16015-12-6

Upstream product

• 100-42-5 styrene 
• 123-31-9 hydroquinone 
• 107-02-8 acrolein 
• 110-87-2 3,4-dihydro-2H-pyran 
• 591-50-4 iodobenzene 
• 124654-51-9 2-(benzenesulphonyl)tetrahydro-6-phenyl-2H-pyran 
• 10413-10-2 6-phenyltetrahydro-2H-pyran-2-ol 
• 98088-48-3 1-(allyloxy)-1-phenylbut-3-ene 
• 126087-54-5 2-phenyl-3,6-dihydro-2H-pyran 
• 80735-94-0 1-Phenyl-3-buten-1-ol 
• 100-52-7 benzaldehyde 
• 10413-17-9 6-phenyltetrahydropyran-2-one 
• 116805-87-9 5-hydroxy-5-phenylpentanoic acid 
• 1501-05-9 5-oxo-5-phenylvaleric acid 

Downstream Products

• 322764-79-4 5-hydroxy-5-phenyl-valeraldehyde 
• 2051-95-8 succinylbenzene 
• 1501-05-9 5-oxo-5-phenylvaleric acid 
• 55066-48-3 3-methyl-5-phenylpentan-1-ol 
• 74457-58-2 4-oxo-2-phenyl-butyric acid 

Relevant academic research and scientific papers

A new synthesis of highly functionalized cyclohexenes via a vinylogous Ferrier-Petasis cyclization reaction

Research on the O→C rearrangement reaction shows that alkoxydienes undergo a smooth rearrangement in a vinylogous manner with a catalytic amount of titanium (IV) chloride, which leads to highly substituted cyclohexenes a particularly useful starting mater

Experimental and Computational Study of an Unexpected Iron-Catalyzed Carboetherification by Cooperative Metal and Ligand Substrate Interaction and Proton Shuttling

An iron-catalyzed cycloisomerization of allenols to deoxygenated pyranose glycals has been developed. Combined experimental and computational studies show that the iron complex exhibits a dual catalytic role in that the non-innocent cyclopentadienone ligand acts as proton shuttle by initial hydrogen abstraction from the alcohol and by facilitating protonation and deprotonation events in the isomerization and demetalation steps. Molecular orbital analysis provides insight into the unexpected and selective formation of the 3,4-dihydro-2H-pyran.

Preparation method of 3-methyl-5-phenyl-amyl alcohol

The invention provides a preparation method of 3-methyl-5-phenyl-amyl alcohol. The preparation method comprises the following steps of phenyl-dihydropyran preparation, wherein the weight ratio of solid acid to 3-methyl-3-butenol is 1:(100-5,000), the weight ratio of xylene to 3-methyl-3-butenol is (0.5-2.0):1.0, and the weight ratio of benzaldehyde to 3-methyl-3-butenol is (1.2-3.0):1.0; a hydrogenation reaction, wherein the hydrogenation reaction is conducted for 1 h to 15 h at the temperature of 45 DEG C to 150 DEG C under the pressure of 0.3 MPa to 2.5 MPa. According to the preparation method, phenyl-dihydropyran is efficiently generated by mainly adopting a vacuum tower type reactor and a negative-pressure cyclization technology; a cocatalyst is added in the hydrogenation reaction, and therefore it is guaranteed that the conversion rate and the selectivity are high, the catalyst is recycled for multiple batches and is low in cost, the yield of the final product is high, and industrialized production can be achieved.

Highly regioselective heck coupling reactions of aryl halides and dihydropyran in the presence of an NHC-pyridine ligand

The Heck coupling reactions of aryl halides and 3,4-dihydro-2H-pyran facilitated the regioselective synthesis of arylated cyclic enol ethers. Good yields were obtained using 5 mol% of an NHC-ligand-Pd-catalyst complex in the presence of K2CO3 in DMF at 100°C. The use of this catalytic system broadens the substrate scope and improves the selectivity for this cross-coupling process. Georg Thieme Verlag Stuttgart.

Ruthenium-catalyzed olefin metathesis double-bond isomerization sequence

A novel ruthenium-catalyzed tandem ring-closing metathesis (RCM) double-bond isomerization reaction is described in this paper. The utility of this method for the efficient syntheses of five-, six-, and seven-membered cyclic enol ethers is demonstrated. It relies on the conversion of a metathesis-active ruthenium carbene species to an isomerization-active ruthenium-hydride species in situ. This conversion is achieved by using various additives. Scope and limitations of the different protocols are discussed, and some mechanistic considerations based on 31P and 1H NMR spectroscopic studies are presented.

In situ conversion of a Ru metathesis catalyst to an isomerization catalyst

Addition of alcohols and substoichiometric amounts of a base to a metathesis reaction induces conversion of the metathesis-active carbene catalyst to an isomerization-active hydride species.

An olefin metathesis/double bond isomerization sequence catalyzed by an in situ generated ruthenium hydride species

The direct conversion of allyl ethers to cyclic enol ethers using an olefin metathesis/double bond migration sequence is described. Ruthenium carbene complexes were activated to catalyze the double bond migration step by addition of hydride sources, such

New tandem catalysis: Preparation of cyclic enol ethers through a ruthenium-catalyzed ring-closing metathesis-olefin isomerization sequence

Tandem reactions that proceed with a single metal catalyst precursor offer novel opportunities for developing efficient new reaction sequences. In this regard, reaction conditions have been identified that allows for a tandem ring-closing metathesis-olefi

Substituent dependence of the diastereofacial selectivity in iodination and bromination of glycals and related cyclic enol ethers

The stereochemical course of the electrophilic iodination and bromination of tri-O-benzyl-D-glucal under various conditions has been compared to that of substituted dihydropyrans 2-5. IN3 addition in acetonitrile affords trans-α-iodoazides (80-87%), besides small amounts of trans-β-adducts, in the presence or the absence of benzyloxy substituents at C-3 or C-4, and in agreement with bridged iodonium ion intermediates. In contrast, the diastereofacial selectivity of bromine addition in dichloroethane going through open bromo oxocarbenium ions depends strongly on the substituents. Whereas the trans-α-dibromides are the main (85-95%) adducts in the absence of C-4 and C-5 substituents, in their presence a moderate to exclusive selectivity for cis-α-addition (60-99%) is observed. The predominance of trans-α-addition is again observed whatever the substituents when the bromination is carried out in the same solvent but with a tribromide ion salt, supporting a concerted addition of the two bromine atoms under these conditions. Finally, bromine addition in methanol exhibits a completely different behavior with the nonselective formation of trans-α- and trans-β-methoxybromides and a small dependence on the substituents. In agreement with the absence of azide trapping of any cationic intermediate, it is concluded that these brominations which do not go through an ionic intermediate are concerted additions of bromine and methanol with very loose rate- and product-determining transition states. Finally, the substituent conformation at C-4 influences drastically the stereoselectivity in all these brominations. Evidence for α-anomeric control of the nucleophile approach at C-1 is given by the highly predominant formation of α-adducts, except in the methanolic bromination. The factors determining the versatile selectivity of the electrophile approach are discussed in terms of PPFMO theory and of the special mechanisms of glycal reactions.

SUBSTITUTION REACTIONS OF 2-BENZENESULPHONYL CYCLIC ETHERS WITH CARBON NUCLEOPHILES

Direct substitution of 2-benzenesulphonylcyclic ethers was studied using a variety of carbon nucleophiles.These nucleophiles included organozinc reagents (derived from aryl, vinyl and alkynyl Grignard reagents) or silyl enol ethers, silyl ketene acetals,