35376-41-1

Usage

Synthesis Reference(s)

Journal of Heterocyclic Chemistry, 24, p. 497, 1987 DOI: 10.1002/jhet.5570240237

Upstream product

• 111602-13-2 d'ethoxy-2 methyl-6 phenyl-4 dihydro-3,4 2H-pyranne 
• 107-93-7 (E)-but-2-enoic acid 
• 140-10-3 (E)-3-phenylacrylic acid 
• 116428-46-7 trans-3-phenyl-5-(trimethylsilyl)-cyclohexanone 
• 493-72-1 5-phenyl-cyclohexane-1,3-dione 
• 14371-10-9 (E)-3-phenylpropenal 
• 73291-51-7 (E)-1-phenylpenta-1,4-dien-3-one 
• 5208-89-9 (E)-1-phenyl-1,4-pentadien-3-ol 
• 20795-53-3 3-phenylcyclohexanone 
• 92251-17-7 5-ethoxy-1,6-dihydro-[1,1'-biphenyl]-3(2H)-one 
• 5323-87-5 3-Ethoxycyclohex-2-en-1-one 
• 100-58-3 phenylmagnesium bromide 
• 35225-79-7 dibenzylideneacetone 
• 353764-38-2 1,5-diphenyl-1,7-octadien-3-one 

Downstream Products

• 117894-23-2 (-)-(R)-5-phenylcyclohex-2-enone 
• 26114-87-4 cis-1,2,3,6-tetrahydro-[1,1'-biphenyl]-3-ol 
• 117894-26-5 (S)-(+)-5-phenyl-2-cyclohexen-1-one 
• 26114-89-6 cis-1,2,3,6-tetrahydro-[1,1'-biphenyl]-3-yl acetate 
• 26114-89-6 trans-5-phenyl-2-cyclohexen-1-yl acetate 
• 93468-54-3 N,N-dimethyl-(2-c-chloro-6-t-phenyl-1-r-cyclohexyl)methylamine 
• 93468-58-7 1,6-trans-N,N-dimethyl-(6-phenyl-2-cyclohexenyl)methylamine 
• 54928-82-4 Cyano-(3-phenyl-cyclohex-1-enyl)-acetic acid methyl ester 
• 54928-83-5 Cyano-[3-phenyl-cyclohex-(E)-ylidene]-acetic acid methyl ester 

Relevant academic research and scientific papers

Conversion of an amine-substituted amine-manganese tricarbonyl complex to a functionalized cyclohexenone

The synthesis of functionalized cyclohexenones can be achieved via double nucleophile addition, with intermediate reactivation by ligand exchange, to aminoarene-manganese tricarbonyl cationic complexes by adjusting the electron donating power of the amine.

Enantioselective Synthesis of γ-Functionalized Cyclopentenones and δ-Functionalized Cycloheptenones Utilizing a Redox-Relay Heck Strategy

In this report, the desymmetrization of cyclic enones under relay Heck conditions with an array of aryl boronic acids, alkenyl triflates and indole derivatives is described. This method grants facile access to diverse γ-functionalized cyclopentenones and δ-functionalized cycloheptenones. Using this approach, a formal synthesis of (S)-baclofen was completed in high yield and excellent enantioselectivity. (Figure presented.).

CeO2-Supported Pd(II)-on-Au Nanoparticle Catalyst for Aerobic Selective α,β-Desaturation of Carbonyl Compounds Applicable to Cyclohexanones

Direct selective desaturation of carbonyl compounds to synthesize α,β-unsaturated carbonyl compounds represents an environmentally benign alternative to classical stepwise procedures. In this study, we designed an ideal CeO2-supported Pd(II)-on-Au nanoparticle catalyst (Pd/Au/CeO2) and successfully achieved heterogeneously catalyzed selective desaturation of cyclohexanones to cyclohexenones using O2 in air as the oxidant. Besides cyclohexenones, various bioactive enones can also be synthesized from the corresponding saturated ketones under open air conditions in the presence of Pd/Au/CeO2. Preliminary mechanistic studies revealed that α-C-H bond cleavage in the substrates is the turnover-limiting step of this desaturation reaction.

Metal-Free I2-Catalyzed Highly Selective Dehydrogenative Coupling of Alcohols and Cyclohexenones

The I2 catalyzed highly selective oxidative condensation of cyclohexenones and alcohols for the synthesis of aryl alkyl ethers has been described. DMSO is employed as the mild terminal oxidant. This novel methodology offers a metal-free reaction condition, operational simplicity and broad substrate scope to afford valuable products from inexpensive reagents. Various meta-substituted aromatic ethers which are hardly synthesized from the reported methods requiring meta-substituted phenols, are efficiently prepared by the present protocol.

Iodine-Promoted Semmler–Wolff Reactions: Step-Economic Access to meta-Substituted Primary Anilines via Aromatization

An atom- and step-economic access to an array of unprotected meta-substituted primary anilines was disclosed using the Semmler–Wolff reaction, promoted by molecular iodine. Therein, noble metal catalysts and inert atmosphere are unnecessary while the forcing reaction conditions and the lengthy synthesis can be avoided. The synthetic utility of this approach is evident in the de novo syntheses of three bioactive molecules with good total yields.

Experimental studies on the selective β-c-h halogenation of enones

Here we describe the realization of a one-pot protocol for the β-C-H halogenation of cyclic enones via umpolung of the β-carbon. The developed method includes hydrazone formation and selective β-halogenation (bromination, chlorination) with N-bromosuccini

Catalytic Enantioselective Nitroso Diels-Alder Reaction

The nitroso Diels-Alder (NDA) reaction is an attractive strategy for the synthesis of 3,6-dihydro-1,2-oxazines and 1-amino-4-hydroxy-2-ene derivatives. Herein we report the Cu(I)-DTBM-Segphos catalyzed asymmetric intermolecular NDA reaction of variously substituted cyclic 1,3-dienes using highly reactive nitroso compounds derived from pyrimidine and pyridazine derivatives. In most of the cases studied, the cycloadducts were obtained in high yields (up to 99%) with very high regio-, diastereo-, and enantioselectivities (up to regioselectivity > 99:1, d.r. > 99:1, and >99% ee). As an application of this methodology, formal syntheses of conduramine A-1 and narciclasine were accomplished.

Silver(I)-catalyzed ring-contractive rearrangement: A new entry to 5-alkylidene-2-cyclopentenones

A novel silver(I)-catalyzed ring-contractive rearrangement of 5-substituted 6-diazo-2-cyclohexenones has been developed, providing a new and efficient access to 5-alkylidene-2-cyclopentenones. The AgOTf-catalyzed reaction proceeds through metal-carbenoid formation followed by endocyclic allyl [1,2] migration with excellent stereoselectivity and broad substrate scope.

Hydroxy-rhodium(I) catalyzed regioselective Michael addition of cyclic enones

Hydroxy-rhodium catalyzed dimerization of various cyclic enones to the corresponding α-enone adducts is developed. The key feature of this method is that the base-sensitive, highly substituted enones also undergo dimerization and the resultant products ar

Synthesis of cyclic enones via direct palladium-catalyzed aerobic dehydrogenation of ketones

α,β-Unsaturated carbonyl compounds are versatile intermediates in the synthesis of pharmaceuticals and biologically active compounds. Here, we report the discovery and application of Pd(DMSO)2(TFA)2 as a catalyst for direct dehydrogenation of cyclohexanones and other cyclic ketones to the corresponding enones, using O2 as the oxidant. The substrate scope includes heterocyclic ketones and several natural-product precursors.