diethyl 1-(furan-2-ylmethyl)aziridin-2-ylphosphonate | 1309980-45-7

• 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 1-(furan-2-ylmethyl)aziridin-2-ylphosphonate
• 英文别名: 2-Diethoxyphosphoryl-1-(furan-2-ylmethyl)aziridine
• CAS: 1309980-45-7
• 化学式: C₁₁H₁₈NO₄P
• 分子量: 259.242
• InChiKey: KTPPXAYMISNBOE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  17
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.64
• 拓扑面积：
  51.7
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  diethyl 1-(furan-2-ylmethyl)aziridin-2-ylphosphonate 在 lithium hydroxide monohydrate 作用下， 以 四氢呋喃 、 甲醇 、 水 为溶剂， 反应 3.0h， 生成
  参考文献：
  名称：

  新型氮丙啶基膦酸衍生物的合成，表征和细胞毒活性评估。

  摘要：

  通过将膦酸乙烯基酯或α-甲苯磺酰基乙烯基膦酸酯与伯胺或手性胺的改性Gabriel-Cromwell反应获得的氮丙啶2-膦酸酯单水解制备新的氮丙啶2-膦酸。使用MTT测定法测试了这些化合物对HCT-116结肠直肠癌细胞系和CCD-18Co正常结肠成纤维细胞系的细胞毒性。三种合成的膦酸衍生物2e（乙基氢{（（2S）-1-[（1S）-1-（萘-2-基）乙基]叠氮吡啶-2-基}膦酸酯）2h（乙基氢（1-苄基氮丙啶-2-基）膦酸酯和2i（乙基氢（1-环己基氮丙啶-2-基）膦酸酯）显示出比参考癌症治疗药物依托泊苷更高的细胞毒性。细胞死亡是通过强烈诱导凋亡，甚至比依托泊苷更有效，

  DOI：

  10.1002/cbdv.201900375
• 作为产物：
  描述：

  乙烯基磷酸二乙酯 在 溴 、 三乙胺 作用下， 以 二氯甲烷 、 乙腈 为溶剂， 反应 3.0h， 生成 diethyl 1-(furan-2-ylmethyl)aziridin-2-ylphosphonate
  参考文献：
  名称：

  Synthesis of 2-aziridinyl phosphonates by modified Gabriel–Cromwell reaction and their antibacterial activities

  摘要：

  A set of new aziridinyl phosphonates (4a-g) were synthesized by using the Gabriel-Cromwell reaction and its modified version developed in this study and their structures confirmed by HRMS, IR. and NMR spectra. All the compounds were screened for their antibacterial activity. They all showed comparable moderate to good growth inhibitory activity in reference to ampicillin and streptomycin. (C) 2011 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2011.03.037

文献信息

• Synthesis of <i>β</i>-chloro-<i>α</i>-aminophosphonate derivatives via the regioselective ring opening of unactivated aziridine-2-phosphonates
  作者：Sidika Polat-Cakir、Nurzhan Beksultanova、Özdemir Dogan

  DOI：10.1080/10426507.2018.1513521

  日期：2018.12.2

  Abstract A series of unactivated racemic and chiral aziridine-2-phosphonates were synthesized by modified Gabriel-Cromwell reaction. Ring opening reaction of the synthesized phosphonates by gaseous HCl provided access to a wide range of biologically interesting novel β-chloro-α-aminophosphonates. All reactions toward each of the above-mentioned products can be conducted regioselectively in high yields

  摘要 通过改良的加布里埃尔-克伦威尔反应合成了一系列未活化的外消旋和手性氮丙啶-2-膦酸酯。合成的膦酸盐通过气态 HCl 的开环反应提供了广泛的生物学上有趣的新型 β-氯-α-氨基膦酸盐。针对上述每种产物的所有反应都可以以高产率区域选择性地进行。图形概要
• Synthesis of Functionalized Novel <i>α</i> ‐Amino‐ <i>β</i> ‐alkoxyphosphonates through Regioselective Ring Opening of Aziridine‐2‐phosphonates
  作者：Sidika Polat‐Cakir、Nurzhan Beksultanova、Özdemir Dogan

  DOI：10.1002/hlca.201900199

  日期：2019.11

  Aziridines are highly useful compounds as building blocks for the synthesis of important organic compounds. Amino acid synthesis by aziridine ring opening reaction is a good example to the use of aziridines. Although this reaction is studied by many groups, the synthesis of amino phosphonic acids is less explored. In this study, we have carried out the ring opening reaction of aziridinyl phosphonates

  氮丙啶是非常有用的化合物，可作为重要有机化合物合成的基础。通过氮丙啶开环反应合成氨基酸是使用氮丙啶的一个很好的例子。尽管该反应已被许多研究小组研究，但氨基膦酸的合成研究却很少。在这项研究中，我们已经进行了氮丙啶基膦酸酯与多种醇（包括功能更强的炔丙醇和烯丙基醇）的开环反应。这些反应以40-91％的产率提供了功能化的α-氨基-β-烷氧基膦酸酯。
• Synthesis of 2-aziridinyl phosphonates by modified Gabriel–Cromwell reaction and their antibacterial activities
  作者：Özdemir Doğan、Hakan Babiz、Ayşe Gül Gözen、Songül Budak

  DOI：10.1016/j.ejmech.2011.03.037

  日期：2011.6

  A set of new aziridinyl phosphonates (4a-g) were synthesized by using the Gabriel-Cromwell reaction and its modified version developed in this study and their structures confirmed by HRMS, IR. and NMR spectra. All the compounds were screened for their antibacterial activity. They all showed comparable moderate to good growth inhibitory activity in reference to ampicillin and streptomycin. (C) 2011 Elsevier Masson SAS. All rights reserved.
• Synthesis, Characterization and Evaluation of Cytotoxic Activities of Novel Aziridinyl Phosphonic Acid Derivatives
  作者：Rehan Khan、Sinem Ulusan、Sreeparna Banerjee、Özdemir Dogan

  DOI：10.1002/cbdv.201900375

  日期：2019.11

  New aziridine 2-phosphonic acids were prepared by monohydrolysis of the aziridine 2-phosphonates that were obtained by the modified Gabriel-Cromwell reaction of vinyl phosphonate or α-tosylvinyl phosphonate with a primary amine or a chiral amine. The cellular cytotoxicity of these compounds was tested against the HCT-116 colorectal cancer cell lines and the CCD-18Co normal colon fibroblast lines using

  通过将膦酸乙烯基酯或α-甲苯磺酰基乙烯基膦酸酯与伯胺或手性胺的改性Gabriel-Cromwell反应获得的氮丙啶2-膦酸酯单水解制备新的氮丙啶2-膦酸。使用MTT测定法测试了这些化合物对HCT-116结肠直肠癌细胞系和CCD-18Co正常结肠成纤维细胞系的细胞毒性。三种合成的膦酸衍生物2e（乙基氢（（2S）-1-[（1S）-1-（萘-2-基）乙基]叠氮吡啶-2-基}膦酸酯）2h（乙基氢（1-苄基氮丙啶-2-基）膦酸酯和2i（乙基氢（1-环己基氮丙啶-2-基）膦酸酯）显示出比参考癌症治疗药物依托泊苷更高的细胞毒性。细胞死亡是通过强烈诱导凋亡，甚至比依托泊苷更有效，