bis(2-ethoxyethyl) phosphite | 6163-84-4

• 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: bis(2-ethoxyethyl) phosphite
• 英文别名: di-(2-ethoxy)ethyl phosphite；di-(2-ethoxyethyl) phosphite；phosphonic acid bis-(2-ethoxy-ethyl) ester；phosphorous acid bis-(2-ethoxy-ethyl) ester；phosphonic acid bis-(2-ethoxy-ethyl ester)；Phosphonsaeure-bis-(2-aethoxy-aethylester)；1-Ethoxy-2-(2-ethoxyethoxyphosphonoyloxy)ethane
• CAS: 6163-84-4
• 化学式: C₈H₁₉O₅P
• 分子量: 226.21
• InChiKey: NSAXMBYHZUBQAQ-UHFFFAOYSA-N

物化性质

• 沸点：
  156-157 °C(Press: 13 Torr)
• 密度：
  1.088 g/cm3

计算性质

• 辛醇/水分配系数(LogP)：
  -0.1
• 重原子数：
  14
• 可旋转键数：
  10
• 环数：
  0.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  54
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  bis(2-ethoxyethyl) phosphite 在 氨 、 sulfur 作用下， 以 二氯甲烷 为溶剂， 生成 O.O-Bis-<2-aethoxy-aethyl>-thiophosphat
  参考文献：
  名称：

  Pesin,V.G.; Khaletskii,A.M., Journal of general chemistry of the USSR, 1961, vol. 31, p. 2337 - 2343

  摘要：

  DOI：
• 作为产物：
  描述：

  乙二醇乙醚 在 三氯氧磷 作用下， 生成 bis(2-ethoxyethyl) phosphite
  参考文献：
  名称：

  物理性质和化学组成。第XLIX部分。某些有机磷化合物的折射率，密度和表面张力

  摘要：

  亚磷酸三正烷基酯，正膦酸二正烷基酯，正烷基膦酸二正丙基酯，正磷酸三正烷基酯（丁基至庚基）的正膦酸二正烷基酯（甲基至辛基），亚磷酸三-2-正烷氧基乙基酯（甲氧基-己氧基），亚磷酸二-2-正烷氧基乙基酯（甲氧基-庚氧基-）和2-正烷氧基-4-甲基-1,3,2已经制备了-二氧杂膦酸酯（甲氧基-至己氧基-），并确定了它们在20°的折射率以及在一定温度范围内的密度和表面张力：详细测量了许多代表性化合物的红外光谱。键（P O），（P–O），（P–C），（P–H）和1,3,2-二氧杂膦环的抛物线，折射和分子折射系数已通过新的实验数据。

  DOI：

  10.1039/j19660000249

文献信息

• Synthesis, Antiviral and Antifungal Bioactivity of 2-Cyano-acrylate Derivatives Containing Phosphonyl Moieties
  作者：Yin-Pu Lv、Xian-You Wang、Bao-An Song、Song Yang、Kai Yan、Guang-Fang Xu、Pinaki S Bhadury、Fang Liu、Lin-Hong Jin、De-Yu Hu

  DOI：10.3390/12050965

  日期：——

  Alkyl 2-cyano-3-methylthio-3-phosphonylacrylates were synthesized by the reaction of alkyl 2-cyano-3,3-dimethylthioacrylates with dialkyl phosphites. The structures of the new compounds were characterized by elemental analyses, IR, 1H-, 13C- and 31P-NMR spectral data. These compounds were tested in vitro against pathogenic fungi, namely, Fusarium graminearum, Cytospora mandshurica and Fusarium oxysporum. Amongst all compounds, 2d and 2t were found to be effective against the tested fungi at 50μg/mL. A half-leaf method was used to determine the in vivo protective, inactivation and curative efficacies of the title products against tobacco mosaic virus (TMV). Title compounds 2a and 2b were found to possess good in vivo curative, protection and inactivation effects against TMV with inhibitory rates at 500 mg/L of 60.0, 89.4 and 56.5 and 64.2, 84.2 and 61.2 %, respectively. To the best of our knowledge, this is the first report on the antiviral and antifungal activity of alkyl 2-cyano-3-methylthio-3-phosphonylacrylates.

  烷基2-氰基-3-甲基硫代-3-膦酰基丙烯酸酯通过烷基2-氰基-3,3-二甲基硫代丙烯酸酯与二烷基亚磷酸酯反应合成。新化合物的结构通过元素分析、IR、1H-、13C-和31P-NMR光谱数据表征。这些化合物在体外对病原真菌，即禾赤色镰孢、山里白棒孢和尖孢镰刀菌进行测试。在所有化合物中，2d和2t在50μg/mL时对测试的真菌有效。半叶法用于测定标题化合物对烟草花叶病毒（TMV）的田间保护、失活和治疗效果。标题化合物2a和2b被发现对TMV具有良好的田间治疗、保护和失活效果，抑制率在500 mg/L时分别为60.0、89.4和56.5以及64.2、84.2和61.2%。据我们所知，这是关于烷基2-氰基-3-甲基硫代-3-膦酰基丙烯酸酯抗病毒和抗真菌活性的首次报道。
• Synthesis and Antiviral Bioactivities of α-Aminophosphonates Containing Alkoxyethyl Moieties
  作者：Yingshu Xu、Kai Yan、Baoan Song、Gangfang Xu、Song Yang、Wei Xue、Deyu Hu、Ping Lu、Guiping Ouyang、Linhong Jin、Zhuo Chen

  DOI：10.3390/11090666

  日期：——

  A simple, efficient, and general method has been developed for the synthesis ofvarious α-aminophosphonate derivatives 4a-4l by treatment of substituted benzaldehydes andaniline with bis(2-methoxyethyl)- or bis(2-ethoxyethyl) phosphite under microwaveirradiation without solvents and catalysts. The products were characterized by elementalanalysis, IR, 1H-NMR, 13C- and 31P-NMR spectra. The X-ray crystallographic data of therepresentative compound 4l was determined. The new α-aminophosphonate derivatives werefound to possess moderate to good antiviral activity.

