7299-55-0

Usage

Uses

Used in Chemical Synthesis:
Pent-3-yn-2-one is used as a chemical intermediate for the synthesis of various organic compounds, such as pharmaceuticals, agrochemicals, and specialty chemicals. Its unique triple bond and ketone functional groups make it a versatile building block in organic synthesis.
Used in Flavor and Fragrance Industry:
Pent-3-yn-2-one is used as a flavoring agent and a fragrance ingredient due to its ability to impart specific aromas and tastes to various products. Its chemical reactivity allows for the creation of unique and complex scents and flavors.
Used in Material Science:
Pent-3-yn-2-one is used as a precursor in the development of advanced materials, such as polymers and coatings, that exhibit unique properties, such as high thermal stability and resistance to degradation. Its reactive nature enables the formation of novel materials with tailored characteristics for specific applications.

InChI:InChI=1/C5H6O/c1-3-4-5(2)6/h1-2H3

Upstream product

• 98135-76-3 methyl-(1-methylene-but-2-ynyl)-ether 
• 590-14-7 1-bromo-1-propene 
• 57984-70-0 Pent-3-yn-2-ol 
• 74142-35-1 ethyl-(1-methylene-but-2-ynyl)-ether 
• 627-21-4 2-Pentyne 
• 108-24-7 acetic anhydride 
• 74-99-7 prop-1-yne 
• 64-17-5 ethanol 
• 74142-33-9 1-(1-Propinyl)vinyl-triflat 
• 75-89-8 2,2,2-trifluoroethanol 
• 83182-16-5 (Z)-3-phenylsulphinyl-4-trimethylsilylpent-3-en-2-one 
• 83182-19-8 (E)-3-phenylsulphinyl-4-trimethylsilylpent-3-en-2-one 
• 71870-52-5 2-(2-Methylcyclopropyl)-3-pentin-2-ol 
• 6224-91-5 trimethyl(prop-1-ynyl)silane 

Downstream Products

• 67-51-6 3,5-dimethyl-1H-pyrazole 
• 107-87-9 2-Pentanone 
• 123-54-6 acetylacetone 
• 102369-89-1 1-(2-methyl-cyclohexa-1,4-dienyl)-ethanone 
• 23157-63-3 (1-hydroxy-1-methyl-but-2-ynyl)-phosphonic acid dimethyl ester 
• 61858-84-2 5-Acetyl-3-aethyl-4-methylisoxazol 
• 80992-51-4 (2R,3R,4S)-2,3,4-Trimethyl-2-prop-1-ynyl-oxetane 
• 80992-51-4 (2R,3R,4R)-2,3,4-Trimethyl-2-prop-1-ynyl-oxetane 
• 80992-50-3 (2S,3S)-2,3,5-Trimethyl-4-vinyl-2,3-dihydro-furan 
• 80992-50-3 (2R,3S)-2,3,5-Trimethyl-4-vinyl-2,3-dihydro-furan 
• 80992-51-4 (2S,3R,4S)-2,3,4-Trimethyl-2-prop-1-ynyl-oxetane 
• 85336-13-6 Cyclohexyl-[1-methyl-but-2-yn-(Z)-ylidene]-amine 
• 110258-85-0 (-)-(R)-p-tolylsulfinyl-1 methyl-2 pentene-1(Z) yne-3 
• 110258-91-8 (-)-(R)-p-tolylsulfinyl-1 methyl-2 pentene-1(E) yne-3 

Relevant academic research and scientific papers

Oxidative methoxycarbonylation of propyne and allene with carbon monoxide and methanol in the presence of copper-palladium catalyst

A direct oxidative methoxycarbonylation of propyne with carbon monoxide in methanol medium in the presence of copper-palladium catalytic system results in methyl 2-butynoate in 18-31% yield. Depending on reaction conditions allene provides either a mixture of methyl 2-(chloromethyl)acrylate and methyl 2-(methoxymethyl)acrylate (～3-4:1) in overall yield 16-23%, or methyl 2-(methoxymethyl)acrylate in 19% yield.

Covalent Adaptable Networks with Tunable Exchange Rates Based on Reversible Thiol–yne Cross-Linking

The design of covalent adaptable networks (CANs) relies on the ability to trigger the rearrangement of bonds within a polymer network. Simple activated alkynes are now used as versatile reversible cross-linkers for thiols. The click-like thiol–yne cross-linking reaction readily enables network synthesis from polythiols through a double Michael addition with a reversible and tunable second addition step. The resulting thioacetal cross-linking moieties are robust but dynamic linkages. A series of different activated alkynes have been synthesized and systematically probed for their ability to produce dynamic thioacetal linkages, both in kinetic studies of small molecule models, as well as in stress relaxation and creep measurements on thiol–yne-based CANs. The results are further rationalized by DFT calculations, showing that the bond exchange rates can be significantly influenced by the choice of the activated alkyne cross-linker.

