4-[2-(diethoxyphosphoryl)-2-fluoroethyl]-2,2-dimethoxyoxazolidine-3-carboxylic acid tert-butyl ester | 925706-68-9

• 分子结构分类: 有机化合物 - 有机酸及其衍生物
• 英文名称: 4-[2-(diethoxyphosphoryl)-2-fluoroethyl]-2,2-dimethoxyoxazolidine-3-carboxylic acid tert-butyl ester
• CAS: 925706-68-9
• 化学式: C₁₆H₃₁FNO₆P
• 分子量: 383.397
• InChiKey: ZFIAUAVLHGVNEY-PZORYLMUSA-N

物化性质

• 沸点：
  437.8±40.0 °C(Predicted)
• 密度：
  1.118±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.31
• 重原子数：
  25.0
• 可旋转键数：
  7.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.94
• 拓扑面积：
  74.3
• 氢给体数：
  0.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  4-[2-(diethoxyphosphoryl)-2-fluoroethyl]-2,2-dimethoxyoxazolidine-3-carboxylic acid tert-butyl ester 在 jones reagent 、 benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate 、 N,N-二异丙基乙胺 作用下， 以 二氯甲烷 、 丙酮 为溶剂， 反应 24.0h， 生成
  参考文献：
  名称：

  Synthesis and biological evaluation of γ-aminophosphonates as potent, subtype-selective sphingosine 1-phosphate receptor agonists and antagonists

  摘要：

  The synthesis of N-arylamide phosphonates and related arylether and arylamine analogues provided potent, subtype-selective agonists and antagonists of the five known sphingosine I-phosphate (SIP) receptors (S1P(1-5)). To this end, the syntheses of phosphoserine mimetics-selectively protected and optically active phosphonoserines-are described. In vitro binding assays showed that the implementation of phosphonates as phosphate mimetics provided compounds with similar receptor binding affinities as compared to their phosphate precursors. meta-substituted arylamide phosphonates were discovered to be antagonists of the S1P(1) and S1P(3) receptors. When administered to mice, an antagonist blocked the lymphopenia evoked by a SIP receptor agonist and caused capillary leakage in both lung and kidney. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2006.10.060
• 作为产物：
  描述：

  4-[2-(diethoxyphosphoryl)-2-fluorovinyl]-2,2-dimethoxyoxazolidine-3-carboxylic acid tert-butyl ester 在 palladium on activated charcoal 氢气 作用下， 以 乙醇 为溶剂， 反应 12.0h， 以88%的产率得到4-[2-(diethoxyphosphoryl)-2-fluoroethyl]-2,2-dimethoxyoxazolidine-3-carboxylic acid tert-butyl ester
  参考文献：
  名称：

  Synthesis and biological evaluation of γ-aminophosphonates as potent, subtype-selective sphingosine 1-phosphate receptor agonists and antagonists

  摘要：

  The synthesis of N-arylamide phosphonates and related arylether and arylamine analogues provided potent, subtype-selective agonists and antagonists of the five known sphingosine I-phosphate (SIP) receptors (S1P(1-5)). To this end, the syntheses of phosphoserine mimetics-selectively protected and optically active phosphonoserines-are described. In vitro binding assays showed that the implementation of phosphonates as phosphate mimetics provided compounds with similar receptor binding affinities as compared to their phosphate precursors. meta-substituted arylamide phosphonates were discovered to be antagonists of the S1P(1) and S1P(3) receptors. When administered to mice, an antagonist blocked the lymphopenia evoked by a SIP receptor agonist and caused capillary leakage in both lung and kidney. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2006.10.060