4-[(3-nitrophenyl)amino]pent-3-en-2-one | 68903-25-3

• 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: 4-[(3-nitrophenyl)amino]pent-3-en-2-one
• 英文别名: 4-(3-nitrophenylamino)-3-penten-2-one；4-[(3-Nitrophenyl)amino]-3-penten-2-one；4-(3-nitroanilino)pent-3-en-2-one
• CAS: 68903-25-3
• 化学式: C₁₁H₁₂N₂O₃
• 分子量: 220.228
• InChiKey: RKODTPIHPRNNHD-UHFFFAOYSA-N

物化性质

• 熔点：
  78-80 °C
• 沸点：
  362.4±42.0 °C(Predicted)
• 密度：
  1.242±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  74.9
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  4-[(3-nitrophenyl)amino]pent-3-en-2-one 在 硫酸 、 溶剂黄146 作用下， 反应 0.77h， 生成 3-acetyl-2-methyl-1-(3-nitrophenyl)-4-oxa-1-azacyclopenta[a]naphthalen-5-one
  参考文献：
  名称：

  Facile synthesis of substituted pyrrole-fused isocoumarins from ninhydrin

  摘要：

  A simple and efficient procedure has been developed for the synthesis of substituted pyrrole-fused isocoumarins from easily available ninhydrin. The cyclic hemiaminal dihydroxy-indenopyrroles, the adducts of ninhydrin with enamines of acetylacetone, give pyrrole-fused isocournarins upon heating in acidic medium. The process constitutes an interesting acid-catalyzed rearrangement to eight-membered lactams followed by intramolecular cyclization involving the amino and keto groups. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2011.07.133
• 作为产物：
  描述：

  间硝基苯胺 、 乙酰丙酮 以65%的产率得到4-[(3-nitrophenyl)amino]pent-3-en-2-one
  参考文献：
  名称：

  Reactions of 4-Amino-3-penten-2-one and Its NSubstituted Derivatives with Diazonium Ions

  摘要：

  苯重氮盐与取代的4-氨基-3-戊烯-2-酮发生偶联反应，反应发生在C-3原子上。使用¹H和¹³C核磁共振光谱技术研究了起始烯胺酮和偶联产物的结构。在CDCl₃中，3-(4-氯苯基偶氮)-2-(4-甲基苯基亚胺)-4-戊酮以偶氮形式存在，而4-氨基-3-(4-氯苯基偶氮)-3-戊烯-2-酮以两种偶氮化合物的混合物形式存在，这两种化合物可能在分子内氢键排列上有所不同。偶氮偶联反应动力学在醋酸盐缓冲液和甲醇-水或tert-丁醇-水混合物中进行了研究。偶联速率发现与pH和缓冲液浓度无关。已确定了与起始化合物相关的反应级数，并提出了反应机理。根据Hammett或Yukawa-Tsuno方程式，发现了log k_obs与取代基常数之间的线性依赖关系。

  DOI：

  10.1135/cccc19951367

文献信息

• A Mild and Efficient Method for Synthesis of b-Enaminones using Melamine-Formaldehyde Resin Supported H+ Under Solvent Free Conditions
  作者：Ramin Rezaei、Mozhdeh Shakeri

  DOI：10.14233/ajchem.2013.14436

  日期：——

  A green and efficient practical approach is developed for the synthesis of b-enaminones using melamine-formaldehyde resin supported H+ (MFRH) as a mild and inexpensive catalyst in solvent-free media. The present method was performed by combining low cost and readily available amines, 1,3-dicarbonyls and melamine-formaldehyde resin supported H+ (MFRH) as a catalyst. This method is applicable to both cyclic and acyclic ketones with aromatic and aliphatic amines, and provides several advantages such as environmental friendliness, low cost, good yields and simple workup procedure.

  一种绿色高效的实用方法被开发用于合成β-烯胺酮，采用甲醛-三聚氰胺树脂支持的H+（MFRH）作为温和且廉价的催化剂，且在无溶剂条件下进行。该方法结合了低成本和易于获取的胺、1,3-二酮和作为催化剂的甲醛-三聚氰胺树脂支持H+（MFRH）。此方法适用于芳香和脂肪胺的环状和非环状酮，并提供了诸多优点，如环境友好、成本低、产率良好及操作简便。
• Freezing the Bioactive Conformation to Boost Potency: The Identification of BAY 85-8501, a Selective and Potent Inhibitor of Human Neutrophil Elastase for Pulmonary Diseases
  作者：Franz von Nussbaum、Volkhart M.-J. Li、Swen Allerheiligen、Sonja Anlauf、Lars Bärfacker、Martin Bechem、Martina Delbeck、Mary F. Fitzgerald、Michael Gerisch、Heike Gielen-Haertwig、Helmut Haning、Dagmar Karthaus、Dieter Lang、Klemens Lustig、Daniel Meibom、Joachim Mittendorf、Ulrich Rosentreter、Martina Schäfer、Stefan Schäfer、Jens Schamberger、Leila A. Telan、Adrian Tersteegen

  DOI：10.1002/cmdc.201500131

  日期：2015.7

  Human neutrophil elastase (HNE) is a key protease for matrix degradation. High HNE activity is observed in inflammatory diseases. Accordingly, HNE is a potential target for the treatment of pulmonary diseases such as chronic obstructive pulmonary disease (COPD), acute lung injury (ALI), acute respiratory distress syndrome (ARDS), bronchiectasis (BE), and pulmonary hypertension (PH). HNE inhibitors

  Human neutrophil elastase (HNE) is a key protease for matrix degradation. High HNE activity is observed in inflammatory diseases. Accordingly, HNE is a potential target for the treatment of pulmonary diseases such as chronic obstructive pulmonary disease (COPD), acute lung injury (ALI), acute respiratory distress syndrome (ARDS), bronchiectasis (BE), and pulmonary hypertension (PH). HNE inhibitors
• 1 4-dihydro-1 4-diphenylpyridine derivatives
  申请人：Gielen -Haertwig Heike

  公开号：US20050165014A1

  公开（公告）日：2005-07-28

  The invention relates to novel 1,4-dihydro-1,4-diphenylpyridine derivatives, processes for their preparation, and their use in medicaments, especially for the treatment of chronic obstructive pulmonary diseases.

  本发明涉及新型1,4-二氢-1,4-二苯基吡啶衍生物，其制备方法以及它们在药物中的应用，尤其是用于慢性阻塞性肺疾病的治疗。
• 1,4-dihydro-1,4-diphenylpyridine derivatives
  申请人：Bayer HealthCare AG

  公开号：US07199136B2

  公开（公告）日：2007-04-03

  The invention relates to novel 1,4-dihydro-1,4-diphenylpyridine derivatives of formula (I) wherein the variable groups are as defined in the text and claims. Processes for their preparation, pharmaceutical compositions containing them, and methods of treatment of inflammatory processes, expecially chronic obstructive pulmonary diseases, using them are also disclosed and claimed.

  本发明涉及新型1,4-二氢-1,4-二苯基吡啶衍生物的公式（I），其中变量基团如文本和权利要求中所定义。本发明还揭示和声明了它们的制备过程、含有它们的药物组合物，以及使用它们治疗炎症过程，特别是慢性阻塞性肺部疾病的方法。