diethyl 3-hydroxy-5-nitro-2-oxoindolin-3-ylphosphonate | 1236200-85-3

• 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-5-nitro-2-oxoindolin-3-ylphosphonate
• 英文别名: diethyl 3-hydroxy-5-nitro-2-oxindolin-3-ylphosphonate；3-diethoxyphosphoryl-3-hydroxy-5-nitro-1H-indol-2-one
• CAS: 1236200-85-3
• 化学式: C₁₂H₁₅N₂O₇P
• 分子量: 330.234
• InChiKey: KYBJHZRMGCQNMQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.1
• 重原子数：
  22
• 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：
  131
• 氢给体数：
  2
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  5-硝基靛红 、 亚磷酸三乙酯 在 水 作用下， 反应 10.0h， 以93%的产率得到diethyl 3-hydroxy-5-nitro-2-oxoindolin-3-ylphosphonate
  参考文献：
  名称：

  的α的合成1使用聚乙二醇（PEG-400）作为一种高效和可回收的反应介质无催化剂的条件下，羟吲哚-α-hydroxyphosphonates

  摘要：

  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。

  DOI：

  10.1016/j.tetlet.2012.01.045

文献信息

• 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。
• 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.
• Nano-rod ZnO as a novel and reusable catalyst for C−P bond formation and hydrophosphonation of isatin derivatives under solvent-free conditions
  作者：Mona Hosseini-Sarvari、Mina Tavakolian

  DOI：10.1139/cjc-2011-0432

  日期：2013.11

  A highly efficient method for the synthesis of α¹-oxindole-α-hydroxyphosphonates via nano-rod ZnO catalyzed hydrophosphonation of isatin derivatives was developed. The reaction products are in excellent yields using the catalytic system nano-rod ZnO (25 mol%) under solvent-free conditions at room temperature. The catalyst can be reused several times without any significant loss of its activity.

  通过纳米棒ZnO催化的吲哚酮衍生物水合磷酸化反应，开发了一种合成α1-氧杂-α-羟基膦酸酯的高效方法。在室温下无溶剂条件下，使用催化体系纳米棒ZnO（25 mol％），反应产物收率极高。催化剂可以重复使用多次，没有明显的活性损失。
• Amberlyst-15 Catalyzed Synthesis of α′-Oxindole-α-Hydroxyphosphonates under Ultrasonic Irradiation
  作者：Kunda Uma Maheswara Rao、Guda Dinneswara Reddy、Chan-Moon Chung

  DOI：10.1080/10426507.2012.736099

  日期：2013.8.1

  An efficient and environment friendly protocol for the synthesis of -oxindole--hydroxyphosphonates by the condensation of substituted isatin and dialkylphosphite in the presence of amberlyst-15 is reported. This reaction gives good to excellent yields of products under heating and sonication conditions. Supplementary materials are available for this article. Go to the publisher's online edition of Phosphorus, Sulfer, and Silicon and the Related Elements for the following free supplemental files: Additional figures.
• Novel aqueous phase supramolecular synthesis of α 1 -oxindole-α-hydroxyphosphonates
  作者：J. Shankar、K. Karnakar、B. Srinivas、Y.V.D. Nageswar

  DOI：10.1016/j.tetlet.2010.05.096

  日期：2010.7

  alpha(1)-Oxindole-alpha-hydroxyphosphonates were synthesized for the first time in water under neutral conditions mediated by beta-cyclodextrin in high yields. The beta-cyclodextrin can be recovered and reused without any loss of activity. (C) 2010 Elsevier Ltd. All rights reserved.