2,3,6-tribromo-1-methyl-1H-indole | 70063-24-0

• 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: 2,3,6-tribromo-1-methyl-1H-indole
• 英文别名: 1-methyl-2,3,6-tribromoindole；2,3,6-tribromo-1-methylindole；2,3,6-tribromo-N-methylindole；N-methyl-2,3,6-tribromoindole；2,3,6-tribromo-1-methyl-indole
• CAS: 70063-24-0
• 化学式: C₉H₆Br₃N
• 分子量: 367.865
• InChiKey: VNXWBQUYRZQEEF-UHFFFAOYSA-N

物化性质

• 熔点：
  89-90 °C
• 沸点：
  411.4±40.0 °C(Predicted)
• 密度：
  2.18±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  13
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  4.9
• 氢给体数：
  0
• 氢受体数：
  0

反应信息

• 作为反应物：
  描述：

  2,3,6-tribromo-1-methyl-1H-indole 在 溴 作用下， 以 甲酸 、 溶剂黄146 为溶剂， 反应 2.0h， 以67%的产率得到2,3,5,6-tetrabromo-1-methyl-1H-indole
  参考文献：
  名称：

  Syntheses of Polybrominated Indoles from the Red Alga Laurencia brongniartii and the Brittle Star Ophiocoma erinaceus

  摘要：

  The red alga Laurencia brongniartii and brittle star Ophiocoma erinaceus metabolites 2,3,6-tribromo-1-methylindole (1) and 2,3,5,6-tetrabromo-1-methylindole (2) are easily synthesized selectively from 2,3-dibromo-1-methylindole (5), which in turn is prepared from indole (3) in one continuous sequence in 92% yield. Moreover, 2 can be made from both 1 and 5 in 67% and 65% yields, respectively.

  DOI：

  10.1021/np010610s
• 作为产物：
  描述：

  2,3,5,6-tetrabromo-1-methyl-1H-indole 在 sodium tetrahydroborate 、 N-溴代丁二酰亚胺(NBS) 、 1,1'-双(二苯膦基)二茂铁二氯化钯(II)二氯甲烷复合物 、 四甲基乙二胺 作用下， 以 四氢呋喃 为溶剂， 反应 24.0h， 生成 2,3,6-tribromo-1-methyl-1H-indole
  参考文献：
  名称：

  多溴化吲哚的区域选择性加氢脱溴

  摘要：

  硼氢化钠和 N,N,N',N'-四甲基乙二胺与钯催化剂的混合物是一种温和有效的系统，用于区域选择性加氢脱溴的多溴化吲哚具有 N-供体和 N-撤回取代基 [N-甲基- 和 N-（甲氧基羰基）吲哚，分别]。

  DOI：

  10.1002/ejoc.201400032

文献信息

• Synthesis of carbazoles and 1,2-dihydrocarbazoles by domino ‘twofold Heck/6π-electrocyclization’ reactions of di-, tri- and tetrabromoindoles
  作者：Munawar Hussain、Serge-Mithérand Tengho Toguem、Rasheed Ahmad、Đặng Thanh Tùng、Ingo Knepper、Alexander Villinger、Peter Langer

  DOI：10.1016/j.tet.2011.05.014

  日期：2011.7

  palladium(0)-catalyzed Heck cross-coupling reactions of di-, tri- and tetrabromo-N-methylindoles. The reactions were carried out at 90 °C using a novel biaryl monophosphine ligand developed by Buchwald and co-workers. 1,2-Dihydrocarbazoles were formed by a domino ‘twofold Heck/6π-electrocyclization’ when the reaction was carried out at higher temperature. The regioselectivity of the Heck reaction of 2,3,6-tr

  二，三和四烯基吲哚是通过钯（0）催化的二，三和四溴-N-甲基吲哚的Heck交叉偶联反应制备的。使用Buchwald及其同事开发的新型联芳基单膦配体在90°C下进行反应。当在较高温度下进行反应时，通过多米诺“双重Heck /6π-电环化”形成1,2-二氢咔唑。2,3,6-三溴-N-甲基吲哚的Heck反应的区域选择性有利于碳原子C-2和C-3。通过Pd / C催化的脱氢，将1，2-二氢咔唑高产率地转化为相应的咔唑。
• Synthesis of Carbazoles and 1,2-Dihydrocarbazoles by Domino ‘Twofold Heck-6π-Electrocyclization’ Reactions of Di- and Tribromo-N-methylindoles
  作者：Peter Langer、Munawar Hussain、Đãng Tùng

