18315-84-9

Usage

Uses

Used in Pharmaceutical Synthesis:
(E)-1-Phenyl-2-nitro-1-propene is utilized as a key intermediate in the synthesis of a wide range of pharmaceuticals. Its unique chemical structure allows for the creation of various medicinal compounds, contributing to the development of new treatments and therapies.
Used in Organic Chemical Reactions:
As a reactive compound, (E)-1-Phenyl-2-nitro-1-propene is employed in numerous organic chemical reactions, facilitating the formation of complex molecules and structures. Its versatility in these reactions makes it a valuable tool in the field of organic chemistry.
Used in Dye and Perfume Production:
(E)-1-Phenyl-2-nitro-1-propene serves as a precursor in the production of dyes and perfumes, where its chemical properties are harnessed to create a variety of colors and fragrances. This application highlights its importance in the chemical industry and the creation of consumer products.
Used in Biological and Pharmacological Research:
The potential biological and pharmacological activities of (E)-1-Phenyl-2-nitro-1-propene have made it a subject of interest for researchers. It is used in the study of various biological processes and the development of new drugs, further expanding its utility in the scientific community.

Upstream product

• 79-24-3 Nitroethane 
• 1077-18-5 N-benzylidenebutan-1-amine 
• 66618-80-2 acetic acid-((1RS,2RS)-2-nitro-1-phenyl-propyl ester) 
• 100-52-7 benzaldehyde 
• 766-90-5 cis-1-phenyl-1-propylene 
• 637-50-3 1-phenylpropene 
• 26251-08-1 2-nitro-1-phenylpropan-1-ol 
• 75-52-5 nitromethane 
• 98-86-2 acetophenone 
• 873-66-5 1-propenylbenzene 
• 1895-97-2 2-methyl-3-phenylacrylic acid 
• 100-51-6 benzyl alcohol 
• 60593-26-2 (1-nitroethyl)-phosphonic acid diethyl ester 
• 66618-80-2 1-phenyl-2-nitro-1-propanol acetate 

Downstream Products

• 408314-96-5 5-methyl-5-nitro-4-phenyl-4,5-dihydro-1H-pyrazole 
• 28612-58-0 4-((1RS,2SR)-2-nitro-1-phenyl-propyl)-morpholine 
• 28612-58-0 4-((1RS,2RS)-2-nitro-phenyl-propyl)-morpholine 
• 93159-92-3 (2-oxo-1-phenyl-propyl)-malonic acid diethyl ester 
• 546103-01-9 2-acetyl-4-nitro-3-phenyl-valeric acid ethyl ester 
• 92851-01-9 (2-nitro-1-phenyl-propyl)-phenyl sulfide 
• 83465-97-8 (4R,4aS,7aS)-3-Methyl-4-phenyl-7a-piperidin-1-yl-4,4a,5,6,7,7a-hexahydro-cyclopenta[e][1,2]oxazine 2-oxide 
• 83465-96-7 (4R,4aS,8aS)-3-Methyl-4-phenyl-8a-piperidin-1-yl-4a,5,6,7,8,8a-hexahydro-4H-benzo[e][1,2]oxazine 2-oxide 
• 28612-51-3 (4R,4aS,8aS)-3-Methyl-4-phenyl-8a-pyrrolidin-1-yl-4a,5,6,7,8,8a-hexahydro-4H-benzo[e][1,2]oxazine 2-oxide 
• 28557-75-7 (4R,4aS,7aS)-3-Methyl-7a-morpholin-4-yl-4-phenyl-4,4a,5,6,7,7a-hexahydro-cyclopenta[e][1,2]oxazine 2-oxide 
• 28612-50-2 (4R,4aS,8aS)-3-Methyl-8a-morpholin-4-yl-4-phenyl-4a,5,6,7,8,8a-hexahydro-4H-benzo[e][1,2]oxazine 2-oxide 
• 98-87-3 benzylidene dichloride 
• 100-52-7 benzaldehyde 
• 90-02-8 salicylaldehyde 

Relevant academic research and scientific papers

Microwave-Assisted Henry Reaction: Solventless Synthesis of Conjugated Nitroalkenes

In a solventless system and under microwave irradiation, nitroalkanes react with arylaldehydes in the presence of a catalytic amount of ammonium acetate to afford, in one step, conjugated nitroalkenes without the isolation of intermediary β-nitro alcohols. - Key Words: Arylaldehydes; Nitroalkanes; Ammonium acetate; Conjugated nitroalkenes; Henry reaction; Microwave irradiation

Solvent-free nucleophilic addition of N-alkylhydroxylamines to substituted nitroolefins: Formation of nitrones by a tandem process

Nucleophilic addition of 1-methyl-2-arylethylhydroxylamine to substituted β-nitrostyrene under solvent-free conditions has led to unexpected nitrones via a tandem process involving 1,4-addition and elimination. Copyright Taylor & Francis Group, LLC.

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.

