dimethoxymethyl phosphonic acid dimethyl ester | 30410-95-8

• 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: dimethoxymethyl phosphonic acid dimethyl ester
• 英文别名: dimethyl (dimethoxymethyl)phosphonate；dimethyl (dimetoxymethyl)phosphonate；Dimethoxy-methanphosphonsaeure-dimethylester；Dimethoxymethan-phosphonsaeure-dimethylester；Dimethoxymethylphosphonsaeure-dimethylester；dimethoxyphosphoryl(dimethoxy)methane
• CAS: 30410-95-8
• 化学式: C₅H₁₃O₅P
• 分子量: 184.129
• InChiKey: DTILCMQFCUCGAG-UHFFFAOYSA-N

物化性质

• 沸点：
  65 °C(Press: 1 Torr)
• 密度：
  1.143±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.6
• 重原子数：
  11
• 可旋转键数：
  5
• 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：

  dimethoxymethyl phosphonic acid dimethyl ester 在 N-溴代丁二酰亚胺(NBS) 作用下， 以 苯 为溶剂， 反应 1.0h， 以80%的产率得到甲膦酸三乙酯
  参考文献：
  名称：

  Livantsov, M. V.; Proskurnina, M. V.; Prishchenko, A. A., Journal of general chemistry of the USSR, 1984, vol. 54, # 11, p. 2237 - 2249

  摘要：

  DOI：
• 作为产物：
  描述：

  原甲酸三甲酯 在 亚磷酸 作用下， 生成 dimethoxymethyl phosphonic acid dimethyl ester
  参考文献：
  名称：

  Gross,H.; Costisella,B., Journal fur praktische Chemie (Leipzig 1954), 1974, vol. 316, p. 550 - 556

  摘要：

  DOI：

文献信息

• Dealkylation Reaction of Acetals, Phosphonate, and Phosphate Esters with Chlorotrimethylsilane/Metal Halide Reagent in Acetonitrile, and Its Application to the Synthesis of Phosphonic Acids and Vinyl Phosphates
  作者：Tsuyoshi Morita、Yoshiki Okamoto、Hiroshi Sakurai

  DOI：10.1246/bcsj.54.267

  日期：1981.1

  A mild and efficient method has been developed for carbon-oxygen bond cleavage using chlorotrimethylsilane/sodium iodide in acetonitrile. It was applied to synthetic transformation under nonaqueous and neutral conditions, such as acetal deprotection and the synthesis of phosphonic acids from the corresponding dialkyl phosphonates via methanolysis of their silyl esters. Effectiveness of various kinds

  已经开发出一种在乙腈中使用三甲基氯硅烷/碘化钠进行碳氧键断裂的温和有效的方法。它被应用于非水和中性条件下的合成转化，如缩醛脱保护和从相应的膦酸二烷基酯通过其甲硅烷基酯的甲醇分解合成膦酸。通过 1 H NMR 在乙腈溶液中检测了各种金属碘化物或碘化铵对此类脱烷基作用的有效性。用碘化锂或碘化钾代替碘化钠也获得了令人满意的结果。然而，铜（I）或碘化季铵是无效的。乙腈中的氯三甲基硅烷/溴化锂对多功能膦酸酯或二烷基乙烯基磷酸酯的选择性脱烷基作用有效。
• The Preparation of Phosphonic Acids Having Labile Functional Groups
  作者：Tsuyoshi Morita、Yoshiki Okamoto、Hiroshi Sakurai

  DOI：10.1246/bcsj.51.2169

  日期：1978.7

  Phosphonic acids having labile functional groups have been prepared quantitatively by the hydrolysis of bis(trimethylsilyl) phosphonates, were prepared by the reaction under mild conditions of the corresponding dialkyl phosphonates with bromotrimethylsilane.

