1-methoxy-3-methoxycarbonyl-1-oxophosphorinan-4-one | 183558-71-6

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 乙烯基酸
• 英文名称: 1-methoxy-3-methoxycarbonyl-1-oxophosphorinan-4-one
• 英文别名: methyl 4-hydroxy-1-methoxy-1-oxo-3,6-dihydro-2H-1lambda5-phosphinine-5-carboxylate；methyl 4-hydroxy-1-methoxy-1-oxo-3,6-dihydro-2H-1λ5-phosphinine-5-carboxylate
• CAS: 183558-71-6
• 化学式: C₈H₁₃O₅P
• 分子量: 220.162
• InChiKey: UQRNSUQDWHOCDI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.4
• 重原子数：
  14
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  72.8
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  1-methoxy-3-methoxycarbonyl-1-oxophosphorinan-4-one 在 盐酸 作用下， 反应 72.0h， 生成 1-methoxy-1-oxo-phosphorinan-4-one
  参考文献：
  名称：

  1-Oxo-2-oxa-1-phosphabicyclo[2.2.2]octane：磷酸酯碱性水解的新机制探针

  摘要：

  从次磷酸开始以多步顺序完成标题化合物2的合成。在强碱中，双环次膦酸盐 2 的水解速度比双环磷酸盐 OP(OCH2)3CCH3 (1a) 快 2 个数量级，并且加速完全是焓。这种速率提高归因于 2 更容易实现五坐标过渡态。与 1a 相比，通过 X 射线方法确定的 2 的分子结构显示在任一双环框架内都没有应变的迹象。观察到的加速度不支持立体电子效应对六元环磷酸酯水解的贡献。

  DOI：

  10.1021/ja9611147
• 作为产物：
  描述：

  3-(methoxyphosphinyl)propanoic acid methyl ester 在 sodium methylate 、 sodium tert-pentoxide 作用下， 以 苯 为溶剂， 生成 1-methoxy-3-methoxycarbonyl-1-oxophosphorinan-4-one
  参考文献：
  名称：

  Inhibition of glutamate racemase by substrate–product analogues

  摘要：

  D-Glutamate is an essential biosynthetic building block of the peptidoglycans that encapsulate the bacterial cell wall. Glutamate racemase catalyzes the reversible formation of D-glutamate from L-glutamate and, hence, the enzyme is a potential therapeutic target. We show that the novel cyclic substrate-product analogue (R,S)-1-hydroxy-1-oxo-4-amino-4-carboxyphosphorinane is a modest, partial noncompetitive inhibitor of glutamate racemase from Fusobacterium nucleatum (FnGR), a pathogen responsible, in part, for periodontal disease and colorectal cancer (K-i = 3.1 +/- 0.6 mM, cf. K-m = 1.41 +/- 0.06 mM). The cyclic substrate- product analogue (R, S)-4-amino-4-carboxy-1,1-dioxotetrahydro-thiopyran was a weak inhibitor, giving only similar to 30% inhibition at a concentration of 40 mM. The related cyclic substrate-product analogue 1,1-dioxo-tetrahydrothiopyran-4-one was a cooperative mixed-type inhibitor of FnGR (K-i = 18.4 +/- 1.2 mM), while linear analogues were only weak inhibitors of the enzyme. For glutamate racemase, mimicking the structure of both enantiomeric substrates (substrate-product analogues) serves as a useful design strategy for developing inhibitors. The new cyclic compounds developed in the present study may serve as potential lead compounds for further development. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2013.12.114