diethyl 1-(diethylphosphono)ethylphosphate | 4470-71-7

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 有机磷酸及其衍生物
• 英文名称: diethyl 1-(diethylphosphono)ethylphosphate
• 英文别名: diethyl(1-diethylphosphorylethyl)phosphonate；Phosphorsaeure-1-(diethoxyphosphinyl)ethyl-diethylester；diethyl 1-(diethylphosphonoylethyl)phosphate；1-(diethoxyphosphoryl)ethyl diethyl phosphate；Phosphorsaeure-(1-diethylphosphono-ethyl)-diethylester；<1-(O,O-Diaethyl-phosphonooxy)-aethyl>-phosphonsaeure-diaethylester；Diethyl-<1-(O,O-diethyl-phosphono)-ethyl>-phosphat；Phosphorsaeure-diethyl-(1-diethylphosphono-ethyl)-ester；Diethyl-(α-diethylphosphon)-ethylphosphat；1-(Diaethoxyphosphinyl)-aethyl-diaethylphosphat；1--1--ethan；1--ethylphosphonsaeure-diethylester；Diaethyl-<1-(diaethyl-phosphono)-aethyl>-phosphat；Diethyl-<1-(diethoxyphosphinyl)-ethyl>-phosphat；1-Diethylphosphonooxy-1-diethylphosphono-ethan；(1-Diaethoxyphosphoryloxy-aethyl)-phosphonsaeure-diaethylester；phosphoric acid 1-diethoxyphosphoryl-ethyl ester diethyl ester；(1-diethoxyphosphoryloxy-ethyl)-phosphonic acid diethyl ester；Phosphoric acid, 1-(diethoxyphosphinyl)ethyl diethyl ester；1-diethoxyphosphorylethyl diethyl phosphate
• CAS: 4470-71-7
• 化学式: C₁₀H₂₄O₇P₂
• 分子量: 318.244
• InChiKey: GWHBHPUCUQJEEH-UHFFFAOYSA-N

物化性质

• 沸点：
  151-152 °C(Press: 1 Torr)
• 密度：
  1.1542 g/cm3

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  19
• 可旋转键数：
  11
• 环数：
  0.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  80.3
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  diethyl 1-(diethylphosphono)ethylphosphate 生成 (1-chloro-ethyl)-phosphonic acid
  参考文献：
  名称：

  N.m.r. Study of the P-C(OH)-P to P-C-O-P Rearrangement: Tetraethyl 1-Hydroxyalkylidenediphosphonates

  摘要：

  DOI：

  10.1021/ja00869a022
• 作为产物：
  描述：

  (1-hydroxyethylidene)-1,1-bisphosphonic acid tetraethyl ester 在 sodium ethanolate 作用下， 以 乙醇 为溶剂， 生成 diethyl 1-(diethylphosphono)ethylphosphate
  参考文献：
  名称：

  N.m.r. Study of the P-C(OH)-P to P-C-O-P Rearrangement: Tetraethyl 1-Hydroxyalkylidenediphosphonates

  摘要：

  DOI：

  10.1021/ja00869a022

文献信息

• Tetraalkyl Hydroxymethylene-bisphosphonate and Dialkyl 1-Diphenylphosphinoyl-1-hydroxy-ethylphosphonate Derivatives by the Pudovik Reaction and Their Rearranged Products
  作者：Zsuzsanna Szalai、György Keglevich

  DOI：10.3390/molecules26247575

  日期：——

  The reaction of diethyl α-oxoethylphosphonate and diethyl oxobenzylphosphonate with diethyl phosphite, dimethyl phosphite, and diphenylphosphine oxide affords, depending on the substrates and conditions (nature and quantity of the amine catalyst, temperature, and solvent), the Pudovik adduct and/or the corresponding >P(O)–CH–O–P(O)< product formed by rearrangement. The nature of the substituent on

  α-氧代乙基膦酸二乙酯和氧代苄基膦酸二乙酯与亚磷酸二乙酯、亚磷酸二甲酯和氧化二苯基膦的反应根据底物和条件（胺催化剂的性质和数量、温度和溶剂）提供 Pudovik 加合物和/或相应的 >P(O)–CH–O–P(O)< 重排产物。中心碳原子上的取代基（甲基或苯基）的性质影响重排的倾向。具有不同 P(O)Y 函数（Y = RO 或 Ph）的不对称产物（加合物或重排物质）表现出有趣的 NMR 特征。
• Synthesis of α-hydroxy-methylenebisphos-phonates by the microwave-assisted reaction of α-oxophosphonates and dialkyl phosphites under solventless conditions
  作者：Alajos Grün、István Gábor Molnár、Béla Bertók、István Greiner、György Keglevich

  DOI：10.1002/hc.20558

  日期：——

  The synthesis of hydroxy-methylenebisphosphonates (2a–c) by the addition of dialkyl phosphite to the carbonyl group of the corresponding α-oxophosphonate (1a–c) was studied under microwave irradiation (MW) and solventless conditions in the presence of dialkylamine as the catalyst. After optimization, products 2a and 2b were obtained selectively and in good yields avoiding the formation of the phosphonate-phosphate

