diethyl [1-(3-nitrophenyl)]-N-(3-nitroanilino)methanesulfonate

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: diethyl [1-(3-nitrophenyl)]-N-(3-nitroanilino)methanesulfonate
• 英文别名: N-[diethoxyphosphoryl-(3-nitrophenyl)methyl]-3-nitroaniline
• 化学式: C₁₇H₂₀N₃O₇P
• 分子量: 409.335
• InChiKey: RUBJFCGRBSMQCE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  28
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  139
• 氢给体数：
  1
• 氢受体数：
  8

反应信息

• 作为产物：
  描述：

  间硝基苯甲醛 、 间硝基苯胺 、 亚磷酸三乙酯 在 silica-supported polyphosphoric acid 作用下， 反应 1.92h， 以92%的产率得到diethyl [1-(3-nitrophenyl)]-N-(3-nitroanilino)methanesulfonate
  参考文献：
  名称：

  Silica supported polyphosphoric acid (PPA-SiO_2): an efficient and reusable heterogeneous catalyst for the one-pot synthesis of \alpha -amino phosphonates

  摘要：

  在 80 °C 无溶剂条件下，在 PPA-SiO_2 存在下，采用醛、胺和三烷基膦酸盐之间的单锅三组分缩合反应，描述了制备 \alpha -氨基膦酸盐的高效绿色方案。本方法具有产率高、反应时间短、无毒、可回收和催化剂可重复使用等优点。

  DOI：

  10.3906/kim-0910-28

文献信息

• Nitroanilinomethanephosphonates derived from ferrocene and nitrobenzaldehyde
  作者：Jaros?aw Lewkowski、Monika Rze?niczak、Romuald Skowro?ski

  DOI：10.1002/hc.10128

  日期：——

  A series of new aminophosphonates derived from ferrocene and nitrobenzene were synthesized. They were characterized by means of the 1H and 31P NMR spectroscopy as well as by their elemental analysis. Synthesis of esters was carried out without solvent as refluxing of the reagents in toluene or in acetonitrile gave no results. © 2003 Wiley Periodicals, Inc. Heteroatom Chem 14:144–148, 2003; Published

  合成了一系列以二茂铁和硝基苯为原料的新型氨基膦酸酯。通过 1H 和 31P NMR 光谱以及元素分析对它们进行表征。酯的合成在没有溶剂的情况下进行，因为试剂在甲苯或乙腈中回流没有得到结果。© 2003 Wiley Periodicals, Inc. 杂原子化学 14:144–148, 2003; 在线发表于 Wiley InterScience (www.interscience.wiley.com)。DOI 10.1002/hc.10128
• Silica supported polyphosphoric acid (PPA-SiO_2): an efficient and reusable heterogeneous catalyst for the one-pot synthesis of \alpha -amino phosphonates
  作者：MALEK TAHER MAGHSOODLOU、SAYYED MOSTAFA HABIBI-KHORASSANI、REZA HEYDARI、NOUROLLAH HAZERI、SEYED SAJAD SAJADIKHAH、MOHSEN ROSTAMIZADEH、LEILA KEISHAMS

  DOI：10.3906/kim-0910-28

  日期：——

  An efficient green protocol is described for the preparation of \alpha -amino phosphonates, employing a one-pot three-component condensation reaction between aldehydes, amines, and trialkyl phosphites in the presence of PPA-SiO_2 under solvent-free conditions at 80 °C. The present procedure offer advantages such as high to excellent yields, short reaction time, inexpensiveness, recovery, and reusability of catalyst.

  在 80 °C 无溶剂条件下，在 PPA-SiO_2 存在下，采用醛、胺和三烷基膦酸盐之间的单锅三组分缩合反应，描述了制备 \alpha -氨基膦酸盐的高效绿色方案。本方法具有产率高、反应时间短、无毒、可回收和催化剂可重复使用等优点。
• Al(H₂PO₄)₃as an Efficient and Reusable Catalyst for One-pot Three-component Synthesis of<i>α</i>-Amino Phosphonates under Solvent-free Conditions
  作者：Malek Taher Maghsoodlou、Sayyed Mostafa Habibi-Khorassani、Reza Heydari、Nourollah Hazeri、Seyed Sajad Sajadikhah、Mohsen Rostamizadeh

  DOI：10.1002/cjoc.201090067

  日期：2010.2

  Synthesis of α‐amino phosphonates is described under solvent‐free conditions at 100°C from reaction between aldehydes and amines in the presence of trialkyl phosphites using Al(H2PO4)3 as an efficient and reusable heterogeneous catalyst. The advantages of this procedure are short reaction time, flexibility and having high to excellent yields.

  描述了在无溶剂条件下，在亚磷酸三烷基酯存在下，使用Al（H 2 PO 4）3作为有效且可重复使用的多相催化剂，醛与胺之间的反应，在无溶剂条件下合成α-氨基膦酸酯的方法。该方法的优点是反应时间短，柔韧性好并且产率高至优异。
• One-Pot, Three-Component Synthesis of <font>α</font>-Amino Phosphonates Using NaHSO₄-SiO₂ as an Efficient and Reusable Catalyst
  作者：Malek Taher Maghsoodlou、Reza Heydari、Sayyed Mostafa Habibi-Khorassani、Nourallah Hazeri、Seyed Sajad Sajadikhah、Mohsen Rostamizadeh、Mojtaba Lashkari

  DOI：10.1080/00397911.2010.523153

  日期：2012.1.1

  environmentally benign method has been developed for the synthesis of α-amino phosphonates. One-pot, three-component reaction of aldehyds, amines, and trialkylphosphite in the presence of silica-supported sodium hydrogen sulfate (NaHSO4-SiO2) as an inexpensive and reusable catalyst under solvent-free conditions at 80 °C affords the corresponding α-amino phosphonates in good yields and short reaction times. GRAPHICAL

  摘要 已开发出一种简单、高效且环境友好的合成α-氨基膦酸酯的方法。在二氧化硅负载的硫酸氢钠 (NaHSO4-SiO2) 作为廉价且可重复使用的催化剂存在下，在 80 °C 无溶剂条件下，醛、胺和亚磷酸三烷基酯的一锅三组分反应得到相应的 α-氨基膦酸盐，收率高，反应时间短。图形概要
• Xanthan Sulfuric Acid as an Efficient Biodegradable and Recyclable Catalyst for the One-Pot Synthesis of α-Amino Phosphonates
  作者：Guo-Ying Sun、Jun-Tao Hou、Jing-Jie Dou、Jun Lu、Yong-Jie Hou、Tuo Xue、Zhan-Hui Zhang

  DOI：10.1002/jccs.201000194

  日期：2010.12

  convenient and efficient procedure for the synthesis of α‐amino phosphonates by a one‐pot, three‐component condensation of aldehydes, amine, and diethyl phosphite in the presence of xanthan sulfuric acid as a bio‐supported catalyst under solvent‐free conditions has been developed. A wide range of α‐amino phosphonates have been obtained in high to excellent yields. Furthermore, the catalyst can be recovered

  在无溶剂条件下，以黄原酸作为生物负载催化剂，通过醛，胺和亚磷酸二乙酯的一锅，三组分缩合反应合成α-氨基膦酸酯的便捷高效方法具有已开发。以高到极好的产率获得了各种各样的α-氨基膦酸酯。此外，可以简单地回收催化剂，并在随后的反应中重复使用几次。