7,10-dimethyl-5-(phenylsulfonyl)-5H-benzo[b]carbazole | 1072096-77-5

• 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: 7,10-dimethyl-5-(phenylsulfonyl)-5H-benzo[b]carbazole
• 英文别名: 5-(Benzenesulfonyl)-7,10-dimethylbenzo[b]carbazole
• CAS: 1072096-77-5
• 化学式: C₂₄H₁₉NO₂S
• 分子量: 385.486
• InChiKey: OOIKRRFSYICVFU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.2
• 重原子数：
  28
• 可旋转键数：
  2
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  47.4
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  diethyl 2-((3-(2,5-dimethylbenzyl)-1-(phenylsulfonyl)-1H-indol-2-yl)methylene)malonate 在 zinc dibromide 作用下， 以 1,2-二氯乙烷 为溶剂， 反应 1.0h， 以67%的产率得到7,10-dimethyl-5-(phenylsulfonyl)-5H-benzo[b]carbazole
  参考文献：
  名称：

  Dhayalan, Vasudevan; Sureshbabu, Radhakrishnan; Mohanakrishnan, Arasambattu K., Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 2011, vol. 50, # 6, p. 843 - 857

  摘要：

  DOI：

文献信息

• A Versatile Synthesis of Annulated Carbazole Analogs Involving a Domino Reaction of Bromomethylindoles with Arenes/Heteroarenes
  作者：Vasudevan Dhayalan、J. Arul Clement、Radhakrishnan Jagan、Arasambattu K. Mohanakrishnan

  DOI：10.1002/ejoc.200801018

  日期：2009.2

  A ZnBr2-mediated arylation of aryl/heteroaryl methyl bromides with arenes at 80 °C led to the formation of arylated products, which underwent subsequent 1,5-sigmatropic rearrangement followed by electrocyclization and aromatization with loss of a diethylmalonate unit to afford the corresponding annulated products. (© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2009)

  ZnBr2 介导的芳基/杂芳基甲基溴与芳烃在 80°C 的芳基化形成芳基化产物，随后进行 1,5-σ 重排，然后进行电环化和芳构化，失去丙二酸二乙酯单元，得到相应的环化产物。产品。(© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2009)
• Synthesis of Annulated Carbazoles via FeCl3/SnCl4‑Mediated Domino Reaction of Vinyl Ketone Tethered Bromomethylindoles with Arenes and Heteroarenes
  作者：Arasambattu K. Mohanakrishnan、Velu Saravanan

  DOI：10.1055/a-1387-9479

  日期：2021.7

  One-pot synthesis of aryl- as well as heteroaryl-annulated carbazoles was achieved from 2/3-bromomethylindoles involving Lewis acid mediated domino reaction with arenes as well as heteroarenes via successive Friedel–Crafts intermolecular as well as intramolecular alkylations followed by elimination of acetone. Further, the bis-domino reaction of 2,5-bis(bromomethyl)pyrrole was also carried out with

  一锅合成芳基和杂芳基环化的咔唑是通过2 / 3-溴甲基吲哚，涉及路易斯酸介导的与芳烃的多米诺反应以及杂芳烃，通过连续的Friedel-Crafts分子间以及分子内烷基化，然后消除丙酮进行的。此外，还用选择的杂芳烃进行了2，5-双（溴甲基）吡咯的双多米诺反应。此外，合成的噻吩并咔唑和噻吩并二苯并呋喃已成功用于第二代多米诺骨牌反应。
• Lewis Acid Mediated One-Pot Synthesis of Aryl/Heteroaryl-Fused Carbazoles Involving a Cascade Friedel-Crafts Alkylation/Electrocyclization/Aromatization Reaction Sequence
  作者：Radhakrishnan Sureshbabu、Velu Saravanan、Vasudevan Dhayalan、Arasambattu K. Mohanakrishnan

  DOI：10.1002/ejoc.201001309

  日期：2011.2

  ]-fused carbazoles has been developed startingfrom suitably substituted 2/3-(bromomethyl)indoles and ar-enes under Lewis acid catalysis. The attractive feature ofthis protocol is the fact that a wide variety of π-conjugatedannulated carbazoles can be readily accessed by the appro-priate choice of arenes and heteroarenes. The annulationprotocol has been extended to (bromomethyl)benzene aswell as 2,

  在路易斯酸催化下，以适当取代的 2/3-（溴甲基）吲哚和芳烯为原料开发了]-稠合咔唑。本协议的有吸引力的特征是，可以通过竞争和杂种丁烯的应用选择可以容易地访问各种π缀合的咔唑。环化协议已扩展到（溴甲基）苯以及 2,5-双（溴甲基）噻吩。发现吲哚基-2-甲基乙酸酯的环化不如相应的2-(溴甲基)吲哚合适。然而，在苄体系的情况下，发现相应的醋酸盐更适用。在这项工作中开发的路易斯酸介导的级联环化序列可能会导致在多环芳香杂环领域的新应用。
• A one pot synthesis of annulated carbazole analogs
  作者：Arasambattu K. Mohanakrishnan、Vasudevan Dhayalan、J. Arul Clement、Ramalingam Balamurugan Radhakrishn Sureshbabu、Natarajan Senthil Kumar

  DOI：10.1016/j.tetlet.2008.07.036

  日期：2008.10.6

  A ZnBr2-mediated arylation of N-protected 2/3-bromomethylindoles containing an electron-deficient malonylidene unit with arenes at 80 degrees C led to the formation of arylated products, which on Unprecedented 1,5-sigmatropic rearrangement followed by electrocyclization and subsequent aromatization with loss of diethylmalonate furnished the corresponding annulated carbazoles in reasonable yields. (C) 2008 Published by Elsevier Ltd.