116505-07-8

Upstream product

• 6051-13-4 2-cyclohexylpropanoic acid 
• 77124-22-2 2-cyclohexylidenepropanoic acid 
• 31042-01-0 methyl (1-hydroxy-α-methylcyclohexane)acetate 
• 40556-79-4 methyl 2-cyclohexylpropionate 
• 14352-61-5 methyl cyclohexylacetate 
• 3451-36-3 (2R)-2-cyclohexylpropanoic acid 
• 5292-21-7 Cyclohexylacetic acid 
• 108-94-1 cyclohexanone 
• 62184-70-7 methyl 2-(1-cyclohexenyl)propanoate 

Downstream Products

• 65426-80-4 2-Cyclohexyl-propancarbonsaeure-p-nitrophenylester 
• 116505-08-9 (5S,6R)-6-((R)-1-Cyclohexyl-ethyl)-5-methyl-4-pyrrolidin-1-yl-5,6-dihydro-pyran-2-one 
• 116505-08-9 (5S,6R)-6-((S)-1-Cyclohexyl-ethyl)-5-methyl-4-pyrrolidin-1-yl-5,6-dihydro-pyran-2-one 
• 20474-46-8 cyclohexyl-3 butanone-2 
• 185199-40-0 3-cyclohexyl-1,3-dimethyloxindole 
• 1425052-38-5 2-cyclohexyl-N-(2,3,5,6-tetrafluoro-4-(trifluoromethyl)phenyl)propanamide 
• 28523-32-2 (R)-2-cyclohexyl-propionic acid amide 
• 1534433-51-6 2-cyclohexyl-3-(4-methoxyphenyl)-N-(quinolin-8-yl)propanamide 
• 1534433-39-0 2-cyclohexyl-N-(quinolin-8-yl)propanamide 

Relevant academic research and scientific papers

Catalytic enantioselective desymmetrization of cyclobutane-1,3diones by carbonyl-amine condensation

A chiral phosphoric acid-catalyzed enantioselective condensation of 2,2-disubstituted cyclobutane-1,3-diones with a primary amine is described. This reaction offered a mild and efficient protocol for constructing quaternary carbon-containing cyclobutanes

1-Aminopyridinium Ylides as Monodentate Directing Groups for sp3 C-H Bond Functionalization

1-Aminopyridinium ylides are efficient directing groups for palladium-catalyzed β-arylation and alkylation of sp3 C-H bonds in carboxylic acid derivatives. The efficiency of these directing groups depends on the substitution at the pyridine moiety. The unsubstituted pyridine-derived ylides allow functionalization of primary C-H bonds, while methylene groups are unreactive in the absence of external ligands. 4-Pyrrolidinopyridine-containing ylides are capable of C-H functionalization in acyclic methylene groups in the absence of external ligands, thus rivaling the efficiency of the aminoquinoline directing group. Preliminary mechanistic studies have been performed. A cyclopalladated intermediate has been isolated and characterized by X-ray crystallography, and its reactivity was studied.

Pd(II)-Catalyzed Direct Sulfonylation of Unactivated C(sp3)-H Bonds with Sodium Sulfinates

A Pd(II)-catalyzed sulfonylation of unactivated C(sp3)-H bonds with sodium arylsulfinates using an 8-aminoquinoline auxiliary is described. This reaction demonstrates excellent functional group tolerance with respect to both the caboxamide starting material and the sodium arylsulfinate coupling partner, affording a broad range of aryl alkyl sulfones. Moreover, the late-stage modification of complex molecules was achieved via this sulfonylation protocol.

Nickel-catalyzed direct arylation of C(sp3)-H bonds in aliphatic amides via bidentate-chelation assistance

The Ni-catalyzed, direct arylation of C(sp3)-H (methyl and methylene) bonds in aliphatic amides containing an 8-aminoquinoline moiety as a bidentate directing group with aryl halides is described. Deuterium-labeling experiments indicate that the C-H bond cleavage step is fast and reversible. Various nickel complexes including both Ni(II) and Ni(0) show a high catalytic activity. The results of a series of mechanistic experiments indicate that the catalytic reaction does not proceed through a Ni(0)/Ni(II) catalytic cycle, but probably through a Ni(II)/Ni(IV) catalytic cycle.

Ligand-promoted alkylation of C(sp3)-H and C(sp2)-H bonds

9-Methylacridine was identified as a generally effective ligand to promote a Pd(II)-catalyzed C(sp3) - H and C(sp2) - H alkylation of simple amides with various alkyl iodides. This alkylation reaction was applied to the preparation of unnatural amino acids and geometrically controlled tri- and tetrasubstituted acrylic acids.

Lewis acid-promoted ketene-alkene [2 + 2] cycloadditions

Described are the first examples of ketene-alkene [2 + 2] cycloadditions promoted by Lewis acids. Notable features of this method include (1) substantial rate acceleration relative to traditional thermal reactions, (2) good diastereoselectivities and yields for the formation of the cyclobutanone products, and (3) inverse diastereoselectivity compared with related thermal cycloadditions for many examples. These studies not only provide access to synthetically versatile cyclobutanones that cannot be prepared by traditional thermal cycloadditions but also address important mechanistic questions regarding ketene-alkene [2 + 2] cycloaddition reactions.