3-fluoro-6H-isoindolo[2,1-a]indol-6-one | 891202-83-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 异吲哚及其衍生物
• 英文名称: 3-fluoro-6H-isoindolo[2,1-a]indol-6-one
• 英文别名: 3-Fluoroisoindolo[2,3-a]indol-6-one
• CAS: 891202-83-8
• 化学式: C₁₅H₈FNO
• 分子量: 237.233
• InChiKey: NQJLSGXDRAMWCN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  18
• 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：
  22
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  3-fluoro-6H-isoindolo[2,1-a]indol-6-one 、 N,N-二乙基乙二胺 反应 96.0h， 以88%的产率得到N-[2-(diethylamino)ethyl]-2-(6-fluoroindol-2-yl)benzenecarboxamide
  参考文献：
  名称：

  Synthesis and biological activity of 6H-isoindolo[2,1-a]indol-6-ones, analogues of batracylin, and related compounds

  摘要：

  Closely related to batracylin, 6H-isoindolo[2,1-a]indol-6-ones including 2-nitro- 13a, 2-amino- 14, and 2-diethylaminopropionamide derivative 16 as well as D-ring substituted 13b, 13c or A-ring substituted 13d and 20 analogues, were synthesised and evaluated against L1210 leukaemia. Subsequent treatment of 13b and 13c with NN-diethylethylenediarnine at 180 degrees C, led to compounds 17a and 17b arising from an unexpected opening of the pyrrolidinone ring and amidification of the keto group. Under the same conditions, the dichloro derivative 13d led to the monoalkyl compound 20 which was the most cytotoxic of the series. (c) 2006 Elsevier SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2005.10.008
• 作为产物：
  描述：

  5-氟-2-甲基苯胺 在 N-溴代丁二酰亚胺(NBS) 、 溶剂黄146 、 三乙胺 、 过氧化苯甲酰 作用下， 以 四氯化碳 、 甲苯 为溶剂， 反应 37.0h， 生成 3-fluoro-6H-isoindolo[2,1-a]indol-6-one
  参考文献：
  名称：

  Synthesis and biological activity of 6H-isoindolo[2,1-a]indol-6-ones, analogues of batracylin, and related compounds

  摘要：

  Closely related to batracylin, 6H-isoindolo[2,1-a]indol-6-ones including 2-nitro- 13a, 2-amino- 14, and 2-diethylaminopropionamide derivative 16 as well as D-ring substituted 13b, 13c or A-ring substituted 13d and 20 analogues, were synthesised and evaluated against L1210 leukaemia. Subsequent treatment of 13b and 13c with NN-diethylethylenediarnine at 180 degrees C, led to compounds 17a and 17b arising from an unexpected opening of the pyrrolidinone ring and amidification of the keto group. Under the same conditions, the dichloro derivative 13d led to the monoalkyl compound 20 which was the most cytotoxic of the series. (c) 2006 Elsevier SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2005.10.008

文献信息

• 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：2024.10

  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。