O,O'-diisopropyl (N,N-diethyl-aminomethyl)phosphonate | 118896-15-4

• 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: O,O'-diisopropyl (N,N-diethyl-aminomethyl)phosphonate
• 英文别名: diisopropyl (N,N-diethylaminomethyl)phosphonate；diisopropyl N,N-diethylaminomethylphosphonate；N-[di(propan-2-yloxy)phosphorylmethyl]-N-ethylethanamine
• CAS: 118896-15-4
• 化学式: C₁₁H₂₆NO₃P
• 分子量: 251.306
• InChiKey: FRPCGMYHJLDOHO-UHFFFAOYSA-N

物化性质

• 沸点：
  81-82 °C(Press: 0.47 Torr)
• 密度：
  0.985±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  16
• 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：
  38.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  O,O'-diisopropyl (N,N-diethyl-aminomethyl)phosphonate 在 potassium tert-butylate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成 diisopropyl 1-(N,N-diethylamino)-3-methyl-3-butenylphosphonate
  参考文献：
  名称：

  Makomo, Hubert; Saquet, Monique; Simeon, Fabrice, Phosphorus, Sulfur and Silicon and the Related Elements, 1996, vol. 109, # 1-4, p. 445 - 448

  摘要：

  DOI：
• 作为产物：
  描述：

  二乙基(异丙氧基甲基)胺 、 异丙醇 在 phosphorus 、 sodium isopropylate 作用下， 反应 240.0h， 以26%的产率得到O,O'-diisopropyl (N,N-diethyl-aminomethyl)phosphonate
  参考文献：
  名称：

  Reaction of Elemental (White) Phosphorus with (Alkoxymethyl)dialkylamines

  摘要：

  The reaction of elemental (white) phosphorus with (alkoxymethyl)dialkylamines in the presence of sodium alkoxide results in complete conversion of P-4 in proton-donor solvents only. P-31 NMR spectroscopy allowed detection of the initial formation of P-III compounds whose subsequent transformations primarily provide phosphinate and phosphonate structures. Under the reaction conditions, trialkyl phosphites further react with (alkoxymethyl)dialkylamines to form dialkyl (dialkylamino)methylphosphonates.

  DOI：

  10.1023/b:rugc.0000015981.21117.9f

文献信息

• Catalyst-Free and Selective C–N Bond Functionalization: Stereospecific Three-Component Coupling of Amines, Dichloromethane, and >P(O)H Species Affording α-Aminophosphorus Compounds
  作者：Yalei Zhao、Xiuling Chen、Tieqiao Chen、Yongbo Zhou、Shuang-Feng Yin、Li-Biao Han

  DOI：10.1021/jo501961h

  日期：2015.1.2

  and selective C–N bond functionalization has been achieved through three-component coupling of amines, dihalomethane, and >P(O)H species. This reaction takes place stereospecifically with retention of configuration at phosphorus, which can produce various new optically active phosphorus analogues of α-amino acids.

  通过胺，二卤甲烷和> P（O）H物质的三组分偶联，实现了无催化剂和选择性C–N键的官能化。该反应立体定向地进行，并且保留了在磷处的构型，这可以产生各种新的α-氨基酸的旋光性磷类似物。
• Chemoselective Reduction of the P=O Bond in the Presence of P-O and P-N Bonds in Phosphonate and Phosphinate Derivatives
  作者：Sylwia Sowa、K. Michał Pietrusiewicz

  DOI：10.1002/ejoc.201801518

  日期：2019.2.7

  The chemoselective reduction of P=O bond in α‐hydroxy and α‐amino phosphonic/phosphinic acid derivatives can be achieved without concomitant scission of their ester and amide bonds using commercially available BH3 complexes. The reduction involves an intramolecular assistance by the proximal OH or NH groups enabling preferential removal of the phosphoryl oxygen.

  使用市售BH 3络合物，无需伴随其酯键和酰胺键的断裂即可实现α-羟基和α-氨基膦酸/次膦酸衍生物中P = O键的化学选择性还原。还原涉及通过近端的OH或NH基团的分子内协助，从而能够优先去除磷酰氧。
• Synthesis and Acid-Base Properties of  -Aminophosphoryl Compounds
  作者：S. V. Zakharov、G. Kh. Nuriazdanova、A. R. Garifzyanov、V. I. Galkin、R. A. Cherkasov

  DOI：10.1023/b:rugc.0000042422.61124.b3

  日期：2004.6

  alpha-Aminophosphoryl compounds of the phosphonate, phosphine oxide, and alpha,omega-bis(phosphine oxide) series and some of their thiophosphoryl analogs were synthesized. Potentiometric measurements of the pK(a) of the conjugate acids revealed an insignificant effect of variation of substituents on the phosphorus, nitrogen, and alpha-carbon atoms on the basicity of the phosphorylated amines. The latter are weak bases. Organophosphorus groups decrease the basicity of the amines by almost 5 pK(a) units. The role of the hydrophobic effect and intramolecular H-bonding in the obtained substances was discussed.
• Kaushik; Charandabi; Ettel, Inorganic Chemistry, 1989, vol. 28, # 5, p. 897 - 899
  作者：Kaushik、Charandabi、Ettel、Lofthouse、Morse

  DOI：——

  日期：——
• Charandabi, M. R. M. D.; Ettel, M. L.; Kaushik, M. P., Phosphorus, Sulfur and Silicon and the Related Elements, 1989, vol. 44, p. 223 - 234
  作者：Charandabi, M. R. M. D.、Ettel, M. L.、Kaushik, M. P.、Huffman, J. H.、Morse, K. W.

  DOI：——

  日期：——