81640-05-3

Basic information

• Product Name: Cycloheptanone, 2-[(R)-hydroxyphenylmethyl]-, (2R)-rel-
• CAS NO: 81640-05-3
• Molecular Formula: C14H18O2
• Molecular Weight: 218.296
• Mol File: 81640-05-3.mol

Chemical Properties

• CAS DataBase Reference: Cycloheptanone, 2-[(R)-hydroxyphenylmethyl]-, (2R)-rel-(CAS DataBase Reference)
• NIST Chemistry Reference: Cycloheptanone, 2-[(R)-hydroxyphenylmethyl]-, (2R)-rel-(81640-05-3)
• EPA Substance Registry System: Cycloheptanone, 2-[(R)-hydroxyphenylmethyl]-, (2R)-rel-(81640-05-3)

Safety Data

• Hazardous Substances Data: 81640-05-3(Hazardous Substances Data)

Upstream product

• 22081-48-7 (cyclohept-1-en-1-yloxy)(trimethyl)silane 
• 100-52-7 benzaldehyde 
• 219583-59-2 trichloro<(cycloheptenyl)oxy>silane 
• 36504-15-1 cycloheptanone lithium enolate 
• 1121-66-0 2-Cyclohepten-1-one 

Relevant articles and documents

Photocontrolled Cobalt Catalysis for Selective Hydroboration of α,β-Unsaturated Ketones

Selectivity between 1,2 and 1,4 addition of a nucleophile to an α,β-unsaturated carbonyl compound has classically been modified by the addition of stoichiometric additives to the substrate or reagent to increase their “hard” or “soft” character. Here, we demonstrate a conceptually distinct approach that instead relies on controlling the coordination sphere of a catalyst with visible light. In this way, we bias the reaction down two divergent pathways, giving contrasting products in the catalytic hydroboration of α,β-unsaturated ketones. This includes direct access to previously elusive cyclic enolborates, via 1,4-selective hydroboration, providing a straightforward and stereoselective route to rare syn-aldol products in one-pot. DFT calculations and mechanistic experiments confirm two different mechanisms are operative, underpinning this unusual photocontrolled selectivity switch.

Synthesis of cyclobutanones and four-membered enol ethers by using a rearrangement reaction of enol triflates

A new synthetic method of cyclobutanone derivatives and four-membered enol ethers via an intramolecular cyclization of a ketone enolate was developed. The cyclization precursors, enol triflates having a silyloxy group at the β′-position, were synthesized from the corresponding β-hydroxy ketones, which were prepared via an aldol reaction of a cycloalkanone and an aldehyde. Under the influence of TBAF, the enol triflates afforded a cyclobutanone or a four-membered enol ether through rearrangement of the trifluoromethanesulfonyl group followed by an intramolecular C- or O-alkylation reaction.

Scope and limitations of chiral B-[3,5-bis(trifluoromethyl)phenyl]oxazaborolidine catalyst for use in the Mukaiyama aldol reaction

A new chiral oxazaborolidine catalyst was prepared in situ from 3,5-bis(trifluoromethyl)phenylboron dichloride and N-(p-toluenesulfonyl)-(S)-tryptophan. This catalyst is much more active than Corey's original catalyst for the Mukaiyama aldol reaction of a

Asymmetric aldol additions catalyzed by chiral phosphoramides: Electronic effects of the aldehyde component

The trichlorosilyl enolates of cyclopentanone and cycloheptanone were prepared by a mercury(II)-catalyzed metathesis from their TMS enol ethers in good yield. These enolates undergo spontaneous addition to aldehydes to provide the aldol adducts syn-4, 5a-

Surface-mediated solid phase reaction. I. Aldol reaction of silyl enol ethers with aldehydes on a solid surface of neutral alumina: Selectivity for anti aldols

The aldol reaction of trimethyl silyl enol ethers with aldehydes on the solid surface of neutral alumina under sonication without any solvent is found to proceed providing cross aldol products with anti selectivity.

Asymmetric aldol reaction: A highly erythro-selective aldol reaction between tricarbonyl(A-trimethylsilylbenzaldehyde derivative )-chromium (0) complexes and cyclic silyl enol ethers

Reaction of (±)-chromium (0) -complexes 4e-g with 5-7 gave the erythro isomers in a highly selective manner. This aldol reaction was successfully applied to the asymmetric one. The absolute configuration was determined by X-ray analysis of (-)-erythro-8e.

Fluoride Ion Catalyzed Aldol Reaction between Enol Silyl Ethers and Carbonyl Compounds

A new aldol reaction effected by the reaction of enol trimethylsilyl ethers and a quarternary ammonium fluoride is reported.Under the influence of a catalytic amount of tetrabutylammonium fluoride at low temperatures, enol silyl ethers react with various aldehydes to give the corresponding aldol trimethylsilyl ethers in fair to good yields.The silyl group of these products can be smoothly removed under mild conditions.Ketones, epoxides, and esters do not serve as electrophiles in this reaction.The reaction proceeds in a regiospecific manner with respect to the enol silyl ethers; the reactions of two regioisomers of 2-methylcyclohexanone with benzaldehyde cleanly give the respective regioisomeric aldol products.The reaction of 4-tert-butyl-1-methyl-2-(trimethylsiloxy)cyclohexene proceeds exclusively by the axial attack of the electrophile, making a strong contrast with the related cases reported on this cyclohexanone system.The aldol addition of a ketone and an aldehyde can be performed without the isolation of the enol silyl ether of the ketone by effecting both the silylation of the ketone and the aldol reaction with the aid of a fluoride anion.The characteristic behavior of the enolate species in this reaction can be rationalized by considering a mobile equilibrium in which the combination of fluorotrimethylsilane and a quarternary ammonium enolate functions as key controlling factor.

ERYTHRO SELECTIVE ALDOL CONDENSATION USING TITANIUM ENOLATES

Titanium enolates derived from ketones and esters react with aldehydes to afford erythro adducts with high diastereoselection.