N-cyclopropyl-N-(2,4-dinitrophenyl)amine | 31846-29-4

• 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: N-cyclopropyl-N-(2,4-dinitrophenyl)amine
• 英文别名: N-cyclopropyl-2,4-dinitroaniline
• CAS: 31846-29-4
• 化学式: C₉H₉N₃O₄
• mdl: MFCD02039796
• 分子量: 223.188
• InChiKey: UUSBBZCYYXEBJV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.333
• 拓扑面积：
  104
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  N-cyclopropyl-N-(2,4-dinitrophenyl)amine 在 硫酸 、 铁粉 、 溶剂黄146 、 potassium nitrate 作用下， 生成 1-Cyclopropyl-6,7-dinitro-1,4-dihydro-quinoxaline-2,3-dione
  参考文献：
  名称：

  Pyrrolylquinoxalinediones: A new class of AMPA receptor antagonists

  摘要：

  Pyrrolylquinoxalinediones were synthesized and their affinities for the AMPA receptor were determined. Most compounds showed moderate to good affinities. The acetic acid derivative 8b exhibited a K-i value of 70 nM and was equipotent to NBQX 1. Structure activity relationships are discussed. Selected compounds were tested for their potency to inhibit AMPA induced lethal convulsions in mice. In this in vivo model the compounds showed improved potency compared with NBQX. Copyright (C) 1996 Elsevier Science Ltd

  DOI：

  10.1016/s0960-894x(96)00534-3
• 作为产物：
  描述：

  2,4-二硝基苯磺酸二水合物 、 环丙胺 以 四氢呋喃 为溶剂， 反应 0.5h， 以92%的产率得到N-cyclopropyl-N-(2,4-dinitrophenyl)amine
  参考文献：
  名称：

  磺酸的异丙基亲核取代合成邻硝基硝基芳基胺

  摘要：

  描述了一种温和，有效和环保的方法，该方法用于通过邻氨基芳基的ipso亲核芳基取代反应，由邻硝基芳基磺酸合成邻硝基芳基胺。无需任何金属，活化剂或有毒氧化剂的帮助，即可在室温下以高收率获得产品。该方法可用于无消旋地合成N-芳基氨基酸酯。

  DOI：

  10.1021/acs.orglett.8b03730

文献信息

• A New Leaving Group in Nucleophilic Aromatic Substitution Reactions (S_NAr)
  作者：Mehdi Bakavoli、Mehdi Pordel、Mohammad Rahimizadeh、Pooneh Jahandari

  DOI：10.3184/030823408x338693

  日期：2008.8

  Nucleophilic aromatic substitution of a 2,4-dinitrophenyl substituted pyrazole 1 with primary amines leads to substitution of the pyrazolo substituent. In these nucleophilic aromatic substitution reactions (SNAr), 5-amino-1H-4-pyrazolecarbonitrile (3) acts as a new leaving group.

  2,4-二硝基苯基取代的吡唑 1 与伯胺的亲核芳族取代导致吡唑基取代基的取代。在这些亲核芳香取代反应 (SNAr) 中，5-氨基-1H-4-吡唑甲腈 (3) 作为新的离去基团。
• Pyrrolylquinoxalinediones: A new class of AMPA receptor antagonists
  作者：W. Lubisch、B. Behl、H.P. Hofmann

  DOI：10.1016/s0960-894x(96)00534-3

  日期：1996.12

  Pyrrolylquinoxalinediones were synthesized and their affinities for the AMPA receptor were determined. Most compounds showed moderate to good affinities. The acetic acid derivative 8b exhibited a K-i value of 70 nM and was equipotent to NBQX 1. Structure activity relationships are discussed. Selected compounds were tested for their potency to inhibit AMPA induced lethal convulsions in mice. In this in vivo model the compounds showed improved potency compared with NBQX. Copyright (C) 1996 Elsevier Science Ltd
• Synthesis of <i>o</i>-Nitroarylamines via Ipso Nucleophilic Substitution of Sulfonic Acids
  作者：Srinivasa Rao Manne、Jyoti Chandra、Bhubaneswar Mandal

  DOI：10.1021/acs.orglett.8b03730

  日期：2019.2.1

  and eco-friendly method for the synthesis of o-nitroarylamine from o-nitroaryl sulfonic acid via ipso nucleophilic aryl substitution by amine is described. The products have been obtained with good yields at room temperature without the assistance of any metal, activating agent, or toxic oxidant. This method is useful for racemization-free synthesis of N-aryl amino acid esters.

  描述了一种温和，有效和环保的方法，该方法用于通过邻氨基芳基的ipso亲核芳基取代反应，由邻硝基芳基磺酸合成邻硝基芳基胺。无需任何金属，活化剂或有毒氧化剂的帮助，即可在室温下以高收率获得产品。该方法可用于无消旋地合成N-芳基氨基酸酯。