6-methyl-11-phenyl-5H-benzo[b]carbazole | 414868-64-7

• 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-11-phenyl-5H-benzo[b]carbazole
• CAS: 414868-64-7
• 化学式: C₂₃H₁₇N
• 分子量: 307.395
• InChiKey: RZQYTZDPLWCQCI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.3
• 重原子数：
  24
• 可旋转键数：
  1
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.04
• 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-(2-phenylethynyl)phenyl]propaneselenoimidate 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 48.0h， 以55%的产率得到6-methyl-11-phenyl-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

• 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。
• Synthesis of Ellipticine:  A Radical Cascade Protocol to Aryl- and Heteroaryl-Annulated[<i>b</i>]carbazoles
  作者：Jan M. Pedersen、W. Russell Bowman、Mark R. J. Elsegood、Anthony J. Fletcher、Peter J. Lovell

  DOI：10.1021/jo0519920

  日期：2005.12.1

  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.