11-methyl-5H-benzo[b]carbazole | 120211-14-5

• 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: 11-methyl-5H-benzo[b]carbazole
• CAS: 120211-14-5
• 化学式: C₁₇H₁₃N
• 分子量: 231.297
• InChiKey: AUEDAUAYPTXPDK-UHFFFAOYSA-N

物化性质

• 熔点：
  231-233 °C
• 沸点：
  466.3±14.0 °C(Predicted)
• 密度：
  1.240±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  18
• 可旋转键数：
  0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  15.8
• 氢给体数：
  1
• 氢受体数：
  0

反应信息

• 作为产物：
  描述：

  (Z)-phenyl 2-phenyl-N-[2-(prop-1-ynyl)phenyl]ethaneselenoimidate 在 三乙基硼 、 三正丁基氢锡 作用下， 以 正己烷 、 甲苯 为溶剂， 反应 24.0h， 以15%的产率得到11-methyl-5H-benzo[b]carbazole
  参考文献：
  名称：

  Synthesis of Ellipticine:  A Radical Cascade Protocol to Aryl- and Heteroaryl-Annulated[b]carbazoles

  摘要：

  Imidoyl selanides, synthesized from amides, have been used as radical precursors of imidoyl radicals in cascade reactions. The novel radical cascade has been developed for the simple synthesis of the medicinally important aryl-annulated[b]-carbazoles. The protocol has been exemplified with the high-yielding total synthesis of the anticancer alkaloid ellipticine.

  DOI：

  10.1021/jo0519920

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。
• Synthesis of carbazoles related to carbazomycin, hyellazole and ellipticine.
  作者：Jan Bergman、Benjamin Pelcman

  DOI：10.1016/s0040-4020(01)86029-4

  日期：1988.1

  2-disubstituted carbazoles are described. The first involves condensation of 2-alkyl-substituted indoles with 2,3-unsaturated ketones in the presence of Pd/C and molecular sieves, the second is based on the reaction of a 2-vinylic indole with the Vilsmeier reagent. The vinylic indoles were prepared by a Fischer indole synthesis, or via 1-benzenesulphonyl-2-lithioindole.

  描述了两种合成1,2-二取代咔唑的途径。第一个涉及在Pd / C和分子筛的存在下2-烷基取代的吲哚与2,3-不饱和酮的缩合，第二个基于2-乙烯基吲哚与Vilsmeier试剂的反应。乙烯基吲哚通过Fischer吲哚合成或通过1-苯磺酰基-2-硫代吲哚制备。
• BERGMAN, JAN;PELCMAN, BENJAMIN, TETRAHEDRON., 44,(1988) N 16, C. 5215-5228
  作者：BERGMAN, JAN、PELCMAN, BENJAMIN

  DOI：——

  日期：——