6-bromo-2,3,4,9-tetrahydro-3-methyl-1H-carbazole | 433725-14-5

• 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: 6-bromo-2,3,4,9-tetrahydro-3-methyl-1H-carbazole
• 英文别名: 6-bromo-3-methyl-tetrahydrocarbazole；6-Bromo-3-methyl-2,3,4,9-tetrahydro-1H-carbazole
• CAS: 433725-14-5
• 化学式: C₁₃H₁₄BrN
• 分子量: 264.165
• InChiKey: ROOYQDWBKVLILV-UHFFFAOYSA-N

物化性质

• 沸点：
  380.2±37.0 °C(Predicted)
• 密度：
  1.428±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  15
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.38
• 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：

  6-bromo-2,3,4,9-tetrahydro-3-methyl-1H-carbazole 在 高碘酸 作用下， 以 甲醇 为溶剂， 以69%的产率得到6-Bromo-3-methyl-2,3,4,9-tetrahydrocarbazol-1-one
  参考文献：
  名称：

  通过分子碘改性的芳构化全合成各种含氧咔唑

  摘要：

  对于1-氧四氢咔唑的单和双氧化咔唑生物碱，已经开发了一种简便的方法。合成路线的关键步骤是使用分子碘进行的1-氧四氢咔唑的芳香化工艺。据我们所知，这是第一个通过费歇尔-保时捷方法从易得的含酯结构单元中直接合成克劳斯碱E，鼠李糖碱，鼠李酸和鼠李碱的报告。

  DOI：

  10.1016/j.tetlet.2016.01.002
• 作为产物：
  描述：

  4-溴苯肼盐酸盐 、 4-甲基环己酮 在 溶剂黄146 作用下， 以 环己烷 为溶剂， 反应 22.0h， 以77%的产率得到6-bromo-2,3,4,9-tetrahydro-3-methyl-1H-carbazole
  参考文献：
  名称：

  Synthesis of carbazole-linked cyclic and acyclic peptoids with antibacterial activity

  摘要：

  This paper describes the synthesis of several novel cyclic and acyclic peptoids, the former structurally comprising a tripeptide moiety linked through a carbazole scaffold. In a key step, a ring-closing metathesis reaction was used giving efficient access to this new class of cyclic peptoids. The target compounds were tested against Staphylococcus aureus (ATCC 6538P) and their minimum inhibitory concentration (MIC) values were determined. These compounds showed moderate to poor activities with MIC values ranging from 15-250 mug/mL. (C) 2003 Elsevier Ltd. All richts reserved.

  DOI：

  10.1016/j.tet.2003.09.034

文献信息

• Modification of biologically active amides and amines with fluoro-containing heterocycles 11. Tetrahydrocarbazoles modified with 2-(5-fluoropyridin-3-yl)ethyl fragment
  作者：V. B. Sokolov、A. Yu. Aksinenko、N. S. Nikolaeva、V. V. Grigor’ev、A. S. Kinzirsky、S. O. Bachurin

  DOI：10.1007/s11172-014-0561-3

  日期：2014.5

  A method for the modification of tetrahydrocarbazoles with the 2-(5-fluoropyridin-3-yl)ethyl fragment was suggest, which consists in the reaction of 5-fluoro-3-vinylpyridine with tetrahydrocarbazoles under conditions of fluoride ion catalysis and leads to the earlier unknown 9-[2-(5-fluoropyridin-3-yl)ethyl]-2,3,4,9-tetrahydro-1H-carbazoles. Method of radioligand binding was used to study the influence of compounds synthesized on neuronal NMDA-receptors.

  提出了一种通过2-(5-氟吡啶-3-基)乙基片段修饰四氢咔唑的方法，该方法在氟离子催化条件下使5-氟-3-乙烯基吡啶与四氢咔唑反应，生成迄今未知的9-[2-(5-氟吡啶-3-基)乙基]-2,3,4,9-四氢-1H-咔唑。采用放射配体结合法研究了所合成化合物对神经元NMDA受体的影响。
• Total synthesis of diverse oxygenated carbazoles by modified aromatization using molecular iodine
  作者：Vivek T. Humne、Mahavir S. Naykode、Monica H. Ghom、Pradeep D. Lokhande

  DOI：10.1016/j.tetlet.2016.01.002

  日期：2016.2

  A convenient route has been developed for mono and dioxygenated carbazole alkaloids from 1-oxotetrahydrocarbazoles. The key step of the synthetic route is the aromatic process of 1-oxotetrahydrocarbazoles using molecular iodine. To our knowledge, this is the first report to manifest a direct synthesis of clausine E, mukonine, mukoeic acid and mukoline, from readily available ester-containing building

  对于1-氧四氢咔唑的单和双氧化咔唑生物碱，已经开发了一种简便的方法。合成路线的关键步骤是使用分子碘进行的1-氧四氢咔唑的芳香化工艺。据我们所知，这是第一个通过费歇尔-保时捷方法从易得的含酯结构单元中直接合成克劳斯碱E，鼠李糖碱，鼠李酸和鼠李碱的报告。
• The Synthesis of a Novel Carbazole-linked Cyclic Peptoid with Antibacterial Activity
  作者：John B. Bremner、Jonathan A. Coates、Paul A. Keller、Stephen G. Pyne、Helen M. Witchard

  DOI：10.1055/s-2002-19754

  日期：——

  This paper describes the synthesis of a novel cyclic peptoid 11, structurally comprising a tripeptide moiety linked through a carbazole scaffold. In a key step, a ring-closing metathesis reaction was used giving efficientaccess to a new class of cyclic peptoids.

  本文描述了一种新型环状 peptoid 11 的合成，其结构上包含通过咔唑支架连接的三肽部分。在一个关键步骤中，使用闭环复分解反应可以有效地获得一类新的环状拟肽。
• Peptoid compounds
  申请人：Bremner John

  公开号：US20050043509A1

  公开（公告）日：2005-02-24

  The invention relates to new peptoid compounds of formula (I), as well as their use in the treatment of bacterial infections, such as those caused by vancomycin resistant microorganisms, and to compositions thereof.

  本发明涉及公式（I）的新型肽酸类化合物，以及它们在治疗细菌感染中的应用，例如由万古霉素耐药微生物引起的感染，以及它们的组合物。
• PEPTOID COMPOUNDS
  申请人：BREMNER John

  公开号：US20120108499A1

  公开（公告）日：2012-05-03

  The invention relates to new peptoid compounds of formula (I), as well as their use in the treatment of bacterial infections, such as those caused by vancomycin resistant microorganisms, and to compositions thereof.

  本发明涉及公式（I）的新型肽状化合物，以及它们在治疗细菌感染方面的应用，例如由万古霉素耐药微生物引起的感染，以及它们的组成物。