18325-75-2

Upstream product

• 37609-34-0 cyclohex-1-en-1-yllithium 
• 98-86-2 acetophenone 
• 555-31-7 aluminum isopropoxide 
• 67-63-0 isopropyl alcohol 
• 932-66-1 1-cyclohexenyl methyl ketone 
• 90087-64-2 1-(1-nitroethyl)cyclohexene 
• 62-53-3 aniline 
• 76888-38-5 1-(1-cyclohexenyl)ethanol 
• 1192-88-7 1-cyclohexene-1-carboxaldehyde 
• 544-97-8 dimethyl zinc(II) 
• 108-30-5 succinic acid anhydride 
• 108-22-5 Isopropenyl acetate 
• 105-38-4 vinyl propionate 
• 74-89-5 methylamine 

Downstream Products

• 18325-75-2 (S)-1-(1-cyclohex-1-enyl)ethanol 
• 98559-23-0 1-ethylidene-2-bromo-cyclohexane 
• 94733-50-3 <2-Aethyliden-cyclohexyl>-aceton 
• 3991-31-9 (+/-)-<1-(Cyclohex-1-enyl)-aethyl>-vinyl-aether 
• 216174-33-3 methyl 2-(2-ethylidenecyclohexyl)-3-methoxypropionate 
• 146513-64-6 1-(cyclohexenyl)ethyl N-phenylcarbamate 
• 3817-85-4 O-(1-(1-cyclohexenyl)-ethyl) S-methyl dithiocarbonate 
• 79605-68-8 (1R)-1-(cyclohex-1-en-1-yl)ethan-1-ol 
• 325490-27-5 N-1-(1-cyclohexenyl)ethylphthalimide 
• 932-66-1 1-cyclohexenyl methyl ketone 
• 863319-14-6 (+)‐(R)‐1‐(cyclohex‐1‐en‐1‐yl)ethyl propionate 
• 60073-34-9 ethylidene-2 cyclohexylamine (E) 
• 325490-26-4 1-(cyclohex-1-en-1-yl)ethan-1-amine 

Relevant academic research and scientific papers

Tin(II) chloride dihydrate reduction of β,γ-unsaturated nitro-alkenes

β,γ-Unsaturated nitro-alkenes have been converted into α,β-unsaturated ketones in good yield by tin(II) chloride dihydrate in tetrahedrofuran.

Highly enantio- and diastereoselective one-pot synthesis of acyclic epoxy alcohols and allylic epoxy alcohols

In this report, we outline a highly enantio- and diastereoselective one-pot method for the efficient synthesis of synthetically useful acyclic epoxy alcohols and allylic epoxy alcohols. Our method takes advantage of a highly enantioselective C-C bond-form

Chemoenzymatic synthesis of enantiomeric, bicyclic δ-halo-γ-lactones with a cyclohexane ring, their biological activity and interaction with biological membranes

Starting from 1-acetyl-1-cyclohexene, three enantiomeric pairs (ee ≥99%) of bicyclic δ-halo-γ-lactones with cyclohexane ring were obtained in five-step synthesis. The key stereochemical steps were lipase-catalyzed kinetic resolution of racemic 1-(cyclohex-1-en-1-yl) ethanol followed by transfer of chirality to ethyl 2-(2-ethylidenecyclohexyl) acetate in the Johnson–Claisen rearrangement. Synthesized halolactones exhibited antiproliferative activity towards canine B-cell leukemia cells (GL-1) and canine B-cell chronic leukemia cells (CLB70) and the most potent (IC50 18.43 ± 1.46 μg/mL against GL-1, IC50 11.40 ± 0.40 μg/mL against CLB70) comparable with the control etoposide, was (1R,6R,1’S)-1-(1’-chloroethyl)-9- oxabicyclo[4.3.0]nonan-8-one (8b). All halolactones did not have a toxic effect on erythrocytes and did not change the fluidity of membranes in the hydrophobic region of the lipid bilayer. Only weak changes in the hydrophilic area were observed, like the degree of lipid packing and associated hydration. The racemic halolactones were also tested for their antimicrobial properties and found to exhibit selectivity towards bacteria, in particular, towards Proteus mirabilis ATCC 35659.

