diisopropyl vinyloxymethanephosphonate | 183197-20-8

• 分子结构分类: 有机化合物 - 有机酸及其衍生物
• 英文名称: diisopropyl vinyloxymethanephosphonate
• 英文别名: diisopropyl vinyloxymethylphosphonate；2-[ethenoxymethyl(propan-2-yloxy)phosphoryl]oxypropane
• CAS: 183197-20-8
• 化学式: C₉H₁₉O₄P
• 分子量: 222.221
• InChiKey: KWIZPWYZAVVSAD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.15
• 重原子数：
  14.0
• 可旋转键数：
  7.0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.78
• 拓扑面积：
  44.76
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  diisopropyl vinyloxymethanephosphonate 在 N-碘代丁二酰亚胺 、 caesium carbonate 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 24.0h， 生成
  参考文献：
  名称：

  2′-C-ALKOXY AND 2′-C-ARYLOXY DERIVATIVES OFN-(2-PHOSPHONOMETHOXYETHYL)-PURINES AND -PYRIMIDINES: SYNTHESIS AND BIOLOGICAL ACTIVITY

  摘要：

  A series of novel, unusual type of acyclic phosphonate-based nucleotide analogues related to well-known antivirals (PMEA and HPMPA) was synthesized using easily available synthon. These compounds, which are distinguished for the presence of phosphonomethyl acetal linkage, form a group of derivatives that contribute to the understanding of structure-activity relationship within the area of acyclic nucleotide analogues.

  DOI：

  10.1081/ncn-100105244
• 作为产物：
  描述：

  三异丙基亚磷酸酯 在 potassium tert-butylate 作用下， 以 四氢呋喃 为溶剂， 反应 4.33h， 生成 diisopropyl vinyloxymethanephosphonate
  参考文献：
  名称：

  2′-C-ALKOXY AND 2′-C-ARYLOXY DERIVATIVES OFN-(2-PHOSPHONOMETHOXYETHYL)-PURINES AND -PYRIMIDINES: SYNTHESIS AND BIOLOGICAL ACTIVITY

  摘要：

  A series of novel, unusual type of acyclic phosphonate-based nucleotide analogues related to well-known antivirals (PMEA and HPMPA) was synthesized using easily available synthon. These compounds, which are distinguished for the presence of phosphonomethyl acetal linkage, form a group of derivatives that contribute to the understanding of structure-activity relationship within the area of acyclic nucleotide analogues.

  DOI：

  10.1081/ncn-100105244

文献信息

• 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
• 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.
• Rejman, Dominik; Rosenberg, Ivan, Collection of Czechoslovak Chemical Communications, 1996, vol. 61, p. S122 - S123
  作者：Rejman, Dominik、Rosenberg, Ivan

  DOI：——

  日期：——