diethyl allyloxymethylphosphonate | 64226-00-2

• 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 allyloxymethylphosphonate
• 英文别名: allyloxymethyl-phosphonic acid diethyl ester；Diethyl ((allyloxy)methyl)phosphonate；3-(diethoxyphosphorylmethoxy)prop-1-ene
• CAS: 64226-00-2
• 化学式: C₈H₁₇O₄P
• 分子量: 208.194
• InChiKey: HPNNWVDRZWKNEV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  13
• 可旋转键数：
  8
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.75
• 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 allyloxymethylphosphonate 在 甲醇 、 过氧化苯甲酰 作用下， 反应 22.0h， 生成
  参考文献：
  名称：

  Synthesis of novel partially fluorinated phosphonic/sulfonic acids

  摘要：

  A new-synthesis of (EtO)2P(O)CH2OCH2CH = CH2 (1) has been developed. Addition of I(CF2)4SO2F or I(CF2)2O(CF2)2SO2F to 1 followed by hydrolysis, reduction and ion exchange of the addition adducts gave (HO)2P(O)CH2O(CH2)3(CF2)4SO3H.2H2O and (HO)2P-(O)CH2O(CH2)3(CF2)2O(CF2)2SO3H.3H2O, respectively.

  DOI：

  10.1016/s0022-1139(00)80100-1
• 作为产物：
  描述：

  羟甲基膦酸二乙酯 、 3-溴丙烯 在 PTC 作用下， 以63%的产率得到diethyl allyloxymethylphosphonate
  参考文献：
  名称：

  [2,3] -Wittig重排在α-烯丙氧基甲基膦酸酯系列中

  摘要：

  水解后，在-70°C下用两当量的二异丙基氨基锂在THF中处理一些（α-烯丙氧基甲基）膦酸二乙酯，得到相应的（[2,3]- α-金属化的起始膦酸酯的维蒂希重排。

  DOI：

  10.1016/0022-328x(94)87023-3

文献信息

• Purine derivatives having antiviral activity
  申请人：Beecham Group P.l.c.

  公开号：US05055458A1

  公开（公告）日：1991-10-08

  Compounds of formula (I) and pharmaceutically acceptable salts thereof: ##STR1## wherein R.sub.1 is hydroxy, amino, chloro or OR.sub.7 wherein R.sub.7 is C.sub.1-6 alkyl, phenyl or phenyl C.sub.1-2 alkyl either of which phenyl moieties may be substituted by one or two substituents selected from halo, C.sub.1-4 alkyl or C.sub.1-4 alkoxy; R.sub.2 amino or, when R.sub.1 is hydroxy or amino, R.sub.2 may also be hydrogen; X is --CH.sub.2 CH.sub.2 -- or a moiety of structure (a), (b) or (c): ##STR2## wherein n is 1 or 2; m is 0, 1 or 2; and R.sub.3 is hydrogen or acyl; R.sub.4 is a group of formula: ##STR3## wherein R.sub.5 and R.sub.6 are independently selected from hydrogen, C.sub.1-6 alkyl and optionally substituted phenyl; having antiviral activity, processes for their preparation and their use as pharmaceuticals.

  式(I)的化合物及其药学上可接受的盐：其中R.sub.1为羟基、氨基、氯基或OR.sub.7，其中R.sub.7为C.sub.1-6烷基、苯基或苯基C.sub.1-2烷基，其中任一苯基基团可被来自卤素、C.sub.1-4烷基或C.sub.1-4烷氧基的一或两个取代基取代；R.sub.2为氨基，或当R.sub.1为羟基或氨基时，R.sub.2也可以是氢原子；X为--CH.sub.2 CH.sub.2 --或结构(a)、(b)或(c)的基团：其中n为1或2；m为0、1或2；R.sub.3为氢原子或酰基；R.sub.4为下式的基团：其中R.sub.5和R.sub.6独立地选自氢原子、C.sub.1-6烷基和可选择取代的苯基；具有抗病毒活性，其制备方法及其作为药物的用途。
• Novel isoxazolidine analogues of homonucleosides and homonucleotides
  作者：Dorota G. Piotrowska、Jan Balzarini、Graciela Andrei、Dominique Schols、Robert Snoeck、Andrzej E. Wróblewski、Joanna Gotkowska

