1,2-dihydro-8-methyl-4(3H)-carbazolone | 153865-32-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 英文名称: 1,2-dihydro-8-methyl-4(3H)-carbazolone
• 英文别名: 1,2,3,9-tetrahydro-8-methyl-4H-carbazol-4-one；8-methyl-1,2-dihydrocarbazol-4(3H)-one；8-methyl-2,3-dihydro-1H-carbazol-4(9H)-one；8-Methyl-1,2,3,9-tetrahydro-4H-carbazol-4-one；8-methyl-1,2,3,9-tetrahydrocarbazol-4-one
• CAS: 153865-32-8
• 化学式: C₁₃H₁₃NO
• 分子量: 199.252
• InChiKey: QFTGKLHYEWRXKN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  15
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  32.9
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  1,2-dihydro-8-methyl-4(3H)-carbazolone 、 正戊烷 、 sodium;hydride 、 溴甲苯 在 溴甲苯 碳酸氢钠 、 乙酸乙酯 、 Sodium sulfate-III 、 Ethyl acetate hexane methylene-chloride 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 19.5h， 以to give 0.2076 g (73%) of the title compound的产率得到9-benzyl-8-methyl-1,2,3,9-tetrahydro-4H-carbazol-4-one
  参考文献：
  名称：

  Aminoalkoxy carbazoles for the treatment of cns diseases

  摘要：

  本发明提供了氨基烷氧基咔唑衍生物，更具体地提供了式(I)中R1、R2、R3、R4、R8和R9所描述的化合物。这些化合物是5-HT配体，可用于治疗需要调节5-HT活性的疾病。

  公开号：

  US06514968B1
• 作为产物：
  描述：

  1-碘-3-甲基-2-硝基苯 在 二(氰基苯)二氯化钯 、 bis(dibenzylideneacetone)-palladium⁽⁰⁾ copper(l) iodide 、 1,10-菲罗啉 、 三苯胂 、 一氧化碳 、 1,3-双(二苯基膦)丙烷 作用下， 以 N-甲基吡咯烷酮 、 N,N-二甲基甲酰胺 为溶剂， 80.0 ℃ 、607.95 kPa 条件下， 生成 1,2-dihydro-8-methyl-4(3H)-carbazolone
  参考文献：
  名称：

  Novel palladium-catalyzed synthesis of 1,2-dihydro-4(3H)-carbazolones

  摘要：

  Two sequential palladium-catalyzed reactions are the key steps in a novel synthetic route to carbazolones, an intermolecular Stille coupling followed by a recently developed palladium-catalyzed reductive N-heteroannulation. A number of functionalized 1,2-dihydro-4(3H)-carbazolones were prepared using this sequence. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(02)00072-2

文献信息

• An Improved Method for the Synthesis of Carbazolones by Palladium/Copper-Catalyzed Intramolecular Annulation of N-Arylenaminones
  作者：Jing-Hua Li、Bojie Weng、Rui Liu

  DOI：10.1055/s-0030-1258141

  日期：2010.9

  via the condensation of arylamines with 1,3-cyclodiketones followed by intramolecular oxidative cyclization catalyzed by palladium acetate and copper acetate in ethanol under an oxygen atmosphere was established. The improved method has the advantage of easily available starting materials and affords good yields. carbazolones - intramolecular oxidative cyclization - oxygen - palladium acetate - copper

  建立了一种改进的合成方法，该方法通过芳基胺与1,3-环二酮的缩合，然后在氧气气氛下由乙酸钯和乙酸铜在乙醇中催化，进行分子内氧化环化反应来合成咔唑酮。改进的方法的优点是容易获得起始原料并提供良好的产率。 卡巴唑酮-分子内氧化环化-氧气-乙酸钯-乙酸铜
• Hypervalent Iodine(III)‐Mediated Counteranion Controlled Intramolecular Annulation of Exocyclic β‐Enaminone to Carbazolone and Imidazo[1,2‐<i>a</i>]pyridine Synthesis
  作者：Dhananjay Bhattacherjee、Shankar Ram、Arvind Singh Chauhan、Yamini、Sheetal、Pralay Das

  DOI：10.1002/chem.201806299

  日期：2019.4.23

  A highly efficient and flexible protocol for intramolecular annulation of exocyclic β‐enaminones has been disclosed for the synthesis of carbazolones and imidazo[1,2‐a]pyridines through a counter‐anion‐controlled free‐radical mechanism promoted by hypervalent iodine(III). The cooperative behavior of HTIB and AgSbF6 plays a crucial role in the intramolecular annulation process through C−C and C−N bond

  为环外β-烯胺酮的分子内环化一个高效和灵活的协议已经公开了carbazolones和咪唑并[1,2的合成一个]吡啶通过高价碘促进的抗衡阴离子控制自由基机理（III） 。HTIB和AgSbF 6的协同行为在通过CC和CN键形成所需的分子内环化过程中起着至关重要的作用。机械学的见解表明，系统中涉及的两个竞争性反应是由抗衡阴离子的性质决定的，抗衡阴离子的性质决定了最终产物的形成。制备并分离了各种咔唑酮和咪唑并[1,2- a ]吡啶分子，收率良好至极佳。
• Complex bases promoted arynic cyclisations of halogenated imines or enamines: A regiochemical synthesis of indole derivatives
  作者：Catherine Caubère、Paul Caubère、Pierre Renard、Jean-Guy Bizot-Espiart、Brigitte Jamart-Grégoire

  DOI：10.1016/s0040-4039(00)91822-7

  日期：1993.10

  The complex base NaNH2-tBuONa allows expeditious synthesis of indole derivatives by arynic cyclization of imines or enamines of chloroanilines. Unstable may be used without purification, complex bases being unsensitive to impurities.

  复杂的碱式NaNH 2 -tBuONa可以通过亚胺或氯苯胺的烯胺的芳基环化反应迅速合成吲哚衍生物。不稳定，无需纯化即可使用，复杂的碱对杂质不敏感。
• Aggregative activation and heterocyclic chemistry I complex bases promoted arynic cyclisation of imines or enaminoketones; regiochemical synthesis of indoles
  作者：Catherine Caubère、Paul Caubère、Sandra Ianelli、Mario Nardelli、Brigitte Jamart-Grégoire

  DOI：10.1016/s0040-4020(01)89304-2

  日期：1994.1

  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.
• Palladium-catalyzed synthesis of 1,2-dihydro-4(3H)-carbazolones. Formal total synthesis of murrayaquinone A
  作者：Tricia L Scott、Björn C.G Söderberg

  DOI：10.1016/s0040-4020(03)00976-1

  日期：2003.8

  Two sequential palladium-catalyzed reactions are the key steps in a novel synthetic route to 1,2-dihydro-4(3H)-carbazolones. The steps are an intermolecular Stille cross-coupling followed by a reductive N-heteroannulation. A formal total synthesis of murrayaquinone A, employing this sequence, is reported. (C) 2003 Elsevier Ltd. All fights reserved.