2345-51-9

Usage

Uses

Used in Pharmaceutical Industry:
3-Butynoic acid is used as a synthetic intermediate for the production of various pharmaceutical compounds. Its unique structure allows for the synthesis of complex molecules with potential therapeutic applications.
Used in Chemical Synthesis:
3-Butynoic acid is used as a key building block in the synthesis of functionalized γ-butyrolactones and tetrahydrofurans via Conia-ene cyclizations. These cyclizations are important reactions in organic chemistry, enabling the formation of complex ring structures with high levels of control over stereochemistry and functionality.
Used in Organic Chemistry:
3-Butynoic acid is used as a precursor for the synthesis of allenoates, which are valuable intermediates in organic chemistry. These allenoates can undergo [2+2] cycloadditions with alkenes, leading to the formation of cyclobutane derivatives with potential applications in material science and pharmaceuticals.
Used in Natural Product Synthesis:
3-Butynoic acid is used in the phosphine-catalyzed synthesis of highly functionalized coumarins. Coumarins are a class of naturally occurring compounds with a wide range of biological activities, including anticoagulant, anti-inflammatory, and antithrombotic properties. The synthesis of these compounds using 3-butynoic acid allows for the development of new drugs and pharmaceutical agents.
Used in Organometallic Chemistry:
3-Butynoic acid is used in the synthesis of various useful organotin reagents via radical hydrostannation. Organotin compounds have a wide range of applications, including as catalysts, stabilizers, and materials for the production of polymers and bioactive compounds. The hydrostannation of 3-butynoic acid provides a convenient route to these valuable organotin reagents.

InChI:InChI=1/C4H4O2/c1-2-3-4(5)6/h1H,3H2,(H,5,6)

Upstream product

• 927-74-2 3-Butyn-1-ol 
• 10024-18-7 bromoallene 
• 124-38-9 carbon dioxide 
• 463-49-0 1,2-propanediene 
• 2936-44-9 allenyl iodide 
• 106-96-7 propargyl bromide 

Downstream Products

• 32804-66-3 methyl 3-butynoate 
• 53841-07-9 ethyl cyanoacetate 
• 107-92-6 butyric acid 
• 109689-37-4 7-hydroxy-7,7-diphenyl-hepta-3,5-diynoic acid 
• 92024-81-2 6-phenyl-hexa-3,5-diynoic acid 
• 124-38-9 carbon dioxide 
• 74-99-7 prop-1-yne 
• 177659-36-8 N-Methyl-N-prop-2-ynylbut-3-ynamide 
• 31983-44-5 (E)-6-[2-(benzo[1,3]dioxol-5-yl)vinyl]pyran-2-one 
• 32065-58-0 (E)-6-(styryl)pyran-2-one 
• 949448-97-9 C₁₆H₁₆O₅ 
• 949448-99-1 C₁₅H₁₃O₄Br 
• 949449-10-9 2-[(2-benzenesulfonyl)vinyl]phenyl allenoate 
• 949449-11-0 C₁₂H₉NO₄ 

Relevant academic research and scientific papers

Some preparation methods of a tricyclo[4.1.0.02,7]hept-4-en-3-one skeleton

β-Elimination of acetic acid was elaborated in our synthetic method of a tricyclo[4.1.0.02,7]hept-4-en-3-one (tropovalene) skeleton. Presented was a new synthetic method of this skeleton, which consists of a reaction sequence of 1,4-addition of propanethiol to bicyclo[3.2.0]hepta-3,6-dien-2-one, photochemical construction of bicyclobutane skeleton, oxidation, and thermal elimination of sulfenic acid.

