5576-97-6

Usage

Uses

Used in Pharmaceutical Industry:
4-METHOXY-BETA-NITROSTYRENE is used as a Michael acceptor for the synthesis of proline-based chiral ionic liquid catalysts with two five-membered unsaturated aza-heterocycles. These catalysts are essential in the development of new pharmaceutical compounds and can improve the efficiency and selectivity of various chemical reactions.
Used in Material Science:
In the field of material science, 4-METHOXY-BETA-NITROSTYRENE acts as a guest molecule and forms co-crystal phases with the d-form of robust syndiotactic polystyrene (sPS). This application is crucial for the development of new materials with enhanced properties, such as improved mechanical strength, thermal stability, and chemical resistance.
General Description:
4-METHOXY-BETA-NITROSTYRENE participates in the Michael reaction on carbapenam intermediate, which is a significant chemical process in the synthesis of various pharmaceutical compounds. Its ability to act as a Michael acceptor makes it a valuable component in the development of new drugs and materials.

Upstream product

• 75-52-5 nitromethane 
• 123-11-5 4-methoxy-benzaldehyde 
• 110-58-7 n-Pentylamine 
• 943-89-5 (E)-3-(4-methoxyphenyl)acrylic acid 
• 2826-26-8 2-(4-methoxyphenylmethylene)malononitrile 
• 1133396-07-2 2-(1-(4-methoxyphenyl)-2-nitroethyl)malononitrile 
• 123-08-0 4-hydroxy-benzaldehyde 
• 38316-05-1 1-(4-methoxy-phenyl)-2-nitro-ethanol 
• 2393-23-9 4-methoxy-benzylamine 
• 24393-56-4 ethyl (E)-3-(4-methoxyphenyl)prop-2-enoate 
• 5153-67-3 nitrostyrene 
• 1309664-93-4 C₃₂H₄₀N₂O₄Si 
• 637-69-4 4-Methoxystyrene 
• 830-09-1 3-(4'-methoxyphenyl)propenoic acid 

Downstream Products

• 52809-71-9 (1-(4-methoxyphenyl)-2-nitroethyl) phenyl sulfide 
• 139032-03-4 2-(4-methoxyphenyl)-2-(pyrid-3-yloxy)-1-nitroethane 
• 95834-32-5 6-Hydrazino-5-[1-(4-methoxy-phenyl)-2-nitro-ethyl]-1,3-dimethyl-1H-pyrimidine-2,4-dione 
• 95834-28-9 6-Hydroxyamino-5-[1-(4-methoxy-phenyl)-2-nitro-ethyl]-1,3-dimethyl-1H-pyrimidine-2,4-dione 
• 99391-20-5 u,l-4a,5,6,7,8,8a-hexahydro-4-(4-methoxyphenyl)-8a-<(trimethylsilyl)oxy>-4H-1,2-benzoxazine-2-oxide 
• 99391-20-5 l,l-4a,5,6,7,8,8a-hexahydro-4-(4-methoxyphenyl)-8a-<(trimethylsilyl)oxy>-4H-1,2-benzoxazine-2-oxide 
• 99391-20-5 u,u-4a,5,6,7,8,8a-hexahydro-4-(4-methoxyphenyl)-8a-<(trimethylsilyl)oxy>-4H-1,2-benzoxazine-2-oxide 
• 142076-19-5 1-((Z)-4-Benzenesulfonyl-3-methyl-1-nitromethyl-but-3-enyl)-4-methoxy-benzene 
• 142076-10-6 1-((E)-4-Benzenesulfonyl-3-methyl-1-nitromethyl-but-3-enyl)-4-methoxy-benzene 
• 128639-80-5 (2R,3S,4R)-6-phenyl-2-p-methoxyphenyl-3,4-dihydro-4-dimethylamino-3-nitro-2H-thiopyran 
• 128639-94-1 (2R,3S,4S)-2-p-methoxyphenyl-4-anilino-3-nitro-6-phenyl-3,4-dihydro-2H-thiopyran 
• 128639-74-7 (2R,3S,4R)-6-p-methylphenyl-2-p-methoxyphenyl-3,4-dihydro-4-dimethylamino-3-nitro-2H-thiopyran 
• 128639-77-0 (2R,3S,4R)-6-p-chlorophenyl-2-p-methoxyphenyl-3,4-dihydro-4-dimethylamino-3-nitro-2H-thiopyran 
• 128639-95-2 (2R,3S,4S)-2-p-methoxyphenyl-4-p-chlorophenyl-3-nitro-6-phenyl-3,4-dihydro-2H-thiopyran 

Relevant academic research and scientific papers

Soluble guanylate cyclase stimulator, trans-4-methoxy-β-nitrostyrene, has a beneficial effect in monocrotaline-induced pulmonary arterial hypertension in rats

The soluble guanylate cyclase (sGC)/GMPc pathway plays an important role in controlling pulmonary arterial hypertension (PAH). We investigated whether the novel sGC stimulator trans-4-methoxy-β-nitrostyrene (T4MN), ameliorates monocrotaline (MCT)-induced

Metal-Free Deoxygenation of Chiral Nitroalkanes: An Easy Entry to α-Substituted Enantiomerically Enriched Nitriles

A metal-free, mild and chemodivergent transformation involving nitroalkanes has been developed. Under optimized reaction conditions, in the presence of trichlorosilane and a tertiary amine, aliphatic nitroalkanes were selectively converted into amines or nitriles. Furthermore, when chiral β-substituted nitro compounds were reacted, the stereochemical integrity of the stereocenter was maintained and α-functionalized nitriles were obtained with no loss of enantiomeric excess. The methodology was successfully applied to the synthesis of chiral β-cyano esters, α-aryl alkylnitriles, and TBS-protected cyanohydrins, including direct precursors of four active pharmaceutical ingredients (ibuprofen, tembamide, aegeline and denopamine).

