4660-17-7

Upstream product

• 10034-09-0 1-methoxy-1,3-butadiene 
• 100-52-7 benzaldehyde 
• 100591-70-6 3-Benzenesulfinyl-6-phenyl-tetrahydro-pyran-2-one 
• 126087-54-5 2-phenyl-3,6-dihydro-2H-pyran 
• 104-53-0 3-phenyl-propionaldehyde 
• 89922-39-4 ethyl 2-(α-hydroxybenzyl)-3-butenoate 
• 80735-94-0 1-Phenyl-3-buten-1-ol 
• 98088-48-3 1-(allyloxy)-1-phenylbut-3-ene 
• 104683-48-9 (Z)-5-phenyl-2-pentene-1,5-diol 
• 72853-47-5 5-hydroxy-5-phenyl-pent-2-enoic acid methyl ester 
• 10413-17-9 6-phenyltetrahydropyran-2-one 
• 19190-80-8 methyl 3-Phenylglycidate 
• 71403-94-6 2,3-epoxy-3-phenylpropanal 
• 100591-59-1 Carbonic acid 4-benzenesulfinyl-1-phenyl-butyl ester methyl ester 

Downstream Products

• 2128-90-7 6-phenyl-2H-pyran-2-one 
• 10413-10-2 6-phenyltetrahydro-2H-pyran-2-ol 

Relevant academic research and scientific papers

Mechanism of Enolate Transfer between Si and Cu

Exchange of X (F, Cl, OMe) and a substituted enolate chain between SiMe3 and various CuI complexes was examined. Reaction mechanisms pass through a cyclic transition state in which the reaction coordinate is associated with rotation of the SiMe3 moiety. The dependence of the thermodynamic and kinetic features on the nature of the active and ancillary ligands was examined. Formation of copper enolate is shown to be favored when stabilized enolates are used. Replacement of F by Cl reverses the preference of the reaction. This is associated with the small difference between the Cu?Cl and Si?Cl bond energies, in contrast to other Si?X bonds, which are systematically stronger than their Cu?X analogues.

Diels-Alder Reactions of 1-Alkoxy-1-amino-1,3-butadienes: Direct Synthesis of 6-Substituted and 6,6-Disubstituted 2-Cyclohexenones and 6-Substituted 5,6-Dihydropyran-2-ones

We report the cycloaddition reactions of 1-alkoxy-1-amino-1,3-butadienes. These doubly activated dienes are prepared on a multigram scale from crotonic acid chloride and its derivatives. The dienes undergo Diels-Alder (DA) and hetero-Diels-Alder (HDA) reactions under mild reaction conditions with a variety of electron-deficient dienophiles to afford cycloadducts in good yields with excellent regioselectivities. The hydrolysis of the DA cycloadducts provides 6-substituted and 6,6-disubstituted 2-cylohexenones, which are versatile building blocks for complex molecule synthesis. The corresponding HDA cycloadducts afford 6-substituted 5,6-dihydropyran-2-ones.

Copper-Catalyzed Desaturation of Lactones, Lactams, and Ketones under pH-Neutral Conditions

A copper-catalyzed desaturation method that is suitable for converting lactones, lactams, and cyclic ketones to their α,β-unsaturated counterparts is reported. The reaction does not require strong base/acid or sulfur/selenium reagents and can be carried out through a simple one-step operation. The protocol uses inexpensive catalysts and reagents and exhibits excellent scalability and functional group tolerance. Notably, tert-butyl alcohol is the only stoichiometric byproduct produced, and overoxidation is not observed. The reaction mechanism has been investigated through control experiments, deuterium labeling, radical clock, electron paramagnetic resonance, high-resolution mass spectrometry, and kinetic studies. The data obtained are consistent with a reaction pathway involving reversible α-deprotonation by a Cu(II)-OtBu species followed by further oxidation of the resulting Cu enolate.

Enzyme mediated kinetic resolution of δ-hydroxy-α,β-unsaturated esters as a route to optically active δ-lactones

A novel synthetic route to optically active saturated and unsaturated δ-lactones based on enzymatic kinetic resolution and ring-closing metathesis reactions has been proposed. The influence of temperature, co-solvent, organic additives and the substrate s

Synthesis and evaluation of (-)-Massoialactone and analogues as potential anticancer and anti-inflammatory agents

(-)-Massoialactone, an α,β-unsaturated δ-lactone isolated from Cryptocarya massoia, and five analogues were synthesized and their antiproliferative and anti-inflammatory activities were evaluated. The lactones were able to mimic the "core" functional grou

One-pot sequential 1,4- and 1,2-reductions of α,β-unsaturated δ-lactones to the corresponding δ-lactols with CuCl and NaBH 4 in methanol

An efficient, one-pot method for the highly chemoselective synthesis of δ-lactols from α,β-unsaturated δ-lactones using CuCl and NaBH4 in methanol was developed. Georg Thieme Verlag Stuttgart. New York.

αβ-Unsaturated δ-valerolactones through RCM-isomerization sequence

αβ-Unsaturated δ-lactones are accessible via a sequential ring-closing metathesis (RCM) double-bond migration reaction starting from butenoates of allyl alcohols. This approach proceeds efficiently with lower catalyst loadings and higher initial substrate concentrations compared to the alternative RCM of acrylates derived from homoallylic alcohols. Georg Thieme Verlag Stuttgart . New York.

Gold-catalyzed intermolecular reactions of propiolic acids with alkenes: [4 + 2] Annulation and enyne cross metathesis

A gold-catalyzed intermolecular reaction of propiolic acids with alkenes led to a [4 + 2] annulation or enyne cross metathesis. The [4 + 2] annulation proceeds with net cis-addition with respect to alkenes and provides an expedient route to α,β-unsaturate

Synthesis of substituted α,β-unsaturated δ-lactones from vinyl tellurides

A new approach for the synthesis of α,β-unsaturated δ-lactones, a unit present in many natural products with interesting biological activities is described. The approach was based on the use of a vinyl telluride, and it is complementary to the methods usi

Synthesis and biological evaluation of α,β-unsaturated lactones as potent immunosuppressive agents

Compounds having α,β-unsaturated lactones display a variety of biological activities. Many research groups have tested both natural and unnatural α,β-unsaturated lactones for as-yet undiscovered biological properties. We synthesized α,β-unsaturated lacton