  在微波辐射 (MW) 和无溶剂条件下，在二烷基胺存在下研究了通过将亚磷酸二烷基酯加成到相应的 α-氧代膦酸酯 (1a-c) 的羰基上合成羟基-亚甲基双膦酸酯 (2a-c)。催化剂。优化后，产物 2a 和 2b 被选择性地以良好的收率获得，避免了由于重排而形成的膦酸盐-磷酸盐副产物（3a 和 3b）。与不太有效的热反应相比，MW 辅助的羟基双膦酸盐（2a 和 2b）合成提供了完全的转化率和 100% 的化学选择性。同时，苯基取代的亚甲基双膦酸酯2c只能以75%的选择性获得。© 2009 Wiley Periodicals, Inc. 杂原子化学 20:350–354, 2009; 在线发表于 Wiley InterScience (www.interscience.wiley.com)。DOI 10.1002/hc.20558
• Phenyl-, benzyl-, and unsymmetrical hydroxy-methylenebisphosphonates as dronic acid ester analogues from α-oxophosphonates by microwave-assisted syntheses
  作者：György Keglevich、Alajos Grün、István Gábor Molnár、István Greiner

  DOI：10.1002/hc.20727

  日期：2011.9

  The microwave (MW)-assisted addition of dialkyl phosphites to α-oxophosphonates was investigated and optimized under solventless conditions to provide the phenyl- and benzyl-hydroxy-methylenebisphosphonates efficiently by suppressing the rearrangement side reaction. Methyl-hydroxy-methylenebisphosphonates with mixed ester functionalities and an analogous diester-diacid were also synthesized. It was

  在无溶剂条件下对亚磷酸二烷基酯与 α-氧代膦酸酯的微波 (MW) 辅助加成进行了研究和优化，以通过抑制重排副反应有效地提供苯基-和苄基-羟基-亚甲基双膦酸酯。还合成了具有混合酯官能团和类似的二酯二酸的甲基-羟基-亚甲基双膦酸酯。发现α-氧代膦酸酯也可以转化为羟基-亚甲基双膦酸酯和/或重排产物，而无需使用亚磷酸二烷基酯作为试剂并小心排除水，只需在室温下静置、热处理或MW辐照。还详细研究了通过前体的受控分解发生并导致中间体形成亚磷酸二烷基酯的这些新反应。© 2011 Wiley Periodicals, Inc. 杂原子化学 22:640–648, 2011; 在 wileyonlinelibrary.com 上在线查看这篇文章。DOI 10.1002/hc.20727
• Oxidative phosphonylation of aromatic compounds
  作者：Franz Effenberger、Hariolf Kottmann

  DOI：10.1016/s0040-4020(01)97192-3

  日期：1985.1

  anodic oxidation proceeds either via phosphinium radical cations, which then attack the arenes electrophilically, or via arene radical cations, which add the trialkylphosphite as nucleophile. Aryl phosphonates are also obtained in good yield by chemical oxidation with peroxodisulfate/AgNO3 in acetonitrile/water or glacial acetic acid. The diethylphosphinium radical cation, formed from diethylphosphite by

  可以通过化学或阳极氧化由相应的芳烃和三或二烷基磷酸酯以高收率制备芳基膦酸酯。阳极氧化可通过基自由基阳离子进行，然后再以亲电子方式攻击芳烃，或通过芳烃基阳离子进行，后者将亚磷酸三烷基酯添加为亲核试剂。通过用过二硫酸盐/ AgNO 3在乙腈/水或冰醋酸中进行化学氧化，也可以以高收率获得芳基膦酸酯。由亚磷酸二乙酯通过用Ag（II）氧化而形成的二乙基phosph自由基阳离子被认为是该过程中的反应性物质。提高银盐浓度导致多膦酰化作用的增加。确定氧化膦酰化过程的选择性比。
• Bisphosphorylation of anhydrides – convenient access to bisphosphonates with a P–O–C–P motif
  作者：Xin-Yue Zhang、Qi-Wei Li、Hui-Qi Yue、Zi-Qian Wu、Ji Li、Ming Li、Lu Lu、Shang-Dong Yang、Bin Yang

  DOI：10.1039/d2cc01472f

  日期：——

  novel strategy of bisphosphorylation of anhydrides with P(O)–H reagents via a DMAP-catalyzed and DBU-promoted process has been developed. These one-step transformations proceed efficiently to provide convenient access to a variety of P–O–C–P motif containing organophosphorus compounds. In addition, the gram-scale synthesis and the efficient recovery of the by-product highlight the sustainability and applicability

  已经开发了一种通过DMAP 催化和 DBU 促进的过程用 P(O)-H 试剂双磷酸化酸酐的新策略。这些一步转换有效地进行，以方便地访问各种含有有机磷化合物的 P-O-C-P 基序。此外，克级合成和副产物的高效回收突出了该方法的可持续性和适用性。