(E)-5-fluoro-3-(2-nitroethenyl)-1H-indole | 214417-26-2

• 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: (E)-5-fluoro-3-(2-nitroethenyl)-1H-indole
• 英文别名: (Ε)-5-fluoro-3-(2-nitroethenyl)-1Η-indole；5-fluoro-3-((E)-2-nitrovinyl)-1H-indole；5-Fluoro-3-(2-nitrovinyl)indole；5-fluoro-3-[(E)-2-nitroethenyl]-1H-indole
• CAS: 214417-26-2
• 化学式: C₁₀H₇FN₂O₂
• 分子量: 206.176
• InChiKey: RFGJWSVNMVSDEH-ONEGZZNKSA-N

物化性质

• 熔点：
  158-160 °C (decomp)
• 沸点：
  409.1±30.0 °C(Predicted)
• 密度：
  1.438±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  15
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  61.6
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (E)-5-fluoro-3-(2-nitroethenyl)-1H-indole 在 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 为溶剂， 以76%的产率得到5-氟色胺
  参考文献：
  名称：

  Enantioselective Brønsted Acid-Catalyzed N-Acyliminium Cyclization Cascades

  摘要：

  An enantioselective Bronsted acid-catalyzed N-acyliminium cyclization cascade of tryptamines with enol lactones to form architecturally complex heterocycles in high enantiomeric excess has been developed. The reaction is technically simple to perform as well as atom-efficient and may be coupled to a gold(1)-catalyzed cycloisomerization of alkynoic acids whereby the key enol lactone reaction partner is generated in situ. Employing up to 10 mol% bulky chiral phosphoric acid catalysts in boiling toluene allowed the product materials to be generated in good overall yields (63-99%) and high enantioselectivities (72-99% ee). With doubly substituted enol lactones, high diastereo- and enantioselectivities were obtained, thus providing a new example of a dynamic kinetic asymmetric cyclization reaction.

  DOI：

  10.1021/ja9024885
• 作为产物：
  描述：

  5-氟吲哚 在 乙酸铵 、 三氯氧磷 作用下， 反应 2.25h， 生成 (E)-5-fluoro-3-(2-nitroethenyl)-1H-indole
  参考文献：
  名称：

  Spadoni, Gilberto; Balsamini, Cesarino; Bedini, Annalida, Medicinal Chemistry Research, 1998, vol. 8, # 9, p. 487 - 498

  摘要：

  DOI：

文献信息

• Chiral Bis‐phosphate Macrocycles for Catalytic, Efficient, and Enantioselective Electrophilic Fluorination
  作者：Lie‐Wei Zhang、Xu‐Dong Wang、Yu‐Fei Ao、De‐Xian Wang、Qi‐Qiang Wang

  DOI：10.1002/chem.202400498

  日期：2024.4.25

  Bis-phosphate macrocycles have been designed with an integrated chiral cavity and two cooperative phosphate sites for accommodating DABCO dications through complementary ion-pair interactions. Only 2 mol% of the macrocycle was necessary for efficiently catalyzing the fluorocyclization of tryptamines in up to 91 % ee, thus significantly outperforming the acyclic counterparts (lower reactivity; <20 %

  双磷酸大环化合物被设计为具有集成的手性空腔和两个协作磷酸位点，用于通过互补离子对相互作用容纳 DABCO 双阳离子。只需 2 mol% 的大环即可有效催化高达 91% ee 的色胺氟环化，因此显着优于无环对应物（较低的反应性；<20% ee）。
• Melatonin Receptor Ligands:  Synthesis of New Melatonin Derivatives and Comprehensive Comparative Molecular Field Analysis (CoMFA) Study
  作者：Marco Mor、Silvia Rivara、Claudia Silva、Fabrizio Bordi、Pier Vincenzo Plazzi、Gilberto Spadoni、Giuseppe Diamantini、Cesarino Balsamini、Giorgio Tarzia、Franco Fraschini、Valeria Lucini、Romolo Nonno、Bojidar Michaylov Stankov

