4591-64-4

Upstream product

• 4687-64-3 4-[6-(2-nitro-1-phenyl-ethyl)-cyclohex-1-enyl]-morpholine 
• 670-80-4 4-cyclohexen-1-ylmorpholine 
• 5153-67-3 nitrostyrene 
• 75-52-5 nitromethane 
• 5682-83-7 (E)-2-benzylidenecyclohexanone 
• 931-57-7 1-methoxy-cyclohex-1-ene 
• 17851-97-7 1-tri(n-butyl)stannyloxy-1-cyclohexene 
• 108-94-1 cyclohexanone 
• 579-71-5 2-nitrostyrene 
• 102-96-5 (2-nitroethenyl)benzene 
• 83976-41-4 (S)-2-methoxymethylpyrrolidine cyclohexanone enamine 
• 233257-14-2 (2R,6S)-2-(tert-Butyl-dimethyl-silanyl)-6-((R)-2-nitro-1-phenyl-ethyl)-cyclohexanone 
• 6651-36-1 1-(Trimethylsilyloxy)cyclohexene 
• 100-52-7 benzaldehyde 

Downstream Products

• 99695-91-7 2-(β-Amino-α-phenylethyl)-cyclohexanol 
• 83976-51-6 (+)-(2S,1'R)-2-(2'-Nitro-1'-phenylaethyl)-cyclohexanon-aethylendithioacetal 
• 1288984-93-9 (1R,2R,3R,4R,4aS,8aS)-8a-hydroxy-2-methyl-3-nitro-4-phenyldecahydronaphthalene-1-carbaldehyde 
• 4591-64-4 (R)-2-((S)-2-nitro-1-phenylethyl)cyclohexanone 
• 1288984-92-8 (1R,2S,3S,4R,4aS,8aS)-8a-hydroxy-3-nitro-2-(4-nitrophenyl)-4-phenyldecahydronaphthalene-1-carbaldehyde 
• 1436787-16-4 (1R,2S,3R,4R,4aS,8aS)-8a-hydroxy-3-nitro-2-(4-nitrophenyl)-4-phenyldecahydronaphthalene-1-carbaldehyde 
• 1436787-12-0 (2R,3R,4S,4aR)-3-nitro-2-(4-nitrophenyl)-4-phenyl-2,3,4,4a,5,6,7,8-octahydronaphthalene-1-carbaldehyde 
• 1436787-20-0 (2R,3S,4S,4aR)-3-nitro-2-(4-nitrophenyl)-4-phenyl-2,3,4,4a,5,6,7,8-octahydronaphthalene-1-carbaldehyde 
• 1436787-84-6 (1R,2S,3R,4R,4aS,8aS)-2-(4-bromophenyl)-8a-hydroxy-3-nitro-4-phenyldecahydronaphthalene-1-carbaldehyde 
• 1288984-86-0 (1R,2S,3S,4R,4aS,8aS)-8a-hydroxy-3-nitro-2,4-diphenyldecahydronaphthalene-1-carbaldehyde 
• 1436786-55-8 (1R,2S,3R,4R,4aS,8aS)-8a-hydroxy-3-nitro-2,4-diphenyldecahydronaphthalene-1-carbaldehyde 
• 1436786-51-4 (2R,3R,4S,4aR)-3-nitro-2,4-diphenyl-2,3,4,4a,5,6,7,8-octahydronaphthalene-1-carbaldehyde 
• 1436786-59-2 (2R,3S,4S,4aR)-3-nitro-2,4-diphenyl-2,3,4,4a,5,6,7,8-octahydronaphthalene-1-carbaldehyde 
• 1436788-23-6 (1R,2S,3R,4R,4aR,8aS)-8a-hydroxy-3-nitro-2,4-diphenyldecahydronaphthalene-1-carbaldehyde 

Relevant academic research and scientific papers

Chiral C2-symmetric bis-thioureas as enzyme mimics in enantioselective Michael addition

We report herein the synthesis and application of enantiopure C2-symmetric primary amine-1,3-bis-thiourea organocatalysts in enantioselective conjugate 1,4-Michael addition of carbonyl containing nucleophiles, to nitroalkenes and N-phenylmaleim

Primary Amine Catalyzed Activation of Carbonyl Compounds: A Study on Reaction Pathways and Reactive Intermediates by Mass Spectrometry

