50675-18-8

Usage

Uses

Used in Pharmaceutical Industry:
Tetrahydropyran-4-carbaldehyde is used as a key intermediate in the synthesis of heterocyclic compounds for pharmaceutical applications. These heterocyclic compounds are essential in the development of new drugs and therapeutic agents, targeting a wide range of medical conditions.
Used in Chemical Industry:
In the chemical industry, Tetrahydropyran-4-carbaldehyde serves as a versatile building block for the creation of various organic compounds. Its aldehyde functional group allows for a wide range of chemical reactions, making it a valuable component in the synthesis of complex molecules and materials.
Used in Research and Development:
Tetrahydropyran-4-carbaldehyde is also utilized in research and development settings, where it is employed to study the properties and reactivity of heterocyclic compounds. This knowledge contributes to the advancement of chemical science and the discovery of novel applications for these compounds.

InChI:InChI=1/C6H10O2/c7-5-6-1-3-8-4-2-6/h5-6H,1-4H2

Upstream product

• 185-72-8 1,6-dioxa-spiro[2.5]octane 
• 5435-44-9 (E)-3-Ureido-but-2-enoic acid ethyl ester 
• 40191-32-0 tetrahydro-2H-pyran-4-carbonylchloride 
• 14774-37-9 (tetrahydro-2H-pyran-4-yl)methanol 
• 101765-10-0 tetrahydro-4-(methoxymethylene)-2H-pyran 
• 2081-44-9 Tetrahydro-pyran-4-ol 
• 110238-91-0 tetrahydropyran-4-carboxylic acid methyl ester 
• 6192-52-5 p-toluenesulfonic acid monohydrate 
• 144-55-8 sodium hydrogencarbonate 
• 50-00-0 formaldehyd 
• 96835-17-5 ethyl tetrahydro-2H-pyran-4-carboxylate 
• 5337-03-1 tetrahydro-2H-pyran-4-carboxylic acid 
• 29943-42-8 Tetrahydro-4H-pyran-4-one 
• 4295-99-2 tetrahydro-2H-pyran-4-carbonitrile 

Downstream Products

• 99228-16-7 tetrahydropyran-4-yl-acrylic acid ethyl ester 
• 265108-10-9 2-(tetrahydro-pyran-4-ylmethylene)-malononitrile 
• 5337-03-1 tetrahydro-2H-pyran-4-carboxylic acid 
• 1057333-60-4 [1-cyano-2-(tetrahydro-pyran-4-yl)-vinyl]-phosphonic acid diethyl ester 
• 1800345-36-1 (S)-(tetrahydro-2H-pyran-4-yl)(phenyl)methanol 
• 1800345-36-1 (R)-(tetrahydro-2H-pyran-4-yl)(phenyl)methanol 
• 40191-32-0 tetrahydro-2H-pyran-4-carbonylchloride 
• 639468-72-7 phenyl(tetrahydro-2H-pyran-4-yl)methanone 
• 216087-92-2 rac-(tetrahydro-2H-pyran-4-yl)(phenyl)methanol 
• 582299-19-2 2-hydroxy-1-phenyl-2-(3,4,5,6-tetrahydro-2H-pyran-4-yl) ethan-1-one 
• 582299-04-5 2-oxo-2-phenyl-1-(3,4,5,6-tetrahydro-2H-pyran-4-yl)ethyl 4-methylbenzene-1-sulfonate 
• 99197-84-9 ethyl 3-(3,4,5,6-tetrahydro-2H-pyran-4-yl) propionate 
• 99197-88-3 ethyl 2-oxo-4-(3,4,5,6-tetrahydro-2H-pyran-4-yl)butyrate 
• 99198-19-3 3(S)-[1(S)-carboxy-3-(3,4,5,6-tetrahydro-2H-pyran-4-yl)propyl]amino-4-oxo-2,3,4,5-tetrahydro-1,5-benzoxazepine-5-acetic acid 

Relevant academic research and scientific papers

SULFONYL-SUBSTITUTED BICYCLIC COMPOUND WHICH ACTS AS ROR INHIBITOR

Provided is a sulfonyl-substituted bicyclic compound (A) which acts as a RORγ inhibitor, said compound has good RORγ inhibitory activity and is expected to be used for treating diseases mediated by a RORγ receptor in mammals.

Axial-to-Central Chirality Transfer for Construction of Quaternary Stereocenters via Dearomatization of BINOLs

All-carbon quaternary stereocenters are versatile building blocks, and their asymmetric construction has attracted much attention. Herein, we disclose an axial-to-central chirality transfer strategy for the synthesis of chiral quaternary stereocenters via dearomatization of (S)-BINOLs. The reaction proceeded smoothly with a wide range of propargyl carbonates to afford chiral spiro-compounds in high yields with excellent enantioselectivities. In addition, the strategy was extended to kinetic resolution of rac-BINOLs albeit with moderate s value.

