2-methoxy-9-tosyl-9H-carbazole | 1174643-97-0

• 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-methoxy-9-tosyl-9H-carbazole
• 英文别名: 2-Methoxy-9-(4-methylphenyl)sulfonylcarbazole；2-methoxy-9-(4-methylphenyl)sulfonylcarbazole
• CAS: 1174643-97-0
• 化学式: C₂₀H₁₇NO₃S
• 分子量: 351.426
• InChiKey: AZXTYICVMILQEQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.9
• 重原子数：
  25
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  56.7
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  N-(3'-methoxy-[1,1'-biphenyl]-2-yl)-4-methylbenzenesulfonamide 在 lithium perchlorate 、 palladium diacetate 、 对甲苯磺酸 、 三氟乙酸 作用下， 以 乙腈 为溶剂， 反应 3.0h， 以75%的产率得到2-methoxy-9-tosyl-9H-carbazole
  参考文献：
  名称：

  2-氨基氨基联芳基的电化学钯催化分子内CH氨基合成咔唑

  摘要：

  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。

  DOI：

  10.1002/cjoc.202000407

文献信息

• Fine-tuning hydroxylamines as single-nitrogen sources for Pd(0)-catalyzed diamination of o-bromo(or chloro)-biaryls
  作者：Pin Ding、Lingbo Han、Jiaxing Bai、Jingjing Liu、Xinjun Luan

  DOI：10.1007/s11426-021-1202-9

  日期：2022.4

  Transition metal-catalyzed diamination by hydroxylamines is a common approach for making three-membered aziridines, while its use for building the larger N-heterocycles is still underdeveloped. Herein, we report an efficient Pd(0)-catalyzed inter-molecular [4+1] annulation of o-bromo(or chloro)-biaryls with bifunctional secondary hydroxylamines for the one-step assembly of synthetically useful carbazoles

  羟胺的过渡金属催化二化是制备三元氮丙啶的常用方法，而其用于构建较大的N-杂环的用途仍未开发。在此，我们报告了一种有效的 Pd(0) 催化的分子间 [4+1] 环化邻溴（或氯）-联芳基与双功能仲羟胺，用于一步组装合成有用的咔唑。值得注意的是，这种多米诺骨牌反应的关键是明智地选择氨基源和 Pd(0)-催化剂，以便在具有不稳定 NO 的羟胺存在下将芳基卤化物氧化加成到 Pd(0)-物种中。键。
• Microwave-assisted reactions of nitroheterocycles with dienes. Diels–Alder and tandem hetero Diels–Alder/[3,3] sigmatropic shift
  作者：M. Victoria Gómez、Ana I. Aranda、Andrés Moreno、Fernando P. Cossío、Abel de Cózar、Ángel Díaz-Ortiz、Antonio de la Hoz、Pilar Prieto

  DOI：10.1016/j.tet.2009.04.065

  日期：2009.7

  the pyrazolate ion, as elucidated by computational studies. Reaction of nitroindole 1 with cyclohexadiene 2 afforded exclusively the endo stereoisomer (10endo) in a tandem hetero Diels–Alder/[3,3] sigmatropic shift, as determined by computational calculations.

  的狄尔斯-阿尔德环加成3-硝基-1-（p甲苯磺酰）吲哚1与二烯2 - 6在微波辐射下无溶剂条件下在消除硝基之后和原位芳构化，得到咔唑衍生物。虽然3-硝基-1-（对甲苯磺酰基）吡咯11提供吲哚衍生物，但是4-硝基-1-（对甲苯磺酰基）吡唑13与环己二烯2没有提供预期的环加合物，而是提供了1-环己烯-2-基吡唑16。该过程是由1-（p（甲苯磺酰基）基团，二烯的质子化和吡唑酸根离子的亲核加成，已通过计算研究得以阐明。硝基吲哚的反应1与环己二烯2排他地，得到内型立体异构体（10内向在串联杂狄尔斯-阿尔德）/ [3,3]σ迁移移，如通过计算机计算确定的。
• Pd-catalyzed three-component [2 + 2 + 1] cycloamination toward carbazoles
  作者：Mingzhu Shen、Min Li、Jingxun Yu

  DOI：10.1039/d4ob00356j

  日期：2024.4.24

  involving sequential nucleophilic and electrophilic C–N bond formations. Herein, we report a novel Suzuki reaction/C–H activation/amination sequence for building a myriad of carbazoles in a single transformation using bifunctional secondary hydroxylamines. It is noteworthy that the synthetic utility of this methodology is highlighted by the total synthesis of clausine V and glycoborine by incorporating

  使用羟胺衍生物作为单一氮源来制备 N-杂环分子的传统方法依赖于涉及连续亲核和亲电 C-N 键形成的两个化学过程。在此，我们报告了一种新颖的铃木反应/C-H活化/胺化序列，用于使用双功能仲羟胺在一次转化中构建无数咔唑。值得注意的是，通过将标题[2 + 2 + 1]环胺化作为关键步骤，克劳辛V和糖硼烷的全合成突出了该方法的合成效用。进行对照实验以更好地了解反应机理。
• 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
• Discovery of novel N-substituted carbazoles as neuroprotective agents with potent anti-oxidative activity
  作者：Daqian Zhu、Meihui Chen、Min Li、Bingling Luo、Yang Zhao、Peng Huang、Fengtian Xue、Simona Rapposelli、Rongbiao Pi、Shijun Wen

  DOI：10.1016/j.ejmech.2013.07.029

  日期：2013.10

  Carbazole moiety is an important scaffold with a variety of biological applications, for example, anti-oxidative stress. Our previous synthesized carbazoles were screened for their neuroprotective properties against two individual oxidative stresses. Some of the new carbazole derivatives were observed with modest to good neuroprotective effects on neuronal cells HT22 against cell injury induced by glutamate or homocysteic acid (HCA). Substituents introduced to the carbazole ring system play crucial roles in their biological activities. In particular, a bulky group favors the neuroprotective activity of the compounds. One of the new compounds, 6, showed the best neuroprotective effects, which might result from its anti-oxidative activity with a GSH-independent mechanism. These findings might provide an alternative strategy for the development of novel carbazole derivatives for the treatment of CNS diseases such as Alzheimer's disease. (C) 2013 Elsevier Masson SAS. All rights reserved.