9-bromo-2-(3-chloro-4-fluorophenyl)-4,4-dimethyl-4,5-dihydropyrrolo[2,3,4-kl]acridin-1(2H)-one | 166883-88-1

• 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: 9-bromo-2-(3-chloro-4-fluorophenyl)-4,4-dimethyl-4,5-dihydropyrrolo[2,3,4-kl]acridin-1(2H)-one
• 英文别名: 3-[(3-Chloro-4-fluorophenyl)amino]-5,5-dimethylcyclohex-2-en-1-one；3-(3-chloro-4-fluoroanilino)-5,5-dimethylcyclohex-2-en-1-one
• CAS: 166883-88-1
• 化学式: C₁₄H₁₅ClFNO
• mdl: MFCD02327216
• 分子量: 267.731
• InChiKey: QVRXIBRZRFFPKA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  29.1
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  9-bromo-2-(3-chloro-4-fluorophenyl)-4,4-dimethyl-4,5-dihydropyrrolo[2,3,4-kl]acridin-1(2H)-one 在 sodium amide 、 sodium t-butanolate 作用下， 以 四氢呋喃 为溶剂， 反应 48.0h， 以58%的产率得到1,2,3,9-tetrahydro-6-fluoro-2,2-dimethyl-4H-carbazol-4-one
  参考文献：
  名称：

  Aggregative activation and heterocyclic chemistry I complex bases promoted arynic cyclisation of imines or enaminoketones; regiochemical synthesis of indoles

  摘要：

  The complex base NaNH2-t-BuONa allowed expeditious syntheses of indoles by arynic cyclisation of imines or enaminoketones prepared from halogeno anilines and carbonyl derivatives. Unstable imines may be used without purification, complex bases being unsensitive to impurities. It is showed that this kind of reaction may be applied to mixture of substrates suitably halogenated on the benzene ring. Formation of three components aggregates is proposed to explain a number of observations.

  DOI：

  10.1016/s0040-4020(01)89304-2
• 作为产物：
  描述：

  3-氯-4-氟苯胺 、 5,5-二甲基-1,3-环己二酮 在 APTS 作用下， 以 苯 为溶剂， 生成 9-bromo-2-(3-chloro-4-fluorophenyl)-4,4-dimethyl-4,5-dihydropyrrolo[2,3,4-kl]acridin-1(2H)-one
  参考文献：
  名称：

  Aggregative activation and heterocyclic chemistry I complex bases promoted arynic cyclisation of imines or enaminoketones; regiochemical synthesis of indoles

  摘要：

  The complex base NaNH2-t-BuONa allowed expeditious syntheses of indoles by arynic cyclisation of imines or enaminoketones prepared from halogeno anilines and carbonyl derivatives. Unstable imines may be used without purification, complex bases being unsensitive to impurities. It is showed that this kind of reaction may be applied to mixture of substrates suitably halogenated on the benzene ring. Formation of three components aggregates is proposed to explain a number of observations.

  DOI：

  10.1016/s0040-4020(01)89304-2

文献信息

• Facile one-pot three-component synthesis of diverse 2,3-disubstituted isoindolin-1-ones using ZrO₂ nanoparticles as a reusable dual acid–base solid support under solvent-free conditions
  作者：Kamalesh Debnath、Sayan Mukherjee、Chandan Bodhak、Animesh Pramanik

  DOI：10.1039/c6ra00870d

  日期：——

  A facile one-pot three-component protocol for the synthesis of a series of multi-functionalized 2,3-disubstituted isoindolin-1-ones has been developed using ZrO2 nanoparticles as a dual acid–base solid support under solvent-free conditions. The surface of the ZrO2 nanoparticles, which is embedded with active hydroxyl groups, oxyanions and Zr4+ ions, efficiently catalyses the condensation of 2-carboxybenzaldehyde

  使用ZrO 2纳米颗粒作为无溶剂条件下的双酸碱固相载体，已经开发了一种简便的一锅三组分规程，用于合成一系列多官能化的2,3-二取代异吲哚啉-1-酮。ZrO 2纳米颗粒的表面嵌入了活性羟基，氧阴离子和Zr 4+离子，可有效催化2-羧基苯甲醛，脂肪族胺与亲核试剂的缩合（烯胺/ 6-氨基1,3-二甲基尿嘧啶/ 1 ，3-环己二酮/吲哚）产生2，3-二取代的异吲哚啉-1-酮。操作简单，减少反应时间和温度，消除溶剂，产品产率高，基材范围更广，ZrO 2的利用 作为固体载体的纳米颗粒及其在重复应用后几乎没有减弱的催化活性是本方法的关键特征。
• Magnetically separable Fe₃O₄–SO₃H nanoparticles as an efficient solid acid support for the facile synthesis of two types of spiroindole fused dihydropyridine derivatives under solvent free conditions
  作者：Kamalesh Debnath、Krishnadipti Singha、Animesh Pramanik