A Deprotonation Approach to the Unprecedented Amino-Trimethylenemethane Chemistry: Regio-, Diastereo-, and Enantioselective Synthesis of Complex Amino Cycles

The first realization of the amino-trimethylenemethane chemistry is reported using a deprotonation strategy to simplify the synthesis of the amino-trimethylenemethane donor in two steps from commercial and inexpensive materials. A broad scope of cycloaddition acceptors (seven different classes) participated in the chemistry, chemo-, regio-, diastereo-, and enantioselectively generating various types of highly valuable complex amino cycles. Multiple derivatization reactions that further elaborated the initial amino cycles were performed without isolation of the crude product. Ultimately, we applied the amino-trimethylenemethane chemistry to synthesize a potential pharmaceutical in 8 linear steps and 7.5 % overall yield, which previously was achieved in 18 linear steps and 0.6 % overall yield.

Catalyst- and Substituent-Controlled Switching of Chemoselectivity for the Enantioselective Synthesis of Fully Substituted Cyclobutane Derivatives via 2 + 2 Annulation of Vinylogous Ketone Enolates and Nitroalkene

The first regioselective, diastereoselective, and enantioselective organocatalyzed Michael-Michael cascade of vinylogous ketone enolates and nitroalkenes for the construction of fully substituted cyclobutanes is achieved by the deployment of the appropriate chiral squaramide catalyst and the pertinent substituent on the substrate. The domino reaction provided cyclobutanes with four contiguous stereocenters, including a quaternary center in good yields with diastereomeric ratio of >20:1 and with enantioselectivities of mostly up to 98% enantiomeric excess (ee). The structures and the absolute configurations of the adducts were confirmed by single-crystal X-ray crystallographic analyses of the appropriate products.

Synthesis, antiproliferative and pro-apoptotic effects of nitrostyrenes and related compounds in Burkitt’s lymphoma

Background: Cancers of the lymphatic cells (lymphomas) account for approximately 12% of malignant diseases worldwide. The nitrostyrene scaffold is identified as a lead target structure for the development of particularly effective compounds targeting Burkitt’s lymphoma (BL). Objectives: The aims of the curent study were to synthesise a panel of nitrostyrene compounds and to evaluate their activity in Burkitt’s lymphoma (BL). Methods: A panel of structurally varied compounds were designed and synthesised using Henry Knoevenagel condensation reactions. Single crystal X-Ray analysis confirmed the E configuration for six examples of these novel structures. A number of nitrostyrene-related compounds were also investigated including 1,3-bis(aryl)-2-nitropropenes together with heterocyclic scaffolds containing the nitrovinyl pharmacophore such as 3-nitro-2-phenyl-2H-chromenes. The antiproliferative activities of the compounds were evaluated using the BL cell lines EBV- MUTU-1 and EBV+ DG-75 (chemoresistant) to establish preliminary structure-activity relationships. Results: Lead compounds with optimized nitrostyrene scaffolds and 3-nitro-2-phenyl-2Hchromene structures were successfully established with typical IC50 values of 0.45 μM and 0.47 μM in MUTU-1 cells and 1.41 μM and 1.92 μM, respectively, in DG-75 cells. The mechanism of cell death was identified as apoptotic and the lead compound was found to elicit comparable apoptotic effects to Taxol in Burkitt’s lymphoma cell lines MUTU-1 and DG-75. Conclusion: This class of pharmaceutically active compounds with potential for the treatment of Burkitt’s lymphoma suggest a potential role for nitrostyrene based agents in chemotherapy.

Electronic effect of substituents on anilines favors 1,4-addition to: Trans -β-nitrostyrenes: Access to N -substituted 3-arylindoles and 3-arylindoles

A simple and an efficient method for the regioselective synthesis of N-alkyl/aryl/H 3-arylindole derivatives from N-substituted anilines and trans-β-nitrostyrenes has been described using 10 mol% of bismuth(iii) triflate as a catalyst in acetonitrile at 80 °C. The present protocol profits from the formation of new C-C and C-N bonds, broad substrate scope and moderate to good yields.

In order to iodide is one pot synthesis nitryl source α, β - unsaturated nitro olefin derivatives (by machine translation)

The present invention discloses a one-pot synthesis nitryl source iodide is α, β - unsaturated nitro olefin derivatives, vinyl compounds containing four aryl ferrous (III), iodide and tertiary-butyl hydrogen peroxide in acetonitrile solution system a pot of reaction, generating α, β - unsaturated nitro olefin derivatives; the method to achieve the under mild reaction conditions, high yield with high stereo selectivity of the E synthesis of α, β - unsaturated nitro olefin. (by machine translation)

Α, β - unsaturated nitro olefin derivative synthesis method (by machine translation)

The invention discloses a α, β - unsaturated nitro olefin derivative synthesis method, vinyl compounds containing four aryl ferrous (III), ammonium halide and tertiary-butyl hydrogen peroxide in the system of the one-pot reaction, generating α, β - unsaturated nitro olefin derivatives; the method to achieve the under mild reaction conditions, high yield with high stereo selectivity of the E synthesis of α, β - unsaturated nitro olefin. (by machine translation)

Catalytic asymmetric Tamura cycloadditions involving nitroalkenes

The first examples of asymmetric Tamura cycloaddition reactions involving singly activated alkenes are reported. Homophthalic anhydride reacts with α-methyl nitrosytrenes in the presence of an alkaloid-based catalyst to generate fused bicyclic aromatic ketone products with three new stereocentres (which are susceptible to subsequent equilibration) in 12-99% ee. An unusual equilibration process which occurs in methanolic medium in the absence of a recognisable base via proton transfer at the α-carbon of an ester was investigated experimentally and computationally.