  具有易变官能团的磷酸已经通过双(trimethylsilyl)磷酸酯的水解定量制备，并通过相应的双烷基磷酸盐与溴代三甲基硅烷在温和条件下反应制备。
• Organophosphorus intermediates. VI. The acid-catalysed reaction of trialkyl orthoformates with phosphinic acid
  作者：MJ Gallagher、H Honegger

  DOI：10.1071/ch9800287

  日期：——

  Trialkyl orthoformates react with phosphinic acid to give the corresponding alkyl phosphinate and alkyl mono- or bis- (dialkoxymethyl)phosphinates; dialkyl phosphonites and phosphine, PH3, are also formed. The formation of P-alkylated products is acid- catalysed and is believed to proceed by alkylation of the trivalent tautomer of phosphinic acid (or its ester) by the dialkoxymethyl carbonium ion arising from the ortho ester in the presence of acid. A comparison with the corresponding reactions of phosphonic acid suggests that the trivalent tautomer of phosphinic acid [HP(OH)2] is formed much more readily than the trivalent form of phosphonic acid [P(OH)3] and this is accounted for by proposing that the equilibria RPH(O)OR′ +H+ ↔ RP+H(OH)OR' ↔ RP(OH)OR'+H+ (R = H, OH; R' = H, alkyl) lie further to the right for R = H than for R = OH because of inductive effects. 31P and 1H n.m.r. data are reported.

  三烷基原甲酸酯 与膦酸反应生成相应的膦酸烷基酯和 烷基单-或双-（二烷氧基甲基）膦酸盐； 还可生成二烷基亚膦酸盐和膦 PH3。P P-烷基化产物的形成是在酸催化下进行的，据信是通过三价膦酸的烷基化进行的。 膦酸的三价同系物（或其酯）通过 的三价同系物（或其酯）发生烷基化的过程。 酸。与膦酸的相应反应相比 表明，膦酸的三价同系物[HP(OH)2]比三价同系物更容易形成。 比三价形式的膦酸 [P(OH)3] 更容易形成。 这可以通过提出以下平衡来解释 rph(o)or′ +h+ ↔ rp+h(oh)or' ↔ rp(oh)or'+h+ （r = h，oh；r' = h、 烷基） 比 R = H 由于感应效应，R = H 时比 R = OH 时更靠右。31P 和 1H n.m.r. 数据。
• Reaction of P(III) chlorides with aldehydes: II. Reaction of primary intermediates with aprotic nucleophiles: Ethylene oxide, acetals, trialkyl orthoformates, and trialkyl phosphites
  作者：M. B. Gazizov、R. A. Khairullin、R. F. Karimova

  DOI：10.1134/s1070363213120116

  日期：2013.12

  Structure of primary intermediates of the reaction of P(III) chlorides with aliphatic aldehydes was confirmed by their reactions with such aprotic reagents like ethylene oxide, trialkyl phosphites, acetals, and trialkyl orthoformates. Principle difference in the reactions of these nucleophiles with intermediates containing active chlorine atom at P(III) and those not containing was established. The

  P（III）氯化物与脂族醛反应的主要中间体的结构已通过其与非质子传递剂（如环氧乙烷，亚磷酸三烷基酯，缩醛和原甲酸三烷基酯）的反应得到证实。确定了这些亲核试剂与在P（III）处含有活性氯原子的中间体和不含有这些中间体的反应的原理差异。前者以及所有其他P（III）氯化物直接与亲核试剂反应，而后者缓慢分解为醛和P（III）氯化物，后者与亲核试剂反应。
• Cathode-catalyzed transesterification of alkylphosphonates
  作者：M. E. Niyazymbetov、B. Kostizella、I. Keitel、K. H. Schwartz

  DOI：10.1007/bf00959658

  日期：1991.1

  The cathodic electrolysis of aliphatic alcohols and alkylphosphonates in acetonitrile with 0.5 N Et4NClO4 as the base electrolyte leads to mono- and ditransesterified phosphonates. The yield and ratio of these products is a function of the nature of the starting reagents and amount of current passed.