Stereoselective Synthesis of the C1-C22 Carbon Framework of (-)-Amphidinolide K

Two stereoselective routes to the C7-C22 subunit of amphidinolide K are disclosed. Jacobsen's hydrolytic kinetic resolution and Sharpless' asymmetric dihydroxylation reactions have been employed for the construction of the tetrahydrofuran ring. The C10-C1

CARM1 INHIBITORS AND USES THEREOF

Provided herein are compounds of Formula (I): and pharmaceutically acceptable salts thereof, and pharmaceutical compositions thereof; wherein X, R1, R1a, R2a, R2b, R2c, R2d, are as defined herein, and Ring HET is a 6-membered monocyclic heteroaryl ring system of Formula: wherein L2, R13, G8, G10, G11, and G12 are as defined herein. Compounds of the present invention are useful for inhibiting CARMl activity. Methods of using the compounds for treating CARMl -mediated disorders are also described.

Spectroscopy and Photochemistry of Triplet 1,3-Dimethylpropynylidene (MeC3Me)

Photolysis (λ > 472 nm) of 2-diazo-3-pentyne (11) affords triplet 1,3-dimethylpropynylidene (MeC3Me, 33), which was characterized spectroscopically in cryogenic matrices. The infrared, electronic absorption, and electron paramagnetic resonance spectra of MeC3Me (33) are compared with those of the parent system (HC3H) to ascertain the effect of alkyl substituents on delocalized carbon chains of this type. Quantum chemical calculations (CCSD(T)/ANO1) predict an unsymmetrical equilibrium structure for triplet MeC3Me (33), but they also reveal a very shallow potential energy surface. The experimental IR spectrum of triplet MeC3Me (33) is best interpreted in terms of a quasilinear, axially symmetric structure. EPR spectra yield zero-field splitting parameters that are typical for triplet carbenes with axial symmetry (|D/hc| = 0.63 cm-1, |E/hc| = β 0 cm-1), while theoretical analysis suggests that the methyl substituents confer significant spin polarization to the carbon chain. Upon irradiation into the near-UV electronic absorption (λmax 350 nm), MeC3Me (33) undergoes 1,2-hydrogen migration to yield pent-1-en-3-yne (4), a photochemical reaction that is typical of carbenes bearing a methyl substituent. This facile process apparently precludes photoisomerization to other interesting C5H6 isomers, in contrast to the rich photochemistry of the parent C3H2 system.

Total synthesis of hematoporphyrin and protoporphyrin; A conceptually new approach

The total synthesis of protoporphyrin IX and its disodium salt using a new alternative method to the classical MacDonald condensation is reported. The key step is the reaction of the new unsymmetrical diiodo dipyrrylmethane 1 with the known dipyrrylmethane 2. Coupling of the two fragments leads directly to porphyrin 3 without the need of an oxidizing agent. The new methodology is well suited for the synthesis of protoporphyrin IX derivatives on a multi-100 g scale in good quality without the need for chromatography. Furthermore, these preparations are completely free of any contaminant of animal origin, which represents a real improvement in the manufacturing of protoporphyrin IX derivatives. Schweizerische Chemische Gesellschaft.

Total synthesis of carolacton, a highly potent biofilm inhibitor

Metals are the key players in the synthesis of caralacton, a strong inhibitor of bacterial biofilms. The total synthesis is based on several metal-mediated key transformations such as the Ley and the Duthaler-Hafner aldol reactions, the Marshall reaction and Breit's substitution, as well as the Nozaki-Hiyama-Kishi and Negishi-Fu C-C coupling reactions. Copyright

Total synthesis of hematoporphyrin and protoporphyrin: A conceptually new approach

The total synthesis of protoporphyrin IX and its disodium salt using a new alternative method to the classical MacDonald condensation is reported. The key step is the reaction of the new unsymmetrical diiodo dipyrrylmethane 1 with the known dipyrrylmethane 2. Coupling of the two fragments leads directly to porphyrin 3 without the need of an oxidizing agent. The new methodology is well suited for the synthesis of protoporphyrin IX derivatives on a multi 100 g scale in good quality without the need for chromatography. Furthermore, these preparations are completely free of any contaminant of animal origin, which represents a real improvement in the manufacturing of protoporphyrin IX derivatives.

Palladium(II)-catalyzed dicarboxymethylation of chiral allylic alcohols: Chirality transfer affording optically active diesters containing three contiguous chiral centers

This manuscript describes the extension of Stille's palladium-catalyzed olefin dicarbonylation reaction to chiral allylic alcohols with chirality transfer to afford the corresponding chiral alcohol functionalized with bis-carbomethoxy esters, containing three contiguous chiral centers, in good to excellent diastereoselectivities (78-98%).

Catalytic enantioselective construction of β-quaternary carbons via a conjugate addition of cyanide to β,β-disubstituted α,β-unsaturated carbonyl compounds

The first general catalytic enantioselective conjugate addition of cyanide to β, β-disubstituted α,β-unsaturated ketones and N-acylpyrroles was developed using a strontium catalyst derived from Sr(O iPr)2 and new chiral ligand 5. The reaction exhibited excellent enantioselectivity and a wide substrate scope using 0.5-10 mol % catalyst. 1,4-Adducts containing β-quaternary carbons were exclusively produced over 1,2-adducts. ESI-MS analysis of the strontium catalyst indicated that the active catalyst was a trimetallic Sr/5 = 3:5 complex. The exclusive 1,4-selectivity was partly due to the ability of the strontium complex to promote both a retro-cyanation reaction from the 1,2-adducts and highly enantioselective conjugate cyanation.