5670-65-5

Usage

Uses

Used in Organic Synthesis:
(Z)-1-Nitro-2-phenyl-1-propene is utilized as a key intermediate in organic synthesis, serving as a building block for the creation of a wide range of chemical products. Its unique structure allows for various chemical reactions, making it a valuable component in the development of new compounds.
Used in Pharmaceutical Industry:
As a precursor for the synthesis of various pharmaceuticals, (Z)-1-Nitro-2-phenyl-1-propene is instrumental in the development of new drugs. Its ability to be transformed into different chemical entities contributes to the advancement of medicinal chemistry and the discovery of novel therapeutic agents.
Used in Fine Chemicals Production:
(Z)-1-Nitro-2-phenyl-1-propene is also employed in the production of fine chemicals, which are high-purity chemicals used in various applications, including the fragrance, flavor, and specialty chemical industries. Its versatility and reactivity make it a sought-after compound in this sector.
Used in Polymer Production:
In the polymer industry, (Z)-1-Nitro-2-phenyl-1-propene serves as a reactant in the production of various polymers. Its integration into polymer chemistry can lead to the development of new materials with unique properties and applications.
Used in Illicit Drug Synthesis (Controlled Substance):
Due to its potential use as a precursor in the synthesis of amphetamines and other psychoactive substances, (Z)-1-Nitro-2-phenyl-1-propene is considered a controlled substance in some countries. Its regulation is tight to prevent its misuse in illegal drug production.

Upstream product

• 98-83-9 isopropenylbenzene 
• 98-86-2 acetophenone 
• 704-80-3 (E)-3-phenyl-2-butenoic acid 
• 945-93-7 ethyl (E)-3-phenylbut-2-enoate 
• 637-50-3 1-phenylpropene 
• 75-52-5 nitromethane 
• 66291-23-4 2-acetoxy-1-nitro-2-phenylpropane 
• 5670-65-5 (E)-1-nitro-2-phenyl-1-propene 
• 704-79-0 3-phenylbut-2-enoic acid 

Downstream Products

• 63278-04-6 Methyl-4-nitro-2-methoxycarbonyl-3-methyl-3-phenylbutyrat 
• 59647-78-8 2-phenylpropanal oxime 
• 7796-75-0 (+)-(R)-1-nitro-2-phenylpropane 
• 746647-15-4 (S)-1-nitro-2-phenylpropane 
• 1246226-31-2 4-p-methoxyphenyl-3-(1-phenylvinyl)-5-(methoxycarbonyl)isoxazoline N-oxide 
• 1246226-37-8 4-propyl-3-(1-phenylvinyl)-5-(methoxycarbonyl)isoxazoline N-oxide 
• 1246226-41-4 4-(2,4-dimethylphenyl)-3-(1-phenylvinyl)-5-(methoxycarbonyl)isoxazoline N-oxide 
• 1246226-40-3 4-o-anisyl-3-(1-phenylvinyl)-5-(methoxycarbonyl)isoxazoline N-oxide 
• 1246226-39-0 4-o-nitrophenyl-3-(1-phenylvinyl)-5-(methoxycarbonyl)isoxazoline N-oxide 
• 1246226-25-4 4-phenyl-3-(1-phenylvinyl)-5-(methoxycarbonyl)isoxazoline N-oxide 

Relevant academic research and scientific papers

1,3-Difunctionalization of β-alkyl nitroalkenes via combination of Lewis base catalysis and radical oxidation

Upon treatment with a Lewis base catalyst, β-alkyl-substituted nitroalkenes could be readily converted into allylic nitro compounds. Examples of either C-1 or C-3 functionalization methods have been reported through nitro-elimination, giving alkene products. In this work, successful 1,3-difunctionalization was achieved through a synergetic Lewis base catalysis and TBHP radical oxidation, giving vinylic alkoxyamines in good to excellent yields. This work further extended the general synthetic application of β-alkyl nitroalkenes.

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).

Highly enantioselective construction of CF3-bearing all-carbon quaternary stereocenters: Hiral spiro-fused bisoxazoline ligands with 1,1′-binaphthyl sidearm for asymmetric Michael-type Friedel-Crafts reaction

A novel class of chiral spiro-fused bisoxazoline ligands possessing a deep chiral pocket was prepared. The developed ligands have been employed in the nickel-catalyzed highly enantioselective Michael-type Friedel-Crafts reaction, affording the products bearing a trifluoromethylated all-carbon quaternary stereocenter with moderate to excellent yields (up to 99%) and good to excellent enantioselectivies (up to > 99.9% ee). Moreover, a proposed model of chiral pocket revealed that the attack of indole from the Re-face of β-CF3-β-disubstituted nitroalkene was favorable.

