diethyl 3-hydroxy-2-oxo-2,3-dihydro-1H-indol-3-yl phosphonate | 5044-62-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 英文名称: diethyl 3-hydroxy-2-oxo-2,3-dihydro-1H-indol-3-yl phosphonate
• 英文别名: diethyl 3-hydroxy-2-oxoindolin-3-ylphosphonate；3-(diethoxyphosphoryl)-3-hydroxyindolin-2-one；(3-hydroxy-2-oxo-2,3-dihydro-indol-3-yl)-phosphonic acid diethyl ester；(2,3-dihydro-3-hydroxy-2-oxo-1H-indol-3-yl)-phosphonic acid, diethylester；diethyl (3-hydroxy-2-oxo-2,3-dihydro-1H-indol-3-yl)phosphonate；3-diethoxyphosphoryl-3-hydroxy-1H-indol-2-one
• CAS: 5044-62-2
• 化学式: C₁₂H₁₆NO₅P
• 分子量: 285.236
• InChiKey: BXIJPYSMEQLHGD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.1
• 重原子数：
  19
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  84.9
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  靛红 、 亚磷酸三乙酯 以 neat liquid 为溶剂， 反应 0.62h， 以86%的产率得到diethyl 3-hydroxy-2-oxo-2,3-dihydro-1H-indol-3-yl phosphonate
  参考文献：
  名称：

  无溶剂条件下超声辅助绿色合成α-羟基膦酸酯

  摘要：

  摘要 通过醛或酮与亚磷酸三烷基酯的反应合成α-羟基膦酸酯的简单，有效，环境友好的方法在超声辐射，无溶剂和无催化剂的条件下有效地实现。这种快速的方法可以高产率和短反应时间生产α-羟基膦酸酯。 图形概要

  DOI：

  10.1007/s11164-015-2420-8

文献信息

• Ketones in the catalytic three-component “one-pot” Kabachnik-Fields synthesis of α-amino phosphonates
  作者：E. D. Matveeva、T. A. Podrugina、M. V. Prisyajnoy、N. S. Zefirov

  DOI：10.1007/s11172-006-0400-2

  日期：2006.7

  Reactions of carbocyclic, heterocyclic, and steroidal ketones with benzylamine and diethyl phosphite in a catalytic three-component “one-pot” synthesis of α-amino phosphonates were studied. The activities of mono-and binuclear complexes of tetra(tert-butyl)phthalocyanines as catalysts for this process were compared.

  研究了碳环、杂环和甾体酮与苄胺和亚磷酸二乙酯在催化三组分“一锅”合成 α-氨基膦酸酯中的反应。比较了作为该过程催化剂的四（叔丁基）酞菁的单核和双核配合物的活性。
• Magnetic Fe₃O₄Nanoparticle-Supported Phosphotungstic Acid as a Recyclable Catalyst for the Kabachnik-Fields Reaction of Isatins, Imines, and Aldehydes under Solvent-Free Conditions
  作者：Mohd Nazish、S. Saravanan、Noor-ul H. Khan、Prathibha Kumari、Rukhsana I. Kureshy、Sayed H. R. Abdi、Hari C. Bajaj

  DOI：10.1002/cplu.201402191

  日期：2014.9.22

  reaction of isatins, imines, and aldehydes using dimethyl and diethyl phosphite as a nucleophile to give the corresponding α‐hydroxy and α‐amino phosphonates in excellent yields for a wide range of substrates. The reaction conditions were simple, green, and efficient. The catalyst was recycled up to five times with retention of its activity. Based on the NMR spectroscopy studies, a probable catalytic cycle