  已经开发出一种简单、高效且通用的方法，用于在微波辐射下，在无溶剂和催化剂的情况下，通过用双（2-甲氧基乙基）或双（2-乙氧基乙基）亚磷酸酯处理取代的苯甲醛和苯胺来合成各种α-氨基膦酸酯衍生物4a-4l。通过元素分析、红外光谱、1H-NMR、13C-和31P-NMR光谱对产物进行了表征。测定了代表性化合物4l的X射线晶体数据。发现新的α-氨基膦酸酯衍生物具有中等至良好的抗病毒活性。
• Novel Sterically Crowded and Conformationally Constrained α-Aminophosphonates with a Near-Neutral pKa as Highly Accurate 31P NMR pH Probes. Application to Subtle pH Gradients Determination in Dictyostelium discoideum Cells
  作者：Caroline Delehedde、Marcel Culcasi、Emilie Ricquebourg、Mathieu Cassien、Didier Siri、Bruno Blaive、Sylvia Pietri、Sophie Thétiot-Laurent

  DOI：10.3390/molecules27144506

  日期：——

  overlapping those of phosphorus metabolites, and spectroscopic sensitivities (i.e., chemical shifts variation Δδab between the acidic and basic forms) ranging from 9.2–10.7 ppm, being fourfold larger than conventional endogenous markers such as inorganic phosphate. X-ray crystallographic studies combined with predictive empirical relationships and ab initio calculations addressed the inductive and

  为了发现新的31 P NMR 标记物用于探测生物环境中的细微 pH 变化（<0.2 pH 单位），合成了 15 种新的构象受限或空间位阻的 α-氨基膦酸盐，它们源自二乙基（2-甲基吡咯烷-2-基）膦酸盐，并测试了它们的 pH 值报告和体外细胞毒性。所有化合物均显示出接近中性的 p K a s（范围为 6.28–6.97）、与磷代谢物不重叠的化学位移和光谱灵敏度（即化学位移变化 Δ δ ab介于酸性和碱性形式之间）范围为 9.2-10.7 ppm，比传统的内源性标记物（如无机磷酸盐）大四倍。X 射线晶体学研究与预测性经验关系和从头计算相结合，解决了与质子化胺功能相关的取代基的诱导和立体化学效应。在 p K a s 与二维结构和磷的金字塔化之间建立了令人满意的相关性，表明磷周围的空间拥挤对于调节 Δ δ ab至关重要。最后，命中31 P NMR pH 探针1b带有未取代的 1,3,2-二氧杂磷环烷环，它具有中等亲脂性，对
• Synthesis and Antiviral Bioactivities of 2-Cyano-3-substituted-amino(phenyl) Methylphosphonylacrylates (Acrylamides) Containing Alkoxyethyl Moieties
  作者：Jia-Qiang Yang、Bao-an Song、Pinaki S. Bhadury、Zhuo Chen、Song Yang、Xue-Jian Cai、De-Yu Hu、Wei Xue

  DOI：10.1021/jf902861m

  日期：2010.3.10

  An efficient reaction under microwave irradiation has been developed for the synthesis of a series of novel 2-cyano-3-substituted-amino(phenyl) methylphosphonylacrylates (acrylamides) II. The products obtained in shorter reaction time with moderate yields are fully characterized by elemental analysis, IR, H-1, C-13, and P-31 NMR spectral data. The role of introducing various substituents and the effect of incorporating alpha-aminophosphonates with an alkoxyethyl moiety into the parent cyanoacrylate (acrylamide) structure are investigated. Among the studied compounds, both II-17 and II-24 displayed good in vivo curative, protection, and inactivation effects, which were comparable to those of the commercial reference ningnanmycin (inhibitory rates of 58.8, 60.2, 78.9% and 60.0, 58.9, 85.5%, respectively, at 500 mg/L against TMV). To the best of the authors' knowledge, this is the first report on the synthesis and antiviral activity of the title compounds II.
• Design, Synthesis, and Antiviral Activity of α-Aminophosphonates Bearing a Benzothiophene Moiety
  作者：Peiwei Zhang、Chenghao Tang、Zhiwei Chen、Bo Wang、Xiang Wang、Linhong Jin、Song Yang、Deyu Hu

  DOI：10.1080/10426507.2013.829837

  日期：2014.4.3

  A series of -aminophosphonates containing a benzothiophene moiety was designed and synthesized. All synthesized compounds were confirmed by H-1 NMR, C-13 NMR, P-31 NMR, infrared spectroscopy, and elemental analysis. The half-leaf method was used to determine the in vivo efficacy of -aminophosphonates bearing a benzothiophene moiety against the tobacco mosaic virus (TMV). Bioassay results showed that all compounds exhibited certain anti-TMV activity at 500g/mL concentration. Compound 2f exhibited a curative effect of up to 48.1% against TMV, which was almost similar to that obtained from the standard ningnanmycin (51.9%). [Supplementary materials are available for this article. Go to the publisher's online edition of Phosphorus, Sulfer, and Silicon and the Related Elements for the following free supplemental files: Additional text, figures, and tables.]