  DOI：10.1039/c5ra00737b

  日期：——

  (N–H or N–R/Ar) two different types of products are formed through three component one-pot condensation reactions. Operational simplicity, reduced reaction time, lower reaction temperature, elimination of solvents, high yields of the products, easy separation of Fe3O4–SO3H nanoparticles by means of an external magnetic bar and recyclability of Fe3O4–SO3H nanoparticles make the present method economical

  发现磁性可分离的Fe 3 O 4 -SO 3 H纳米颗粒可作为一种有效的固体负载酸催化剂，用于轻松合成两种类型的螺吲哚稠合的二氢吡啶衍生物，例如螺[indolo-3,10'-茚并[1,2] -b ]喹啉] -2,4,11'-三酮和茚并喹啉-螺氧并吲哚在无溶剂条件下。根据起始异构素（NH或N-R / Ar）的N取代的性质，可以通过三组分一锅缩合反应形成两种不同类型的产物。操作简单，减少反应时间，降低反应温度，消除溶剂，产物产率高，Fe 3 O 4 -SO 3易于分离H纳米颗粒通过外部磁棒和Fe 3 O 4 -SO 3 H纳米颗粒的可回收性使本方法经济，绿色和可持续。
• 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。
• Microwave-Assisted Improved Synthesis of Pyrrolo[2,3,4-kl]acridine and Dihydropyrrolo[2,3,4-kl]acridine Derivatives Catalyzed by Silica Sulfuric Acid
  作者：Chengpao Cao、Changliang Xu、Wei Lin、Xuemei Li、Minghua Hu、Juxian Wang、Zhibin Huang、Daqing Shi、Yucheng Wang

  DOI：10.3390/molecules18021613

  日期：——

  An improved synthesis of multifunctionalized pyrrolo[2,3,4-kl]acridine derivatives with different substituted patterns using silica sulfuric acid (SSA) as a heterogeneous catalyst under microwave irradiation conditions was developed. The reaction could be conducted by using readily available and inexpensive substrates within short periods of 12–15 min. under microwave irradiation. Compared with the

  开发了使用二氧化硅硫酸 (SSA) 作为非均相催化剂在微波辐射条件下合成具有不同取代模式的多功能吡咯并 [2,3,4-kl] 吖啶衍生物的改进方法。该反应可以通过使用容易获得且价格低廉的底物在 12-15 分钟的短时间内在微波辐射下进行。与传统方法相比，该方法的显着优点是反应条件温和、操作简单、产率高、反应时间短、过程环保。
• Efficient syntheses of novel indeno[1,2-b]chromenone derivatives via hetero-Diels-Alder reactions of 2-(arylmethylene)-1H-indene-1,3(2H)-diones with enaminones
  作者：Kalawati Meena、Sudesh Kumari、Jitender M. Khurana、Amita Malik

  DOI：10.1016/j.tetlet.2018.03.014

  日期：2018.4

  Efficient syntheses of novel 10-aryl-5a-(arylamino)-9-hydroxy-5a,6,7,8-tetrahydroindeno[1,2-b]chromen-11(10H)-one derivatives has been reported by [4+2] cycloaddition reactions of electron-deficient 2-(arylmethylene)-1H-indene-1,3(2H)-dione heterodienes with electron-rich enaminones in [bmim]BF4 at 80 °C and in acetic acid at 80 °C. Dimedone/cyclohexane-1,3-dione enaminones have been used as dienophiles

  新颖10芳基-5-的高效合成一- （芳基氨基）-9-羟基-5-一个，6,7,8-四氢茚并[1,2- b ]苯并吡喃11（10 ħ） -酮衍生物已经报道由[ bmim] BF 4中在80°C和乙酸中，缺电子的2-（芳基亚甲基）-1 H-茚-1,3（2 H）-二酮杂二烯与富电子的烯酮的[4 + 2]环加成反应80°C时呈酸性。在反电子需量异Diels-Alder反应中，二甲酮/环己烷-1,3-二酮烯酮已被用作亲二烯体。通过简单的后处理即可以高收率获得产品。