bis(2-methoxyethyl) phosphite | 6163-85-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: bis(2-methoxyethyl) phosphite
• 英文别名: di-2-methoxyethyl phosphite；bis(2-methoxyethyl) phosphonate；HP(O)(OEtOMe)2；phosphonic acid bis-(2-methoxy-ethyl) ester；phosphorous acid bis-(2-methoxy-ethyl) ester；Phosphonsaeure-bis-(2-methoxy-aethylester)；1-Methoxy-2-[2-methoxyethoxy(oxido)phosphaniumyl]oxyethane；1-methoxy-2-[2-methoxyethoxy(oxido)phosphaniumyl]oxyethane
• CAS: 6163-85-5
• 化学式: C₆H₁₅O₅P
• 分子量: 198.156
• InChiKey: HXCZAFBGXPZLOO-UHFFFAOYSA-N

物化性质

• 沸点：
  257.4±25.0 °C(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.8
• 重原子数：
  12
• 可旋转键数：
  8
• 环数：
  0.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  60
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  bis(2-methoxyethyl) phosphite 在 1,2,3,4,5,6,7,8-八硫杂环辛烷 、 三乙胺 、 盐酸 作用下， 以 乙醚 、 水 为溶剂， 以22%的产率得到O,O-bis(2-methoxyethyl) S-hydrogen phosphorothioate
  参考文献：
  名称：

  Electrophilic Trifluoromethylation of S-Hydrogen Phosphorothioates

  摘要：

  A series of S-hydrogen phosphorothioates have been converted to the corresponding S-trifluoromethyl derivatives upon reaction with the electrophilic trifluoromethylation reagent 1 (trifluoromethyl 1,3-dihydro-3,3-dimethyl-1,2-benziodoxole). Relative rate data were obtained by F-19 NMR monitoring of competition experiments and were evaluated by means of the Taft equation. A high positive polar sensitivity factor of 2.55 was found for electron-rich substrates and a negative one of -0.37 for electron-poor ones, implying the involvement of two different rate-determining steps. Furthermore, the reaction was found to be unaffected by steric factors.

  DOI：

  10.1021/jo200522w
• 作为产物：
  描述：

  乙二醇甲醚 在 三氯化磷 作用下， 以 苯 为溶剂， 反应 2.0h， 以85%的产率得到bis(2-methoxyethyl) phosphite
  参考文献：
  名称：

  聚氧杂烷基磷酸酯与Fe(III)在乙醇中络合反应的动力学研究

  摘要：

  摘要 采用动力学方法、31P NMR和半经验方法研究了Fe(III)阳离子在乙醇中与七种氧杂烷基磷酸酯和磷酸乙酯的络合反应。几乎所有磷酸盐的 ΔG≠ 值都在 53-56 kJ mol-1 的范围内。对于所研究系统的 ΔS≠ 值观察到最大差异，而活化焓 ΔH≠ 由活化熵补偿。讨论了 Fe(III) 阳离子和氧杂烷基磷酸酯之间形成的配合物的结构以及这些反应的机制。

  DOI：

  10.1016/s0022-2860(02)00164-3

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。
• Palladium-catalyzed desulfitative C–P coupling of arylsulfinate metal salts and H-phosphonates
  作者：Junchen Li、Xiaojing Bi、Hongmei Wang、Junhua Xiao

  DOI：10.1039/c4ra01270d

  日期：——

  Catalyzed by palladium(II) chloride, a diverse range of arylsulfinate sodium, potassium, lithium, silver, zinc, and copper salts undergo desulfination/C–P coupling with H-phosphonates, in the presence of silver(I) carbonate as oxidant, to produce useful arylphosphonates under microwave irradiation.

  在碳酸亚银（I）存在下，氯化钯（II）催化多种芳基亚磺酸钠，钾，锂，银，锌和铜盐与H-膦酸酯进行脱硫/ CP偶联，在微波辐射下产生有用的芳基膦酸酯。
• Synthesis and antiviral activity of novel pyrazole amides containing α-aminophosphonate moiety
  作者：Lintao Wu、Baoan Song、Pinaki S. Bhadury、Song Yang、Deyu Hu、Linhong Jin

  DOI：10.1002/jhet.591

  日期：2011.3

  A series of novel pyrazole amides J1, J2, J3, J4, J5, J6, J7, J8, J9, J10, J11, J12, J13, J14, J15 containing an α‐aminophosphonate moiety were synthesized and subsequently characterized by spectral (IR, 1H‐, 13C‐, 31P‐, and 19F‐NMR) data and elemental analysis. The racemic sample of J1 was further separated into its enantiomers under normal‐phase condition on two immobilized polysaccharide‐based chiral

  合成了一系列新颖的吡唑酰胺J1，J2，J3，J4，J5，J6，J7，J8，J9，J10，J11，J12，J13，J14，J15，含有α-氨基膦酸酯部分，并随后通过光谱（IR ，1 H‐，13 C‐，31 P‐和19 F‐NMR）数据和元素分析。J1的外消旋体样品在两个固定的基于多糖的手性固定相（Chiralpak IA和Chiralpak IC）上，在正相条件下将其进一步分离为对映体。合成的化合物在生物测定中显示出一定程度的抗病毒活性。标题化合物（J3，J10和J12）在0.5 mg / mL的浓度下对烟草花叶病毒显示出一定的治愈活性（分别为39.9％，41.8％，50.1％）。杂环化学杂志，00，00（2011）。
• [BMIM]Cl Catalyzed One-Pot Synthesis of α-Aminophosphonate Derivatives Containing a 4-Phenoxyquinazoline Moiety under Microwave Irradiation
  作者：Song Bai、Baoan Song、Pinaki S. Bhadury、Song Yang、Deyu Hu、Wei Xue

  DOI：10.1002/cjoc.201190035

  日期：2011.1

  [BMIM]Cl catalyzed three component Mannich‐type reaction of 4‐(quinazolin‐4‐yloxy)benzenamine and aldehyde with dialkyl phosphite under microwave irradiation has been described. The salient features of the reaction leading to new α‐aminophosphonates include shorter reaction time and good yields. The method is environmentally friendly and does not require toxic catalysts or solvents. To the best of

  [BMIM] Cl在微波辐射下催化了4-（喹唑啉-4-基氧基）苯甲胺和醛与亚磷酸二烷基酯的三组分曼尼希型反应。产生新的α-氨基膦酸酯的反应的显着特征包括较短的反应时间和良好的收率。该方法是环境友好的并且不需要有毒的催化剂或溶剂。据我们所知，这是[BMIM] Cl诱导α-氨基膦酸酯衍生物一锅合成的第一份报告。
• 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。