5153-68-4

Usage

Uses

Used in Pharmaceutical Industry:
TRANS-4-METHYL-BETA-NITROSTYRENE is used as an organic intermediate for the synthesis of various pharmaceutical compounds. Its unique structure makes it a valuable component in the development of new drugs and medications.
Used in Chemical Synthesis:
TRANS-4-METHYL-BETA-NITROSTYRENE is used as a reagent in the synthesis of N-benzylpyrrolomorphinans, a class of compounds with potential applications in various fields. Its asymmetric Michael addition with benzaldehyde in the presence of silylated pyrrolidine catalyst has been reported, showcasing its versatility in chemical reactions.
Additionally, the hydrogenation of TRANS-4-METHYL-BETA-NITROSTYRENE in the presence of Pd(II) complexes of (Z)-2-((quinolin-3-ylimino)methyl)phenol as catalyst has been studied, further demonstrating its utility in chemical synthesis processes.

InChI:InChI=1/C9H9NO2/c1-8-2-4-9(5-3-8)6-7-10(11)12/h2-7H,1H3/b7-6+

Upstream product

• 75-52-5 nitromethane 
• 104-87-0 4-methyl-benzaldehyde 
• 135711-34-1 Butyl-(2-nitro-1-p-tolyl-ethyl)-amine 
• 7559-37-7 1-bromo-1-nitro-2-(4-tolyl)ethene 
• 622-97-9 1-ethenyl-4-methylbenzene 
• 123-08-0 4-hydroxy-benzaldehyde 
• 5736-88-9 p-butoxybenzaldehyde 
• 30669-07-9 4-methoxy-N-[(4-methylphenyl)methylidene]aniline 
• 3395-83-3 4-methylbenzaldehyde dimethylacetal 
• 1355229-73-0 5-(4-methylphenyl)-2-[1-(4-methylphenyl)-2-nitroethoxy]-1,2-oxazolidine-3,3-dicarbonitrile 
• 1866-39-3 4-methylcinnamic acid 
• 28691-43-2 1-(4-methylphenyl)-2-nitroethanol 
• 1866-39-3 trans-p-methylcinnamic acid 
• 104-84-7 para-methylbenzylamine 

Downstream Products

• 135711-34-1 Butyl-(2-nitro-1-p-tolyl-ethyl)-amine 
• 1384456-85-2 (R)-5-ethoxy-4-(2-nitro-1-(p-tolyl)ethyl)furan-3(2H)-one 
• 1448632-13-0 (2'R,3'S,4'S,5'S)-1-benzyl-4'-nitro-5'-phenyl-3'-(p-tolyl)spiro[indoline-3,2'-pyrrolidin]-2-one 
• 1609938-98-8 C₂₁H₁₇NO₄ 
• 1609939-04-9 C₂₂H₁₇NO₆ 
• 1616391-93-5 ethyl 2-p-tolylpyrrolo[1,2-a]quinoline-3-carboxylate 
• 1350971-13-9 (2R,3R,4S,5R)-methyl 4-nitro-5-phenyl-3-(p-tolyl)-pyrrolidine-2-carboxylate 

Relevant academic research and scientific papers

Green sustainable approach for carbon–carbon bond-forming reactions using FeNPs/DETA@rGO nano-catalyst

We have fabricated eccentric highly persuasive bifunctional FeNPs/DETA@rGO (where DETA = diethylenetriamine) nano-catalyst with a dual activation mechanism by presenting aliphatic amine on the basal and/or edges sites offering a base characteristic and Fe

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.

Skeletally Tunable Seven-Membered-Ring Fused Pyrroles

We describe a copper-mediated method that enables the synthesis of seven-membered-ring fused pyrroles (7-mrFPs). The protocol proceeds via an in situ spiro-intermediate ring expansion and tolerates a library of 7-mrFP derivatives with a broad range of functional groups in a simple step with tangible parameters and substrate adaptations. These rare 7-mrFPs are now accessible on a millimolar scale, and selected examples exhibit high antioxidant activity.

Active Base Hybrid Organosilica Materials based on Pyrrolidine Builder Units for Fine Chemicals Production

The catalytic activity of “pyrrolidine type” fragments included or anchored in the mesoporous silica supports or polymeric frameworks have been fully reported for enantioselective transformation. Nevertheless, low attention was focused on their catalytic abilities to perform base-catalyzed reaction. Accordingly, hybrid materials including pyrrolidine fragments in the mesoporous silica supports were prepared following different synthesis methods, such as micellar and fluoride sol-gel routes in absence of structural directing agents. Their great catalytic performance was explored for various base-catalyzed reactions to the formation of C?C bond through Knoevenagel, Claisen-Schmidt and Henry condensations under microwave irradiation. The benefits of microwave irradiation combined with suitable catalytic properties of pyrrolidine hybrid materials with strong base sites and high accessibility to active centers, allowed carrying out successfully base-catalyzed condensation reactions for the production of fine chemicals. Moreover, the hybrid catalyst exhibited high selectivity and good stability over different catalytic cycles contributing to environmental sustainability.

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.

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.

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.

One-pot and metal-free synthesis of 3-arylated-4-nitrophenols via polyfunctionalized cyclohexanones from β-nitrostyrenes

β-Nitrostyrenes underwent a Diels-Alder reaction with Danishefsky's diene to afford cyclohexenes together with the corresponding hydrolyzed products, 3-arylated-5-methoxy-4-nitrocyclohexanones. When the reaction was conducted in the presence of water, the cyclohexenes were efficiently hydrolyzed into cyclohexanones. Subsequent aromatization by heating the cyclohexanone with a catalytic amount of iodine in dimethyl sulfoxide gave 3-arylated-4-nitrophenols. The reaction of nitrostyrenes with Danishefsky's diene could be conducted in one pot to directly afford the corresponding nitrophenols. Moreover, a heteroaryl group, e.g., a thienyl group could be introduced into the nitrophenol framework.