The field of organocatalysis is expanding at a fast pace. Its growth is sustained by major stimuli, such as the effort toward an understanding of the mechanisms of reaction and catalytic processes in general, the elucidation of basic properties leading to stereocontrol and the search for broad applicability and scalability of the synthetic methodology. This paper reports a thorough study based on ESI-MS spectrometry of amino-organocatalyzed model reactions under different experimental conditions. Off-line reaction monitoring of mixtures containing different catalytic systems, by ESI-MSn showed the presence of several putative intermediate species, either in their protonated or sodiated forms. In addition, enantioselective chromatography of crude reactions provides the stereochemical outcome of asymmetric reactions. The bulk of the data collected offers a clue of the intricate pathways occurring in solution for the studied reactions.

Additive and Emergent Catalytic Properties of Dimeric Unnatural Amino Acid Derivatives: Aldol and Conjugate Additions

Different densely substituted L- and D-proline esters were prepared by asymmetric (3+2) cycloaddition reactions catalyzed by conveniently selected EhuPhos chiral ligands. The γ-nitro-2-alkoxycarbonyl pyrrolidines thus obtained in either their endo or exo forms were functionalized and coupled to yield the corresponding γ-dipeptides. The catalytic properties of these latter dimers were examined using aldol and conjugate additions as case studies. When aldol reactions were analyzed, an additive behavior in terms of stereocontrol was observed on going from the monomers to the dimers. In contrast, in the case of the conjugate additions between ketones and nitroalkenes, the monomers did not catalyze this reaction, whereas the different γ-dipeptides promoted the formation of the corresponding Michael adducts. Therefore, in this latter case emergent catalytic properties were observed for these novel γ-dipeptides based on unnatural proline derivatives. Under certain conditions stoichiometric amounts of ketone, acid and nitroalkene), formation of N-acyloxy-2-oxooctahydro-1H-indoles was observed.

A development of a reusable copper supported imidazolium functionalized ionic liquid catalyzed asymmetric Michael addition reaction

An eco-friendly copper supported Imidazolium functionalized ionic liquid [[Gmim]Cl–Cu (II)] used as green catalyst in solvent free asymmetric Michael addition at 25OC. This technique covers simplified product isolation, high conversion and cata

2-[1-(Dimethylamino)ethyl]ferrocenylphosphinic acid as an organocatalyst of Michael and Friedel—Crafts reactions

Racemic 2-[1-(dimethylamino)ethyl]ferrocenylphosphinic acid was tested as an organocatalyst in the Michael and Friedel—Crafts reactions. The use of this zwitterion provides 78% conversion in the Michael reaction between cyclohexanone and β-nitrostyrene, a

Remarkable Effect of tert-Amine Additives in the Asymmetric Direct Michael Reaction of Ketones with β-Arylnitroethenes Catalyzed by an L-Hydroxyproline-Based Amino Tf-Amide Organocatalyst

A catalytic asymmetric direct Michael reaction of ketones with trans-β-arylnitroethenes can be achieved under the influence of optically pure L-hydroxyproline-based secondary-amino aromatic Tf-amide organocatalyst. The effect of the trialkylamine base additive such as diethylmethylamine is of paramount importance to accomplish high reactivity and enantioselectivity in this asymmetric Michael reaction.

Chiral anthranilic pyrrolidine as custom-made amine catalyst for enantioselective Michael reaction of nitroalkenes with carbonyl compounds

A chiral anthranilic pyrrolidine catalyst as a custom-made amine-catalyst was developed for the enantio- and diastereo selective Michael reaction of nitroalkenes with carbonyl compounds. In particular, a peptide-like catalyst in which an α-amino acid is a

Novel C2-symmetric phenylglycine derivatives as organocatalysts of the Michael reaction between nitroalkenes and ketones

A comprehensive study of the activity of the amide-type organocatalysts based on (R)- and (S)-phenylglycine and 1,2-di(2-pyridyl)-1,2-diaminoethane in the asymmetric Michael reaction between various nitroalkenes and ketones was carried out. The products o

Asymmetric 1,4-Michael Addition in Aqueous Medium Using Hydrophobic Chiral Organocatalysts

Organic transformations exclusively in water as an environmentally friendly and safe medium have drawn significant interest in the recent years. Moreover, transition metal-free synthesis of enantiopure molecules in water will have a great deal of attentio

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.