19752-84-2

Usage

Uses

Used in Pharmaceutical Industry:
TETRAHYDRO-PYRAN-3-OL is used as a key intermediate in the synthesis of CRF1 (corticotropin-releasing factor type 1) receptor antagonists, which are important for the development of drugs targeting stress-related disorders and anxiety.
Used in Agrochemical Industry:
TETRAHYDRO-PYRAN-3-OL is used in the preparation of herbicides, which are essential for controlling unwanted plant growth in agricultural fields and maintaining crop productivity.
Used in Chemical Synthesis:
TETRAHYDRO-PYRAN-3-OL is used as a building block in the synthesis of various organic compounds, including pyrazolothiazole compounds, which have potential applications in different industries such as pharmaceuticals and agrochemicals.

Synthesis Reference(s)

The Journal of Organic Chemistry, 35, p. 2282, 1970 DOI: 10.1021/jo00832a038

InChI:InChI=1/C5H10O2/c6-5-2-1-3-7-4-5/h5-6H,1-4H2

Upstream product

• 1204-56-4 diacetoxy-2,3 tetrahydropyranne 
• 6790-38-1 1,2-epoxy-3-vinylpropane 
• 110-87-2 3,4-dihydro-2H-pyran 
• 27999-93-5 3-tetrahydropyranyl brosylate 
• 64-19-7 acetic acid 
• 78870-52-7 (1SR,6RS)-3,7-dioxa-bicyclo[4.1.0]heptane 
• 14697-46-2 1,2,5-pentanetriol 
• 23462-75-1 5,6-dihydro-2H-pyran-3(4H)-one 

Downstream Products

• 129888-63-7 tetrahydro-2H-pyran-3-yl methanesulfonate 
• 23462-75-1 5,6-dihydro-2H-pyran-3(4H)-one 
• 87011-11-8 3-Phenylmethoxytetrahydropyran 
• 14697-46-2 1,2,5-pentanetriol 
• 1239611-86-9 rac-[1-(4-chloro-phenyl)-2-oxo-2-[4-(tetrahydro-pyran-3-yloxy)-phenyl]-ethyl]-carbamic acid tert-butyl ester 
• 873397-34-3 racemic tetrahydropyran-3-carboxylic acid 
• 1305321-54-3 3-({2-[(benzyloxycarbonyl)amino]-3-phenylpropanoyl}-amino)tetrahydropyran-3-carboxylic acid 
• 89464-26-6 tetrahydropyran-3-carbonitrile 
• 1305321-47-4 N-methyl-N-phenyltetrahydropyran-3-carboxamide 
• 1305321-48-5 N-methyl-N-phenyltetrahydropyran-3-thiocarboxamide 
• 1305321-46-3 N-methyl-N-phenyl-5-oxa-1-azaspiro[2.5]oct-1-en-2-amine 
• 1305321-49-6 N-{3-[(N-methyl-N-phenylamino)thioxomethyl]tetrahydropyran-3-yl}benzamide 

Relevant academic research and scientific papers

Hydroxynitrile lyase catalysed synthesis of heterocyclic (R)- and (S)-cyanohydrins

Heterocyclic saturated five- and six-membered ring ketones sometimes bearing a methyl substituent were reacted with HCN under enzyme catalysis using recombinant hydroxynitrile lyase from Hevea brasiliensis, as a rule (S)-selective, and Prunus amygdalus, (R)-selective. The resulting cyanohydrins were stereochemically characterised. The steric outcome of these transformations was interpreted by molecular modelling. The resulting cyanohydrins were stereochemically characterised and the mechanistic course of the transformations interpreted by molecular modelling.

Hydroboration of Prochiral Olefins with Chiral Lewis Base-Borane Complexes: Relationship to the Mechanism of Hydroboration

Alcohols with up to 19percent enantiomeric excess were obtained on hydroboration/oxidation of representative prochiral olefins using N-isobornyl-N-methylaniline-borane or N-benzyl-N-isopropyl-α-methylbenzylamine-borane indicating that the Lewis base is present in the hydroboration transition state.

Preparation method of 3-hydroxy tetrahydropyran

The invention provides a preparation method of 3-hydroxy tetrahydropyran. The method comprises the following steps: S1, adding an ether solvent, 3,4-dihydro-2H-pyran and alkali metal borohydride into a reaction flask, performing stirring, performing heating to 40-50 DEG C, dropwise adding a mixed solution of protonic acid or ester thereof and the ether solvent, and performing reaction for 8-24 hours while keeping the temperature at 30-60 DEG C; S2, sampling GC, and controlling the content of a raw material 3,4-dihydro-2H-pyran in the GC to be less than 10%; and S3, cooling to room temperature, padding a diatomite, performing filtering, washing a filter cake, dropwise adding a sodium hydroxide solution into filtrate, performing stirring, dropwise adding 30% hydrogen peroxide at a temperature of less than 45 DEG C, performing stirring while keeping the temperature at40-45 DEG C, adding a saturated sodium thiosulfate solution in batches, performing stirring, cooling to 30 DEG C, performing standing for layering, extracting a water layer with an ether solvent, combining organic layers, performing concentration under reduced pressure to remove the solvent, performing distillation under reduced pressure, and performing rectifying to obtain a 3-hydroxy tetrahydropyran product. According to the method, the yield reaches 60%, the purity reaches 99%, a borane-like compound is prepared from the alkali metal hydroboron, the price is low, the use of flammable and expensive borane is avoided, the risk is low, the operation is simple, and the method is suitable for batch production and has obvious economic benefits.