  DOI：10.1021/jm9810093

  日期：1998.9.1

  The CoMFA methodology was applied to melatonin receptor ligands in order to establish quantitative structure-affinity relationships. One hundred thirty-three compounds were considered: they were either collected from literature or newly synthesized in order to gain information about the less explored positions. To this end, various melatonin derivatives were prepared and their affinity for quail optic tecta melatonin receptor was tested. Compounds were aligned on the putative active conformation of melatonin proposed by our previously reported pharmacophore search, and their relative affinities were calculated from the displacement of 2-[I-125]-iodomelatonin on different tissues expressing aMT receptors. Compounds were grouped into three sets according to their topology. Subset A: melatonin-like compounds; subset B: N-acyl-2-amino-8-methoxytetralins and related compounds; subset C: N-acyl-phenylalkylamines and related compounds. CoMFA models were derived for each set, using the steric, electrostatic, and lipophilic fields as structural descriptors; the PLS analyses were characterized by good statistical parameters, taking into account the heterogeneity of the binding data, obtained with different experimental protocols. From the CoMFA model for the melatonin-like compounds, besides the well-known positive effect of 2-substitution, a low steric tolerance for substituents in 1, 6, and 7, and a negative effect of electron-rich 4-substituents were observed; the information provided by the newly synthesized compounds was essential for these results. Moreover, a comprehensive model for the 133 compounds, accounting for a common alignment and a common mode of interaction at the melatonin receptor, was derived (Q(2) = 0.769, R-2 = 0.905). This model validates our previously reported pharmacophore search and offers a clear depiction of the structure-affinity relationships for the melatonin receptor ligands.
• Diastereoselective Three-Component 1,3-Dipolar Cycloaddition to Access Functionalized β-Tetrahydrocarboline- and Tetrahydroisoquinoline-Fused Spirooxindoles
  作者：Yongchao Wang、Yu Chen、Shengli Duan、Yiyang Cao、Wenjin Sun、Mei Zhang、Delin Zhao、Donghua Hu、Jianwei Dong

  DOI：10.3390/molecules29081790

  日期：——

  A chemselective catalyst-free three-component 1,3-dipolar cycloaddition has been described. The unique polycyclic THPI and THIQs were creatively employed as dipolarophiles, which led to the formation of functionalized β-tetrahydrocarboline- and tetrahydroisoquinoline-fused spirooxindoles in 60–94% of yields with excellent diastereoselectivities (10: 1−>99: 1 dr). This reaction not only realizes a concise THPI- or THIQs-based 1,3-dipolar cycloaddition, but also provides a practical strategy for the construction of two distinctive spirooxindole skeletons.
• Enantioselective Brønsted Acid-Catalyzed <i>N</i>-Acyliminium Cyclization Cascades
  作者：Michael E. Muratore、Chloe A. Holloway、Adam W. Pilling、R. Ian Storer、Graham Trevitt、Darren J. Dixon

  DOI：10.1021/ja9024885

  日期：2009.8.12

  An enantioselective Bronsted acid-catalyzed N-acyliminium cyclization cascade of tryptamines with enol lactones to form architecturally complex heterocycles in high enantiomeric excess has been developed. The reaction is technically simple to perform as well as atom-efficient and may be coupled to a gold(1)-catalyzed cycloisomerization of alkynoic acids whereby the key enol lactone reaction partner is generated in situ. Employing up to 10 mol% bulky chiral phosphoric acid catalysts in boiling toluene allowed the product materials to be generated in good overall yields (63-99%) and high enantioselectivities (72-99% ee). With doubly substituted enol lactones, high diastereo- and enantioselectivities were obtained, thus providing a new example of a dynamic kinetic asymmetric cyclization reaction.
• Spadoni, Gilberto; Balsamini, Cesarino; Bedini, Annalida, Medicinal Chemistry Research, 1998, vol. 8, # 9, p. 487 - 498
  作者：Spadoni, Gilberto、Balsamini, Cesarino、Bedini, Annalida、Carey, Aedin、Diamantini, Giuseppe、Di Giacomo, Barbara、Tontini, Andrea、Tarzia, Giorgio、Nonno, Romolo、Lucini, Valeria、Pannacci, Marilou、Michaylov Stankov, Bojidar、Fraschini, Franco

  DOI：——

  日期：——