[(4-methoxyphenyl)(phenylamino)methyl]phosphonic acid diisopropyl ester | 5308-60-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: [(4-methoxyphenyl)(phenylamino)methyl]phosphonic acid diisopropyl ester
• 英文别名: diisopropyl [(4-methoxyphenyl)(phenylamino)methyl]phosphonate；Dipropan-2-yl [anilino(4-methoxyphenyl)methyl]phosphonate；N-[di(propan-2-yloxy)phosphoryl-(4-methoxyphenyl)methyl]aniline
• CAS: 5308-60-1
• 化学式: C₂₀H₂₈NO₄P
• 分子量: 377.42
• InChiKey: GMHJKLKSBBMHBE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  26
• 可旋转键数：
  9
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  56.8
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  亚磷酸二异丙酯 、 N-(4-甲氧亚苄基)苯胺 在 水 作用下， 以 异丙醇 为溶剂， 生成 [(4-methoxyphenyl)(phenylamino)methyl]phosphonic acid diisopropyl ester
  参考文献：
  名称：

  Kinetics and mechanism of the Pudovik reaction in the azomethine series: III. Acid-catalyzed hydrophosphorylation of imines

  摘要：

  A complex spectral (UV, IR, and P-31 NMR), preparative, and kinetic investigation of the mechanism of the noncatalytic variant of the Pudovik reaction in the series of imines was carried out. The reaction proceeds through a four-center cyclic transition state. The transition state is highly labile, which determines its high sensitivity to the structure of the reagents, the nature of the solvent and catalyst, and some other factors. The necessary condition for the hydrophosphorylation of imines to occur is the participation of proton-donor reagents and acidic admixtures, specifically hydrolysis products of dialkyl hydrogen phosphites, such as monoalkyl dihydrogen phosphates and phosphorous acid, which act as acid catalysts. When the starting, reagents are thoroughly purified and no such catalysts are present, the Pudovik reaction fails to occur in the imine series.

  DOI：

  10.1134/s1070363206030121

文献信息

• 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。
• An Extremely Efficient Three-Component Reaction of Aldehydes/Ketones, Amines, and Phosphites (Kabachnik−Fields Reaction) for the Synthesis of α-Aminophosphonates Catalyzed by Magnesium Perchlorate
  作者：Srikant Bhagat、Asit K. Chakraborti

  DOI：10.1021/jo062140i

  日期：2007.2.1

  an extremely efficient catalyst for the synthesis of α-aminophosphonates. A three-component reaction (3-CR) of an amine, an aldehyde or a ketone, and a di-/trialkyl phosphite (Kabachnik−Fields reaction) took place in one pot under solvent-free conditions to afford the corresponding α-aminophosphonates in high yields and short times. The use of solvent retards the rate of the reaction and requires a

  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
• Copper (I) Iodide-Catalyzed Solvent-Free Synthesis of α-Aminophosphonates
  作者：Hua Fang、Xuanling Xie、Bihong Hong、Yufen Zhao、Meijuan Fang

  DOI：10.1080/10426507.2011.590561

  日期：2011.11.1
• Kinetics and mechanism of the Pudovik reaction in the azomethine series: III. Acid-catalyzed hydrophosphorylation of imines
  作者：A. A. Sobanov、A. V. Zolotukhin、I. V. Galkina、V. I. Galkin、R. A. Cherkasov

  DOI：10.1134/s1070363206030121

  日期：2006.3

  A complex spectral (UV, IR, and P-31 NMR), preparative, and kinetic investigation of the mechanism of the noncatalytic variant of the Pudovik reaction in the series of imines was carried out. The reaction proceeds through a four-center cyclic transition state. The transition state is highly labile, which determines its high sensitivity to the structure of the reagents, the nature of the solvent and catalyst, and some other factors. The necessary condition for the hydrophosphorylation of imines to occur is the participation of proton-donor reagents and acidic admixtures, specifically hydrolysis products of dialkyl hydrogen phosphites, such as monoalkyl dihydrogen phosphates and phosphorous acid, which act as acid catalysts. When the starting, reagents are thoroughly purified and no such catalysts are present, the Pudovik reaction fails to occur in the imine series.