590-37-4

Usage

Uses

Used in Chemical Synthesis:
2-METHYLPENT-4-YN-2-OL is utilized as a solvent and an intermediate in the production of various chemicals, playing a crucial role in the synthesis of pharmaceuticals and agricultural chemicals. Its versatility in chemical reactions makes it a valuable component in the development of new compounds.
Used in Pharmaceutical Industry:
In the pharmaceutical sector, 2-METHYLPENT-4-YN-2-OL is used as a building block for the creation of new medicinal agents. Its unique properties allow it to be integrated into the structures of potential drugs, contributing to the advancement of pharmaceutical research and development.
Used in Fragrance Industry:
2-METHYLPENT-4-YN-2-OL also finds application in the fragrance industry, where its mild and slightly sweet odor is harnessed to create or enhance the scent profiles of various perfumes and scented products.
Used in Research and Development:
This organic compound is employed in research and development settings to explore its potential in creating new chemical entities. Its use in this context aids in the discovery and innovation of novel applications across different industries.

InChI:InChI=1/C6H10O/c1-4-5-6(2,3)7/h1,7H,5H2,2-3H3

Upstream product

• 106-96-7 propargyl bromide 
• 67-64-1 acetone 
• 28750-44-9 2-chloromethylene-1,1-dimethyl-cyclopropane 
• 18295-60-8 allenylmagnesium bromide 
• 22665-30-1 allenylzinc bromide 
• 60-29-7 diethyl ether 
• 123-91-1 1,4-dioxane 
• 79015-61-5 2-methyl-5-trimethylsilanyl-pent-4-yn-2-ol 
• 558-30-5 2-methyl-1,2-epoxypropane 
• 1066-26-8 sodium acetylide 
• 18295-60-8 propargyl magnesium bromide 

Downstream Products

• 819-71-6 4-Methylpent-4-en-1-yne 
• 1595-53-5 4-methylpent-3-en-1-yne 
• 16176-79-7 all-trans-OH-Spirilloxanthin 
• 34255-08-8 spirilloxanthin 
• 141-79-7 4-methyl-pent-3-en-2-one 
• 624-97-5 2-methylpent-4-en-2-ol 

Relevant academic research and scientific papers

Synthesis and absolute stereochemistry of spiroacetals in rove beetles (Coleoptera: Staphylinidae)

The unusual branched-carbon chain spiroacetal, 2,2,8-trimethyl-1,7-dioxaspiro[5.5]undecane, has been synthesised as its racemate and (6S,8R)-isomer. The natural compound, identified in the rove beetle, Ontholestes murinus (L.) proved to be the (6R,8S)-isomer. (E,E)-2,8-Dimethyl-1,7-dioxaspiro[5.5]undecane, a major component of the volatiles from the same insect, is the (2S,6R,8S)-isomer, but is largely racemic in Ontholestes tesselatus (Geoffr. Fourcr.).

Synthesis of Cyclopropanes via 1,3-migration of acyloxy groups triggered by formation of α-Imino Rhodium Carbenes

A novel and highly efficient synthetic approach to cyclopropanes was realized via 1,3-migration of acyloxy groups triggered by α-imino rhodium carbenes. Excellent chemoselectivity ensured broad compatibility of common functional groups. Merits such as readily available substrates, mild reaction conditions, and time-saving processes qualified this transformation as an attractive alternative strategy to synthesize multifunctionalized cyclopropanes. Primary investigations and discussion on the mechanism are presented.

Enantioselective Construction of Tertiary Fluoride Stereocenters by Organocatalytic Fluorocyclization

1,1-Disubstituted styrenes with internal oxygen and nitrogen nucleophiles undergo oxidative fluorocyclization reactions with in situ generated chiral iodine(III)-catalysts. The resulting fluorinated tetrahydrofurans and pyrrolidines contain a tertiary carbon-fluorine stereocenter. Application of a new 1-naphthyllactic acid-based iodine(III)-catalyst allows the control of tertiary carbon-fluorine stereocenters with up to 96% ee. Density functional theory calculations are performed to investigate the details of the mechanism and the factors governing the stereoselectivity of the reaction.

