149713-23-5

Usage

Uses

Used in Pharmaceutical Industry:
(2R,4S)-4-methyl-2-phenyl-tetrahydropyran serves as a valuable building block in organic synthesis, particularly for the preparation of pharmaceuticals. Its distinct structure and stereochemistry make it instrumental in the development of new drugs with specific therapeutic properties.
Used in Agrochemical Industry:
In the agrochemical sector, (2R,4S)-4-methyl-2-phenyl-tetrahydropyran is utilized as a key intermediate in the synthesis of various agrochemicals. Its chiral nature allows for the creation of targeted and effective products for agricultural applications.
Used in Flavoring Agent for Food Industry:
(2R,4S)-4-methyl-2-phenyl-tetrahydropyran also finds use as a flavoring agent in the food industry. Its unique properties contribute to the development of distinct flavors and scents in food products, enhancing the overall consumer experience.
Used in Organic Synthesis:
As a versatile compound, (2R,4S)-4-methyl-2-phenyl-tetrahydropyran is widely used in organic synthesis for the preparation of complex organic molecules. Its stereochemistry plays a significant role in the design and synthesis of these molecules, making it an essential tool for chemists.

Upstream product

• 135569-04-9 <<<(3-methyl-1-phenyl-3-butenyl)oxy>methyl>seleno>benzene 
• 78-79-5 isoprene 
• 73408-01-2 3-methyl-5-phenyl-4-pentenol 
• 172295-01-1 (E)-3-methyl-5-phenyl-4-penten-1-ol 
• 100-52-7 benzaldehyde 
• 476687-78-2 (E)-3-methyl-5-phenyl-2-pentene-1,5-diol 
• 201145-41-7 (E)-5-hydroxy-3-methyl-5-phenyl-pent-2-enal 
• 39652-50-1 5-hydroxy-3-methyl-5-phenyl-pent-2-enoic acid methyl ester 
• 19041-17-9 methyl 4-bromo-3-methylbut-2-enoate 
• 1610378-61-4 C₁₉H₂₀O₃ 
• 100-42-5 styrene 
• 3240-30-0 3-methyl-1-phenyl-pent-4-en-1-one 
• 98-86-2 acetophenone 

Relevant academic research and scientific papers

Catalytic Diastereoselective Hetero-Diels-Alder Reaction of α-Haloacroleins with Alkenes: Construction of 3,4-Dihydropyran

In this Letter, a catalytic diastereoselective hetero-Diels-Alder reaction of α-haloacroleins with less polarized alkenes was developed, and the resulting 3,4-dihydropyrans were produced in high yields with a broad substate scope. Mechanism studies showed that 3,4-dihydropyran was produced from the ring expansion of cyclobutane, which was generated in the ring contraction of the initially formed unstable 3,4-dihydropyran conformer.

Water-Accelerated Nickel-Catalyzed α-Crotylation of Simple Ketones with 1,3-Butadiene under pH and Redox-Neutral Conditions

We report a nickel/NHC-catalyzed branched-selective α-crotylation of simple ketones using 1,3-butadiene as the alkylation agent. This reaction is regioselective and operated under pH and redox-neutral conditions. Water was used as the sole additive, which significantly accelerates the transformation.

gamma-alkenyl ketone and preparation method thereof

The invention discloses a gamma-alkenyl ketone preparation method, wherein the target product can be obtained at high yield and high regioselectivity by using acetophenone and 1,3-butadiene as raw materials in the presence of an organic solvent, a catalyst, an additive and a ligand. According to the invention, the method has advantages of high atom economy, high regioselectivity, high yield and the like, can achieve the efficient conversion from a cheap basic organic chemical product 1,3-butadiene to high-added-value gamma-alkenyl ketone, and uses the cheap catalyst, so that the reaction conditions are neutral and mild, and the experimental operation is safe and simple; and the synthesized gamma-alkenyl ketone is a useful synthetic intermediate, can be subjected to a series of conversionsto obtain a series of drug molecule precursors or key intermediates, and has wide application prospect.

Catalytic asymmetric [4+2]-cycloaddition of dienes with aldehydes

Despite its significant potential, a general catalytic asymmetric [4+2]-cycloaddition of simple and electronically unbiased dienes with any type of aldehyde has long been unknown. Previously developed methodologies invariably require activated, electronically engineered substrates. We now provide a general solution to this problem. We show that highly acidic and confined imidodiphosphorimidates (IDPis) are extremely effective Br?nsted acid catalysts of the hetero-Diels-Alder reaction of a wide variety of aldehydes and dienes to give enantiomerically enriched dihydropyrans. Excellent stereoselectivity is generally observed and a variety of scents and natural products can be easily accessed.

Enantioselective cascade formal reductive insertion of allylic alcohols into the C(O)-C bond of 1,3-diketones: Ready access to synthetically valuable 3-alkylpentanol units

An unprecedented cascade reaction combining dual iron-amine-catalyzed enantioselective functionalization of allylic alcohols and chemoselective acyl transfer is presented. It allows, from diketones and allylic alcohols, preparation of efficiently function

Aluminium triflate catalysed cyclisation of unsaturated alcohols: novel synthesis of rose oxide and analogues

Aluminium trifluoromethanesulfonate was used as an efficient catalyst for the cycloisomerisation of several unsaturated alcohols into cyclic ethers such as rose oxide and some of its ether analogues.

Regio- and stereoselective nickel-catalyzed homoallylation of aldehydes with 1,3-dienes

Ni(acac)2 catalyzes homoallylation of aldehydes with 1,3-dienes in the presence of triethylborane. Triethylborane serves as a reducing agent delivering a formal hydride to the C2 position of 1,3-dienes, thus generating a formal homoallyl anion species and enabling the novel homoallylation of aldehydes. The reaction proceeds smoothly at room temperature in the absence of any phosphane or nitrogen ligands and is highly regioselective and stereoselective for a wide variety combination of aldehydes and 1,3-dienes: e.g., isoprene and benzaldehyde combine to give a mixture of anti- and syn-1-phenyl-3-methyl-4-penten-1-ol (2.2) in a ratio of 15:1 in 90% yield. Under the conditions, sterically congested aliphatic aldehydes and ketones show low yields. In such cases, diethylzinc serves as a substitute for triethylborane and yields the expected products in good yields with similarly high regio- and stereoselectivity. 1,3-Cyclohexadiene is one exception among 24 kinds of dienes examined and undergoes allylation (not homoallylation) selectively.

Biocatalyzed preparation of the optically enriched stereoisomers of 4-methyl-2-phenyl-tetrahydro-2H-pyran (Doremox)

The four stereoisomers of the rose oxide analogue Doremox were prepared in enantiomerically enriched form by enantiospecific bakers' yeast reduction of suitable derivatives and by lipase-mediated kinetic resolution of diol precursors.