5153-69-5

Usage

Uses

Used in Pharmaceutical Industry:
Trans-4-fluoro-beta-nitrostyrene is used as a key intermediate in the enantioselective synthesis of cyclohexenol derivatives. These derivatives are important building blocks for the development of pharmaceutical compounds, particularly those targeting various diseases and conditions. The enantioselective synthesis allows for the creation of chiral molecules with specific configurations, which can have significant implications for the efficacy and safety of the resulting drugs.
Used in Chemical Synthesis:
In the field of chemical synthesis, trans-4-fluoro-beta-nitrostyrene serves as a valuable precursor for the production of various organic compounds. Its unique structure allows for a range of reactions, including addition, substitution, and rearrangement, making it a versatile component in the synthesis of complex molecules.
Used in Material Science:
The unique properties of trans-4-fluoro-beta-nitrostyrene also make it a candidate for the development of new materials with specific characteristics. For example, its fluorine-containing structure may contribute to enhanced chemical stability, thermal resistance, or other desirable properties in the resulting materials.

InChI:InChI=1/C8H6FNO2/c9-8-3-1-7(2-4-8)5-6-10(11)12/h1-6H/b6-5+

Upstream product

• 75-52-5 nitromethane 
• 459-57-4 4-fluorobenzaldehyde 
• 135711-36-3 Butyl-[1-(4-fluoro-phenyl)-2-nitro-ethyl]-amine 
• 5676-81-3 4-fluorobenzalaniline 
• 405-99-2 para-fluorostyrene 
• 140-75-0 para-fluorobenzylamine 
• 67-56-1 methanol 
• 79-24-3 Nitroethane 
• 462-06-6 fluorobenzene 
• 459-32-5 (E)-4-fluorocinnamic acid 
• 459-32-5 4-fluorocinnamic acid 

Downstream Products

• 92774-81-7 2-[1-(4-Fluoro-phenyl)-2-nitro-ethyl]-3-hydroxy-cyclopent-2-enone 
• 124401-37-2 N,N-bis<3-(4-fluorophenyl)-4-(methoxycarbonyl)-5-methyl-2,3-dihydrofuran-2-yl>hydroxylamine 
• 124401-50-9 ethyl 1,2-diisopropyl-4-(4-fluorophenyl)-1H-pyrrole-3-carboxylate 
• 135711-36-3 Butyl-[1-(4-fluoro-phenyl)-2-nitro-ethyl]-amine 
• 77484-26-5 chloro-3 fluoro-6 indolinone-2 
• 77484-36-7 acide N-acetyl chloro-2 (p.fluorophenyl)-2 acetohydroxamique 
• 77484-46-9 chlorure de l'acide N-acetoxy chloro-2 (p.fluorophenyl)-2 acetohydroximique 
• 4137-46-6 1-Chlor-2,2-bis-<4-fluor-phenyl>-1-oximino-aethan 
• 37709-91-4 3-(4-Fluoro-phenyl)-4-nitro-2-(triphenyl-λ⁵-phosphanylidene)-butyric acid ethyl ester 
• 4099-59-6 1-Chlor-2-<4-fluor-phenyl>-1-oximino-2-phenyl-aethan 
• 1537-28-6 2,2-Bis-<2-nitro-1-(4-fluor-phenyl)-ethyl>-indandion-(1,3) 
• 123494-30-4 1-[(E)-(but-1-en-1-yl)]-4-fluorobenzene 
• 917472-96-9 4-(4-Fluoro-phenyl)-7-(3-piperidin-1-yl-propoxy)-1,2,3,4-tetrahydro-[2,6]naphthyridine 
• 833-18-1 3-(4-Fluorophenyl)succinic acid 

Relevant academic research and scientific papers

A robust heterogeneous Co-MOF catalyst in azide-alkyne cycloaddition and Friedel-Crafts reactions as well as hydrosilylation of alkynes

Organic reactions using metal-organic frameworks (MOFs) as catalysts are promising with regard to their environmentally friendly features and potential catalyst recyclability. A robust Co(ii)-MOF {[Co2(l-mac)(4,4-bpt)(H2O)]·3.5H2O}n (1) and its enantiomer {[Co2(d-mac)(4,4-bpt)(H2O)]·3.5H2O}n (2) (l/d-mac = basic forms of l/d-malic acid, 4,4-Hbpt = 3,5-di(pyridin-4-yl)-4H-1,2,4-triazole) have been gram-scale prepared under solvothermal conditions. Structural analysis reveals that mac manages Co(ii) ions to form 1-D chains, which are further extended via 4,4-bpt connectors into a noninterpenetrating 3D framework architecture. It was found that 1 can be as a heterogeneous catalyst for multiple organic reactions, such as azide-alkyne cycloaddition and Friedel-Crafts reactions with good isolated yields and good recycle runs (at least five times without substantial degradation). Additionally, 1 can promote hydrosilylation of alkynes under harsh conditions with moderate yield. This journal is

Rationalizing the Unprecedented Stereochemistry of an Enzymatic Nitrile Synthesis through a Combined Computational and Experimental Approach

In this contribution, the unique and unprecedented stereochemical phenomenon of an aldoxime dehydratase-catalyzed enantioselective dehydration of racemic E- and Z-aldoximes with selective formation of both enantiomeric forms of a chiral nitrile is rationalized by means of molecular modelling, comprising in silico mutations and docking studies. This theoretical investigation gave detailed insight into why with the same enzyme the use of racemic E- and Z-aldoximes leads to opposite forms of the chiral nitrile. The calculated mutants with a larger or smaller cavity in the active site were then prepared and used in biotransformations, showing the theoretically predicted decrease and increase of the enantioselectivities in these nitrile syntheses. This validated model also enabled the rational design of mutants with a smaller cavity, which gave superior enantioselectivities compared to the known wild-type enzyme, with excellent E-values of up to E>200 when the mutant OxdRE-Leu145Phe was utilized.

