2-(2-(5-氟-1H-吲哚-3-基)乙基)异吲哚啉-1,3-二酮 | 1198292-69-1

• 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
• 中文名称: 2-(2-(5-氟-1H-吲哚-3-基)乙基)异吲哚啉-1,3-二酮
• 英文名称: 2-(2-(5-fluoro-1H-indol-3-yl)ethyl)isoindoline-1,3-dione
• CAS: 1198292-69-1
• 化学式: C₁₈H₁₃FN₂O₂
• 分子量: 308.312
• InChiKey: LLYOFFYHQXVQSJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.15
• 重原子数：
  23.0
• 可旋转键数：
  3.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  53.17
• 氢给体数：
  1.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  2-(2-(5-氟-1H-吲哚-3-基)乙基)异吲哚啉-1,3-二酮 在 肼 作用下， 以 乙醇 为溶剂， 生成 5-氟色胺
  参考文献：
  名称：

  The discovery of tetrahydro-β-carbolines as inhibitors of the kinesin Eg5

  摘要：

  A series of tetrahydro-beta-carbolines were identified by HTS as inhibitors of the kinesin Eg5. Molecular modeling and medicinal chemistry techniques were employed to explore the SAR for this series with a focus of removing potential metabolic liabilities and improving cellular potency. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2009.11.012
• 作为产物：
  描述：

  4-(1,3-二氧代异吲哚啉-2-基)丁醛 、 2-碘-4-氟苯胺 在 三乙烯二胺 、 palladium diacetate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 0.33h， 以49%的产率得到2-(2-(5-氟-1H-吲哚-3-基)乙基)异吲哚啉-1,3-二酮
  参考文献：
  名称：

  Palladium-catalyzed synthesis of tryptamines and tryptamine homologues: synthesis of psilocin

  摘要：

  A new Pd-catalyzed method for the synthesis of tryptamines is developed, and its applications to the synthesis of Corey's aspidophytine tryptamine 15 and psilocin 20 are also described. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2009.09.050

文献信息

• Enantioselective Total Synthesis and Absolute Configuration Assignment of (+)‐Tronocarpine Enabled by an Asymmetric Michael/Aldol Reaction
  作者：Dong‐Xing Tan、Jie Zhou、Chao‐You Liu、Fu‐She Han

  DOI：10.1002/anie.201914868

  日期：2020.3.2

  We present the first asymmetric total synthesis and absolute configuration determination of (+)-tronocarpine. The [6.5.7.6.6] pentacyclic core was constructed at an early stage by using a sequential cyclization strategy through a newly developed catalytic asymmetric Michael/aldol cascade to build the aza[3.3.1]-bridged cycle and a tandem reduction/hemiamidation procedure to assemble the seven-membered

  我们提出（+）-tronocarpine的第一个不对称总合成和绝对构型确定。[6.5.7.6.6]五环核是通过采用新开发的催化不对称Michael / aldol级联反应通过连续环化策略构建aza [3.3.1]桥连环和串联还原/半酰胺化而在早期阶段构建的组装七元内酰胺的程序。在温和条件下，通过几种适当的精心安排的操作，在后期加入了侧链功能。对映体纯的（+）-香豆蔻碱的合成是通过从色胺中获得的20步最长的线性序列完成的。
• Asymmetric Synthesis of Tetrahydro-β-carbolines <i>via</i> Chiral Phosphoric Acid Catalyzed Transfer Hydrogenation Reaction
  作者：Qin Yin、Shou-Guo Wang、Shu-Li You

  DOI：10.1021/ol400995c

  日期：2013.6.7

  Chiral phosphoric acid catalyzed enantioselective transfer hydrogenation of hydroxylactams has been realized to provide enantioenriched tetrahydro-β-carbolines in dioxane at room temperature (up to 94% yield, 90% ee).

  已经实现了手性磷酸催化羟基内酰胺的对映选择性转移氢化反应，可以在室温下在二恶烷中提供对映体富集的四氢-β-咔啉（最高收率94％，ee 90％）。
• Syntheses of Tetracyclic Indoline Derivatives Via Gold(I)-Catalyzed Hydroamination/Cycloisomerization Cascade of 2-Ethynyltryptamides
  作者：Jiang Zhu、Lu Yang、Hairui Liu、Shitao Sun、Jiaji Li、Lianjie Zhang、Hanyang Sun、Maosheng Cheng、Bin Lin、Yongxiang Liu

  DOI：10.1021/acs.joc.3c02784

  日期：2024.3.1

  A gold(I)-catalyzed hydroamination/cycloisomerization cascade reaction was developed to yield indolizino[8,7-b]indole and indolo[2,3-a]-quinolizine derivatives from 2-ethynyltryptamides. The optimal conditions were determined by condition screening, and the functional group tolerances of these reactions were explored based on synthetic substrates. An insight into the explanation on the selectivity

  开发了金(I)催化的加氢胺化/环化异构化级联反应，从2-乙炔基色酰胺中产生吲哚并[8,7- b ]吲哚和吲哚[2,3- a ]-喹嗪衍生物。通过条件筛选确定了最佳条件，并根据合成底物探索了这些反应的官能团耐受性。通过密度泛函理论计算，深入了解了闭环选择性的解释。提出了级联反应的合理机制。吲哚并[8,7- b ]吲哚的衍生化和诺环定的全合成证明了该策略的实用性。