5,6-dimethoxycarbonylindolo<2,3-a>carbazole | 144823-23-4

• 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: 5,6-dimethoxycarbonylindolo<2,3-a>carbazole
• 英文别名: 5,6-dicarbomethoxyindolo<2,3-a>carbazole；Dimethyl 11,12-dihydroindolo[2,3-a]carbazole-5,6-dicarboxylate
• CAS: 144823-23-4
• 化学式: C₂₂H₁₆N₂O₄
• 分子量: 372.38
• InChiKey: PZSMWNWSDDNEMF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  28
• 可旋转键数：
  4
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.09
• 拓扑面积：
  84.2
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  5,6-dimethoxycarbonylindolo<2,3-a>carbazole 在 sodium tetrahydroborate 、 盐酸甲胺 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 生成 14-Hydroxy-13-methyl-3,13,23-triazahexacyclo[14.7.0.02,10.04,9.011,15.017,22]tricosa-1,4,6,8,10,15,17,19,21-nonaen-12-one
  参考文献：
  名称：

  Simple Synthesis of 2,2'-Bisindole from Indigo and Its Application for the Syntheses of Indolo[2,3-a]pyrrolo[3,4-c]carbazole-5,7-(6H)dione and -5-(6H)one Derivatives

  摘要：

  Indigo was converted to 2,2'-bisindole, from which 6-substituted indolo[2,3-a]pyrrolo[3,4-c]carbazole-5,7-(6H)dione and -5-(6H)one derivatives were prepared in short steps. Bromination of 6-methylindolo[2,3-a]pyrrolo[3,4-c]carbazole5,7-(6H)dione is also reported.

  DOI：

  10.3987/com-95-7192
• 作为产物：
  描述：

  马来酸二甲酯 在 polyphosphoric acid trimethylsilyl ester 、 间氯过氧苯甲酸 作用下， 以 硝基甲烷 、 甲苯 为溶剂， 反应 13.5h， 生成 5,6-dimethoxycarbonylindolo<2,3-a>carbazole
  参考文献：
  名称：

  Synthetic Approaches to Indolo[2,3-a]carbazole alkaloids. Syntheses of arcyriaflavin A and AT2433-B aglycone

  摘要：

  Ozonolysis of tetrahydrophthalimides 17 and 18 or cyclohexane diester 25 and treatment of the intermediate dialdehydes (19, 20, 26) with an arylhydrazine affords the corresponding bis-arylhydrazones (21-24, 27, 28). Exposure of 21 and 23 to PPSE in CH3NO2 gives the indolo[2,3-a]carbazole alkaloids arcyriaflavin A (8) and AT2433-B aglycone (29) in low yield. bis-Phenylhydrazones (osazones) (33, 34, 42, 44) of cyclohexandiones were synthesized by m-CPBA oxidation of 4,5-bis(trimethylsilyloxy)tetrahydrophthalimides followed by treatment of the presumed intermediate 1,2-cyclohexanediones with an arylhydrazine. These osazones were cyclized to the corresponding indolo[2,3-a]carbazoles with PPSE.

  DOI：

  10.1016/s0040-4020(01)81986-4

文献信息

• Coupling reactions of indole-3-acetic acid derivatives. Synthesis of arcyriaflavin A
  作者：Jan Bergman、Eva Koch、Benjamin Pelcman

  DOI：10.1039/b004029k

  日期：——

  The bisindolesuccinic acid methyl ester 10 was obtained by an iodine-promoted coupling of the dianion 9. The diester was converted to the N-benzylimide 12, which was oxidatively cyclized to the indolo[2,3-a]pyrrolo[3,4-c]carbazole 15. The diester 10 could be directly transformed to the known indolocarbazole diester 27via acid-induced intramolecular cyclization in TFA. The same methodology gave arcyriaflavin A 4 from the succinimide 18b.

  双吲哚基琥珀酸甲酯10是通过碘促进的双阴离子9的耦合反应获得的。该二酯被转化为N-苄基亚胺12，随后经过氧化环合得到吲哚[2,3-a]吡咯[3,4-c]咔唑15。二酯10可以直接通过三氟乙酸中的酸诱导分子内环合反应转化为已知的吲哚咔唑二酯27。同样的合成方法从琥珀酰亚胺18b得到了亮菌素A 4。
• Reactions of indole-3-acetic acid derivatives in trifluoroacetic acid
  作者：Jan Bergman、Eva Koch、Benjamin Pelcman

  DOI：10.1016/0040-4039(95)00648-v

  日期：1995.5

  TFA-induced dimerization of indole-3-acetic acid (IAA) gave 5a. The corresponding methyl ester gave the diester 5b or the lactam 6. Similar treatment of the 2,3-bis-(3-indolyl)-succinic ester 4b gave the tetrahydroindolo[2,3-a]carbazole derivative 10. The relation of these compounds to indolocarbazole alkaloids is discussed.

  TFA诱导的吲哚-3-乙酸（IAA）的二聚反应得到5a。相应的甲酯得到二酯5b或内酰胺6。对2，3-双-（3-吲哚基）-琥珀酸酯4b进行类似处理，得到四氢吲哚并[2，3- a ]咔唑衍生物10。讨论了这些化合物与吲哚咔唑生物碱的关系。
• Molecular Iodine Assisted Electrocyclisation: Synthesis of Arcyriaflavin A and Formal Synthesis of Staurosporinone
  作者：Santosh Tilve、Prachi Torney、Rajendra Shirsat

  DOI：10.1055/s-0034-1378536

  日期：——

  A new method for the synthesis of the indolocarbazole alkaloid arcyriaflavin A is described. The synthetic strategy employs a graphite-catalysed alkenation, one-pot oxidation–Wittig reaction, iodine-catalysed electrocyclisation and nitrene insertion as the key steps. The strategy also constitutes a formal synthesis of another indolocarbazole alkaloid staurosporinone.

  描述了一种合成吲哚咔唑生物碱 arcyriaflavin A 的新方法。合成策略采用石墨催化的烯化、一锅氧化-Wittig 反应、碘催化的电环化和氮烯插入作为关键步骤。该策略还构成了另一种吲哚咔唑生物碱星形孢菌素的正式合成。
• A Novel Synthesis of 2,2'-Bisindole and Its Application for the Synthesis of Indolo[2,3-a]carbazole Derivatives
  作者：Masanori Somei、Atsushi Kodama

  DOI：10.3987/com-92-6044

  日期：——

  A novel oxidative coupling method of 2-lithio-1-methoxyindole was developed resulting in the formation of 2,2'-bis(l-methoxyindole) (6). Catalytic hydrogenation of 6 produced 2,2'-bisindole (9). Diels-Alder reaction of 9 with dienophiles afforded indolo-[2,3-a]carbazole derivatives.
• Short Step Syntheses of Indolo[2,3-a]carbazoles Carrying an Alkyl, Allyl, or a Glycosyl Group at the 11-Position and a Novel 6,7-Dihydro-13H-cyclopentano[mn]indolo[3,2-c]acridine Derivative
  作者：Masanori Somei、Fumio Yamada、Jun Kato、Yoshiaki Suzuki、Yoshinori Ueda

  DOI：10.3987/com-01-s(k)40

  日期：——

  Novel 1-alkyl-, 1-allyl-, and 1-beta-glycosyl-2,2'-biindolyls are prepared. Their Diels-Alder reaction produced 11-alkyl-, 11-allyl-, and 11-beta-glycosylindolo[2,3-a]carbazoles. Formation of a novel 6,7-dihydro-13H-cyclopentano[mn]indolo[3,2-c]acridine derivative is also reported.