Potent Phosphoantigens Inducing Selective Activation of Human Vγ9Vδ2 T Lymphocytes

  摘要：

  gamma9delta2T cells represent the most abundant population of human blood gammadeltaT lymphocytes. They produce and promote strong cytotoxic activity against many pathogens that are implicated in several human infectious diseases. Their activation requires their exposure to small phosphorus-containing antigens in the family of prenyl pyrophosphates and their related biosynthetic precursors such as isopentenyl pyrophosphate (IPP) and dimethylallyl pyrophosphate (DMAPP), which are naturally occurring metabolites in mycobacteria and several other microbial pathogens. The broad specificity in the recognition of these molecules by the T-lymphocyte population expressing a Vgamma9Vdelta2 cell receptor might facilitate their manipulation by designing small potent synthetic agonist ligands. In this paper, we describe the synthesis and the biological evaluation of new pyrophosphonate compounds as new isosteric analogues of natural prenyl pyrophosphates. Several prenyl and alkenyl pyrophosphonate with different chain lengths and degrees of insaturation (24-28, 48-50, and 64-66) were tested as well as the alkoxymethylpyrophosphonic analogue of IPP (compound 76) as its closest isostere. Several of them appeared to be better activators of Vgamma9Vdelta2 T cell proliferation than IPP. These results open the perspective of a potential use of isoprenoides pyrophosphonates as specific immunoregulatory molecules.

  DOI：

  10.1021/jm049861z
• 作为产物：
  描述：

  diethyl (4-methylpent-3-en-1-yl)phosphonate 在 吡啶 、 三甲基溴硅烷 作用下， 以 二氯甲烷 为溶剂， 反应 6.0h， 以69%的产率得到4-methyl-3-pentenylphosphonic acid
  参考文献：
  名称：

  Synthesis of Prenyl Pyrophosphonates as New Potent Phosphoantigens Inducing Selective Activation of Human Vγ9Vδ2 T Lymphocytes

  摘要：

  gamma9delta2T cells represent the most abundant population of human blood gammadeltaT lymphocytes. They produce and promote strong cytotoxic activity against many pathogens that are implicated in several human infectious diseases. Their activation requires their exposure to small phosphorus-containing antigens in the family of prenyl pyrophosphates and their related biosynthetic precursors such as isopentenyl pyrophosphate (IPP) and dimethylallyl pyrophosphate (DMAPP), which are naturally occurring metabolites in mycobacteria and several other microbial pathogens. The broad specificity in the recognition of these molecules by the T-lymphocyte population expressing a Vgamma9Vdelta2 cell receptor might facilitate their manipulation by designing small potent synthetic agonist ligands. In this paper, we describe the synthesis and the biological evaluation of new pyrophosphonate compounds as new isosteric analogues of natural prenyl pyrophosphates. Several prenyl and alkenyl pyrophosphonate with different chain lengths and degrees of insaturation (24-28, 48-50, and 64-66) were tested as well as the alkoxymethylpyrophosphonic analogue of IPP (compound 76) as its closest isostere. Several of them appeared to be better activators of Vgamma9Vdelta2 T cell proliferation than IPP. These results open the perspective of a potential use of isoprenoides pyrophosphonates as specific immunoregulatory molecules.

  DOI：

  10.1021/jm049861z

文献信息

• Phosphonates useful as modulators of t $g(g)9$g(d)2 lymphocyte activity
  申请人：Montero Jean-Louis

  公开号：US20060241087A1

  公开（公告）日：2006-10-26

  The invention concerns novel phosphonate derivatives, preparation method, use thereof as ligands modulating T γ9δ2 lymphocyte activity and pharmaceutical compositions comprising them.

  这项发明涉及新型膦酸酯衍生物，其制备方法，以及将其用作调节T γ9δ2淋巴细胞活性的配体和包含它们的药物组合物。
• [EN] METAL-FREE DIRECT ARYLATION OF DIALKYL PHOSPHONATES FOR THE SYNTHESIS OF MIXED ALKYL ARYL PHOSPHONATES<br/>[FR] ARYLATION DIRECTE SANS MÉTAL DE PHOSPHONATES DE DIALKYLE POUR LA SYNTHÈSE DE PHOSPHONATES D'ARYLE ALKYLE MIXTES
  申请人：THE BOARD OF REGENTS OF THE NEVADA SYSTEM OF HIGHER EDUCATION ON BEHALF OF THE UNIV OF NEVADA LAS VE

  公开号：WO2019028391A1

  公开（公告）日：2019-02-07

  Provided herein are phosphates, thiophosphates, phosphonates, and phosphinates, methods of making same, and methods of using these compounds and methods for the generation of pharmaceutically relevant phosphate, phosphonate, and phosphinate analogs. This abstract is intended as a scanning tool for purposes of searching in the particular art and is not intended to be limiting of the present invention.

  本文提供了磷酸盐、硫代磷酸盐、膦酸盐和膦酸盐，以及制备这些化合物的方法，以及使用这些化合物和用于生成与药用相关的磷酸盐、膦酸盐和膦酸盐类似物的方法。此摘要旨在作为搜索特定领域的扫描工具，并不限制本发明。
• [EN] PHOSPHONATES USEFUL AS MODULATORS OF T DOLLAR G(G)9 DOLLAR G(D)2 LYMPHOCYTE ACTIVITY<br/>[FR] PHOSPHONATES UTILES COMME MODULATEURS DE L'ACTIVITE DES LYMPHOCYTES t-GAMMA-9-DELTA-2
  申请人：MAYOLY SPINDLER LAB

  公开号：WO2003050128A1

  公开（公告）日：2003-06-19

  L'invention se rapporte à de nouveaux dérivés phosphonate, à leur procédé de préparation, à leur utilisation comme ligands modulateurs des lymphocytes T Ϝ9δ2 et aux compositions pharmaceutiques les comprenant.

  该发明涉及新的膦酸酯衍生物，其制备方法，其作为调节T细胞Ϝ9δ2的配体的用途以及包含它们的制药组合物。
• Phosphonates useful as modulators of T-gamma-9-delta-2 activity
  申请人：Montero Jean-Louis

  公开号：US20100204184A1

  公开（公告）日：2010-08-12

  The invention concerns novel phosphonate derivatives, preparation method, use thereof as ligands modulating T γ9δ2 lymphocyte activity and pharmaceutical compositions comprising them.

  这项发明涉及新型膦酸盐衍生物、其制备方法，以及将其用作调节T γ9δ2淋巴细胞活性的配体和包含它们的制药组合物。
• Metal-free direct arylation of dialkyl phosphonates for the synthesis of mixed alkyl aryl phosphonates
  申请人：The Board of Regents of the Nevada System of Higher Education on Behalf of the University of Nevada, Las Vegas

  公开号：US10927135B2

  公开（公告）日：2021-02-23

  Provided herein are phosphates, thiophosphates, phosphonates, and phosphinates, methods of making same, and methods of using these compounds and methods for the generation of pharmaceutically relevant phosphate, phosphonate, and phosphinate analogs. This abstract is intended as a scanning tool for purposes of searching in the particular art and is not intended to be limiting of the present invention.

  本发明提供了磷酸盐、硫代磷酸盐、膦酸盐和膦酸盐、其制造方法、使用这些化合物的方法以及生成药用磷酸盐、膦酸盐和膦酸盐类似物的方法。本摘要旨在作为在特定技术领域进行搜索的扫描工具，并非对本发明的限制。