diethyl (N,N-dimethylaminomethyl)phosphonate | 3958-40-5

• 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: diethyl (N,N-dimethylaminomethyl)phosphonate
• 英文别名: Diethyl <(Dimethylamino)methyl>phosphonate；(N,N-dimethylaminomethyl)phosphonate de diethyle；Dimethylamino-methan-phosphonsaeure-diethylester；diethyl N,N-dimethylaminomethanephosphonate；diethyl N,N-dimethylaminomethylphosphonate；diethyl((dimethylamino)methyl)phosphonate；1-diethoxyphosphoryl-N,N-dimethyl-methanamine；1-diethoxyphosphoryl-N,N-dimethylmethanamine
• CAS: 3958-40-5
• 化学式: C₇H₁₈NO₃P
• 分子量: 195.199
• InChiKey: VHKHQYDKHMKDOB-UHFFFAOYSA-N

物化性质

• 沸点：
  72-77 °C(Press: 0.4 Torr)
• 密度：
  1.037±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.3
• 重原子数：
  12
• 可旋转键数：
  6
• 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

安全信息

• 海关编码：
  2931900090

反应信息

• 作为反应物：
  描述：

  diethyl (N,N-dimethylaminomethyl)phosphonate 生成 1-Phenyl-2-diethylphosphono-2-dimethylamino-ethylen
  参考文献：
  名称：

  Eine einfache Methode zur Herstellung von 1-Phosphonatoenaminen

  摘要：

  DOI：

  10.1055/s-1977-24389
• 作为产物：
  描述：

  四乙基焦亚磷酸盐 、 四甲基甲烷二胺 生成 diethyl (N,N-dimethylaminomethyl)phosphonate
  参考文献：
  名称：

  Boehme,H.; Meyer-Dulheuer,K.-H., Justus Liebigs Annalen der Chemie, 1965, vol. 688, p. 78 - 93

  摘要：

  DOI：

文献信息

• Catalyst-Free and Selective C–N Bond Functionalization: Stereospecific Three-Component Coupling of Amines, Dichloromethane, and &gt;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。
• Dimethylaminomethylphosphonic Acid Derivatives-Promoted CuI-Catalyzed Synthesis of Aryl Ethers
  作者：Hua Fu、Ying Jin、Jinyong Liu、Yingwu Yin、Yuyang Jiang、Yufen Zhao

  DOI：10.1055/s-2006-941587

  日期：2006.6

  An inexpensive and efficient catalyst system for synthesis of aryl ethers has been developed by using 20 mol% CuI as the catalyst, 30 mol% dimethylaminomethylphosphonic acid derivatives as the new ligands, K2CO3 as the base and toluene as the ­solvent. This is the first example using aminophosphonates as the ligands for Ullmann ether coupling reaction.

  一种廉价且高效的催化剂系统用于合成芳基醚，使用20 mol%的CuI作为催化剂，30 mol%的二甲氨基甲基膦酸衍生物作为新配体，K2CO3作为碱，甲苯作为溶剂。这是首次将氨基膦酸酯作为Ullmann醚偶联反应的配体。
• Utilisation en synthese du cation iminium genere in situ par oxydation electrochimique d'amines tertiaires
  作者：Gérard Bidan、Martial Genies

  DOI：10.1016/s0040-4020(01)97987-6

  日期：1981.1

  The electrochemical oxidation in acetonitrile of aliphatic amines (ACH3) in presence of a non-nucleophilic base (2,4,6-collidine) and of compounds containing weakly-activated hydrogens (RH) such as diethyl phosphonate and diethyl malonate gives the substituted derivatives ACH2R. These compounds result from the addition of the anion R− to the iminium cation ACH2+. Such a reaction is obtained with tribenzylamine

  在非亲核碱（2,4,6-可力丁）和含有弱活化氢（RH）的化合物（如膦酸二乙酯和丙二酸二乙酯）存在下，脂肪胺（ACH 3）在乙腈中的电化学氧化会产生取代基衍生物ACH 2 R.这些化合物导致从添加阴离子的R -对亚铵阳离子ACH 2 +。用三苄基胺和N，N-二甲基-对甲苯胺获得这种反应。此外（CH 3）2 NCH 2 -CH（CO 2 C 2 H 5）2脱氨基和通过连续迈克尔反应的其它取代的丙二酸酯也与亚胺阳离子（CH反应给出3）2 N + CH 2。
• Development of a one-pot method for the homologation of aldehydes to carboxylic acids
  作者：James McNulty、Priyabrata Das

  DOI：10.1016/j.tet.2009.07.032

  日期：2009.9

  A highly efficient method is described for the one-carbon homologation of aldehydes to carboxylic acid derivatives employing the reaction of a 1,1-bis-dimethylphosphonate derivative with the aldehyde and controlled acid hydrolysis of the derived α-phosphonoenamine intermediate.

  描述了一种高效的方法，该方法利用1，1-双-二甲基膦酸酯衍生物与醛的反应和衍生的α-膦烯胺中间体的受控酸水解，将醛类一碳均化为羧酸衍生物。
• An improved synthesis of α-phosphonoenamines based on a modified Peterson olefination
  作者：James McNulty、Priyabrata Das、Don Gosciniak

  DOI：10.1016/j.tetlet.2007.11.066

  日期：2008.1

  An efficient, stereoselective method for the synthesis of α-phosphonoenamines based on a modified Peterson olefination is described. The carbanion derived from isolatable intermediate 2 reacts with aromatic or aliphatic aldehydes selectively eliminating in Peterson fashion to deliver functionally rich α-phosphonoenamines 3. The synthetic utility of these enamines is demonstrated by their hydrolysis

  描述了一种基于改进的彼得森烯化合成α-膦烯胺的有效的立体选择方法。衍生自可分离中间体2的碳负离子与芳族或脂族醛反应，以Peterson方式选择性地消除，从而生成功能丰富的α-膦烯胺3。这些烯胺的合成效用通过其水解以良好的产率产生同源羧酸来证明。