Substituted pyridine compound and its method and use thereof

The invention relates to a novel substitutive pyridine compound, and a pharmaceutically acceptable salt and a pharmaceutical preparation of the substitutive pyridine compound for regulating the activity of protein kinases and regulating signal responses between cells or in the cells. Meanwhile, the invention further relates to a pharmaceutical composition containing the compound provided by the invention, and a method for treating high proliferative diseases of mammals, especially human with the pharmaceutical composition.

Method for synthesizing tetrahydro-2H-pyran-3-one and key intermediates thereof

The invention discloses a method for synthesizing tetrahydro-2H-pyran-3-one and key intermediates thereof. The method is characterized by comprising the following steps: a, dissolving a compound I in anhydrous tetrahydrofuran under nitrogen protection, cooling to 0 DEG C, dropwise adding a borane-tetrahydrofuran complex to maintain the temperature of about 0 DEG C, stirring for 2 hours, dropwise adding an aqueous solution of NaOH at room temperature, dropwise adding hydrogen peroxide after dropwise adding completion, controlling the temperature to be 50 DEG C or less, stirring at room temperature for 10 hours after dropwise adding completion so as to obtain a compound II; and b, dissolving the compound II in dichloromethane, adding sodium acetate and TEMPO, adding sodium dichloro isocyanurate in batches at the temperature of below 30 DEG C, maintaining the temperature of 30 DEG C for 2 hours, thereby obtaining a compound III. According to the method disclosed by the invention, 3,4-dihydro-2H-pyran is selected as an initial raw material, the key intermediate tetrahydro-2H-pyran-3-ol of tetrahydro-2H-pyran-3-one is prepared through a hydroboration-oxidation method, and the tetrahydro-2H-pyran-3-ol is oxidized so as to obtain the tetrahydro-2H-pyran-3-one. The synthetic method is simple in operation and readily available in raw materials and can be applicable to large-scale industrial production.

N-methyl-N-phenyl-5-oxa-1-azaspiro[2.5]oct-1-en-2-amine - Synthesis and reactions of a synthon for AN UNKNOWN α-AMINO ACID

The synthesis of the heterospirocyclic amino azirine N-methyl-N-phenyl-5- oxa-1-azaspiro[2.5]oct-1-en-2-amine (6a) was achieved from 3,4-dihydro-2H-pyrane (7) via N-methyl-N-phenyltetrahydropyran-3-thiocarboxamide (11). The reactions of 6a with thiobenzoic acid and Z-Phe-OH, respectively, leading to the corresponding 3-benzoylaminotetrahydropyran-3-thiocarboxamide (13) and the diastereoisomeric dipeptide amides (14), respectively, demonstrate that 6a is a valuable synthon for the hitherto unknown 3-aminotetrahydropyrane-3-carboxylic acid. The structure of 13 was established by X-Ray crystallography. The Japan Institute of Heterocyclic Chemistry.

PYRAZINE COMPOUNDS AS PHOSPHODIESTERASE 10 INHIBITORS

Pyrazine compounds, and compositions containing them, and processes for preparing such compounds. Provided herein also are methods of treating disorders or diseases treatable by inhibition of PDE10, such as obesity, non-insulin dependent diabetes, schizophrenia, bipolar disorder, obsessive-compulsive disorder, and the like.

AMINOPYRIDINE AND CARBOXYPYRIDINE COMPOUNDS AS PHOSPHODIESTERASE 10 INHIBITORS

Pyridine and pyrimidine compounds: or a pharmaceutically acceptable salt thereof, wherein m, n, R1, R2, R3, R4, R5, R6, R7, X1, X2, X3, X4, X5, X6, X7, X8, and Y are as defined in the specification; or a pharmaceutically acceptable salt thereof, wherein ring A, m, n, y, R2, R3, R4, R5, R6, R7, R8, R9, X1, X2, and ring A are as defined in the specification; and or a pharmaceutically acceptable salt thereof, wherein m, n, y, R2, R3, R4, R5, R6, R7, R9, X1, X2, and ring A are as defined in the specification; compositions containing them, and processes for preparing such compounds. Provided herein also are methods of treating disorders or diseases treatable by inhibition of PDE10, such as obesity, non-insulin dependent diabetes, schizophrenia, bipolar disorder, obsessive-compulsive disorder, and the like.

Enhancement of cyclic ether formation from polyalcohol compounds in high temperature liquid water by high pressure carbon dioxide

Cyclic ethers were produced by a dehydration reaction of polyalcohol compounds in high temperature liquid water, which was accelerated by the presence of carbon dioxide dissolved in the water. 3-hydroxytetrahydrofuran was produced by the dehydration of 1,2,4-butanetriol. Both tetrahydrofurfuryl alcohol and 3-hydroxytetrahydropyran were produced by the dehydration of 1,2,5-pentanetriol. Five-membered cyclic ethers were formed faster than six-membered cyclic ethers and the formation rates of the cyclic ethers depended strongly on the structure of the polyalcohol compounds. The position of the hydroxyl groups is crucial for the efficient intramolecular dehydration.

Thermodynamic equilibria between polyalcohols and cyclic ethers in high-temperature liquid water

Thermodynamic equilibrium constants between polyalcohols and cyclic ethers in water at 573 K were determined by measuring their concentrations after the long-term reaction in a batch reactor. Intramolecular dehydration reactions of polyalcohols were important for conversion of biomass-derived carbohydrates; however, the yields of products were limited by thermodynamic equilibria between polyalcohols and products. All the thermodynamic equilibrium constants were estimated by the long-term dehydration reaction of 1 mol ·dm-3 polyalcohol aqueous solutions at 573 K. The thermodynamic equilibrium constants between butanepolyols or pentanepolyols and five-membered or six-membered cyclic ethers were within a range from (39 to 337) mol ·dm-3.