dimethyl [(2-methoxyphenyl)(pyrrolidin-1-yl)methyl]phosphonate

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: dimethyl [(2-methoxyphenyl)(pyrrolidin-1-yl)methyl]phosphonate
• 英文别名: dimethyl (2-methoxyphenyl)(pyrrolidin-1-yl)methylphosphonate；dimethyl [(2-methoxyphenyl)(pyrrolidino)methyl]phosphonate；1-[Dimethoxyphosphoryl-(2-methoxyphenyl)methyl]pyrrolidine
• 化学式: C₁₄H₂₂NO₄P
• 分子量: 299.307
• InChiKey: IVXQGYSAQLOVMX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  20
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  48
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  四氢吡咯 、 邻甲氧基苯甲醛 、 三甲氧基磷 在 lithium perchlorate 作用下， 以 乙醚 为溶剂， 反应 0.25h， 以96%的产率得到dimethyl [(2-methoxyphenyl)(pyrrolidin-1-yl)methyl]phosphonate
  参考文献：
  名称：

  LPDE介导的一锅三组分偶联法合成叔α-氨基膦酸酯

  摘要：

  据报道，通过醛，仲胺和亚磷酸三烷基酯在高氯酸锂LPDE的乙醚溶液中于环境温度下高产率地反应，可以合成一种非常温和，高效且简单的方法。

  DOI：

  10.1016/s0040-4020(03)00759-2

文献信息

• Lithium Perchlorate-Catalyzed Three-Component Coupling: A Facile and General Method for the Synthesis ofα-Aminophosphonates under Solvent-Free Conditions
  作者：Najmedin Azizi、Mohammad R. Saidi

  DOI：10.1002/ejoc.200300479

  日期：2003.12

  A simple, efficient, and general method has been developed for the synthesis of α-aminophosphonates in the presence of solid lithium perchlorate under solvent-free conditions. Thus secondary and tertiary α-aminophosphonates were synthesized relatively quickly in good yields at room temperature. (© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2003)

  已开发出一种在固体高氯酸锂存在下，在无溶剂条件下合成 α-氨基膦酸盐的简单、有效和通用的方法。因此，在室温下以良好的产率相对较快地合成仲和叔α-氨基膦酸酯。(© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2003)
• Ultrasonic and Lewis acid ionic liquid catalytic system for Kabachnik-Fields reaction
  作者：Sadegh Rostamnia、Mojtaba Amini

  DOI：10.2478/s11696-013-0516-4

  日期：2014.1.1

  A combination of ultrasonic (US) and [bmim]AlCl4 ionic liquid is used as an alternative to conventional acid catalysts in the Kabachnik-Fields reaction of an amine and aryl aldehyde with phosphite leading to the formation of aminophosphonates. The reaction time was significantly reduced and the reaction progressed very smoothly.

  摘要：在Kabachnik-Fields反应中，将超声波（US）和[bmim]AlCl4离子液体组合使用作为传统酸催化剂的替代品，反应胺和芳香醛与亚磷酸酯形成氨基膦酸盐。反应时间显著缩短，反应进行非常顺利。
• Pvp-based deep eutectic solvent polymer: Sustainable Brønsted-Lewis acidic catalyst in the synthesis of α-aminophosphonate and bisindole
  作者：Mehran Shahiri Haghayegh、Najmedin Azizi、Soulmaz Seyyed Shahabi、Yanlong Gu

  DOI：10.1016/j.molliq.2023.122677

  日期：2023.10

  biologically significant scaffolds via a multicomponent reaction of aldehydes, amines, and tri(alkyl/aryl)phosphites to synthesize secondary and tertiary α-aminophosphonates (APs), in addition to a carbon–carbon bond-forming reaction to synthesizing bis(indolyl)methanes (BIMs) from aldehydes and indolyl compounds. PDESs proved to be highly efficient catalysts for these transformations, providing mild

  聚合物低共熔溶剂 (PDES) 的出现，增强了低共熔溶剂 (DES) 作为可持续材料类别的功能。考虑到PDES对深度共晶单体原位聚合的常见合成限制，本文中，我们采用线性聚乙烯吡咯烷酮（PVP）来开发一种易于制备、原子经济、成本效益高且环境友好的布朗斯台德-通过ZnCl 2和季铵化过程生成路易斯酸性PDES。通过 SEM、EDS、元素图、FT-IR 和 TGA 技术对制备的 PDES 进行了表征。该方法通过改变 ZnCl 2的摩尔比来实现 PDES 的物理化学调节为 PVP 单体重复单元。PDES 被用作非均相催化剂，通过醛、胺和三（烷基/芳基）亚磷酸酯的多组分反应，除了碳之外，还可以合成仲和叔 α-氨基膦酸酯（AP），从而促进具有生物学意义的支架的绿色方法。 –从醛和吲哚基化合物合成双（吲哚基）甲烷（BIM）的碳键形成反应。事实证明，PDES 是这些转变的高效催化剂，为广泛的 AP 和 BIM
• Simultaneously application of SBA-15 sulfonic acid nanoreactor and ultrasonic irradiation as a very useful novel combined catalytic system: An ultra-fast, selective, reusable and waste-free green approach
  作者：Sadegh Rostamnia、Hongchuan Xin、Xiao Liu、Kamran Lamei

  DOI：10.1016/j.molcata.2013.03.017

  日期：2013.8

  Sonicated catalytically amount of the SBA-15/SO3H nanoreactor with organic substrate was found to be an efficient, ultra-fast and waste-free green approach for the synthesis of the indazolophthalazinetriones, polyhydroquinolines and alpha-aminophosphonates as models of organic reactions. The advantages of present combined method are the use of a low scale catalyst, simple procedure with an easy filterable work-up method, waste-free, green and direct synthetic entry to excellent yield of products in a high reusability and a short reaction time. SBA-15 nanoreactor anchored covalently bonded PrSO3H organic groups, to produce organic-inorganic mesochannels, in reaction condition (combined ultrasound/nanoreactor system) as catalyst provide a synergistic means of an efficient approach of the reactants to acidic sites, and suitable mesochannels to drive out the products and water for next recycles. (C) 2013 Elsevier B.V. All rights reserved.
• Simultaneous application of ultrasonic irradiation and immobilized ionic liquid onto the SBA-15 nanoreactor (US/[MPIm]Cl@SBA-15): A robust, recyclable, and useful combined catalytic system for selective and waste-free Kabachnik Fields reaction
  作者：Sadegh Rostamnia、Hongchuan Xin

  DOI：10.1016/j.molliq.2014.01.031

  日期：2014.7

  Simultaneous application of the ultrasonic irradiation (US) and immobilized ionic liquid (IL@SBA-15) is used as an alternative to conventional catalysts in the Kabachnik-Fields reaction of an amine, aldehyde with phosphite leading to the formation of (alpha-aminoalkyl)phosphonate. The reaction time is reduced drastically and the reaction is progressed in an environmentally friendly way. The yields are around 93-96%. (C) 2014 Elsevier B.V. All rights reserved.