1-methyl-9H-carbazole-2,3-dicarboxylic acid-dimethyl ester | 59774-12-8

• 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: 1-methyl-9H-carbazole-2,3-dicarboxylic acid-dimethyl ester
• 英文别名: 9H-methyl-1 carbazole dicarboxylate de methyle-2,3；dimethyl 1-methyl-9H-carbazole-2,3-dicarboxylate；1-methyl-carbazole-2,3-dicarboxylic acid dimethyl ester；dimethyl 1-methylcarbazole-2,3-dicarboxylate；1-Methyl-carbazol-dicarbonsaeure-(2,3)-dimethylester
• CAS: 59774-12-8
• 化学式: C₁₇H₁₅NO₄
• 分子量: 297.31
• InChiKey: XCHURAGJTJRNJL-UHFFFAOYSA-N

物化性质

• 熔点：
  184-185 °C
• 沸点：
  459.5±40.0 °C(Predicted)
• 密度：
  1.303±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  22
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  68.4
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  1-methyl-9H-carbazole-2,3-dicarboxylic acid-dimethyl ester 在 N-溴代丁二酰亚胺(NBS) 、 溶剂黄146 作用下， 反应 1.0h， 以68%的产率得到dimethyl 6-bromo-1-methyl-9H-carbazole-2,3-dicarboxylate
  参考文献：
  名称：

  Electrophilic Substitution of Dimethyl 1-Methylcarbazole-2,3-dicarboxylate: Synthesis of Newb-Fused Carbazoles as Potential Antitumor Agents

  摘要：

  1-Methylcarbazole-2,3-dicarboxylic acid dimethyl ester, a key intermediate in the synthesis of b-fused carbazoles, was successfully transformed into its 6-bromo and 6-nitro derivative via electrophilic substitution in acetic acid solution, using N-bromosuccinimide or urea nitrate, respectively, as reagents. With N-chlorosuccinimide, a 6,8-dichloro congener was also obtained in substantial amounts. The 6-substituted carbazolediesters were used as building blocks for the preparation of several new pyridazine-or pyrrole-fused carbazoles with basic side chains, featuring the core structure of previously developed antitumor compounds.

  DOI：

  10.5935/0103-5053.20140178
• 作为产物：
  描述：

  3-吲哚乙酸 在 三氟化硼乙醚 作用下， 生成 1-methyl-9H-carbazole-2,3-dicarboxylic acid-dimethyl ester
  参考文献：
  名称：

  Electrophilic Substitution of Dimethyl 1-Methylcarbazole-2,3-dicarboxylate: Synthesis of Newb-Fused Carbazoles as Potential Antitumor Agents

  摘要：

  1-Methylcarbazole-2,3-dicarboxylic acid dimethyl ester, a key intermediate in the synthesis of b-fused carbazoles, was successfully transformed into its 6-bromo and 6-nitro derivative via electrophilic substitution in acetic acid solution, using N-bromosuccinimide or urea nitrate, respectively, as reagents. With N-chlorosuccinimide, a 6,8-dichloro congener was also obtained in substantial amounts. The 6-substituted carbazolediesters were used as building blocks for the preparation of several new pyridazine-or pyrrole-fused carbazoles with basic side chains, featuring the core structure of previously developed antitumor compounds.

  DOI：

  10.5935/0103-5053.20140178

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。
• Isoindole derivatives and salts thereof and antitumor agent comprising
  申请人：Toyama Chemical Co., Ltd.

  公开号：US05166204A1

  公开（公告）日：1992-11-24

  A novel isoindole derivative represented by general formula [1] or a salt thereof: ##STR1## which has an excellent antitumor activity and low toxicity.

  由一般式[1]表示的新型异吲哚衍生物或其盐：##STR1##具有优异的抗肿瘤活性和低毒性。
• Diels-alder reactions of pyrano[3,4-b]indol-3-ones with olefinic compounds : Synthesis of (1,2-dihydro)carbazoles
  作者：P. Van Doren、D. Vanderzande、S. Toppet、G. Hoornaert

  DOI：10.1016/s0040-4020(01)89146-8

  日期：1989.1

  The Diels-Alder reaction of substituted pyrano [3, 4-b]indol-3-ones with olefinic dienophiles is described. The role of the substitution pattern on the stability of the obtained 1, 2-dihydrocarbazoles is interpreted in terms of electronic and steric effects on the aromatization to the corresponding carbazoles.

  描述了取代的吡喃并[3，4-b]吲哚-3-酮与烯属亲二烯物的Diels-Alder反应。取代模式对所获得的1，2-二氢咔唑的稳定性的作用是根据电子和位阻作用对相应咔唑的芳构化作用来解释的。
• Synthesis and pharmacology of pyridazino(4,5-b) carbazoles.
  作者：Henriette LANDELLE、Daniel LADUREE、Michel CUGNON DE SEVRICOURT、Max ROBBA

  DOI：10.1248/cpb.37.2679

  日期：——

  Cyclization reaction of hydrazine with carbazole-2,3-methyl dicarboxylates gave 1,4-dioxo-1,2,3,4-tetrahydropyridazino[4,5-b]carbazoles. Chlorodehydroxylation provided 1,4-dichloropyridazino[4,5-b]carbazoles and nucleophilic substitution gave 1,4-dialkoxy pyridazino[4,5-b]carbazoles. These compounds were tested for cytotoxic activity against L1210 leukemia in mice.

  肼与咔唑-2，3-甲基二羧酸酯的环化反应得到1，4-二氧-1,2,3,4-四氢吡啶并[4,5-b]咔唑。进行氯去羟基化，得到1,4-二氯哒嗪[4,5-b]咔唑，亲核取代得到1,4-二烷氧基哒嗪[4,5-b]咔唑。测试了这些化合物对小鼠的L1210白血病的细胞毒活性。
• [EN] HIV INTEGRASE INHIBITORS<br/>[FR] INHIBITEURS D'INTEGRASE VIH
  申请人：TIBOTEC PHARM LTD

  公开号：WO2004096807A3

  公开（公告）日：2005-01-06