膦酸,[苯基[(苯基甲基)氨基]甲基]-,二甲基酯 | 192868-43-2

• 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
• 中文名称: 膦酸,[苯基[(苯基甲基)氨基]甲基]-,二甲基酯
• 英文名称: (benzylamino-phenyl-methyl)-phosphonic acid dimethyl ester
• 英文别名: dimethyl ((benzylamino)(phenyl)methyl)phosphonate；dimethyl [(benzylamino)(phenyl)methyl]phosphonate；dimethyl[(benzylamino)(phenyl)methyl]phosphonate；dimethyl N-benzylamino(phenyl)methylphosphonate；dimethyl (benzylaminophenylmethyl)phosphonate；Phosphonic acid, [phenyl[(phenylmethyl)amino]methyl]-, dimethyl ester；N-benzyl-1-dimethoxyphosphoryl-1-phenylmethanamine
• CAS: 192868-43-2
• 化学式: C₁₆H₂₀NO₃P
• 分子量: 305.313
• InChiKey: IEJNNVNNBLGRLL-UHFFFAOYSA-N

物化性质

• 熔点：
  77-78 °C(Solv: chloroform (67-66-3))
• 沸点：
  422.6±40.0 °C(Predicted)
• 密度：
  1.163±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  21
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.25
• 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：

  (E)-N-benzylidenebenzylamine 在 碳酸氢钠 作用下， 以 二氯甲烷 为溶剂， 反应 24.0h， 生成 膦酸,[苯基[(苯基甲基)氨基]甲基]-,二甲基酯
  参考文献：
  名称：

  Boduszek, Polish Journal of Chemistry, 2001, vol. 75, # 5, p. 663 - 672

  摘要：

  DOI：

文献信息

• Phenylphosphonic Acid as Efficient and Recyclable Catalyst in the Synthesis of α-Aminophosphonates under Solvent-Free Conditions
  作者：Mario Ordóñez、Mercedes Bedolla-Medrano、Eugenio Hernández-Fernández

  DOI：10.1055/s-0033-1341069

  日期：——

  Phenylphosphonic acid is an efficient, friendly and reusable heterogeneous catalyst for the synthesis of α-aminophosphonates through a ‘one-pot’ three-component reaction of amines, carbonyl compounds and dialkyl phosphites under solvent-free conditions. This methodology illustrates a very simple procedure, with wide applicability, extending the scope to aliphatic and aromatic amines, aliphatic and

  苯基膦酸是一种高效、友好且可重复使用的多相催化剂，用于在无溶剂条件下通过胺、羰基化合物和亚磷酸二烷基酯的“一锅法”三组分反应合成 α-氨基膦酸酯。该方法说明了一个非常简单的程序，具有广泛的适用性，将范围扩展到脂肪族和芳香族胺、脂肪族和芳香族醛以及脂肪族酮。它还能够大规模合成 α-氨基膦酸盐，清洁转化，易于后处理和纯化。在每种情况下都获得了优异的结果，以中等至良好的产率获得了所需化合物。
• New Catalyst for Phosphonylation of C˭X Electrophiles
  作者：Oleg I. Kolodiazhnyi、Olga O. Kolodiazhna

  DOI：10.1080/00397911.2010.542602

  日期：2012.6

  recyclable catalyst for the reaction of trialkyl phosphites with various C˭X electrophiles (aldehydes, ketones, ketophosphonates, imines, isocyanates, isothiocyanates, activated alkenes) to afford corresponding α-substituted phosphonates in good yields. The main advantages of the new catalyst is strong activity, accessibility, good yields of products, and gentle conditions of reaction. GRAPHICAL ABSTRACT

  摘要 高氯酸吡啶是一种高效且可回收的催化剂，可用于亚磷酸三烷基酯与各种 C˭X 亲电子试剂（醛、酮、酮膦酸酯、亚胺、异氰酸酯、异硫氰酸酯、活性烯烃）反应，以良好的收率得到相应的 α-取代膦酸酯。 . 新型催化剂的主要优点是活性强、易接近、产物收率好、反应条件温和。图形概要
• Enantioselective Reductive Cyanation and Phosphonylation of Secondary Amides by Iridium and Chiral Thiourea Sequential Catalysis
  作者：Dong‐Huang Chen、Wei‐Ting Sun、Cheng‐Jie Zhu、Guang‐Sheng Lu、Dong‐Ping Wu、Ai‐E Wang、Pei‐Qiang Huang

  DOI：10.1002/anie.202015898

  日期：2021.4.12

  and phosphonylation of secondary amides have been accomplished for the first time for the synthesis of enantioenriched chiral α‐aminonitriles and α‐aminophosphonates. The protocol is highly efficient and enantioselective, providing a novel route to the synthesis of optically active α‐functionalized amines from the simple, readily available feedstocks. In addition, the reactions are scalable and the

  过渡金属催化和有机催化的结合为化学家提供了实现各种前所未有的化学转化的机会。通过将铱与手性硫脲催化结合，首次实现了仲酰胺的直接对映选择性还原性氰化和膦酰化，以合成富含对映体的手性α-氨基腈和α-氨基膦酸酯。该方案高效且对映选择性良好，为从简单易得的原料合成旋光性α-官能化胺提供了一条新颖的途径。另外，反应是可扩展的，并且硫脲催化剂可以再循环和再利用。
• Synthesis of novel α-hydroxyphosphonates along with α-aminophosphonates as intermediates
  作者：Petra R. Varga、Alexandra Belovics、Gerhard Hägele、György Keglevich

  DOI：10.1080/10426507.2021.2008927

  日期：2022.6.3

  Abstract New phosphoryl α-hydroxyphosphonates, their acylated derivatives, as well as α-aminophosphonates were synthesized as potentionally biologycally active substrates. The reverzible formation of α-hydroxyphosphonates allowing a few interesting side-reactions was also observed.

  摘要 合成了新的磷酰基 α-羟基膦酸酯、它们的酰化衍生物以及 α-氨基膦酸酯作为潜在的生物学活性底物。还观察到允许一些有趣的副反应的 α-羟基膦酸盐的可逆形成。
• 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。