6-methyl-5H-benzocarbazole | 77507-61-0

• 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: 6-methyl-5H-benzocarbazole
• 英文别名: 6-methyl-5H-benzo[b]carbazole
• CAS: 77507-61-0
• 化学式: C₁₇H₁₃N
• 分子量: 231.297
• InChiKey: UDOOURMQSUGKLQ-UHFFFAOYSA-N

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：

  3-Methyl-2-(1-phenyl-vinyl)-1H-indole 反应 0.05h， 以26%的产率得到6-methyl-5H-benzocarbazole
  参考文献：
  名称：

  New synthesis of the antitumor 6H-pyrido[4,3-b]carbazole alkaloid ellipticine

  摘要：

  DOI：

  10.1021/jo00327a031

文献信息

• Diels–Alder reactivity of pyrano[3,4-b]indol-3-ones, stable, synthetic equivalents of indole-2,3-quinodimethanes
  作者：Christopher J. Moody

  DOI：10.1039/c39840000925

  日期：——

  Pyrano[3,4-b]indol-3-ones (5), synthetic equivalents of indole-2,3-quinodimethanes, undergo Deils–Alder reaction with acetylenes and with benzyne to give carbazoles and benzo[b]carbozoles respectively.

  吡喃并[3,4- b ]吲哚-3-酮（5）是吲哚-2,3-喹二甲烷的合成等价物，与乙炔和苯并炔进行Deils-Alder反应，分别得到咔唑和苯并[ b ]咔唑。
• 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 ellipticine and olivacine by the thermal electrocyclic reaction<i>via</i>pyridine 3,4-quinodimethane intermediates
  作者：S. Hibino、E. Sugino

  DOI：10.1002/jhet.5570270645

  日期：1990.9

  A synthesis of the antitumor alkaloids ellipticine 1 and olivacine 2 is reported. The route involves a thermal electrocyclic reaction of conjugated hexatriene system 4 derived from 2-alkenylindole derivatives 5. Heating of the 2-alkenylindole derivative 5b at 450–460° gave ellipticine 1 (30%) and 11-demethylellipticine 14 (43%). In a similar manner, the thermolysis of the 2-alkenylindole 5c afforded

  报道了抗肿瘤生物碱玫瑰树碱1和olivacine 2的合成。该路线涉及衍生自2-烯基吲哚衍生物5的共轭己三烯系统4的热电环反应。将2-烯基吲哚衍生物5b在450–460°加热，得到玫瑰树碱1（30％）和11-去甲基玫瑰树碱14（43％）。以类似的方式，对2-烯基吲哚5c进行热解，得到了olivacine 2（57％）。
• A synthesis of 6,11-disubstituted benzo[<i>b</i>]carbazoles
  作者：Heidi L Fraser、Gordon W Gribble

  DOI：10.1139/v01-127

  日期：2001.11.1

  Sequential regioselective addition of organolithium reagents to indolo[1,2-b]isoquinoline-6,11-quinone (7) followed by sodium borohydride reduction of the intermediate diol 10, which is not isolated, affords 6,11-disubstituted 5H-benzo[b]carbazoles 11. The tandem combination of methyllithium and lithium triethylborohydride (Super Hydride) gives 6-methylbenzo[b]carbazole (24).Key words: benzo[b]carbazole, organolithiums, indolo[1,2-b]isoquinoline-6,11-quinone, ellipticine, indole.

  有机锂试剂的顺序区域选择性加成到吲哚[1,2-b]异喹啉-6,11-醌（7），随后钠硼氢化物还原中间体二醇10（未分离），得到6,11-二取代的5H-苯并[b]咔唑11。甲基锂和三乙基硼氢化锂（超级氢化物）的串联组合反应可以得到6-甲基苯并[b]咔唑（24）。关键词：苯并[b]咔唑，有机锂试剂，吲哚[1,2-b]异喹啉-6,11-醌，椭圆嘧啶，吲哚。
• Moody, Christopher J., Journal of the Chemical Society. Perkin transactions I, 1985, p. 2505 - 2508
  作者：Moody, Christopher J.

  DOI：——

  日期：——