1574-86-3

Upstream product

• 75-52-5 nitromethane 
• 1896-62-4 (E)-benzalacetone 
• 25854-38-0 sodium nitromethane 
• 67-56-1 methanol 
• 122-57-6 1-Phenylbut-1-en-3-one 
• 5153-67-3 nitrostyrene 
• 67-64-1 acetone 
• 100-52-7 benzaldehyde 
• 128134-88-3 5-Nitro-4-phenyl-1-pentyne 
• 102-96-5 (2-nitroethenyl)benzene 

Downstream Products

• 6947-14-4 2-methyl-4-phenyl-pyrrolidine 
• 308289-02-3 5-aci-nitro-4-phenylpentan-2-one trimethylsilyl ester 
• 308289-04-5 2-phenylpropenal oxime trimethylsilyl ether 
• 24038-13-9 2-phenylpropenal oxime 
• 177597-89-6 5,5-dimethyl-3-phenyl-N-hydroxypyrroline-1-oxide 
• 177597-90-9 3,5-diphenyl-5-methyl-N-hydroxypyrrolidine 
• 13673-03-5 2-methyl-4-phenyl-1-pyrroline 
• 55091-68-4 3-phenyl-5-methyl-2,5-dihydrofuran-2-one 
• 40923-67-9 5-methyl-3-phenyldihydrofuran-2(3H)-one 
• 20272-25-7 cis-4-methyl-2-phenyl-γ-butyrolactone 
• 20272-25-7 trans-4-methyl-2-phenyl-γ-butyrolactone 
• 89885-33-6 5-nitroso-4-phenylpentan-2-one 

Relevant academic research and scientific papers

Synthesis of michael adducts as key building blocks for potential analgesic drugs: In vitro, in vivo and in silico explorations

Background: Organocatalytic asymmetric Michael addition is a strong approach for C-C bond formation. The objective of the study is to design molecules by exploiting the efficiency of Michael Adducts. We proceeded with the synthesis of Michael adducts by tailoring the substitution pattern on maleimide and trans-β-nitro styrene as Michael accep- tors. The synthesized compounds were evaluated for dual cyclooxygenases (COX) and lipoxygenase (LOX) inhibition. Methods: The compounds (4, 9-11) were synthesized through Michael additions. The cyclooxygenases (COX-1 and 2) and lipoxygenase (5-LOX) assays were used for in vitro evaluations of compounds. After the acute toxicity studies, the in vivo analgesic potential was determined with acetic acid induced writhing, tail immersion, and formalin tests. Furthermore, the possible roles of adrenergic and dopaminergic receptors were also studied. Extensive computational studies were performed to get a better understanding regarding the binding of this compound with protein target. Results: Four Michael adducts (4, 9-11) were synthesized. Compound 4 was obtained in enantio- and diastereopure form. The stereopure compound 4 showed encouraging COX-1 and-2 inhibitions with IC50 values of 128 and 65 μM with SI of 1.94. Benzyl derivative 11 showed excellent COX-2 inhibition with the IC50 value of 5.79 μM and SI value 7.96. Compounds 4 and 11 showed good results in in vivo models of analgesia like acetic acid test, tail immersion, and formalin tests. Our compounds were not active in dopaminergic and adrenergic pathways and so were acting centrally. Through extensive computational studies, we computed binding energies, and pharmacokinetic predictions. Conclusion: Our findings conclude that our synthesized Michael products (pyrrolidinedione 4 and nitroalkane 11) can be potent centrally acting analgesics. Our in silico predictions suggested that the compounds have excellent pharmacokinetic properties. It is concluded here that dual inhibition of COX/LOX pathways provides a convincing step towards the discovery of safe lead analgesic molecules.

A Bifunctional B,N-Based Asymmetric Catalytic Nitrostyrene-Michael Addition Acting through a 10-Membered Ring Cyclic Transition State

The B,N-bifunctional catalyst homoboroproline has been applied to a catalytic asymmetric nitroalkene-Michael addition to β-nitrostyrene analogues, showing broad substrate tolerance, high conversions and moderate to good asymmetric induction. The ability o

Interlocking the Catalyst: Thread versus Rotaxane-Mediated Enantiodivergent Michael Addition of Ketones to β-Nitrostyrene

Fumaramide threads bearing one l-prolinamide fragment have been designed as templates for promoting the efficient formation of novel Leigh's [2]rotaxanes. Both threads and rotaxanes are shown to catalyze the asymmetric addition of ketones to β-nitrostyren

C2-symmetric sulfonamides as homogeneous and heterogeneous organocatalysts that mimic enzymes in enantioselective Michael additions