Manganese Catalyzed Asymmetric Transfer Hydrogenation of Ketones Using Chiral Oxamide Ligands

The asymmetric transfer hydrogenation of ketones using isopropyl alcohol (IPA) as hydrogen donor in the presence of novel manganese catalysts is explored. The selective and active systems are easily generated in situ from [MnBr(CO)5] and inexpensive C2-symmeric bisoxalamide ligands. Under the optimized reaction conditions, the Mn-derived catalyst gave higher enantioselectivity compared with the related ruthenium catalyst.

Enantioselective Hydrogenation of Ketones using Different Metal Complexes with a Chiral PNP Pincer Ligand

The synthesis of different metal pincer complexes coordinating to the chiral PNP ligand bis(2-((2R,5R)-2,5-dimethyl-phospholanoethyl))amine is described in detail. The characterized complexes with Mn, Fe, Re and Ru as metal centers showed good activities regarding the reduction of several prochiral ketones. Comparing these catalysts, the non-noble metal complexes produced best selectivities not only for aromatic substrates, but also for different kinds of aliphatic ones leading to enantioselectivities up to 99% ee. Theoretical investigations elucidated the mechanism and rationalized the selectivity. (Figure presented.).

Cucurbit[5]uril-mediated electrochemical hydrogenation of α,β-unsaturated ketones

The potential of cucurbit[5]uril to be used as inverse phase transfer catalyst in electrocatalytic hydrogenation of α,β-unsaturated ketones is illustrated. The interaction behavior among isophorone and cucurbit[5]uril was also investigated using cyclic voltammetry and UV/vis absorption spectroscopy. The results concerning to both techniques revealed an enhancement in the intensity of the absorption peak and also in the current cathodic peak of isophorone in presence of cucurbit[5]uril. This achievement is related to the increase of the isophorone solubility in the medium being an indicative of a host-guest complex formation. The electrochemical hydrogenation of isophorone using cucurbit[5]uril was more efficient than others well-stablish methodologies. Regarding to (R)-(+)-pulegone and (S)-(+)-carvone, the use of cucurbit[5]uril leads to an increase of 17% and 9%, on average, respectively, in the yields when compared to the control reaction. The efficiency of selective C=O bond hydrogenation of 1-acetyl-1-cyclohexene was evaluated. The presence of cucurbit[5]uril increased by 12% the hydrogenations yields of 1-acetyl-1-cyclohexene when compared to the control reaction. In this sense, these results open up an opportunity to carry out electrocatalytic reactions within the cucurbit[5]uril environment.

Pyrrolidines and Piperidines by Ligand-Enabled Aza-Heck Cyclizations and Cascades of N-(Pentafluorobenzoyloxy)carbamates

Ligand-enabled aza-Heck cyclizations and cascades of N-(pentafluorobenzoyloxy)carbamates are described. These studies encompass the first examples of efficient non-biased 6-exo aza-Heck cyclizations. The methodology provides direct and flexible access to carbamate protected pyrrolidines and piperidines.

CHIRAL METAL COMPLEX COMPOUNDS

The invention comprises novel chiral metal complex compounds of the formula (I) wherein M, PR2, R3 and R4 are outlined in the description, its stereoisomers, in the form as a neutral complex or a complex cation with a suitable counter ion. The chiral metal complex compounds can be used in asymmetric reactions, particularly in asymmetric reductions of ketones, imines or oximes.

Selective Hydrogenation of α,β-Unsaturated Aldehydes and Ketones by Air-Stable Ruthenium NNS Complexes

The selective hydrogenation of the carbonyl functionality of α,β-unsaturated aldehydes and ketones is catalysed by ruthenium dichloride complexes bearing a tridentate NNS ligand as well as triphenylphosphine. The tridentate ligand backbone is flexible, as evidenced by the equilibrium observed in solution between the cis- and trans-isomers of the dichloride precatalysts, as well as crystal structures of several of these complexes. The complexes are activated by base in the presence of hydrogen and readily hydrogenate carbonyl functionalities under mild conditions. Despite the activation by base, side reactions are negligible, even for aldehyde substrates, because of the low amount of base. Thus, the corresponding allylic alcohols can be isolated in very good yields on a 10–25 mmol scale. Turnover numbers up to 200 000 were achieved.

SELECTIVE REDUCTION OF ALDEHYDES AND KETONES

The present invention relates to a selective reduction of specific aldehydes and ketones to their corresponding alcohols.