indolo<1,2-b>isoquinoline-6,11-quinone | 143706-92-7

• 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: indolo<1,2-b>isoquinoline-6,11-quinone
• 英文别名: indolo<1,2-b>isoquinoline-5,12-dione；indolo[1,2-b]isoquinoline-6,11-quinone；indolo[1,2-b]isoquinoline-6,11-dione；indolo[1,2-b]isoquinolin-6,11-dione
• CAS: 143706-92-7
• 化学式: C₁₆H₉NO₂
• 分子量: 247.253
• InChiKey: UDXNTEWKAAEEOR-UHFFFAOYSA-N

物化性质

• 沸点：
  372.5±25.0 °C(Predicted)
• 密度：
  1.36±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  19
• 可旋转键数：
  0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  39.1
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  indolo<1,2-b>isoquinoline-6,11-quinone 在 sodium tetrahydroborate 作用下， 以 乙醇 为溶剂， 反应 24.0h， 以86%的产率得到11,11a-dihydroindolo[1,2-b]isoquinoline-6,11-hydroquinone
  参考文献：
  名称：

  A synthesis of 6,11-disubstituted benzo[b]carbazoles

  摘要：

  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。

  DOI：

  10.1139/v01-127
• 作为产物：
  描述：

  1H-吲哚-2-羧酸肼 在 lead(IV) tetraacetate 、 2-碘酰基苯甲酸 作用下， 以 四氢呋喃 、 乙醇 、 二甲基亚砜 、 乙酸乙酯 为溶剂， 反应 8.0h， 生成 indolo<1,2-b>isoquinoline-6,11-quinone
  参考文献：
  名称：

  Calothrixins 和 Ellipticines 的多样性导向合成

  摘要：

  通过四乙酸铅介导的氧化重排邻羟基酮单酰基腙，利用邻二酰基芳烃作为关键中间体的一锅形成，完成了calothrixins和玫瑰树碱的不同合成。

  DOI：

  10.1002/ejoc.201402837

文献信息

• Studies on the Chemistry of 2-[3-(2-Nitrophenyl)-2-oxopropyl]benzaldehydes: Novel Syntheses of 5H-Benzo[b]carbazole-6,11-diones and Indolo[1,2-b]isoquinoline-6,11-diones
  作者：Marcos Fernández

  DOI：10.1055/s-0029-1216919

  日期：2009.9

  Syntheses of 5H-benzo[b]carbazole-6,11-diones and indolo[1,2-b]isoquinoline-6,11-diones are described. Both compounds are synthesized from 2-[3-(2-nitrophenyl)-2-oxopropyl]benzaldehydes, which were obtained from commercially available indan-1-ones in six steps.

  描述了5H-苯并[b]咔唑-6,11-二酮和吲哚[1,2-b]异喹啉-6,11-二酮的合成方法。这两种化合物均由2-[3-(2-硝基苯基)-2-氧代丙基]苯甲醛合成，后者是通过商业上可获得的茚-1-酮经过六步反应得到的。
• Rhodium-Catalyzed Decarbonylative Intramolecular Arylation of 2-(1H-Indole-1-carbonyl)benzoic Acids
  作者：Hirotsugu Suzuki、Takanori Matsuda、Yosuke Takemura

  DOI：10.1055/a-2278-5797

  日期：——

  We developed a redox-neutral synthesis of isoindoloindolone via intramolecular arylation of 2-(1H-indole-1-carbonyl)benzoic acids. This protocol facilitates the formation of various substituted isoindoloindolones in yields ranging from 17% to 80%. Our mechanistic investigations indicate the pivotal role of NaI: the iodide anion promotes the formation of the desired isoindoloindolone, and the sodium

  我们通过 2-(1 H-吲哚-1-羰基)苯甲酸的分子内芳基化开发了异吲哚并吲哚酮的氧化还原中性合成。该方案促进了各种取代异吲哚并吲哚酮的形成，产率范围为 17% 至 80%。我们的机理研究表明 NaI 的关键作用：碘化物阴离子促进所需异吲哚并吲哚酮的形成，钠阳离子抑制酰化副产物的形成，从而能够以可接受的产率选择性形成异吲哚并吲哚酮。
• 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.
• Synthesis of Indolo[1,2-b]isoquinolinediones; Reduction of 2-[(Substituted Phenyl)methylidene]-3-oxo-2,3-dihydroindole
  作者：Jean-Yves Mérour、Simone Piro鼠le、Fran腔ise Cossais

  DOI：10.3987/com-92-6286

  日期：——

  Indolo[1,2-b]isoquinoline-5,12-dione and the isomeric 6,12-dione have been prepared respectively from 1-sulfonylindole and 1-acetyl-2-[(2-methoxycarbonyl phenyl)methylidene]-3-oxo-2,3-dihydroindole; the reduction of 1-acetyl-2-[(substituted phenyl)methylidene]-3-oxo-2,3-dihydroindole and their oxygen analogs with sodium borohydride have been studied.
• Diversity-Oriented Synthesis of Calothrixins and Ellipticines
  作者：Dattatraya H. Dethe、Ganesh M. Murhade

  DOI：10.1002/ejoc.201402837

  日期：2014.11

  The divergent synthesis of calothrixins and ellipticines has been accomplished by utilising the one-pot formation of o-diacylarenes as a key intermediate through rearrangement of o-hydroxy ketone monoacyl hydrazones by lead tetraacetate mediated oxidation.

  通过四乙酸铅介导的氧化重排邻羟基酮单酰基腙，利用邻二酰基芳烃作为关键中间体的一锅形成，完成了calothrixins和玫瑰树碱的不同合成。