Herein, we report the synthesis of C2-symmetric sulfonamides as homogeneous and heterogeneous organocatalysts and their application in the enantioselective conjugate 1,4-Michael addition of carbonylic nucleophiles to β-nitrostyrene. Organocatal

Concentration Effect in the Asymmetric Michael Addition of Acetone to β-Nitrostyrenes Catalyzed by Primary Amine Thioureas

Bifunctional primary amine thiourea (PAT) organocatalysts show remarkable improvement in enantioselectivity and catalytic activity (turnover frequency) in the asymmetric Michael addition of acetone to β-nitrostyrenes upon dilution. Mechanistic investigati

Enantiocomplementary synthesis of γ-nitroketones using designed and evolved carboligases

Artificial enzymes created by computational design and directed evolution are versatile biocatalysts whose promiscuous activities represent potentially attractive starting points for divergent evolution in the laboratory. The artificial aldolase RA9S.5-8, for example, exploits amine catalysis to promote mechanistically diverse carboligations. Here we report that RA95.5-8 variants catalyze the asymmetric synthesis of γ-nitroketones via two alternative enantiocomplementary Michael-type reactions: enamine-mediated addition of acetone to nitrostyrenes, and nitroalkane addition to conjugated ketones activated as iminium ions. In addition, a cascade of three aldolasecatalyzed reactions enables one-pot assembly of γ-nitroketones from three simpler building blocks. Together, our results highlight the chemical versatility of artificial aldolases for the practical synthesis of important chiral synthons.

2-methyl-4-phenyl-1-pyrroline preparation method

The invention discloses a 2-methyl-4-phenyl-1-pyrroline preparation method which includes the steps: S1, preparing phenyl nitro ethylene from benzaldehyde and nitromethane under catalysis of alkali metal hydroxide; S2, performing addition reaction on the phenyl nitro ethylene and acetone under catalysis of L-proline; S3, performing reduction and ring-closure on an addition product to obtain a target product. According to the preparation method, synthetic raw materials are easily obtained and low in price, and operation conditions are mild. Routes are simple and convenient in synthesis, silica-gel column chromatography is omitted after each step of reaction, and the preparation method is suitable for scientific research of laboratory mini-preparation and industrial production and amplification. Technical improvement of related drugs can be promoted, and various rich routes are provided for synthesis of the drugs.

A kind of T-leucine derivative of the chiral amine compound and its preparation method and application

The invention discloses a tertiary leucine derived chiral amine compound as well as a preparation method and application thereof. The chiral amine compound contains a tert-butyl group, a primary amine, a secondary amine or a tertiary amine functional group and has the structural formula as shown in the specification; and chiral amine and salts thereof are prepared through simple preparation steps by taking common tert-leucine as the raw material to form the chiral amine compound. The chiral amine and the salts thereof can be used for the asymmetrical Michael additive reaction between alpha, beta-unsaturated ketone and a nucleophilic reagent such as nitrocarbol, malonic ester, substituted oxazolone and the like and the asymmetrical cascade reaction between the alpha, beta-unsaturated ketone and fifth-position unsaturated rhodanine, between fifth-position unsaturated hydantoin and the alpha, beta-unsaturated ketone; and the tertiary leucine derived chiral amine compound has very high catalytic activity and stereoselectivity as well as the highest diastereoselectivity of 30/1 and the highest enantioselectivity of 99%, and is wide in oligomer range.

(1R,2R)-(+)-(1,2)-DPEN-Bonded Sulfonic Acid Resin: A Trifunctional Heterogeneous Catalyst for Asymmetric Michael Additions of Acetone to Nitroolefins

Based on (1R,2R)-(+)-(1,2)-DPEN skeleton, a series of primary amine-sulfamide bifunctional catalysts were synthesized, which exhibited excellent catalytic performance in the Michael addition of acetone to β-nitrostyrene. Therefore, a trifunctional heterogeneous catalyst was designed and prepared by simple N-sulfonyl reaction of (1R,2R)-(+)-(1,2)-DPEN and sulfonyl chloride resin. It was employed for the aforementioned addition without any additive and satisfactory results (80.5% conversion; 84.3% ee) were obtained. Meanwhile, the structural and textural properties of the catalyst were characterized by infrared spectroscopy (FT-IR), elemental analysis, SEM, and N2 adsorption and desorption experiments. Finally, the generality of the catalyst was investigated.

Enantioselective addition of aryl ketones and acetone to nitroalkenes organocatalyzed by carbamate-monoprotected cyclohexa-1,2-diamines

Enantiomerically pure carbamate-monoprotected trans-cyclohexane-1,2-diamines are used as chiral organocatalysts for the addition of aryl ketones and acetone to nitroalkenes to give enantioenriched β-substituted γ-nitroketones. The reaction was performed i