33414-62-9

Usage

Uses

Used in Organic Synthesis:
2-(Tetrahydrofuran-2-yl)acetonitrile is utilized as a building block in the synthesis of more complex organic molecules. Its unique structure, which includes the tetrahydrofuran ring and the cyano group, makes it a valuable intermediate in the creation of a variety of compounds.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, 2-(Tetrahydrofuran-2-yl)acetonitrile is used as a key intermediate for the synthesis of various drug molecules. Its versatility in forming different types of chemical bonds and its reactivity make it a preferred choice for developing new pharmaceutical compounds.
Used in Chemical Research:
2-(Tetrahydrofuran-2-yl)acetonitrile is also employed in academic and industrial research settings for studying the properties and reactions of nitriles and tetrahydrofuran-containing compounds. Its unique structure allows researchers to explore new reaction pathways and mechanisms, potentially leading to the discovery of novel chemical processes and applications.

InChI:InChI=1/C6H9NO/c7-4-3-6-2-1-5-8-6/h6H,1-3,5H2

Upstream product

• 1192-30-9 tetrahydrofurfuryl bromide 
• 151-50-8 potassium cyanide 
• 5371-52-8 2-hydroxytetrahydrofuran 
• 2537-48-6 diethyl 1-cyanomethylphosphonate 
• 773837-37-9 sodium cyanide 
• 34583-63-6 rac-(tetrahydrofuran-2-yl)methyl 4-methylbenzenesulfonate 
• 72641-13-5 tetrahydro-2-furanmethanol methanesulfonate (ester) 
• 97-99-4 Tetrahydrofurfuryl alcohol 

Downstream Products

• 116349-04-3 (6S)-(-)-methyl 6,8-dihydroxyoctanoate 
• 98277-97-5 2-(tetrahydrofuran-2-yl)ethylamine 
• 2434-00-6 (tetrahydro-furan-2-yl)-acetic acid 

Relevant academic research and scientific papers

INDOLIZINE DERIVATIVES WHICH ARE APPLICABLE TO NEURODEGENERATIVE DISEASES

The present invention relates to indolizine compounds, and pharmaceutically acceptable compositions thereof, useful as antagonists of P2X7, and for the treatment of P2X7-related disorders.

A metal-ligand cooperative pathway for intermolecular oxa-michael additions to unsaturated nitriles

An unprecedented catalytic pathway for oxa-Michael addition reactions of alcohols to unsaturated nitriles has been revealed using a PNN pincer ruthenium catalyst with a dearomatized pyridine backbone. The isolation of a catalytically competent Ru-dieneamido complex from the reaction between the Ru catalyst and pentenenitrile in combination with DFT calculations supports a mechanism in which activation of the nitrile through metal-ligand cooperativity is a key step. The nitrile-derived Ru-N moiety is sufficiently Br?nsted basic to activate the alcohol and initiate conjugate addition of the alkoxide to the α,β-unsaturated fragment. This reaction proceeds in a concerted manner and involves a six-membered transition state. These features allow the reaction to proceed at ambient temperature in the absence of external base.

[3 + 2] Cycloreversion of Bicyclo[m.3.0]alkan-3-on-2-yl-1-oxonium Ylides to Alkenyloxyketenes. Stereospecific Aspect

Rhodium(II)-catalyzed intramolecular reaction of diazoketones 1 bearing a cyclic ethereal moiety transiently formed bicyclo[m.3.0]octan-3-one-1-oxonium-2-ylides (2), which underwent sigmatropic and stereospecific [3 + 2] cycloreversion reaction to form alkenyloxyketenes 3. The ketenes were efficiently trapped by methanol to form the corresponding esters 4. Mechanistic studies revealed that the size of ethereal ring can be variable at least from THF to the THP, oxepane, and oxocane moiety, i.e., m = 3-6. On the other hand, the size of the ylide ring containing the carbonyl unit is limited to a five-membered ring. The cycloreversion was found to be stereospecific as was proven by the reactions of diastereoisomeric pairs bearing a methyl group at the bond-cleaving position. From threo isomers 7, (E)-alkenyloxyacetates 15 were exclusively formed (77-84%), whereas from erythro isomers 8, (Z)-isomers 16 were formed (80-88%). Mechanism of the cleavage from diazoacetonyl-substituted cyclic ethers to alkenyloxyketenes via bicyclic oxonium ylides was analyzed on the basis of calculations employing the hybrid density functional B3LYP and the highly correlated quadratic configuration interaction QCISD method to reveal that the concerted [3 + 2] cycloreversion is the key step of this reaction.

Pyrimidine derivatives as IL-8 receptor antagonists

Compounds containing the pyrimidine nucleus and their use to treat diseases and conditions related to inappropriate Interleukin-8 receptor activity are disclosed. The compounds are of the formula I In these compounds, Q is preferably unsubstituted and substituted heterocyclyl; U is usually hydrogen or fluorine; and V is preferably hydrogen, halogen, alkyl, —O—alkyl or —S-alkyl. A representative example is:

Chemoenzymatic Synthesis of Methyl (6S)-(-)-6,8-Dihydroxyoctanoate: A Precursor to (R)-(+)-α-Lipoic Acid

A short synthetic sequence for the preparation of methyl (6S)-(-)-6,8-dihydroxyoctanoate, the precursor to (R)-(+)-α-lipoic acid is described starting from (2S)-(+)-2-(tetrahydro-2-furyl)ethanol.

Synthesis of some 2-cyanomethyltetrahydrofuran and 2-cyanomethyltetrahydropyran derivatives

2-cyanomethyltetrahydrofuran and 2-cyanomethyltetrahydropyran derivatives, useful in the synthesis of 3(5)-aminopyrazoles and 5-aminoisoxazoles have been prepared starting from corresponding lactones, via DIBAL-H reduction to lactols, and olefination by Wittig reaction to α, β-unsatured cyanoderivatives. These undergo instantaneous cyclization to tetrahydrofuran and tetrahydropyran derivatives.

Substituted hexahydropyrrolo[1,2-a]-quinolines, hexahydro-1H-pyrido[1,2-a]-q

Tricyclic benzo fused compounds of the formula STR1 and pharmaceutically acceptable cationic and acid addition salts thereof, wherein n is zero, 1 or 2, and t is 1 or 2; M is CH or N, R1 is H or certain acyl groups; Q is CO2 R4, COR5, C(OR7)R5 R6, CN, CONR9 R10, CH2 NR9 R10, CH2 NHCOR11, CH2 NHSO2 R12, 5-tetrazolyl or when n is 1, Q and OR1 together form a lactone or certain reduced derivatives thereof; and Z is certain alkyl, alkoxy, alkoxyalkyl, aralkyl, aralkoxy, aryloxyalkyl or aralkoxyalkyl groups, are valuable central nervous system active agents, methods for their use, pharmaceutical compositions containing them and certain intermediates therefor.