Ionic-Liquid Controlled Nitration of Double Bond: Highly Selective Synthesis of Nitrostyrenes and Benzonitriles

Unprecedented in literature, the conversion of aryl alkenes into β-nitrostyrenes (2) or benzonitriles (3) with sodium nitrite can be governed by an appropriate choice of ionic liquid (IL) medium. A general trend was found for the selectivity of these processes, which depends on the nature of IL, with imidazolium-based ILs, such as [Bmim]Cl, that favor the C–H nitration leading to β-nitrostyrenes, while tetraalkylammonium-based ILs, such as TBAA, privilege the C=C bond cleavage affording benzonitriles. Besides a substrate scope, mechanistic hypotheses were provided on the origin of the different selectivity in the two kinds of ILs, based on their own tunable properties such as polarity, viscosity, and solvent cage effects.

Light-Enabled Enantiodivergence: Stereospecific Reduction of Activated Alkenes Using a Single Organocatalyst Enantiomer

Light-enabled enantiodivergence is demonstrated in which the alkene substrate configuration is manipulated (E → Z) prior to organocatalytic reduction with a chiral thiourea and Hantzsch ester. This allows stereodivergent reduction to be regulated at the substrate level with high fidelity and mitigates the need for a second, enantiomeric catalyst (up to 93:07 and 95:5 er). The synthetic utility of this strategy has been demonstrated in the synthesis of the weight-loss drug (R)-Lorcaserin (Belviq) and a potent AMPA modulator.

Synthetic Diversity from a Versatile and Radical Nitrating Reagent

We leverage the slow liberation of nitrogen dioxide from a newly discovered, inexpensive succinimide-derived reagent to allow for the C?H diversification of alkenes and alkynes. Beyond furnishing a library of aryl β-nitroalkenes, this reagent provides unparalleled access to β-nitrohydrins and β-nitroethers. Detailed mechanistic studies strongly suggest that a mesolytic N?N bond fragmentation liberates a nitryl radical. Using in situ photo-sensitized, electron paramagnetic resonance spectroscopy, we observed direct evidence of a nitryl radical in solution by nitrone spin-trapping. To further exhibit versatility of N-nitrosuccinimide under photoredox conditions, the late-stage diversification of an extensive number of C?H partners to prepare isoxazolines and isoxazoles is presented. This approach allows for the formation of an in situ nitrile oxide from a ketone partner, the presence of which is detected by the formation of the corresponding furoxan when conducted in the absence of a dipolarophile. This 1,3-dipolar cycloaddition with nitrile oxides and alkenes or alkynes proceeds in a single-operational step using a mild, regioselective, and general protocol with broad chemoselectivity.

Metal-free, room temperature, acid-K2S2O8 mediated method for the nitration of olefins: An easy approach for the synthesis of nitroolefins

Here, we have developed a simple, room temperature method for the nitration of olefins by using inexpensive sodium nitrite as a source of nitro groups in the presence of trifluoroacetic acid (TFA) and potassium persulfate (K2S2O8) under an open atmosphere. Styrenes and mono-substituted olefins give stereo-selective corresponding E-nitroolefins under optimized conditions, however, 1,1-bisubstituted olefins give a mixture of E- and Z-nitroolefins. The optimized conditions work well with electron-donating, electron-withdrawing, un-substituted and heterocyclic styrenes and mono-substituted olefins and give corresponding nitroolefins with good to excellent yields.

Poly(ethylene glycol) supported metal nitrates as well-organized reagents for hunsdiecker conversion of α,β-unsaturated acids to β-nitrostyrenes under solvent and acid-free conditions

Poly(ethylene glycol) (PEG) supported metal nitrates such as ferric nitrate and manganese nitrate were accomplished as well-organized reagents for Hunsdiecker conversion of α,β-unsaturated acids to β-nitrostyrenes under acid-free and solvent free conditions using grindstone technique. However, in the case of unsaturated aliphatic acids, nitro alkene derivatives were obtained as products. PEG-400 was found the best among the other PEGs (PEG-200,300, 400, 600, 3000 and 6000) used in this protocol.

Copper-Promoted Regioselective Synthesis of Polysubstituted Pyrroles from Aldehydes, Amines, and Nitroalkenes via 1,2-Phenyl/Alkyl Migration

The facile copper-catalyzed synthesis of polysubstituted pyrroles from aldehydes, amines, and β-nitroalkenes is reported. Remarkably, the use of α-methyl-substituted aldehydes provides efficient access to a series of tetra- and pentasubstituted pyrroles via an overwhelming 1,2-phenyl/alkyl migration. The present methodology is also accessible to non α-substituted aldehydes, yielding the corresponding trisubstituted pyrroles. On the contrary, the use of ketones, in place of aldehydes, does not promote the organic transformation, signifying the necessity of α-substituted aldehydes. The reaction proceeds under mild catalytic conditions with low catalyst loading (0.3-1 mol %), a broad scope, very good functional-group tolerance, and high yields and can be easily scaled up to more than 3 mmol of product, thus highlighting a useful synthetic application of the present catalytic protocol. Based on formal kinetic studies, a possible radical pathway is proposed that involves the formation of an allylic nitrogen radical intermediate, which in turn reacts with the nitroalkene to yield the desired pyrrole framework via a radical 1,2-phenyl or alkyl migration.