diethyl (4-methyl-2-oxa-4-pentenyl)phosphonate | 108070-91-3

• 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: diethyl (4-methyl-2-oxa-4-pentenyl)phosphonate
• 英文别名: Diethyl 4-methyl-2oxa-pent-4-enylphosphonate；3-(diethoxyphosphorylmethoxy)-2-methylprop-1-ene
• CAS: 108070-91-3
• 化学式: C₉H₁₉O₄P
• 分子量: 222.221
• InChiKey: WMJSBPRKDZPLBX-UHFFFAOYSA-N

物化性质

• 沸点：
  280.3±23.0 °C(Predicted)
• 密度：
  1.032±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  14
• 可旋转键数：
  8
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.78
• 拓扑面积：
  44.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  diethyl (4-methyl-2-oxa-4-pentenyl)phosphonate 在 吡啶 、 三正丁胺 、 三甲基溴硅烷 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 8.5h， 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：

  羟甲基膦酸二乙酯 、 3-氯-2-甲基丙烯 在 sodium hydride 作用下， 以 四氢呋喃 为溶剂， 反应 1.5h， 以95%的产率得到diethyl (4-methyl-2-oxa-4-pentenyl)phosphonate
  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。
• 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。
• Phosphonates useful as modulators of T-γ-9-δ-2 activity
  申请人：Innate Pharma, S.A.

  公开号：US08017596B2

  公开（公告）日：2011-09-13

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

  本发明涉及新型膦酸酯衍生物、其制备方法、用作调节T γ9δ2淋巴细胞活性的配体以及包含它们的制药组合物。
• WILSON J. R. H., J. CHEM. SOC. PERKIN TRANS.,(1986) N 6, 1065-1068
  作者：WILSON J. R. H.

  DOI：——

  日期：——
• US8017596B2
  申请人：——

  公开号：US8017596B2

  公开（公告）日：2011-09-13