  磁性纳米颗粒负载的磷钨酸已被用于以亚磷酸二甲酯和亚磷酸二乙酯为亲核试剂，有效地催化靛红，亚胺和醛的加氢膦酰化反应，从而在宽范围内以优异的收率得到相应的α-羟基和α-氨基膦酸酯。的基板。反应条件简单，绿色，高效。在保持活性的情况下，将催化剂再循环至五次。基于NMR光谱学研究，提出了可能的催化循环。
• Synthesis of α1-oxindole-α-hydroxyphosphonates under catalyst-free conditions using polyethylene glycol (PEG-400) as an efficient and recyclable reaction medium
  作者：Lingaiah Nagarapu、Raghu Mallepalli、U. Nikhil Kumar、P. Venkateswarlu、Rajashaker Bantu、Lingappa Yeramanchi

  DOI：10.1016/j.tetlet.2012.01.045

  日期：2012.4

  A simple, efficient, eco-friendly, and cost-effective method has been developed for the synthesis of α1-oxindole-α-hydroxyphosphonate derivatives (3a–o) by a one-pot reaction of isatins (1a–o) with trialkyl phosphites (2a–o) under catalyst-free-conditions using inexpensive, non-toxic polyethylene glycol (PEG-400) in excellent yields (82–92%). The present methodology offers an environmental acceptability;

  一个简单的，高效的，环保的，并且成本有效的方法已被开发用于α的合成1羟吲哚-α-hydroxyphosphonate衍生物（3a中- Ö由靛红的一锅反应（）1A - ö）与三烷基使用廉价，无毒的聚乙二醇（PEG-400）在无催化剂条件下制备亚磷酸酯（2a – o），产率高（82–92％）。本方法提供了环境可接受性；PEG-400的低成本，高收率和可回收性是该协议的重要特征。
• Magnetic nanoparticle γ-Fe₂O₃-immobilized 1,5,7-triazabicyclo[4.4.0]dec-5-ene as a highly recyclable and efficient nanocatalyst for the synthesis of α′-oxindole-α-hydroxyphosphonates
  作者：Xiao Juan Yang

  DOI：10.1002/aoc.3147

  日期：2014.7

  Magnetic nanoparticle γ‐Fe2O3‐immobilized 1,5,7‐triazabicyclo[4.4.0]dec‐5‐ene as a novel magnetic nanocatalyst was synthesized and characterized. The nanoparticle reagent catalyzed efficiently the synthesis of α′‐oxindole‐α‐hydroxyphosphonates from isatins and dimethyl phosphate under solvent‐free conditions at 60 °C. More importantly, the catalyst could be easily recovered by an external magnet and

  磁性纳米颗粒了γ-Fe 2 ö 3固定化1,5,7-三氮杂双环[4.4.0]癸-5-烯作为一种新的磁性纳米催化剂的合成和表征。纳米粒子试剂可在无溶剂条件下于60°C下有效催化由靛红和磷酸二甲酯合成α'-羟吲哚-α-羟基膦酸酯。更重要的是，该催化剂可以很容易地被外部磁体回收并重复使用六次而不会显着降低活性。版权所有©2014 John Wiley＆Sons，Ltd.
• <i>n</i>-BuLi as a Highly Efficient Precatalyst for Hydrophosphonylation of Aldehydes and Unactivated Ketones
  作者：Chengwei Liu、Yu Zhang、Qinqin Qian、Dan Yuan、Yingming Yao

  DOI：10.1021/ol5030713

  日期：2014.12.5

  as highly efficient precatalysts for the hydrophosphonylation reactions of aldehydes and unactivated ketones with dialkyl phosphite under mild conditions. For ketone substrates, a reversible reaction was observed, and the influence of catalyst loading and reaction temperature on the reaction equilibrium was studied in detail. Overall, the hydrophosphonylation reactions catalyzed by 0.1 mol % n-BuLi

  首次发现有机碱金属化合物可作为醛和未活化酮与亚磷酸二烷基酯在温和条件下进行氢膦酰化反应的高效预催化剂。对于酮类底物，观察到可逆反应，并详细研究了催化剂负载量和反应温度对反应平衡的影响。总体而言，由0.1 mol％n- BuLi催化的加氢羰基化反应可在5分钟内完成，适用于多种底物，并以高收率产生了一系列α-羟基膦酸酯。