147068-27-7

Upstream product

• 25308-75-2 1-Phenylcycloheptene 
• 68099-19-4 (RS)-1-phenyl-cyclohept-2-en-1-ol 
• 1121-66-0 2-Cyclohepten-1-one 
• 1194-18-9 cycloheptane-1,3-dione 
• 100-58-3 phenylmagnesium bromide 
• 86616-78-6 3-ethoxycyclohept-2-en-1-one 
• 98-80-6 phenylboronic acid 

Downstream Products

• 501919-44-4 (R)-3-phenyl-cycloheptanone 
• 1186225-58-0 3-isobutyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)cyclopentanone 
• 211447-08-4 Trimethyl-(6-phenyl-cyclohepta-1,6-dienyloxy)-silane 

Relevant academic research and scientific papers

Enantioselective Hydrogenation of Endocyclic Enones: the Solution to a Historical Problem?

The enantioselective hydrogenation of endocyclic enones has been a historical problem for homogeneous catalysis. We herein report an efficient method to reduce endocyclic enones with molecular hydrogen. Catalyzed by a rhodium/Zhaophos complex, a variety of enones with five-, six- or seven-member ring were hydrogenated with high enantioselectivity (92%—99% ee). Excellent chemo- and enantioselectivity demonstrated this method was successfully applied in the enantioselective hydrogenation of citral to produce enantio-enriched citronellal.

An elusive thermal [2 + 2] cycloaddition driven by visible light photocatalysis: Tapping into strain to access C 2-symmetric tricyclic rings

A mild and operationally simple methodology is reported for the synthesis of cyclobutane rings imbedded within a C2-symmetric tricyclic framework. The method uses visible light and an iridium-based photocatalyst to drive the oft-stated "forbidden" thermal

Synthesis of β-Substituted Cyclic Enones via Phosphonium Salt-Activated, Palladium-Catalyzed Cross-Coupling of Cyclic 1,3-Diones

Phosphonium salt-activated, Pd-catalyzed Suzuki-Miyaura and Sonogashira cross-coupling reactions of cyclic 1,3-diones in the synthesis of β-substituted cyclic enones are described. These transformations exhibit good isolated yield and high generality with respect to both substrates and coupling partners. Extension of the substrate scope to cyclic 1,3-dione equivalents, such as 2-cyanocyclohexanone (4), is also briefly examined.

Palladium-catalyzed oxidative rearrangement of tertiary allylic alcohols to enones with oxygen in aqueous solvent

A one-pot procedure for Pd(TFA)2-catalyzed 1,3-isomerization of tertiary allylic alcohols to secondary allylic alcohols followed by a Pd(TFA)2/neocuproine-catalyzed oxidative reaction to β-disubstituted-α,β-unsaturated kenones was developed. (Chemical Equation Presented).

Pt-catalyzed oxidative rearrangement of cyclic tertiary allylic alcohols to enones using aqueous hydrogen peroxide

An oxidative rearrangement of cyclic tertiary allylic alcohols to β-disubstituted α,β-unsaturated ketones by Pt black catalyst with aqueous hydrogen peroxide is described. The reaction proceeds under organic solvent- and halide-free conditions and gives only water as a coproduct. The Pt black catalyst is commercially available and can be reused at least four times.

IBS-catalyzed oxidative rearrangement of tertiary allylic alcohols to enones with oxone

A 2-iodoxybenzenesulfonic acid (IBS)-catalyzed oxidative rearrangement of tertiary allylic alcohols to enones with powdered Oxone in the presence of potassium carbonate and tetrabutylammonium hydrogen sulfate has been developed.

Oxidative rearrangement of tertiary allylic alcohols employing oxoammonium salts

(Chemical Equation Presented) Practical and highly efficient methods for oxidative rearrangement of tertiary allylic alcohols to β-substituted α,β-unsaturated carbonyl compounds employing oxoammonium salts are described. The methods developed are applicable to acyclic substrates as well as medium membered ring substrates and macrocyclic substrates. The counteranion of the oxoammonium salt plays crucial roles on this oxidative rearrangement.

TEMPO/NaIO4-SiO2: A catalytic oxidative rearrangement of tertiary allylic alcohols to β-substituted α,β-unsaturated ketones

(Chemical Equation Presented) The novel catalytic method for the oxidative rearrangement of tertiary allylic alcohols to β-substituted α,β-unsaturated ketones is described. TEMPO/NaIO4-SiO 2 causes facile and efficient oxidative rearrangement of various acyclic substrates as well as medium-sized and macrocyclic substrates.

Oxidative rearrangement of cyclic tertiary allylic alcohols with IBX in DMSO

(Chemical Equation Presented) A practical and environmentally friendly method for oxidative rearrangement of five- and six-membered cyclic tertiary allylic alcohols to β-disubstituted α,β-unsaturated ketones by the IBX/DMSO reagent system is described. Several conventional protecting groups (e.g., Ac, MOM, and TBDPS) are compatible under the reaction conditions prescribed.

Ring size effect in oxidation of 1-phenylcycloalkenes with chromic anhydride-pyridine complex: Preferential formation of epoxide with increase in ring size

A marked ring size effect in the oxidation of 1-phenylcycloalkenes (1) with chromic anhydride-pyridine complex has been observed.While 1-phenylcyclopentene (1a) and 1-phenylcyclohexene (1b) give the expected α,β-unsaturated cyclic ketones (2a,b) 1-phenylcycloheptene (1c) and 1-phenylcyclooctene (1d) furnish epoxides (5c,d) as the major products.