8H-indolo[2,3-b]benzo[h]quinoline | 1190844-48-4

• 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: 8H-indolo[2,3-b]benzo[h]quinoline
• 英文别名: 12H-benzo[h]indolo[2,3-b]quinoline；10,12-Diazapentacyclo[11.8.0.03,11.04,9.014,19]henicosa-1,3(11),4,6,8,12,14,16,18,20-decaene
• CAS: 1190844-48-4
• 化学式: C₁₉H₁₂N₂
• 分子量: 268.318
• InChiKey: JSUVLMUHZAPZLH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.2
• 重原子数：
  21
• 可旋转键数：
  0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  28.7
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  1-溴-2-萘甲醛 在 四氢吡咯 、 盐酸 、 四(三苯基膦)钯 作用下， 以 甲醇 、 乙醇 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 32.17h， 生成 8H-indolo[2,3-b]benzo[h]quinoline
  参考文献：
  名称：

  钯催化的双重环空法：去甲隐油菜碱的合成方法

  摘要：

  报道了一种新型的钯催化双环合反应合成壬基隐油菜碱衍生物的新方法，该过程涉及两个中心杂环的协同构建。去甲隐油菜籽进一步的甲基化以提供其生物碱类似物新隐油菜籽暗示了各种新隐油菜籽衍生物的合成是可行的。根据机理研究表明，Pd（0）的氧化加成是激活腈分子内加成的关键步骤。

  DOI：

  10.1021/acs.orglett.9b00287

文献信息

• Microwave-induced bismuth(III)-catalyzed synthesis of linear indoloquinolines
  作者：Prakash T. Parvatkar、P.S. Parameswaran、Debasish Bandyopadhyay、Sanghamitra Mukherjee、Bimal K. Banik

  DOI：10.1016/j.tetlet.2017.06.040

  日期：2017.7

  Bi(NO3)3-catalyzed one-pot synthesis of a series of linear indoloquinolines is accomplished under mild reaction conditions. While majority of these examples were carried out under solvent-free conditions, in a few cases, minimal quantity of THF is used as solvent. The methodology involves several unique reaction pathways, providing different linear indolo[2,3-b]quinolines in good yields from readily

  微波诱导的Bi（NO 3）3催化一锅合成一系列线性吲哚喹啉在温和的反应条件下完成。尽管这些示例中的大多数都是在无溶剂条件下进行的，但在少数情况下，使用的THF量很少。该方法涉及几种独特的反应途径，从容易获得的起始原料中以高收率提供不同的线性吲哚并[2,3- b ]喹啉，并使用对环境无害的Bi（NO 3）3 ·5H 2 O作为催化剂。
• An Expeditious I₂-Catalyzed Entry into 6<i>H</i>-Indolo[2,3-<i>b</i>]quinoline System of Cryptotackieine
  作者：Prakash T. Parvatkar、Perunninakulath S. Parameswaran、Santosh G. Tilve

  DOI：10.1021/jo901361x

  日期：2009.11.6

  A synthesis of a series of novel 6H-indolo[2,3-b]-quinolines with different substituents on the quinoline ring is described. The method involves reaction of indole-3-carboxyaldehyde with aryl amines in the presence of a catalytic amount of iodine in refluxing diphenyl ether to yield indolo[2,3-b]quinolines in one-pot. The present approach provides a new route for the synthesis of polycyclic structures related to an alkaloid cryptotackieine (neocryptolepine).
• N-Bromosuccinimide as an efficient catalyst for the synthesis of indolo[2,3-b]quinolines
  作者：Ramin Ghorbani-Vaghei、Seyedeh Mina Malaekehpoor

  DOI：10.1016/j.tetlet.2012.06.125

  日期：2012.8

  The use of N-bromosuccinimide as a catalyst promoted the synthesis of polycyclic indolo[2,3-b]quinoline derivatives in good to high yields in the reactions of various aryl amines with indole-3-carbaldehyde at room temperature under mild conditions. (c) 2012 Elsevier Ltd. All rights reserved.
• Ruthenium-exchanged FAU-Y zeolite catalyzed improvement in the synthesis of 6H-indolo[2,3-b]quinolines
  作者：Alireza Khorshidi、Khalil Tabatabaeian

  DOI：10.1016/j.molcata.2011.05.010

  日期：2011.6

  Ruthenium-exchanged FAU-Y zeolite (RuY) was used as a recyclable catalyst for preparation of 6H-indolo[2,3-b]quinolines from the reaction of indole-3-carbaldehyde with aryl amines in refluxing dioxane. Under the above mentioned conditions, reasonable yields of the desired products with different substituents on the quinoline ring were obtained. (C) 2011 Elsevier B.V. All rights reserved.
• Palladium-Catalyzed Dual Annulation: A Method for the Synthesis of Norneocryptolepine
  作者：Li-Hsuan Yeh、Hung-Kai Wang、Gangaram Pallikonda、Yu-Lun Ciou、Jen-Chieh Hsieh

  DOI：10.1021/acs.orglett.9b00287

  日期：2019.3.15

  Pd-catalyzed dual annulation reaction to synthesize the norneocryptolepine derivatives involving the concerted construction of two central heterocycles is reported. The further methylation of the norneocryptolepine to afford its alkaloid analog neocryptolepine implies that synthesis of various neocryptolepine derivatives is feasible. The oxidative addition of Pd(0) is indicated as the key step to activate the

  报道了一种新型的钯催化双环合反应合成壬基隐油菜碱衍生物的新方法，该过程涉及两个中心杂环的协同构建。去甲隐油菜籽进一步的甲基化以提供其生物碱类似物新隐油菜籽暗示了各种新隐油菜籽衍生物的合成是可行的。根据机理研究表明，Pd（0）的氧化加成是激活腈分子内加成的关键步骤。