  DOI：10.1055/s-0029-1217357

  日期：2009.7

  palladium(0)-catalyzed Heck cross-coupling reaction of 2,3-dibromo- and 2,3,6-tribromo-N-methylindole, using Pd(OAc) 2 as the catalyst and a novel biaryl monophosphine ligand developed by Buchwald and co-workers, afforded the corresponding di- and trialkenylindoles in high yields. The formation of 1,2-dihydrocarbazoles by a domino 'twofold Heck―6π-electrocyclization' was observed when the reaction was carried

  钯 (0) 催化的 2,3-二溴-和 2,3,6-三溴-N-甲基吲哚的 Heck 交叉偶联反应，使用 Pd(OAc) 2 作为催化剂和 Buchwald 开发的新型联芳基单膦配体和同事，以高产率提供了相应的二烯基吲哚和三烯基吲哚。当反应在 120 °C 而不是 90 °C 下进行时，观察到通过多米诺“双重 Heck-6π-电环化”形成 1,2-二氢咔唑。
• Synthesis of Bromoindole Alkaloids from <i>Laurencia </i><i>brongniartii</i>
  作者：Oscar R. Suárez-Castillo、Lidia Beiza-Granados、Myriam Meléndez-Rodríguez、Alejandro Álvarez-Hernández、Martha S. Morales-Ríos、Pedro Joseph-Nathan

  DOI：10.1021/np060406a

  日期：2006.11.1

  A regioselective synthesis of N-carbomethoxy-2,3,5-tribromoindole (6) via a sequential one-pot bromination-aromatization-bromination of N-carbomethoxyindoline (2) is described. The process for the transformation of 2 into 6 permitted the isolation of stable reaction intermediates N-carbomethoxy-5-bromoindoline (3), N-carbomethoxy-5-bromoindole (4), and N-carbomethoxy-3,5-dibromoindole (5). Compound

  描述了通过N-羰基甲氧基二氢吲哚（2）的顺序一锅式溴化-芳构化-溴化，N-羰基甲氧基-2,3,5-三溴吲哚（6）的区域选择性合成。将2转化为6的过程可分离出稳定的反应中间体N-羰基甲氧基-5-溴吲哚（3），N-羰基甲氧基-5-溴吲哚（4）和N-羰基甲氧基-3,5-二溴吲哚（5 ）。化合物6用于完成天然产物1b和1c的总合成。另外，将N-甲氧基吲哚（11）溴化，得到N-甲氧基-2,3,6-三溴吲哚（13），由此合成了天然产物1a。
• One-pot synthesis of arylated 1-methyl-1H-indoles by Suzuki–Miyaura cross-coupling reactions of 2,3-dibromo-1-methyl-1H-indole and 2,3,6-tribromo-1-methyl-1H-indole
  作者：Muhammad Farooq Ibad、Dhafer Saber Zinad、Munawar Hussain、Asad Ali、Alexander Villinger、Peter Langer

  DOI：10.1016/j.tet.2013.05.100

  日期：2013.9

  Arylated 1-methyl-1H-indoles were prepared by Suzuki-Miyaura cross-coupling reactions of 2,3-dibromo-1-methyl-1H-indole and 2,3,6-tribromo-1-methyl-1H-indole. The reactions proceed with very good regioselectivity in favour of position 2. (C) 2013 Elsevier Ltd. All rights reserved.
• Simple and efficient procedures for selective preparation of 3-haloindoles and 2,3-dihaloindoles by using 1,3-dibromo-5,5-dimethylhydantoin and 1,3-dichloro-5,5-dimethylhydantoin
  作者：Jianwei Yan、Tianjun Ni、Fulin Yan

  DOI：10.1016/j.tetlet.2015.01.080

  日期：2015.2

  Simple and efficient synthetic procedures for the selective preparation of 3-bromo/3-chloroindoles and 2,3-dibromo/2,3-dichloroindoles by using 1,3-dibromo-5,5-dimethylhydantoin (DBDMH) and 1,3-dichloro-5,5-dimethylhydantoin (DCDMH) were developed. Using 1,4-dioxane as the solvent, a variety of indoles, treated with 0.55 equiv DBDMH/DCDMH, afford the corresponding 3-bromo/3-chloroindoles selectively in 82-99% yield. In 1,2-dichloroethane (DCE), a series of 2,3-dichloro/2,3-dibromoindoles were selectively obtained in 84-95% yield by treating with DBDMH/DCDMH. All the processes do not need extra catalysts, dry solvents, or harsh reaction conditions. (C) 2015 Elsevier Ltd. All rights reserved.

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