(1-benzylamino-cyclohexyl)-phosphonic acid dimethyl ester | 31003-27-7

• 分子结构分类: 有机化合物 - 有机酸及其衍生物
• 英文名称: (1-benzylamino-cyclohexyl)-phosphonic acid dimethyl ester
• 英文别名: (1-benzylaminocyclohexyl)phosphonic acid dimethyl ester；N-benzyl-1-dimethoxyphosphorylcyclohexan-1-amine
• CAS: 31003-27-7
• 化学式: C₁₅H₂₄NO₃P
• 分子量: 297.334
• InChiKey: FKEZPMMIMFTKCV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  20
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.6
• 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：

  N-benzylcyclohexylimine 、 亚磷酸二甲酯 生成 (1-benzylamino-cyclohexyl)-phosphonic acid dimethyl ester
  参考文献：
  名称：

  DE2022228

  摘要：

  公开号：

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。
• 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
• <i>P</i>-Dodecylbenzenesulfonic Acid: A Highly Efficient Catalyst for One-Pot Synthesis of α-Aminophosphonates in Aqueous Media
  作者：Barahman Movassagh、Saba Alapour

  DOI：10.1002/hc.21079

  日期：2013.5

  A highly efficient one-pot three-component reaction of aldehydes or ketones, amines, and trimethyl or triethyl phosphite catalyzed by p-dodecylbenzensulfonic acid is developed for the synthesis of α-aminophosphonates at room temperature in water. © 2013 Wiley Periodicals, Inc. Heteroatom Chem 24:174–178, 2013; View this article online at wileyonlinelibrary.com. DOI 10.1002/hc.21079

  开发了一种由对十二烷基苯磺酸催化的醛或酮、胺和亚磷酸三甲酯或三乙酯的高效一锅三组分反应，用于在室温下在水中合成 α-氨基膦酸酯。© 2013 Wiley Periodicals, Inc. 杂原子化学 24:174–178, 2013; 在 wileyonlinelibrary.com 上在线查看这篇文章。DOI 10.1002/hc.21079
• Phenylboronic Acid as Efficient and Eco-Friendly Catalyst for the One-Pot, Three-Component Synthesis of α-Aminophosphonates under Solvent-Free Conditions
  作者：Mario Ordóñez、Gaurao Tibhe、Mercedes Bedolla-Medrano、Carlos Cativiela

  DOI：10.1055/s-0032-1316558

  日期：2012.8

  A simple, mild, and efficient one-pot, three-component synthetic method has been developed for the preparation of α-aminophosphonates using phenylboronic acid as catalyst under solvent-free conditions at 50 °C. The process involves the reaction of carbonyl compounds (aldehydes or ketones) with benzylamine and dimethyl phosphite. A wide range of carbonyl compounds are compatible with this reaction,

  开发了一种简单、温和、高效的一锅三组分合成方法，以苯基硼酸为催化剂，在 50 °C 无溶剂条件下制备 α-氨基膦酸酯。该过程涉及羰基化合物（醛或酮）与苄胺和亚磷酸二甲酯的反应。广泛的羰基化合物与该反应相容，可在短时间内以中等至极好的收率生产叔和季 α-氨基膦酸酯。