1-Nitro-9-methylcarbazole | 66243-81-0

• 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: 1-Nitro-9-methylcarbazole
• 英文别名: 9-methyl-1-nitro-9H-carbazole；9-Methyl-1-nitrocarbazole
• CAS: 66243-81-0
• 化学式: C₁₃H₁₀N₂O₂
• 分子量: 226.235
• InChiKey: OPXTXOGCNNCVRV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  17
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  50.8
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1-Nitro-9-methylcarbazole 在 palladium on activated charcoal 一水合肼 、 三乙胺 作用下， 以 乙醇 、 二氯甲烷 为溶剂， 反应 20.0h， 生成 N-(9-methylcarbazol-1-yl)-2,2-dimethylpropionamide
  参考文献：
  名称：

  摘要：

  2-, 3- and 4-Pivaloylamino derivatives of dibenzofuran [compounds (5), (4) and (6), respectively] and analogous 3-, 2- and 1-substituted derivatives of 9-methylcarbazole [compounds (8), (7) and (9), respectively] were subjected to lithiation at 0 degreesC and subsequent reaction with dimethylformamide. Aldehyde formation took place at positions alpha to delta to the heteroatom as follows: alpha for (4) and (7); delta for (5); delta and beta (3 : 1) for (8); and alpha' for (6). No formylation occurred with (9).

  DOI：

  10.1071/ch01017
• 作为产物：
  描述：

  咔唑 在 硝酸 作用下， 以 溶剂黄146 为溶剂， 生成 1-Nitro-9-methylcarbazole
  参考文献：
  名称：

  摘要：

  2-, 3- and 4-Pivaloylamino derivatives of dibenzofuran [compounds (5), (4) and (6), respectively] and analogous 3-, 2- and 1-substituted derivatives of 9-methylcarbazole [compounds (8), (7) and (9), respectively] were subjected to lithiation at 0 degreesC and subsequent reaction with dimethylformamide. Aldehyde formation took place at positions alpha to delta to the heteroatom as follows: alpha for (4) and (7); delta for (5); delta and beta (3 : 1) for (8); and alpha' for (6). No formylation occurred with (9).

  DOI：

  10.1071/ch01017

文献信息

• Regioselective Functionalization of 9,9-Dimethyl-9-silafluorenes by Borylation, Bromination, and Nitration
  作者：Masahito Murai、Naoki Nishinaka、Mizuki Kimura、Kazuhiko Takai

  DOI：10.1021/acs.joc.9b00598

  日期：2019.5.3

  Despite the utility of 9-silafluorenes as functional materials and as building blocks, methods for efficient functionalization of their backbone are rare, probably because of the presence of easily cleavable C–Si bonds. Although controlling the regioselectivity of iridium-catalyzed direct borylation of C–H bonds is difficult, we found that bromination and nitration of 2-methoxy-9-silafluorene under

  尽管使用9硅芴作为功能材料和结构单元，但对其骨架进行有效功能化的方法却很少，这可能是由于存在易于裂解的C-Si键所致。尽管很难控制铱催化的C–H键直接硼化的区域选择性，但我们发现2-甲氧基-9-硅芴在温和条件下的溴化和硝化主要发生在富电子位置。具有甲氧基和溴基的所得产物可用作合成不对称取代的含9-硅芴的π-共轭分子的结构单元。
• METHOD FOR PRODUCING AMINOCARBAZOLES
  申请人：——

  公开号：US20010049448A1

  公开（公告）日：2001-12-06

  Disclosed is a method for producing an aminocarbazole by catalytically reducing a nitrocarbazole, wherein as a catalyst is used an active nickel-based catalyst prepared by contacting a nickel-based catalyst with an alkali and an iron compound under a hydrogen gas or inert gas atmosphere in an inert solvent, and according to the method of the present inventions decrease in reaction speed, decrease in yield of a product or the like depending upon the lot of the starting nitrocarbazoles can be prevented, and aminocarbazoles can be produced in a good yield constantly.

  公开了一种通过催化还原硝基咔唑来生产氨基咔唑的方法，其中所使用的催化剂为通过将镍基催化剂与碱和铁化合物接触，在惰性溶剂中在氢气或惰性气氛下制备的活性镍基催化剂。根据本发明的方法，可以预防由于起始硝基咔唑的批次而导致的反应速度减慢、产物收率减少等问题，并且可以持续地以良好的产率生产氨基咔唑。
• A New Method of Nitration of Carbazoles Using Ceric Ammonium Nitrate (CAN)
  作者：Manas Chakrabarty、Archana Batabyal

  DOI：10.1080/00397919408012618

  日期：1994.1

  Abstract A convenient procedure for the mononitration of carbazole and 9-alkylcarbazoles using CAN in CH3CN in presence of SiO2 is reported. The results with 9-acetyl, 9-benzoyl and 9-benzenesulphonylcarbazoles are also discussed.

  摘要 报道了在 SiO2 存在下，在 CH3CN 中使用 CAN 单硝化咔唑和 9-烷基咔唑的简便方法。还讨论了 9-乙酰基、9-苯甲酰基和 9-苯磺酰基咔唑的结果。
• Method for producing aminocarbazoles
  申请人：——

  公开号：US20020183526A1

  公开（公告）日：2002-12-05

  Disclosed is a method for producing an aminocarbazole by catalytically reducing a nitrocarbazole, wherein as a catalyst is used an active nickel-based catalyst prepared by contacting a nickel-based catalyst with an alkali and an iron compound under a hydrogen gas or inert gas atmosphere in an inert solvent, and according to the method of the present invention, decrease in reaction speed, decrease in yield of a product or the like depending upon the lot of the starting nitrocarbazoles can be prevented, and aminocarbazoles can be produced in a good yield constantly.

  本发明揭示了一种通过催化还原硝基咔唑制备氨基咔唑的方法，其中使用的催化剂是通过在惰性溶剂中在氢气或惰性气氛下将镍基催化剂与碱和铁化合物接触制备的活性镍基催化剂。根据本发明的方法，可以防止由于起始硝基咔唑批次的不同导致的反应速度下降、产物收率下降等问题，并且可以持续地高产地生产氨基咔唑。
• 426. Internuclear cyclisation. Part V. The cyclisation of derivatives of diphenylmethane, benzophenone, and N-methyldiphenylamine
  作者：D. H. Hey、R. D. Mulley

  DOI：10.1039/jr9520002276

  日期：——