2-phenyl-9-tosyl-9H-carbazole | 1469876-06-9

• 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: 2-phenyl-9-tosyl-9H-carbazole
• 英文别名: 9-(4-Methylphenyl)sulfonyl-2-phenylcarbazole；9-(4-methylphenyl)sulfonyl-2-phenylcarbazole
• CAS: 1469876-06-9
• 化学式: C₂₅H₁₉NO₂S
• 分子量: 397.497
• InChiKey: RZXSEIHUTKRNNB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.6
• 重原子数：
  29
• 可旋转键数：
  3
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.04
• 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：

  2-甲基吲哚 在 4-二甲氨基吡啶 、 甲基溴化镁 、 碘 、 三乙胺 、 potassium hydroxide 、 palladium dichloride 作用下， 以 四氢呋喃 、 二氯甲烷 、 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 反应 11.5h， 生成 2-phenyl-9-tosyl-9H-carbazole
  参考文献：
  名称：

  钯催化的环烯丙基烷基化反应用于合成苯并环杂芳烃

  摘要：

  为合成咔唑和二苯并噻吩开发了一种概念上新颖的分子内烯丙基烷基化策略。在不寻常的情况下，钯催化相应的（2-甲基吲哚-3-基）烯丙基乙酸酯的π-烯丙基钯络合物的形成，并随后促进苯甲环化过程。

  DOI：

  10.1039/d0cc06695h

文献信息

• Design, synthesis and biological evaluation of <i>N</i>-arylsulfonyl carbazoles as novel anticancer agents
  作者：Xin You、Daqian Zhu、Wenhua Lu、Yichen Sun、Shuang Qiao、Bingling Luo、Yongliang Du、Rongbiao Pi、Yumin Hu、Peng Huang、Shijun Wen

  DOI：10.1039/c8ra02939c

  日期：——

  this work, a set of structurally diverse synthetic carbazoles was screened for their anticancer activities. According to structure–activity relationship studies, carbazoles with an N-substituted sulfonyl group exhibited better anticancer activity. Moreover, compound 8h was discovered to show the most potent anticancer effects on Capan-2 cells by inducing apoptosis and cell cycle arrest in G2/M phase

  在这项工作中，筛选了一组结构多样的合成咔唑的抗癌活性。根据构效关系研究，具有N-取代磺酰基的咔唑表现出更好的抗癌活性。此外，发现化合物8h通过诱导 G2/M 期细胞凋亡和细胞周期停滞对 Capan-2 细胞显示出最有效的抗癌作用。最后，体内研究表明，8h在 PANC-1 和 Capan-2 异种移植模型中阻止了肿瘤生长，没有明显的毒性。
• Electrochemical <scp>Palladium‐Catalyzed</scp> Intramolecular C—H Amination of <scp>2‐Amidobiaryls</scp> for Synthesis of Carbazoles
  作者：Qingqing Wang、Xiaojing Zhang、Pan Wang、Xinlong Gao、Heng Zhang、Aiwen Lei

  DOI：10.1002/cjoc.202000407

  日期：2021.1

  The synthesis of carbazoles based on the electrochemical Pd‐catalyzed intramolecular C—H amination of 2‐amidobiaryls through oxidative cross coupling has been achieved under mild reaction conditions. The reaction can be carried out in undivided cell without the addition of external chemical oxidant. Besides good functional group compatibility, the desired carbazoles can be scaled up and modified easily

  在温和的反应条件下，通过氧化交联的2-位氨基联芳基的电化学Pd催化分子内CH氨基化合成咔唑。该反应可以在不分开的池中进行，而无需添加外部化学氧化剂。除了良好的官能团相容性外，所需的咔唑还可以按比例放大和改性。与以前的方法相比，该协议为咔唑的构建提供了一个简单而可持续的途径。
• C(sp3)–H Activation Enabled by (η3-Indolylmethyl)palladium Complexes: Synthesis of Monosubstituted Tetrahydrocarbazoles
  作者：S. S. V. Ramasastry、Ketan Kumar、T. Vivekanand、Bara Singh

  DOI：10.1055/a-1516-7960

  日期：2022.2

  The synthesis of monosubstituted tetrahydrocarbazoles is achieved via the palladium-catalyzed formal [4+2] cycloaddition of 2-alkyl-3-indolylmethyl carbonates and monosubstituted olefins. The transformation demonstrates an unusual C(sp3)–H activation enabled by (η3-indolylmethyl)palladium complexes. The regioselectivity is found to be dependent on the nature of the substituent across the olefin component

  单取代四氢咔唑的合成是通过钯催化的 2-烷基-3-吲哚基甲基碳酸酯和单取代烯烃的正式 [4+2] 环加成反应来实现的。该转化证明了由（η3-吲哚基甲基）钯配合物实现的不寻常的 C(sp3)-H 活化。发现区域选择性取决于跨烯烃组分的取代基的性质。进行了详细的机理研究，并证明了产品的合成效用。
• Palladium‐Catalyzed Synthesis of Carbazoles by Perester
  作者：Li He、Yongjun Xu

  DOI：10.1002/adsc.202200419

  日期：2022.7.19

  An intramolecular C−H amination for the synthesis of carbazoles with a Pd(II)/TBPB system has been developed. This catalytic amination process forms the carbazole products in good to excellent yields. It is noteworthy that this method implied the advantages of the catalytic mode involving perester with transition metal catalyst in the activation of inert C−H bonds. In addition, the transformation performs

  已经开发了一种用于合成咔唑的分子内 C-H 胺化 Pd(II)/TBPB 系统。这种催化胺化过程以良好至极好的收率形成咔唑产物。值得注意的是，该方法暗示了过酸酯与过渡金属催化剂在惰性C-H键活化中的催化模式的优势。此外，使用水作为溶剂，转化效果很好。
• Synthesis of Carbazoles<i>via</i>One-Pot Copper-Catalyzed Amine Insertion into Cyclic Diphenyleneiodoniums as a Strategy to Generate a Drug-Like Chemical Library
  作者：Daqian Zhu、Qi Liu、Bingling Luo、Meihui Chen、Rongbiao Pi、Peng Huang、Shijun Wen

  DOI：10.1002/adsc.201300271

  日期：2013.8.12

  AbstractCarbazoles have attracted high interest among synthetic chemists due to their unique structural features and potential pharmacological activities. Compared to linear aryliodoniums, cyclic diphenyleneiodoniums are more inert and have not attracted much attention to their application as building blocks. Employing our synthetic strategy, diversified carbazoles can be efficiently obtained from a single cyclic diphenyleneiodonium under mild conditions. The reactions catalyzed by copper(II) acetate have provided a variety of carbazoles in modest to good yields with a broad range of amines including anilines, aliphatic amines and sulfonamides. Moreover, one of the obtained carbazoles has displayed an outstanding ability to protect HT‐22 neuronal cells from the damage induced by neurotoxins glutamate and homocysteic acid.magnified image