5,11-Dimethyl-6H-benzocarbazole | 73326-97-3

• 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: 5,11-Dimethyl-6H-benzocarbazole
• 英文别名: 6,11-dimethyl-5H-benzocarbazole；6,11-dimethyl-5H-benzcarbazole；6,11-dimethyl-5H-benzo[b]carbazole；6,11-dimethyl-5H-benzo[b]carbazole；6,11-Dimethyl-5H-benzocarbazol
• CAS: 73326-97-3
• 化学式: C₁₈H₁₅N
• 分子量: 245.324
• InChiKey: HMGSVDHVYNJVDL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5
• 重原子数：
  19
• 可旋转键数：
  0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.11
• 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：

  5-(Phenylsulfonyl)-6,11-epoxy-6,11-dimethyl-6,11-dihydrobenzocarbazole 在 sodium hydroxide 、 sodium tetrahydroborate 、 三氟乙酸 作用下， 生成 5,11-Dimethyl-6H-benzocarbazole
  参考文献：
  名称：

  Synthesis and Diels-Alder reactions of 1,3-dimethyl-4-(phenylsulfonyl)-4H-furo[3,4-b]indole. A new annulation strategy for the construction of ellipticine and isoellipticine

  摘要：

  DOI：

  10.1021/jo00197a039

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。
• 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。
• 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：——
• A versatile and efficient construction of the 6H-pyrido[4,3-b]carbazole ring system. Syntheses of the antitumor alkaloids ellipticine, 9-methoxyellipticine, and olivacine, and their analogs
  作者：Gordon W. Gribble、Mark G. Saulnier、Judy A. Obaza-Nutaitis、Daniel M. Ketcha

  DOI：10.1021/jo00048a022

  日期：1992.10

  A general and efficient synthesis of the 6H-pyrido[4,3-b]carbazole ring system is described, in which the key steps are (1) regioselective acylation of a 2-lithio-1-(phenylsulfonyl)indole (14) with 3,4-pyridinedicarboxylic acid anhydride (10), (2) cyclization of the deprotected keto acid 17 to keto lactam 19 with acetic anhydride, and (3) the addition of methyllithium to give, after reduction of the intermediate diol 23 with sodium borohydride, the target ring system. In this fashion, ellipticine (1a), 9-methoxyellipticine (1b), and 9-hydroxyellipticine (1c) were synthesized in excellent overall yields from indole. The use of Superhydride, in place of 1 equiv of methyllithium, provided a synthesis of olivacine (2), and the use of phthalic anhydride in the sequence allowed for the preparation of 6,11-dimethylbenzo[b]carbazole (48). The overall yields of ellipticine (1a) (54%) and 9-methoxyellipticine (1b) (47%) in six steps from their respective indoles represent one of the most efficient syntheses of these antitumor alkaloids.