dimethyl (2-benzyl-3-oxo-2,3-dihydro-1H-isoindol-1-yl)phosphonate | 1243585-00-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 异吲哚及其衍生物
• 英文名称: dimethyl (2-benzyl-3-oxo-2,3-dihydro-1H-isoindol-1-yl)phosphonate
• 英文别名: 2-benzyl-3-dimethoxyphosphoryl-3H-isoindol-1-one
• CAS: 1243585-00-3
• 化学式: C₁₇H₁₈NO₄P
• 分子量: 331.308
• InChiKey: YACRSPZMORKTFZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  23
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  55.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  在 K₁₀-FeAA₁₂₀ 作用下， 以 二氯甲烷 为溶剂， 反应 20.0h， 以52%的产率得到dimethyl (2-benzyl-3,5-dioxo-2,3,3a,4,5,7a-hexahydro-1H-isoindol-1-yl)phosphonate
  参考文献：
  名称：

  Experimental and computational study of the ring opening of tricyclic oxanorbornenes to polyhydro isoindole phosphonates

  摘要：

  膦酰化氮杂环是一类重要的化合物，具有作为氨基酸构象限制的生物等排体的高生物潜力。因此，合成构象受限的氨基膦酸盐是很有意义的。我们想要研究通过具有氧杂降冰片烯骨架的 α-氨基膦酸酯开环的可能途径，因为它们可以以高立体选择性合成。这是通过使用不同的路易斯酸实现的，从而产生了一系列产品。在 DFT 理论水平上对 TiCl4 和 FeCl3 的反应进行建模，以深入了解相应产物的途径。为了简化工作，将 Fe(III) 催化剂涂覆在蒙脱石粘土上，但这加速了开环后的芳构化。在硅藻土上猝灭 FeCl3 催化的反应混合物导致完全芳构化。

  DOI：

  10.1039/c002926b

文献信息

• Synthesis of isoindolinone phosphonates and their related derivatives by multicomponent reaction
  作者：Bettina Rávai、Nóra Popovics-Tóth、Ádám Tajti、Erika Bálint

  DOI：10.1080/10426507.2021.2012179

  日期：2022.6.3

  Abstract An efficient catalyst-free microwave (MW)-assisted method was elaborated for the batch and continuous flow synthesis of N-alkyl-isoindolinone phosphonates by the three-component reaction of 2-formylbenzoic acid, primary amines and various dialkyl phosphites. The reaction was also extended to various secondary phosphine oxides and primary amines, as well. In order to obtain more information

  摘要 以 2-甲酰基苯甲酸、伯胺和各种亚磷酸二烷基酯的三组分反应为原料，研究了一种高效的无催化剂微波 (MW) 辅助方法，用于分批和连续流动合成 N-烷基-异吲哚啉酮膦酸酯。该反应还扩展到各种仲氧化膦和伯胺。为了获得有关缩合的更多信息，还通过原位FT-IR光谱研究了反应机理。
• Study on the Microwave-Assisted Batch and Continuous Flow Synthesis of N-Alkyl-Isoindolin-1-One-3-Phosphonates by a Special Kabachnik–Fields Condensation
  作者：Ádám Tajti、Nóra Tóth、Bettina Rávai、István Csontos、Pál Tamás Szabó、Erika Bálint

  DOI：10.3390/molecules25143307

  日期：——

  Kabachnik–Fields reaction of 2-formylbenzoic acid, butylamine and diethyl phosphite was monitored by in situ FT-IR spectroscopy. The novel title compounds could be prepared in high yields at low temperature under a short reaction time. A suitable method could also be developed for the preparation of the isoindolin-1-one-3-phosphonates at a “few g” scale by using a continuous flow MW reactor.

  通过2-甲酰基苯甲酸、脂肪族伯胺和各种亚磷酸二烷基酯的三组分缩合，阐述了一种简单有效的微波（MW）辅助方法，用于无催化剂合成异吲哚啉-1-one-3-膦酸酯。在温度、反应时间和起始材料的摩尔比方面优化间歇和连续流动反应。为了评估 MW 辐射的潜力，还进行了比较热实验。为了获得关于缩合的“实时”信息，通过原位 FT-IR 光谱监测了 2-甲酰基苯甲酸、丁胺和亚磷酸二乙酯的特殊 Kabachnik-Fields 反应。可以在低温、短反应时间内以高收率制备新的标题化合物。
• An efficient, three-component synthesis of isoindolin-1-one-3-phosphonates under mild and solvent-free conditions
  作者：Mehdi Adib、Ehsan Sheikhi、Rozita Yazzaf、Hamid Reza Bijanzadeh、Peiman Mirzaei

  DOI：10.1016/j.tetlet.2015.12.055

  日期：2016.2

  An efficient and mild three-component synthesis of isoindolin-1-one-3-phosphonates is described. The reaction between a 2-formylbenzoic acid, a primary amine, and a trialkyl phosphite proceeded at ambient temperature under catalyst- and solvent-free conditions to afford the desired compounds in excellent yields.