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.

Dipolar HCP materials as alternatives to DMF solvent for azide-based synthesis

Hypercrosslinked polymers HCP-DMF and HCP-DMF-SO3H containing abundant and flexible DMF moieties were designed and synthesized. Benefitting from the solvation microenvironment provided by the pseudo-DMF moities, the polar HCPs manifested outstanding performances in the conversions of NaN3 to benzylic azides and 1,2,3-triazoles in EtOH (95%), respectively, avoiding the use of risky DMF and improving the separation processes of the products.

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.

Molecular Engineering of β-Substituted Oxoporphyrinogens for Hydrogen-Bond Donor Catalysis

A new class of bifunctional hydrogen-bond donor organocatalyst using oxoporphyrinogens having increased intramolecular hydrogen-bond donor distances is reported. Oxoporphyrinogens are highly non-planar rigid macrocycles containing a multiple hydrogen bond-forming binding site. In this work, we describe the first example of non-planar OxPs as hydrogen-bond donor catalysts prepared using a molecular engineering approach of the binding site for dual activation of substrates. The introduction of β-substituents is key to the catalytic activity and the catalysts are able to catalyze 1,4-conjugate additions and sulfa-Michael additions, as well as, Henry and aza-Henry reactions at low catalyst loadings (≤ 1 mol-%) under mild conditions. Preliminary mechanistic studies have been carried out and a possible reaction mechanism has been proposed based on the bi-functional activation of both substrates through hydrogen-bonding interactions.

Biological evaluation and SAR analysis of novel covalent inhibitors against fructose-1,6-bisphosphatase

Fructose-1,6-bisphosphatase (FBPase) is an attractive target for affecting the GNG pathway. In our previous study, the C128 site of FBPase has been identified as a new allosteric site, where several nitrovinyl compounds can bind to inhibit FBPase activity. Herein, a series of nitrostyrene derivatives were further synthesized, and their inhibitory activities against FBPase were investigated in vitro. Most of the prepared nitrostyrene compounds exhibit potent FBPase inhibition (IC50 3, CF3, OH, COOH, or 2-nitrovinyl were installed at the R2 (meta-) position of the benzene ring, the FBPase inhibitory activities of the resulting compounds increased 4.5–55 folds compared to those compounds with the same groups at the R1 (para-) position. In addition, the preferred substituents at the R3 position were Cl or Br, thus compound HS36 exhibited the most potent inhibitory activity (IC50 = 0.15 μM). The molecular docking and site-directed mutation suggest that C128 and N125 are essential for the binding of HS36 and FBPase, which is consistent with the C128-N125-S123 allosteric inhibition mechanism. The reaction enthalpy calculations show that the order of the reactions of compounds with thiol groups at the R3 position is Cl > H > CH3. CoMSIA analysis is consistent with our proposed binding mode. The effect of compounds HS12 and HS36 on glucose production in primary mouse hepatocytes were further evaluated, showing that the inhibition was 71% and 41% at 100 μM, respectively.

Asymmetric synthesis of tetrahydropyran[3,2-c]quinolinones via an organocatalyzed formal [3 + 3] annulation of quinolinones and MBH 2-naphthoates of nitroolefin

An efficient asymmetric and enantio-swithchable organocatalytic [3 + 3] annulation reaction using MBH-2-naphthoates of nitroalkenes and 4-hydroxyquinolin-2(1H)-ones has been developed. Densely substituted tetrahydropyrano[3,2-c]quinolinones scaffolds with two adjacent stereogenic centers are obtained with high yield (up to 95% yield) and good stereoselectivities (up to >20:1 dr and 96% ee) in an enantio-switchable manner. Furthermore, gram scale synthesis was achieved and the nitro group could easily transform into an amino group without any appreciable loss in the diastereo- and enantioselectivity.

A photocatalyst-free photo-induced denitroalkylation of β-nitrostyrenes with 4-alkyl substituted Hantzsch esters at room temperature

A photocatalyst-free stereoselectively photo-induced strategy for the denitroalkylation of β-nitrostyrenes using 4-alkyl substituted Hantzsch esters as the alkyl source under xenon lamp irradiation is developed. The reaction proceeds at room temperature and affords the corresponding products in moderate to excellent yields. The oxidant di-t-butyl peroxide serves as an efficient radical initiator under irradiation of a Xenon lamp, initiating alkyl radicals from the 4-alkyl substituted Hantzsch esters.