2-(4-chlorophenyl)-4,4-dimethyl-4,5-dihydropyrrolo[2,3,4-kl]acridin-1(2H)-one | 1393134-31-0

• 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-chlorophenyl)-4,4-dimethyl-4,5-dihydropyrrolo[2,3,4-kl]acridin-1(2H)-one
• 英文别名: 2-(4-chlorophenyl)-4,5-dihydro-4,4-dimethylpyrrolo[2,3,4-kl]acridin-1(2H)-one；14-(4-Chlorophenyl)-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: 1393134-31-0
• 化学式: C₂₂H₁₇ClN₂O
• 分子量: 360.843
• InChiKey: WLGSHCZGZMWXOL-UHFFFAOYSA-N

物化性质

• 沸点：
  587.9±50.0 °C(predicted)
• 密度：
  1.38±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.2
• 重原子数：
  26
• 可旋转键数：
  1
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  33.2
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-(4-chlorophenyl)-4,4-dimethyl-4,5-dihydropyrrolo[2,3,4-kl]acridin-1(2H)-one 、 丁炔二酸二乙酯 在 异丁酸 作用下， 反应 0.34h， 以58%的产率得到tetraethyl 6-(4-chlorophenyl)-8,8-dimethyl-5-oxo-6,8,8b,9,10,10a-hexahydro-5H-cyclobuta [4,5]pyrrolo[3,2,1-de]pyrrolo[4,3,2-mn]acridine-8b,9,10,10a-tetracarboxylate
  参考文献：
  名称：

  Highly Selective Domino Multicyclizations for Forming Polycyclic Fused Acridines and Azaheterocyclic Skeletons

  摘要：

  Highly selective four-component domino multicyclizations for the synthesis of new fused acridines and azaheterocyclic skeletons have been established by mixing common reactants in isobutyric acid under microwave irradiation. The reactions proceed at fast rates and were conducted to completion within 20-30 min. Up to seven new chemical bonds, four rings, and four stereocenters were assembled in a convenient one-pot operation. The resulting hexacyclic and pentacyclic fused acridines and their stereochemistry have been fully characterized and determined by X-ray structural analysis.

  DOI：

  10.1021/ol400322v
• 作为产物：
  描述：

  3-[(4-氯苯基)氨基]-5,5-二甲基环己-2-烯-1-酮 、 靛红 在 sulfonated carbonaceousmaterial (C-SO₃H) 作用下， 以 水 为溶剂， 反应 8.0h， 以87%的产率得到2-(4-chlorophenyl)-4,4-dimethyl-4,5-dihydropyrrolo[2,3,4-kl]acridin-1(2H)-one
  参考文献：
  名称：

  Single step incorporation of isatin to enaminone: a recyclable catalyst towards assembly of diverse four ring fused pyrrolo[2,3,4-kl]acridin-1-ones

  摘要：

  使用可回收的磺化碳质材料作为非均相催化剂，实现了一步合成四环融合的吡咯并[2,3,4-kl]吖啶酮。

  DOI：

  10.1039/c6ra18048e

文献信息

• 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。
• Amidic C–N bond cleavage of isatin: chemoselective synthesis of pyrrolo[2,3,4-<i>kl</i>]acridin-1-ones using Ag NPs decorated rGO composite as an efficient and recoverable catalyst under microwave irradiation
  作者：Anshu Dandia、Amit Sharma、Vijay Parewa、Begraj Kumawat、Kuldeep S. Rathore、Amit Sharma

  DOI：10.1039/c5ra11747j

  日期：——

  A facile route for the chemo-selective synthesis of pyrrolo[2,3,4-kl]acridin-1-ones via ring-opening or amidic C–N bond cleavage of isatin under microwave irradiation using Ag NPs/rGO composite as an effective and robust catalyst has been described.

  通过微波辐射下使用Ag NPs/rGO复合物作为有效和稳健的催化剂，描述了一种简便的化学选择性合成吡咯并[2,3,4-kl]吖啶-1-酮的方法，通过吲哚酮的环开放或酰胺C-N键裂解。
• A domino synthetic strategy leading to two-carbon-tethered fused acridine/indole pairs and fused acridine derivatives
  作者：Bo Jiang、Xue Wang、Meng-Yuan Li、Qiong Wu、Qin Ye、Hai-Wei Xu、Shu-Jiang Tu

  DOI：10.1039/c2ob26315g

  日期：——

  pairs were synthesized via Brønsted acid-promoted domino reactions between indoline-2,3-dione and C2-tethered indol-3-yl enaminones. The reactions were further expanded to prepare C-tethered fused acridine/pyridine pairs, N-substituted amino acids, N-cyclopropyl and N-aryl substituted fused acridine derivatives, as well as bis-furan-3-yl-substituted indoles. During these reaction processes, the domino

  一系列新型的多官能化的两碳束缚电熔 cr啶/吲哚对通过布朗斯台德酸促进的多米诺骨牌反应合成吲哚啉-2,3-二酮和C 2系联的吲哚-3-基烯胺酮。反应进一步扩大以制备C系链的稠合cr啶/吡啶对，N-取代的氨基酸，N-环丙基和N-芳基取代的稠合a啶衍生物以及双呋喃-3-基取代的吲哚。在这些反应过程中，通过一锅操作很容易实现了稠合的cr啶骨架的多米诺结构以及同时形成的两个新环。该过程是容易的，避免了费时和昂贵的合成，繁琐的后处理和前体纯化。
• 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。