Ethyl 6-cyano-11,12-dihydroindolo[2,3-a]carbazole-5-carboxylate | 210470-17-0

• 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: Ethyl 6-cyano-11,12-dihydroindolo[2,3-a]carbazole-5-carboxylate
• CAS: 210470-17-0
• 化学式: C₂₂H₁₅N₃O₂
• 分子量: 353.38
• InChiKey: GQDOERAZSWHFDD-UHFFFAOYSA-N

物化性质

• 沸点：
  699.5±55.0 °C(Predicted)
• 密度：
  1.43±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  27
• 可旋转键数：
  3
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.09
• 拓扑面积：
  81.7
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  Ethyl 6-cyano-11,12-dihydroindolo[2,3-a]carbazole-5-carboxylate 在 sodium tetrahydroborate 、 cobalt(II) chloride 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 1.0h， 以92%的产率得到6,7,12,13-四氢-5H-吲哚并[2,3-a]吡咯并[3,4-c]咔唑-5-酮
  参考文献：
  名称：

  A new synthesis of staurosporinone

  摘要：

  A new six steps synthesis of staurosporinone 4, starting from 3-cyano-3-(1H-indol-3-yl)-2-oxo-propionic acid ethyl ester 5, is reported. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(98)00372-x
• 作为产物：
  描述：

  diethyl 12-(benzenesulfonyl)-6-cyanoindolo[2,3-a]carbazole-5,11-dicarboxylate 在 sodium ethanolate 作用下， 以 乙醇 为溶剂， 反应 0.5h， 以99%的产率得到Ethyl 6-cyano-11,12-dihydroindolo[2,3-a]carbazole-5-carboxylate
  参考文献：
  名称：

  A new synthesis of staurosporinone

  摘要：

  A new six steps synthesis of staurosporinone 4, starting from 3-cyano-3-(1H-indol-3-yl)-2-oxo-propionic acid ethyl ester 5, is reported. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(98)00372-x

文献信息

• INDOLE-YNONE MEDIATED BENZOANNULATION PROCESS FOR THE PREPARATION OF CARBAZOLES, CARBAZOMYCIN A, CALOTHRIXIN B AND STAUROSPORINONE
  申请人：COUNCIL OF SCIENTIFIC & INDUSTRIAL RESEARCH

  公开号：US20220169609A1

  公开（公告）日：2022-06-02

  The present invention relates to carbazoles of general formula (I), and process for the preparation thereof: wherein ‘R 1 ’ is H, C1-C6 alkyl, benzyl, or allyl; R 2 is H, C1-C6 alkyl, cyclopropyl, phenyl, aryl, heteroaryl, or NO 2 ; R 3 is H, C1-C6 alkyl, cyclopropyl, phenyl aryl, heteroaryl, 4-methoxy phenyl, 4-ethyl phenyl, 2-methyl phenyl, or 2-Fluoro phenyl; R 4 is H, benzoyl, —CO 2 Et, —CHO, Br, or —OMe; R 5 is OH, OMOM, OMe, CN, or OTf; R 6 is H, or O-alkyl; and R 3 -R 4 is —CHNCH2CH2-. This invention also relates to the process for the preparation of carbazomycin A of Formula (1), calothrixin B of Formula (2) and staurosporinone of Formula (3) involving carbazoles of general formula (I) as an intermediate.
• A new synthesis of staurosporinone
  作者：Egle M. Beccalli、Maria Luisa Gelmi、Alessandro Marchesini

  DOI：10.1016/s0040-4020(98)00372-x

  日期：1998.6

  A new six steps synthesis of staurosporinone 4, starting from 3-cyano-3-(1H-indol-3-yl)-2-oxo-propionic acid ethyl ester 5, is reported. (C) 1998 Elsevier Science Ltd. All rights reserved.