  描述了一种高效温和的三组分合成异吲哚啉-1-一-3-膦酸酯的方法。2-甲酰基苯甲酸，伯胺和亚磷酸三烷基酯之间的反应在环境温度下在无催化剂和无溶剂的条件下进行，以优异的收率提供了所需的化合物。
• Multicomponent Synthesis of Potentially Biologically Active Heterocycles Containing a Phosphonate or a Phosphine Oxide Moiety
  作者：Nóra Popovics-Tóth、Erika Bálint

  DOI：10.17344/acsi.2022.7648

  日期：——

  Several multicomponent synthetic approaches were elaborated for plenty of novel nitrogen or oxygen heterocycles containing a phosphonate or a phosphine oxide moiety. All multicomponent reactions were optimized through a model reaction in respect of the heating mode, molar ratio of the starting materials, atmosphere, catalyst, temperature, reaction time and solvent applied, and then, the extended preparation of small libraries of structurally-related compounds was performed. Most of the reactions could be considered as “green syntheses”, as they were carried out in the absence of any catalyst and/or solvent using microwave (MW) irradiation or even at ambient temperature. The scaling-up of a MW-assisted synthesis was also elaborated in a continuous flow MW system. Altogether more than 150 heterocyclic organophosphorus compounds were synthesized, among them several derivatives showed moderate or promising activity against the HL-60 cell line and Bacillus subtilis bacteria.

  为了大量制备含有膦酸盐或氧化膦分子的新型氮杂环或氧杂环，我们精心设计了几种多组分合成方法。所有多组分反应都通过模型反应进行了优化，包括加热方式、起始原料的摩尔比、气氛、催化剂、温度、反应时间和所用溶剂等，然后扩展制备了结构相关的小化合物库。大多数反应可被视为 "绿色合成"，因为它们是在没有任何催化剂和/或溶剂的情况下，利用微波（MW）辐照甚至在环境温度下进行的。此外，还在连续流微波系统中阐述了如何扩大微波辅助合成的规模。总共合成了 150 多种杂环有机磷化合物，其中有几种衍生物对 HL-60 细胞系和枯草芽孢杆菌表现出中等或有希望的活性。
• Experimental and computational study of the ring opening of tricyclic oxanorbornenes to polyhydro isoindole phosphonates
  作者：Diederica D. Claeys、Christian V. Stevens、Bart I. Roman、Pieter Van De Caveye、Michel Waroquier、Veronique Van Speybroeck

  DOI：10.1039/c002926b

  日期：——

  Phosphonylated azaheterocycles are an important class of compounds with high biological potential as conformationally restricted bioisosteres of amino acids. Therefore, it is of interest to synthesize conformationally constrained amino phosphonates. We wanted to investigate possible routes via ring opening of α-amino phosphonates with an oxanorbornene skeleton, as these can be synthesized with high stereoselectivity. This was achieved using different Lewis acids, leading to a range of products. The reaction with TiCl4 and FeCl3 was modelled at a DFT level of theory to get insight in the pathways towards the corresponding products. To ease the work up, the Fe(III) catalyst was coated on montmorillonite clay, but this accelerated aromatization after ring opening. Quenching the FeCl3 catalyzed reaction mixture on celite caused complete aromatization.

  膦酰化氮杂环是一类重要的化合物，具有作为氨基酸构象限制的生物等排体的高生物潜力。因此，合成构象受限的氨基膦酸盐是很有意义的。我们想要研究通过具有氧杂降冰片烯骨架的 α-氨基膦酸酯开环的可能途径，因为它们可以以高立体选择性合成。这是通过使用不同的路易斯酸实现的，从而产生了一系列产品。在 DFT 理论水平上对 TiCl4 和 FeCl3 的反应进行建模，以深入了解相应产物的途径。为了简化工作，将 Fe(III) 催化剂涂覆在蒙脱石粘土上，但这加速了开环后的芳构化。在硅藻土上猝灭 FeCl3 催化的反应混合物导致完全芳构化。