  DOI：10.1016/j.tet.2016.10.073

  日期：2016.12

  Isoxazolidine analogues of homonucleos(t)ides were synthesized from nucleobase-derived nitrones 20a-20e (uracil, 5-fluorouracil, 5-bromouracil, thymine, adenine) employing 1,3-dipolar cycloadditions with allyl alcohol as well as with alkenylphosphonates (allyl-, allyloxymethyl- and vinyloxymethyl- and vinylphosphonate). Besides reactions with vinylphosphonate the additions proceeded regioselectively

  同核苷（酸）化物的异恶唑烷类似物由核碱基衍生的硝酮 20a-20e（尿嘧啶、5-氟尿嘧啶、5-溴尿嘧啶、胸腺嘧啶、腺嘌呤）合成，采用 1,3-偶极环加成与烯丙醇以及烯基膦酸酯（烯丙基-、烯丙氧基甲基-和乙烯基氧基甲基-和乙烯基膦酸酯）。除了与乙烯基膦酸酯的反应外，这些加成还进行区域选择性以产生主要顺式和次要反式 3,5-二取代异恶唑烷的混合物（de 28-82%）。由乙烯基膦酸酯额外生产了高达 10% 的 3,4-二取代异恶唑烷。邻接联轴器，屏蔽效应和 2D NOE 相关性用于构型分配和构象分析，以找出几种异恶唑烷的优选构象，并观察从乙烯基氧基甲基膦酸酯中获得的异头效应（膦酰基甲氧基的假轴取向）。在亚毒性浓度（高达 250 μM）下，所测试的化合物均未在体外对多种 DNA 和 RNA 病毒具有抗病毒活性，也未表现出对 L1210、CEM 和 HeLa 细胞的抗增殖活性（IC50 = ≥100
• Novel compounds
  申请人：BEECHAM GROUP PLC

  公开号：EP0353955A2

  公开（公告）日：1990-02-07

  Compounds of formula (I) and pharmaceutically acceptable salts thereof: wherein R₁ is hydroxy, amino, chloro or OR₇ wherein R₇ is C₁₋₆ alkyl, phenyl or phenyl C₁₋₂ alkyl either of which phenyl moieties may be substituted by one or two substituents selected from halo, C₁₋₄ alkyl or C₁₋₄ alkoxy; R₂ is amino or, when R₁ is hydroxy or amino, R₂ may also be hydrogen; X is -CH₂CH₂- or a moiety of structure (a), (b) or (c): wherein n is 1 or 2; and R₃ is hydrogen or acyl; R₄ is a group of formula: wherein R₅ and R₆ are independently selected from hydrogen, C₁₋₆ alkyl and optionally substituted phenyl; having anitiviral activity, processes for their preparation and their use as pharmaceuticals.

  式 (I) 的化合物及其药学上可接受的盐类： 其中 R₁ 是羟基、氨基、氯或 OR₇ 其中 R₇ 是 C₁₋₆烷基、苯基或苯基 C₁₋₂烷基，其中任一苯基可被一个或两个选自卤代、C₁₋₄ 烷基或 C₁₋₄ 烷氧基的取代基取代； R₂ 是氨基，或者当 R₁ 是羟基或氨基时，R₂ 也可以是氢； X 是-CH₂CH₂- 或结构式(a)、(b)或(c)的分子： 其中 n 是 1 或 2；以及 R₃ 是氢或酰基； R₄ 是式中的基团： 其中 R₅ 和 R₆ 独立选自氢、 C₁₋₆烷基和任选取代的苯基。
• Synthesis of novel isoxazolidine analogues of homonucleosides
  作者：Joanna Gotkowska、Jan Balzarini、Dorota G. Piotrowska

  DOI：10.1016/j.tetlet.2012.10.074

  日期：2012.12

  A general method for the synthesis of nucleobase-derived nitrones 4a-e by treatment of N-(2-oxoethyl)nucleobases with N-methylhydroxylamine is reported. The nitrones 4a-e were applied in the synthesis of isoxazolidine homonucleosides. Moderate diastereoselectivities (de 28-82%) were observed for cycloadditions between nitrones 4a-e and allyl alcohol with cis-isoxazolidines predominating. The stereochemistry of the substituted isoxazolidines was established based on an analysis of 2D NOE experiments for uracil-containing cycloadducts 6a and 7a. Cycloadditions of uracil-based nitrone 4a with vinyl-, allyl-, vinyloxymethyl- and allyloxymethylphosphonates gave the respective phosphonylated cis-isoxazolidines as the major adducts. (C) 2012 Elsevier Ltd. All rights reserved.
• US5055458A
  申请人：——

  公开号：US5055458A

  公开（公告）日：1991-10-08