dimethyl phosphonate | 31682-64-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: dimethyl phosphonate
• 英文别名: dimethyl phosphite；dimethoxyphosphoryl；dimethoxy-phosphanyloxyl
• CAS: 31682-64-1
• 化学式: C₂H₆O₃P
• 分子量: 109.042
• InChiKey: VYEUPWFWPHVSDU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.94
• 重原子数：
  6.0
• 可旋转键数：
  2.0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  35.53
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  (4Z)-2-(4-chlorophenyl)-4-[(4-methoxyphenyl)methylidene]-5-methylpyrazol-3-one 、 dimethyl phosphonate 以70%的产率得到
  参考文献：
  名称：

  ZIMAITY T.; AFSAH E.; ABBAS M., INDIAN J. CHEM., 1978, B 16, 876-879

  摘要：

  DOI：
• 作为产物：
  描述：

  亚磷酸二甲酯 在 二叔丁基过氧化物 作用下， 以 二氯甲烷 为溶剂， 生成 dimethyl phosphonate
  参考文献：
  名称：

  McLauchlan, Keith A.; Simpson, Nigel J. K., Journal of the Chemical Society. Perkin transactions II, 1990, # 8, p. 1371 - 1377

  摘要：

  DOI：

文献信息

• The Reaction of Organophosphorus Radicals With Vinyl Acetate and Acrylonitrile in the Presence of an Aminoxyl Radical Scavenger
  作者：WK Busfield、ID Grice、ID Jenkins

  DOI：10.1071/ch9950625

  日期：——

  The radical-trapping technique employing 1,1,3,3-tetramethyl-1,3-dihydro-2H-isoindol-2-yloxyl (1) as a radical scavenger has been used to study the reaction of diphenylphosphinoyl (2) and dimethoxyphosphinoyl (3) radicals with vinyl acetate and acrylonitrile. The phosphorus- centred radicals were generated by hydrogen abstraction from diphenylphosphine oxide and dimethyl phosphite respectively. Diphenylphosphine oxide was approximately three times as reactive as dimethyl phosphite towards hydrogen abstraction by t- butoxyl radicals and four times as reactive as tetrahydrofuran (towards abstraction of an α-hydrogen). Diphenylphosphinoyl radicals were found to be relatively nucleophilic and, in competition experiments, reacted about an order of magnitude faster with acrylonitrile than with vinyl acetate. Dimethoxyphosphinoyl radicals were rather less nucleophilic and reacted only twice as fast with acrylonitrile as they did with vinyl acetate. In the presence of excess aminoxyl (1), both diphenylphosphinoyl and dimethoxyphosphinoyl radicals were efficiently scavenged to produce stable phosphinic and phosphate esters respectively. The rate of scavenging was close to diffusion-controlled (c. 1.8×109 1. mol-1 s-1).

  以 1,1,3,3-四甲基-1,3-二氢-2H-异吲哚-2-基氧基（1）为自由基清除剂的自由基捕获技术被用于研究二苯基膦酰（2）和二甲氧基膦酰（3）自由基与醋酸乙烯酯和丙烯腈的反应。以磷为中心的自由基分别通过从二苯基氧化膦和亚磷酸二甲酯中抽取氢而生成。 二苯基氧化膦对 t-丁氧自由基析取氢的反应活性大约是亚磷酸二甲酯的三倍，是四氢呋喃（析取 α-氢）的四倍。研究发现，二苯基膦酰基具有较强的亲核性，在竞争实验中，与丙烯腈反应的速度比与醋酸乙烯反应的速度快一个数量级。 二甲氧基膦酰基的亲核性较弱，与丙烯腈反应的速度仅是与醋酸乙烯反应速度的两倍。在存在过量氨基己基（1）的情况下，二苯基膦酰和二甲氧基膦酰自由基都能被有效清除，分别生成稳定的膦酸酯和磷酸酯。清除速率接近于扩散控制（c. 1.8×109 1. mol-1 s-1）。
• Properties and reactions of trimethyl phosphite, trimethyl phosphate, triethyl phosphate, and trimethyl phosphorothionate by ion cyclotron resonance spectroscopy
  作者：Ronald V. Hodges、T. J. McDonnell、J. L. Beauchamp

  DOI：10.1021/ja00524a016

  日期：1980.2
• A catalyst-free, three-component decarboxylative coupling of amino acids with aldehydes and H-dialkylphosphites for the synthesis of α-aminophosphonates
  作者：Babak Kaboudin、Leila Karami、Jun-ya Kato、Hiroshi Aoyama、Tsutomu Yokomatsu

  DOI：10.1016/j.tetlet.2013.06.129

  日期：2013.9

  A simple, efficient, and new method is developed for the synthesis of alpha-aminophosphonates via a three-component, catalyst-free decarboxylative coupling of amino acids with aldehydes and H-dialkyl phosphite. Treatment of amino acids with aldehydes and diethyl phosphite in the absence of catalyst, base, and ligand give alpha-aminophosphonates in moderate to good yields. This method is simple, rapid, and high-yielding. (C) 2013 Elsevier Ltd. All rights reserved.
• One-Carbon Ring Expansion in Cyclopentanones as a Free-Radical Clock
  作者：C. Chatgilialoglu、V. I. Timokhin、M. Ballestri

  DOI：10.1021/jo9716338

  日期：1998.2.1
• EL-HASHASH M.; MAHMOUD M.; EL-FIKY H., REV. ROUM. CHIM., 1979, 24, NO 8, 1191-1202
  作者：EL-HASHASH M.、 MAHMOUD M.、 EL-FIKY H.

  DOI：——

  日期：——

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