Catalytic Asymmetric Construction of Tertiary Carbon Centers Featuring an α-Difluoromethyl Group with CF2H-CH2-NH2as the "building Block"

We report here for the first time a novel difluoromethylated ketimine building block condensed by thioisatin and difluoroethylamine, offering efficient access to a broad range of enantioenriched products bearing difluoroethylamine units (27 examples, ≤98% yield, >99% ee) in the presence of quinine-derived squaramide. Further transformation of the intermediate would generate a variety of versatile functional blocks like α-difluoromethyl amines, β-amino acid, and β-diamine with retention of the enantiomeric excess at the difluoromethyl-bound carbon.

Organocatalytic Asymmetric Synthesis of Aza-Spirooxindoles via Michael/Friedel-Crafts Cascade Reaction of 1,3-Nitroenynes and 3-Pyrrolyloxindoles

An asymmetric [3+3] cyclization of nitroenynes and 3-pyrrolyloxindoles has been realized with a chiral bifunctional squaramide catalyst. This Michael/Friedel-Crafts cascade strategy provides a facile and efficient access to enantioenriched polycyclic aza-spirooxindoles with 32-95% isolated yields and excellent stereocontrol under mild reaction conditions.

Four-Step Domino Reaction Enables Fully Controlled Non-Statistical Synthesis of Hexaarylbenzene with Six Different Aryl Groups**

Hexaarylbenzene (HAB) derivatives are versatile aromatic systems playing a significant role as chromophores, liquid crystalline materials, molecular receptors, molecular-scale devices, organic light-emitting diodes and candidates for organic electronics. Statistical synthesis of simple symmetrical HABs is known via cyclotrimerization or Diels–Alder reactions. By contrast, the synthesis of more complex, asymmetrical systems, and without involvement of statistical steps, remains an unsolved problem. Here we present a generally applicable synthetic strategy to access asymmetrical HAB via an atom-economical and high-yielding metal-free four-step domino reaction using nitrostyrenes and α,α-dicyanoolefins as easily available starting materials. Resulting domino product—functionalized triarylbenzene (TAB)—can be used as a key starting compound to furnish asymmetrically substituted hexaarylbenzenes in high overall yield and without involvement of statistical steps. This straightforward domino process represents a distinct approach to create diverse and still unexplored HAB scaffolds, containing six different aromatic rings around central benzene core.

Exploiting the chiral ligands of bis(Imidazolinyl)-and bis(oxazolinyl)thiophenes—Synthesis and application in Cu-catalyzed friedel–crafts asymmetric alkylation

Five new C2-symmetric chiral ligands of 2,5-bis(imidazolinyl)thiophene (L1–L3) and 2,5-bis(oxazolinyl)thiophene (L4 and L5) were synthesized from thiophene-2,5-dicarboxylic acid (1) with enantiopure amino alcohols (4a–c) in excellent optical purity and chemical yield. The util-ity of these new chiral ligands for Friedel–Crafts asymmetric alkylation was explored. Subse-quently, the optimized tridentate ligand L5 and Cu(OTf)2 catalyst (15 mol%) in toluene for 48 h promoted Friedel–Crafts asymmetric alkylation in moderate to good yields (up to 76%) and with good enantioselectivity (up to 81% ee). The bis(oxazolinyl)thiophene ligands were more potent than bis(imidazolinyl)thiophene analogues for the asymmetric induction of the Friedel–Crafts asymmetric alkylation.

A noncovalent hybrid of [Pd(phen)(OAc)2] and st-DNA for the enantioselective hydroamination of β-nitrostyrene with methoxyamine

We developed a novel Pd-catalysed enantioselective synthesis of C-N bonds using the chiral scaffold of DNA. The non-covalently linked [Pd(phen)(OAc)2] with st-DNA catalysed the Markonicov hydroamination of β-nitrostyrene with methoxyamine for the first time with >75% enantiomeric excess (ee) in an aqueous buffer (pH 7.4) at room temperature.

tert-Butyl Nitrite Mediated Nitro-Nitratosation of Internal Alkenes

In an oxygen atmosphere tert-butyl nitrite (TBN) reacts with unsymmetrical internal benzylic alkenes giving nitro-nitratosation product exclusively. The γ-diaryl-substituted styrenes provided better yields compared to γ-alkyl-aryl-substituted styrenes. The higher yields for the former type of substrates is possibly dictated by the additional stability of benzylic radical due to the anchimeric assistance imparted by the γ-substituted phenyl ring. During oxidative nitration, the nitro (NO2) group adds at the non-benzylic site, whereas the nitrato group (ONO2) is attached at the relatively stable benzylic position. Under similar reaction conditions, α,β-unsaturated carboxylic acids, afforded nitroalkenes as the sole product.

Preparation method of beta-trans-nitroolefin

The invention relates to a preparation method of beta-trans-nitroolefin. The method comprises: sequentially adding an olefin compound, a nitration reagent and a solvent into a reaction container, mixing the substances uniformly, and carrying out constant temperature reaction for 18h under an illumination condition to obtain a reaction solution; and sequentially carrying out drying, concentration and column chromatography treatment on the reaction solution to obtain the beta-trans-nitroolefin compound. The method is simple and practicable, low in cost and high in product yield, can realize large-scale production, and has good industrial application prospects in the aspects of functional organic material, bioactive compound and drug synthesis.