(1-benzylamino-1-phenyl-ethyl)-phosphonic acid diethyl ester | 249889-51-8

• 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: (1-benzylamino-1-phenyl-ethyl)-phosphonic acid diethyl ester
• 英文别名: (1-benzylamino-1-phenylethyl)phosphonic acid diethyl ester；diethyl (1-phenyl-1-benzylaminoeth-1-yl)phosphonate；Phosphonic acid, [1-phenyl-1-[(phenylmethyl)amino]ethyl]-, diethyl ester；N-benzyl-1-diethoxyphosphoryl-1-phenylethanamine
• CAS: 249889-51-8
• 化学式: C₁₉H₂₆NO₃P
• 分子量: 347.394
• InChiKey: PQWYDSHIXWOBEO-UHFFFAOYSA-N

物化性质

• 沸点：
  458.8±40.0 °C(Predicted)
• 密度：
  1.113±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  24
• 可旋转键数：
  9
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.37
• 拓扑面积：
  47.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  二乙基亚磷酸氢酯 、 苯乙酮 、 苄胺 在 magnesium(II) perchlorate 作用下， 以 1,2-二氯乙烷 为溶剂， 反应 2.0h， 以90%的产率得到(1-benzylamino-1-phenyl-ethyl)-phosphonic acid diethyl ester
  参考文献：
  名称：

  高醛酸/醛，酮，胺和亚磷酸酯的三组分极高效反应（Kabachnik-Fields反应），用于合成α-氨基膦酸酯

  摘要：

  据报道，可商购的高氯酸镁是用于合成α-氨基膦酸酯的极其有效的催化剂。胺，醛或酮与亚磷酸二/三烷基酯的三组分反应（3-CR）（Kabachnik-Fields反应）在无溶剂条件下在一锅中进行，得到相应的α-氨基膦酸酯高产和短时间。与纯净条件下相比，溶剂的使用延迟了反应的速度并且需要更长的反应时间。涉及醛，没有任何吸电子取代基的芳族胺和亚磷酸酯的反应在室温下进行。涉及环状酮，具有吸电子取代基的芳族胺和芳基烷基酮（例如苯乙酮）的反应在室温或加热下需要更长的反应时间。在4-甲氧基苯甲醛，2,4-二硝基苯胺和亚磷酸二甲酯的反应过程中，发现高氯酸镁优于其他金属高氯酸盐和三氟甲磺酸盐。抗衡阴离子影响各种镁化合物的催化活性，发现高氯酸镁是最有效的。发现该反应通常与亚磷酸二-/三烷基酯和亚磷酸二芳基酯反应。镁（ClO4）本研究中2催化的α-氨基膦酸酯合成可能代表了真正的三组分反应，因为未观察到亚胺或α-羟基

  DOI：

  10.1021/jo062140i

文献信息

• A Novel Catalytic Three-Component Synthesis (Kabachnick-Fields Reaction) of α-Aminophosphonates from Ketones
  作者：Elena D. Matveeva、Nikolay S. Zefirov、Tatyana A. Podrugina、Elena V. Tishkovskaya、Larisa G. Tomilova

  DOI：10.1055/s-2003-42118

  日期：——

  A novel and highly convenient catalytic variant of the synthesis of α-aminophosphonates on basis of the Kabachnik-Fields reaction [three-component reaction of ketones, diethylphosphite and either benzylamine (series a) ofammonium carbonate (series b)] in the presence of tetra-tert-butylphthalocyanines has been developed. This method affords α-aminophosphonates in acceptable yields for various ketones

  基于 Kabachnik-Fields 反应 [酮、亚磷酸二乙酯和碳酸铵（系列 b）的苄胺（系列 b）的三组分反应]合成 α-氨基膦酸酯的一种新型且非常方便的催化变体-叔丁基酞菁已被开发。该方法以可接受的产率为各种酮提供 α-氨基膦酸酯，包括环状酮、空间位阻酮和笼酮。未取代的α-氨基膦酸也从b系列的相应酯中获得。
• Zirconium(IV) Compounds As Efficient Catalysts for Synthesis of α-Aminophosphonates
  作者：Srikant Bhagat、Asit K. Chakraborti

  DOI：10.1021/jo8009006

  日期：2008.8.1

  Zirconium(IV) compounds are reported as excellent catalysts for a three-component one-pot reaction of an amine, an aldehyde or a ketone, and a di/trialkyl/aryl phosphite to form α-aminophosphonates under solvent-free conditions at rt. Among the various zirconium compounds, ZrOCl2·8H2O and ZrO(ClO4)2·6H2O were most effective. The reactions were faster with dialkyl/diaryl phosphites than with trialkyl/triaryl

  据报道，锆（IV）化合物是胺，醛或酮与亚磷酸二/三烷基酯/芳基酯在室温下在无溶剂条件下形成三组分一锅法反应的极佳催化剂。在各种锆化合物中，ZrOCl 2 ·8H 2 O和ZrO（ClO 4）2 ·6H 2 O最有效。亚磷酸二烷基/二芳基酯的反应比亚磷酸三烷基酯/三芳基酯的反应更快。用芳基甲基醚和甲基酯基团没有发生O -Me裂解。α，β-不饱和羰基部分不与发色部分进行共轭加成。
• General Procedure for the Synthesis of α-Amino Phosphonates from Aldehydes and Ketones Using Indium(III) Chloride as a Catalyst
  作者：Brindaban C. Ranu、Alakananda Hajra、Umasish Jana

  DOI：10.1021/ol990079g

  日期：1999.10.1

  [GRAPHICS]A simple, efficient, and general method has been developed for the synthesis of alpha-amino phosphonates through a one-pot reaction of aldehydes and ketones with amines in the presence of indium(III) chloride as a catalyst.
• Synthesis and 31 P NMR characterization of new low toxic highly sensitive pH probes designed for in vivo acidic pH studies
  作者：Sophie Martel、Jean-Louis Clément、Agnès Muller、Marcel Culcasi、Sylvia Pietri

  DOI：10.1016/s0968-0896(01)00414-x

  日期：2002.5

  With the aim to provide sensitive P-31 NMR probes of intra- and extracellular pH gradients that may reach cellular acidic compartments in biological systems, new 7-aminophosphonates were designed to meet basic requirements such as a low pK(a)s and a great chemical difference (Deltadelta(ab)) between the limiting P-31 NMR chemical shifts in acidic (delta(a)) and basic (delta(b)) media. A series of six phosphorylated pyrrolidines and linear aminophosphonates were synthesized using aminophosphorylation reactions and were screened for cytotoxicity on cultured Muller cells. Among the compounds not being toxic under these conditions. three molecules were selected since they displayed the best in vitro (in several phosphate buffers and in a cytosol-like solution) properties as P-31 NMR acidic pH markers. that is 3, 5 and 9, having the pK(a) values of 3.63, 5.89 and 5.66, respectively. The Deltadelta(ab) values of these pH markers were at least 3 times larger than that of standard P-31 NMR probes, with a low sensitivity to ionic strength changes. From these data. it was proposed that 3, 5 and 9 could be used as reporting probes of subtle proton movements in acidic compartments, an area that still remains poorly investigated using non invasive IT NMR methods. (C) 2002 Elsevier Science Ltd. All rights reserved.