2-(4-methoxyphenyl)-4,4-dimethyl-4,5-dihydropyrrolo[2,3,4-kl]acridin-1(2H)-one | 1393134-36-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 英文名称: 2-(4-methoxyphenyl)-4,4-dimethyl-4,5-dihydropyrrolo[2,3,4-kl]acridin-1(2H)-one
• 英文别名: 14-(4-Methoxyphenyl)-11,11-dimethyl-8,14-diazatetracyclo[7.6.1.02,7.013,16]hexadeca-1(16),2,4,6,8,12-hexaen-15-one；14-(4-methoxyphenyl)-11,11-dimethyl-8,14-diazatetracyclo[7.6.1.02,7.013,16]hexadeca-1(16),2,4,6,8,12-hexaen-15-one
• CAS: 1393134-36-5
• 化学式: C₂₃H₂₀N₂O₂
• 分子量: 356.424
• InChiKey: YAMZDXWYJNVAEC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  27
• 可旋转键数：
  2
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  42.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  3-[(4-甲氧苯基)氨基]-5,5-二甲基-1-环己-2-烯酮 、 靛红 在 silica sulfuric acid 作用下， 以 甲苯 为溶剂， 反应 0.75h， 以91%的产率得到2-(4-methoxyphenyl)-4,4-dimethyl-4,5-dihydropyrrolo[2,3,4-kl]acridin-1(2H)-one
  参考文献：
  名称：

  二氧化硅硫酸催化高效合成吡咯啉系A啶衍生物

  摘要：

  已经建立了一种简单高效的合成方法，该方法通过靛红与二氧化硅硫酸（SSA）催化的烯胺酮的级联反应合成吡咯并[ 2,3,4- kl ] ac啶-1-酮衍生物。在此反应中，SSA具有高度催化性：易于操作，反应时间短，可循环利用，对空气和湿气不敏感以及出色的分离收率。催化剂可以循环至少五次。

  DOI：

  10.1002/jhet.2023

文献信息

• A heteroditopic macrocycle as organocatalytic nanoreactor for pyrroloacridinone synthesis in water
  作者：Piyali Sarkar、Sayan Sarkar、Pradyut Ghosh

  DOI：10.3762/bjoc.15.152

  日期：——

  A heteroditopic macrocycle is reported as an efficient organocatalytic nanoreactor for the synthesis of diversely functionalized pyrroloacridinones in aqueous medium. A library of compounds was synthesized in a one-step pathway utilizing 10 mol % of the nanoreactor following a sustainable methodology in water with high yields.

  一种异二元宏环被报道为在水介质中合成多样官能化吡咯并蒽醌酮的高效有机催化纳米反应器。利用10%的纳米反应器，在水中采用可持续方法一步合成了一系列化合物，收率高。
• One-pot, three-component reaction of dimedone, amines, and isatin in the presence of tris(hydrogensulfato) boron: synthesis of pyrroloacridine derivatives
  作者：Zahed Karimi-Jaberi、Alireza Jaafarizadeh

  DOI：10.1007/s11164-014-1576-y

  日期：2015.7

  three-component reaction of dimedone, anilines. and isatin has been described leading to the synthesis of 2-arylpyrroloacridin-1(2H)-ones in the presence of tris(hydrogensulfato) boron [B(HSO4)3] at reflux in ethanol. However, in the cases of aliphatic amines, tetrahydroxanthene has been obtained from the reaction of isatin and dimedone.

  一锅三组分的二甲酮苯胺反应。并且已经描述了靛红在乙醇中在三（氢硫酸根）硼[B（HSO 4）3 ]存在下导致2-芳基吡咯并olo啶-1（2H）-的合成。但是，在脂肪族胺的情况下，四氢x吨是从靛红和二甲基二酮的反应中获得的。
• A Green Approach for the One-Pot, Three-Component Synthesis of 2-Arylpyrroloacridin-1(2<i>H</i>)-Ones using Lactic Acid as a Bio-based Catalyst under Solvent-Free Conditions
  作者：Maryam Fatahpour、Nourallah Hazeri、Malek Taher Maghsoodlou、Mojtaba Lashkari

  DOI：10.1002/jccs.201700128

  日期：2017.9

  benign synthetic strategy is proposed for the synthesis of 2‐arylpyrroloacridin‐1(2H)‐ones via a lactic acid‐catalyzed three‐component reaction of dimedone, various anilines, and isatins under solvent‐free conditions. Avoidance of hazardous organic solvents, the use of a one‐pot multicomponent procedure for the synthesis of 2‐arylpyrroloacridin‐1(2H)‐ones, operational simplicity, no need for column chromatography

  提出了一种简便而良性的合成策略，用于在无溶剂条件下通过乳酸催化的二甲酮，各种苯胺和靛红的三组分反应合成2-芳基吡咯并rr啶-1（2 H）-酮。避免使用危险的有机溶剂，使用一锅多组分程序合成2-芳基吡咯并ac啶酮-1（2 H）-酮，操作简便，无需柱色谱法，将乳酸用作生物基有机化合物，催化剂的可重复使用性，均质性和市售性以及优异的合成性能是该方法的重要方面，可用于通过潜在的生物支架获得一系列吡咯并cr啶基序。
• An unexpected multicomponent reaction leading to 2-arylpyrrolo[2,3,4-kl]acridin-1(2H)-ones
  作者：Hassan Kefayati、Fataneh Narchin、Kurosh Rad-Moghadam

  DOI：10.1016/j.tetlet.2012.06.070

  日期：2012.8

  An unexpected condensation profile was observed for the three-component reaction of 5,5-dimethyl-1,3-cyclohexadione (dimedone), various anilines, and isatin leading to the synthesis of novel 2-arylpyrrolo [2,3,4-kl]acridin-1(2H)-ones in the ionic liquid [HMIm]HSO4. Regeneration of the enamine group after the initial condensation reaction associated with participation of the restored amine group in translactonization with the pyrrolidone ring are suggested as the main differentiating events being favored over addition of the second dimedone molecule, with respect to similar reported reactions. (C) 2012 Elsevier Ltd. All rights reserved.
• An Efficient Synthesis of Pyrroline-Fused Acridine Derivatives Catalyzed by Silica Sulfuric Acid
  作者：Ming-Hua Hu、Wei Lin、Cheng-Pao Cao、Zhi-Bin Huang、Da-Qing Shi

  DOI：10.1002/jhet.2023

  日期：2014.8

  A simple and efficient synthesis of pyrrolo[2,3,4-kl]acridine-1-one derivatives via the cascade reaction of isatins with enaminones catalyzed by silica sulfuric acid (SSA) has been established. In this reactions, SSA shows a highly catalytic nature: easy to handle procedure, short reaction time, recycle exploitation, insensitivity to air and moisture, and excellent isolated yields. The catalyst could

  已经建立了一种简单高效的合成方法，该方法通过靛红与二氧化硅硫酸（SSA）催化的烯胺酮的级联反应合成吡咯并[ 2,3,4- kl ] ac啶-1-酮衍生物。在此反应中，SSA具有高度催化性：易于操作，反应时间短，可循环利用，对空气和湿气不敏感以及出色的分离收率。催化剂可以循环至少五次。