Synthesis method of 4-ethynyl-tetrahydropyran or 4-ethynyl piperidine

The invention relates to the technical field of organic synthesis. For solving the problems that a conventional synthesis method of 4-ethynyl-tetrahydropyran and 4-ethynyl piperidine is complex in operation, high in cost and unsuitable for industrial production in the prior art, the invention provides a synthesis method of 4-ethynyl-tetrahydropyran or 4-ethynyl piperidine, wherein the synthesis method comprises the following steps: carrying out Wittig reaction on carbonyl of a compound represented by the formula (I) and phosphorus ylide salt under the action of a strong alkali to generate a compound represented by the formula (II), wherein the reaction temperature is 0-50 DEG C; (2) hydrolyzing the compound represented by the formula (II) to generate a compound represented by the formula (III), wherein the reaction temperature is 20-60 DEG C; (3) carrying out a Corey-Fuchs reaction on the compound represented by the formula (III) to obtain a compound represented by the formula (IV), wherein the reaction temperature is -20 to 40 DEG C; and (4) carrying out a reaction of the compound represented by the formula (IV) with a strong alkali, and carrying out a reaction with a silica reagent to generate a compound represented by the formula (V), wherein the reaction temperature is -70 to 20 DEG C. The method has the advantages of simple and accessible raw materials, low cost, simple synthesis steps and high yield, and is suitable for laboratory small-scale preparation and industrial production.

Reduction of N,N-Dimethylcarboxamides to Aldehydes by Sodium Hydride–Iodide Composite

A new and concise protocol for selective reduction of N,N-dimethylamides into aldehydes was established using sodium hydride (NaH) in the presence of sodium iodide (NaI) under mild reaction conditions. The present protocol with the NaH-NaI composite allows for reduction of not only aromatic and heteroaromatic but also aliphatic N,N-dimethylamides with wide substituent compatibility. Retention of α-chirality in the reduction of α-enantioriched amides was accomplished. Use of sodium deuteride (NaD) offers a new step-economical alternative to prepare deuterated aldehydes with high deuterium incorporation rate. The NaH-NaI composite exhibits unique chemoselectivity for reduction of N,N-dimethylamides over ketones.

Polysubstituted-indazole compounds and application of same as IDO inhibitors

The invention discloses polysubstituted-indazole compounds as shown in a formula (I) which is described in the specification, a preparation method for the compounds, and application of the compounds as IDO inhibitors. The compounds provided by the invention can be used for preventing and/or treating a plurality of diseases, such as Alzheimer's disease, cataract, infections related to cellular immune activation, autoimmune diseases, AIDS, cancers, depression, the metabolic disorder of tryptophan or the like.

Aromatic-ring-containing compound, preparation method thereof, pharmaceutical composition and application thereof

The invention discloses an aromatic-ring-containing compound, a preparation method thereof, a pharmaceutical composition and application. The present invention provides the aromatic-ring-containing compound represented by a formula 1, a pharmaceutically acceptable salt thereof, a stereoisomer thereof, a tautomer thereof or a solvate thereof, and the aromatic-ring-containing compound can be effectively bounded to bromodomains of BRD4, BRD3, BRD2, and BRDT in BET family to regulate transcription of downstream gene c-myc and related target genes of the c-myc so as to regulate downstream signalingpathways to play specific roles including treatment of diseases such as inflammatory diseases, cancer, and AIDS. Some of the compounds have high activity, and have good cell activity and metabolic stability, so that the compounds can be an effective drug for treating tumors.

Photochemical Homologation for the Preparation of Aliphatic Aldehydes in Flow

Cheap and readily available aqueous formaldehyde was used as a formylating reagent in a homologation reaction with nonstabilized diazo compounds, enabled by UV photolysis of bench-stable oxadiazolines in a flow photoreactor. Various aliphatic aldehydes were synthesized along with the corresponding derivatized alcohols and benzimidazoles. No transition-metal catalyst or additive was required to affect the reaction, which proceeded at room temperature in 80 min.

METHODS OF MAKING AND USING PDE9 INHIBITORS

The present invention relates to PDE9 inhibitors, their synthesis, and their use for treatment of benign prostate hyperplasia, beta thalassemia, and sickle cell disease.

Metal-free one-pot α-carboxylation of primary alcohols

An efficient metal-free procedure for the formal α-carboxylation of primary alcohols has been developed. The method involves a one-pot oxidation/Passerini/hydrolysis sequence and provides access to α-hydroxy acids bearing a broad range of functional groups. A minor modification to the reaction conditions extends the range of accessible products to α-hydroxy esters.

Difluorocyclobutylacetylenes as positive allosteric modulators of mGluR5 with reduced bioactivation potential

Schizophrenia is a serious illness that affects millions of patients and has been associated with N-methyl-D-aspartate receptor (NMDAR) hypofunction. It has been demonstrated that activation of metabotropic glutamate receptor 5 (mGluR5) enhances NMDA receptor function, suggesting the potential utility of mGluR5 positive allosteric modulators (PAMs) in the treatment of schizophrenia. Herein we describe the optimization of an mGluR5 PAM by replacement of a phenyl with aliphatic heterocycles and carbocycles as a strategy to reduce bioactivation in a biaryl acetylene chemotype. Replacement with a difluorocyclobutane followed by further optimization culminated in the identification of compound 32, a low fold shift PAM with reduced bioactivation potential. Compound 32 demonstrated favorable brain uptake and robust efficacy in mouse novel object recognition (NOR) at low doses.