5,8-dimethyl-2,3,4,9-tetrahydro-1H-carbazole | 36729-38-1

• 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: 5,8-dimethyl-2,3,4,9-tetrahydro-1H-carbazole
• 英文别名: 5,8-dimethyltetrahydrocarbazole；5,8-dimethyl-1,2,3,4-tetrahydro-carbazole；5,8-Dimethyl-1,2,3,4-tetrahydro-carbazol
• CAS: 36729-38-1
• 化学式: C₁₄H₁₇N
• 分子量: 199.296
• InChiKey: BYMKVKXLPSDDSN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  15
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  15.8
• 氢给体数：
  1
• 氢受体数：
  0

反应信息

• 作为反应物：
  描述：

  5,8-dimethyl-2,3,4,9-tetrahydro-1H-carbazole 在 palladium on activated charcoal 三氯氧磷 作用下， 以 various solvent(s) 为溶剂， 反应 8.0h， 生成 3-formyl-1,4-dimethylcarbazole
  参考文献：
  名称：

  Intramolecular cyclization ofortho-(cyclohex-2-enyl)anilines. Modified synthesis of ellipticine

  摘要：

  It was found that the reactions of arylamines with 3-bromocyclohexene afforded hydrocarbazole compounds in 64-78% yields. A modified procedure for the synthesis of antitumor alkaloid ellipticine was proposed.

  DOI：

  10.1007/bf02494860
• 作为产物：
  描述：

  3-氯环己烯 在 palladium dichloride 作用下， 以 硝基苯 为溶剂， 反应 7.0h， 生成 5,8-dimethyl-2,3,4,9-tetrahydro-1H-carbazole
  参考文献：
  名称：

  Intramolecular cyclization ofortho-(cyclohex-2-enyl)anilines. Modified synthesis of ellipticine

  摘要：

  It was found that the reactions of arylamines with 3-bromocyclohexene afforded hydrocarbazole compounds in 64-78% yields. A modified procedure for the synthesis of antitumor alkaloid ellipticine was proposed.

  DOI：

  10.1007/bf02494860

文献信息

• An Electrophilic Bromine Redox Catalysis for the Synthesis of Indole Alkaloid Building Blocks by Selective Aliphatic C−H Amination
  作者：Julien Bergès、Belén García、Kilian Muñiz

  DOI：10.1002/anie.201808939

  日期：2018.11.26

  A new homogeneous bromine(−I/I) redox catalysis is described, which is based on monomeric bromine(I) compounds containing transferable phthalimidato groups. These catalysts enable intermolecular C−H amination reactions at previously unaccessible aliphatic positions and thus enlarge the synthetic potential of direct C−N bond formation, including its application in the synthesis of alkaloid building

  描述了一种新的均相溴（-I / I）氧化还原催化，其基于含有可转移邻苯二甲酰亚胺基的单体溴（I）化合物。这些催化剂能够在以前无法接近的脂肪族位置进行分子间CH氨化反应，从而扩大了直接CN键形成的合成潜力，包括其在生物碱结构单元合成中的应用。这方面通过一种新的合成方法来证明。除了开发催化剂体系外，还充分阐明了所涉及的溴（I）关键催化剂的结构，包括通过X射线分析得出的结果。
• Intramolecular cyclization of ortho-(cyclohex-2-enyl) anilines synthesis of ellipticine
  作者：A. G. Mustafin、I. N. Khalilov、E. V. Tal'vinskii、I. B. Abdrakhmanov、L. V. Spirikhin、G. A. Tolstikov

  DOI：10.1007/bf00630657

  日期：1992.9

  method is proposed for the synthesis of the alkaloid ellipticine, which possesses a pronounced antitumoral activity. The interaction of 3-bromocyclohexene (1 equiv.) and 2,5-xylylidine (4 equiv., 150°C, 5 h) gave a mixture of hexa- and tetrahydrocarbazoles which was dehydrogenated in the presence of Pd/C to the key synthon 1,4-dimethylcarbazole. The formylation of the carbazole by the Vilsmeier-Haack reaction

  提出了一种合成具有显着抗肿瘤活性的生物碱玫瑰树碱的简便方法。3-溴环己烯（1 当量）和 2,5-二甲苯胺（4 当量，150°C，5 小时）的相互作用产生六和四氢咔唑的混合物，在 Pd/C 存在下脱氢成为关键合成子 1,4-二甲基咔唑。通过 Vilsmeier-Haack 反应对咔唑进行甲酰化、与 2,2-二乙氧基乙胺的相互作用以及在雷尼镍上形成的亚胺的还原导致 3-(2,2-二乙氧基乙基氨基甲基)-1,4-二甲基咔唑，沸腾其 N-甲苯磺酸盐以高产率得到玫瑰树碱。
• Ruthenium-Catalyzed Synthesis of Indoles from Anilines and Epoxides
  作者：Miguel Peña-López、Helfried Neumann、Matthias Beller

  DOI：10.1002/chem.201304432

  日期：2014.2.10

  A general synthetic route to indoles from readily available anilines and epoxides by using ruthenium catalysis is described. This straightforward transformation allows a variety of indoles to be obtained in good yields by using [Ru3(CO)12]/1,1′‐bis(diphenylphosphino)ferrocene as the catalytic system. Water and hydrogen are formed as the only stoichiometric by‐products, making this process highly atom

  描述了通过使用钌催化从易得的苯胺和环氧化物制备吲哚的一般合成途径。通过使用[Ru 3（CO）12 ] / 1,1'-双（二苯基膦基）二茂铁作为催化体系，这种简单的转化方法可以高收率获得各种吲哚。水和氢是唯一的化学计量副产物，因此该过程具有很高的原子效率。
• 558. The preparation of tetrahydrocarbazoles from 2-chloro-cyclohexanone
  作者：Neil Campbell、E. B. McCall

  DOI：10.1039/jr9500002870

  日期：——
• A modified synthesis of ellipticine
  作者：A. G. Mustafin、I. N. Khalilov、V. M. Sharafutdinov、D. I. D'yachenko、I. B. Abdrakhmanov、G. A. Tolstikov

  DOI：10.1007/bf02495431

  日期：1997.3