5,6,11-trimethyl-5H-benzo[b]carbazole | 73326-96-2

• 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: 5,6,11-trimethyl-5H-benzo[b]carbazole
• 英文别名: 5,6,11-Trimethyl-5H-benzocarbazol；5,6,11-Trimethylbenzo[b]carbazole
• CAS: 73326-96-2
• 化学式: C₁₉H₁₇N
• 分子量: 259.351
• InChiKey: TVIADLWFFQEKPV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5
• 重原子数：
  20
• 可旋转键数：
  0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.16
• 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：

  5,6,11-trimethyl-5H-benzo[b]carbazole 、 乙酸酐 在 zinc(II) chloride 作用下， 以 氯仿 为溶剂， 反应 0.5h， 以45%的产率得到
  参考文献：
  名称：

  Ring D modifications of ellipticine. Part 2. Chlorination of ellipticine via its N-oxide and synthesis and selective acetylation of 5,6,11-trimethyl-5H-benzo[b]carbazole.

  摘要：

  The N-oxide of ellipticine can be used for the introduction of a chlorine atom at carbon-3 of the ellipticine nucleus. According to modelstudies with 5,8-dimethylisoquinoline-N-oxide the reaction is guided both by steric hindrance and by nitrogen-6 of the ellipticine system. Attempted nucleophilic substitution reactions of 3-chloro-ellipticines failed. The high cytostatic activity observed for 9-acetylellipticine stimulated us to prepare the corresponding deaza analogue. This compound was synthesized in 2 steps starting from 1-methylindole. Regioselective acetylation at C-2 was accomplished using acetic anhydride and ZnCl2 as a catalyst. Under a variety of other conditions the 2,9-diacetylproduct was formed and no 9-monoacetylated compound could be isolated. Just as the parent compound, the acetylated deazaellipticines showed only very low cytostatic activity.

  DOI：

  10.1016/s0040-4020(01)85018-3
• 作为产物：
  描述：

  1-甲基吲哚 、 ethyl 1-(2-ethynylphenyl)ethyl carbonate 在 indium nanofluorobutanesulfonate 作用下， 以 二丁醚 为溶剂， 反应 4.0h， 以44%的产率得到5,6,11-trimethyl-5H-benzo[b]carbazole
  参考文献：
  名称：

  Indium-catalyzed Annulation of Indoles with Ethyl (2-Ethynylaryl)methyl Carbonates: Synthesis and Photoluminescent Properties of Aryl- and Heteroaryl[b]carbazoles

  摘要：

  在铟催化下，吲哚与乙基（2-乙炔基芳基）甲基碳酸酯及其杂芳基类似物进行两次连续的碳-碳键成环反应，得到了具有光致发光性能的芳基和杂芳基咔唑类化合物。随后评估并比较了这些化合物的光致发光性能与相应[a]-和[c]-型化合物，结果显示发光效率的顺序为[a]- < [b]- < [c]-型。

  DOI：

  10.1246/cl.130402

文献信息

• Indium-catalyzed Annulation of Indoles with Ethyl (2-Ethynylaryl)methyl Carbonates: Synthesis and Photoluminescent Properties of Aryl- and Heteroaryl[<i>b</i>]carbazoles
  作者：Yuta Nagase、Takuhiro Miyamura、Kensuke Inoue、Teruhisa Tsuchimoto

  DOI：10.1246/cl.130402

  日期：2013.10.5

  Two successive carbon–carbon bond-forming annulation of indoles with ethyl (2-ethynylaryl)methyl carbonates and their heteroaryl analogs under indium catalysis provided aryl- and heteroaryl[b]carbazoles, photoluminescent properties of which were then evaluated and compared with those of the corresponding [a]- and [c]-types, thereby showing that the order of light-emitting efficiency is [a]- < [b]- < [c]-type.

  在铟催化下，吲哚与乙基（2-乙炔基芳基）甲基碳酸酯及其杂芳基类似物进行两次连续的碳-碳键成环反应，得到了具有光致发光性能的芳基和杂芳基咔唑类化合物。随后评估并比较了这些化合物的光致发光性能与相应[a]-和[c]-型化合物，结果显示发光效率的顺序为[a]- < [b]- < [c]-型。
• Ring D modifications of ellipticine. Part 2. Chlorination of ellipticine via its N-oxide and synthesis and selective acetylation of 5,6,11-trimethyl-5H-benzo[b]carbazole.
  作者：Adrian T. Boogaard、Upendra K. Pandit、Gerrit-Jan Koomen

  DOI：10.1016/s0040-4020(01)85018-3

  日期：1994.4

  The N-oxide of ellipticine can be used for the introduction of a chlorine atom at carbon-3 of the ellipticine nucleus. According to modelstudies with 5,8-dimethylisoquinoline-N-oxide the reaction is guided both by steric hindrance and by nitrogen-6 of the ellipticine system. Attempted nucleophilic substitution reactions of 3-chloro-ellipticines failed. The high cytostatic activity observed for 9-acetylellipticine stimulated us to prepare the corresponding deaza analogue. This compound was synthesized in 2 steps starting from 1-methylindole. Regioselective acetylation at C-2 was accomplished using acetic anhydride and ZnCl2 as a catalyst. Under a variety of other conditions the 2,9-diacetylproduct was formed and no 9-monoacetylated compound could be isolated. Just as the parent compound, the acetylated deazaellipticines showed only very low cytostatic activity.