Catalytic Transformations of Alkynes into either α-Alkoxy or α-Aryl Enolates: Mannich Reactions by Cooperative Catalysis and Evidence for Nucleophile-Directed Chemoselectivity

The catalytic formation of gold enolates from alkynes, nitrones, and nucleophiles is described, and their Mannich reactions result in nucleophile-directed chemoselectivity through cooperative catalysis. For 1-alkyn-4-ols and 2-ethynylphenols, their gold-catalyzed nitrone oxidations afforded N-containing dihydrofuran-3(2H)-ones with syn selectivity. The mechanism involves the Mannich reactions of gold enolates with imines through an O-H-N hydrogen-bonding motif. For aryloxyethynes, their gold enolates react selectively with nitrones to deliver 3-alkylidenebenzofuran-2-ones, as controlled by a C-H-O hydrogen-bonding motif.

1,4-Dihydroindeno[1,2-c]pyrazoles with acetylenic side chains as novel and potent multitargeted receptor tyrosine kinase inhibitors with low affinity for the hERG ion channel

The synthesis of a novel series of 1,4-dihydroindeno[1,2-c]pyrazoles with acetylene-type side chains is described. Optimization of those compounds as KDR kinase inhibitors identified 8, which displayed an oral activity in an estradiol-induced murine uterine edema model (ED50 = 3 mg/kg) superior to Sutent (ED50 = 9 mg/kg) and showed potent antitumor efficacy in an MX-1 human breast carcinoma xenograft tumor growth model (tumor growth inhibition = 90% at 25 mg/kg·day po). The compound was docked into a homology model of the homo-tetrameric pore domain of the hERG potassium channel to identify strategies to improve its cardiac safety profile. Systematic interruption of key binding interactions between 8 and Phe656, Tyr652, and Ser624 yielded 90, which only showed an IC50 of 11.6 μM in the hERG patch clamp assay. The selectivity profile for 8 and 90 revealed that both compounds are multitargeted receptor tyrosine kinase inhibitors with low nanomolar potencies against the members of the VEGFR and PDGFR kinase subfamilies.

FUNGAL CELL WALL SYNTHESIS GENE

A reporter system reflecting the transport process that transports GPI-anchored proteins to the cell wall was constructed and compounds inhibiting this process were discovered. Further, genes conferring resistance to the above compounds were identified and methods of screening for compounds that inhibit the activity of the proteins encoded by these genes were developed.Therefore, through the novel compounds, the present invention showed that antifungal agents having a novel mechanism, i.e. inhibiting the process that transports GPI-anchored proteins to the cell wall, could be achieved.

Synthesis and stereochemistry of insect derived spiroacetals with branched carbon skeletons

About thirty constitutionally different spiroacetals have been characterised from insects but only three have branched carbon skeletons. Two are based on the 1,7-dioxaspiro[5.5]undecane system and are certain stereoisomers of the 2,4,8-trimethyl derivative, from the aposematic shield bug, Cantao parentum (White), and a 2,2,8-trimethyl derivative from the rove beetle, Ontholestes murinus (L). The 1,6-dioxaspiro[4.5]decane system is represented by a stereoisomer of the 2,3,7-trimethyl derivative in the Cantao species. The elucidation of their structures and stereochemistry by spectroscopy, synthesis and enantioselective gas chromatography is described.

SYNTHESE D'ALCOHOLS α-ALLENIQUES PAR REACTION D'ORGANOCHROMIQUES PROPARGYLIQUES SUR LES ALDEHYDES ET LES CETONES

Propargylic bromides can be condensed with aldehydes and ketones in the presence of Hiyama's reagent (2CrCl3+LiAlH4 in THF) leading to α-allenic alcohols, to homopropargylic alcohols or to the mixture of both of them.The selectivity (or specificity) of this reaction depends on the substitution of the propargylic bromide, on the structure of the ketone, and on the presence of HMPT in the reaction mixture.In many cases, α- allenic alcohol has been specifically or very selectively obtained.The mechanism of the reaction and the influence of the various parameters are discussed.