Synthesis and helical structures of poly(ω-alkynamide)s having chiral side chains: Effect of solvent on their screw-sense inversion

New ω-alkynamides, (S)-HC≡CCH2CONHCH2CH-(CH3)CH2CH3 (1) and (S)-HC≡CCH2CH2CONHCH-(CH3)CH2CH2CH2CH2CH3 (2) were synthesized and polymerized with a rhodium catalyst in CHCl3 to obtain cis-stereoregular poly(ω-alkynamide)s (poly(1) and poly(2)). Polarimetric, CD, and IR spectroscopic studies revealed that in solution the polymers adopted predominantly one-handed helical structures stabilized by intramolecular hydrogen bonds between the pendent amide groups. This behavior was similar to that of the corresponding poly(N-alkynylamide) counterparts (poly(3) and poly(4)) reported previously, whereas the helical senses were opposite to each other. The helical structures of the poly(ω-alkynamide)s were stable upon heating similar to those of the poly(N-alkynylamide)s, but the solvent response was completely different. An increase in MeOH content in CHCl3/MeOH resulted in inversion of the predominant screw-sense for poly(1) and poly(2). Conversely, poly(3) was transformed into a random coil, and poly(4) maintained the predominant screw-sense irrespective of MeOH content. The solvent dependence of predominant screw-sense for poly(1) and poly(2) was reasonably explained by molecular orbital studies using the conductor-like screening model (COSMO).

Total Syntheses of Atrovenetin and Atrovenetinone: A Naphthalene-Annulation Approach to a Discoid Tricycle Using Allenic Acid

A total synthesis of atrovenetin has been achieved. The discoid tricyclic motif was constructed by a novel three-carbon annulation of naphthalene derivative and allenic acid under acidic conditions. An effective protocol for the conversion of atrovenetin

Allenamides as orthogonal handles for selective modification of cysteine in peptides and proteins

In this study, a remarkably simple and direct strategy has been successfully developed to selectively label target cysteine residues in fully unprotected peptides and proteins. The strategy is based on the reaction between allenamides and the cysteine thiol, and proceeds swiftly in aqueous medium with excellent selectivity and quantitative conversion, thus forming a stable and irreversible conjugate. The combined simplicity and mildness of the process project allenamide as robust and versatile handles to target cysteines and has potential use in biological systems. Additionally, fluorescent-labeling studies demonstrated that the installation of a C-terminal allenamide moiety onto various molecules of interest may supply a new methodology towards the site-specific labeling of cysteine-containing proteins. Such a new labeling strategy may thus open a window for its application in the field of life sciences.

3D-QSAR assisted identification of FABP4 inhibitors: An effective scaffold hopping analysis/QSAR evaluation

Following on the recent publication of pharmacologically relevant effects, small molecule inhibitors of adipocyte fatty-acid binding protein 4 (FABP4) have attracted high interest. FABP4 is mainly expressed in macrophages and adipose tissue, where it regulates fatty acid storage and lipolysis, being also an important mediator of inflammation. In this regard, FABP4 recently demonstrated an interesting molecular target for the treatment of type 2 diabetes, other metabolic diseases and some type of cancers. In the past years, hundreds of effective FABP4 inhibitors have been synthesized. In this paper, a quantitative structure-activity relationship (QSAR) model has been produced, in order to predict the bioactivity of FABP4 inhibitors. The methodology has been combined with a scaffold-hopping approach, allowing to identify three new molecules that act as effective inhibitors of this protein. These molecules, synthesized and tested for their FABP4 inhibitor activity, showed IC50 values between 3.70 and 5.59 μM, with a high level of agreement with the predicted values.

Tandem Regioselective Hydroformylation-Hydrogenation of Internal Alkynes Using a Supramolecular Catalyst

New supramolecular ligands containing an acyl guanidine function were designed based on the strategy of increasing the π-acceptor ability of phosphine ligands by introducing electron-withdrawing groups. By applying this novel catalytic system, a general protocol for the Rh-catalysed hydroformylation-hydrogenation of unsymmetrical internal alkynes, functionalized with a carboxylic acid, was found to furnish aliphatic aldehydes in high regio- and chemoselectivities. Control experiments confirm the enzyme-like supramolecular catalyst mode of action.

3-butynoic acid preparation method

The present invention discloses a 3-butynoic acid preparation method comprising the following steps: (1) magnesium chips and an organic solvent are added into a reaction vessel, propargyl bromide is added dropwise under nitrogen protection, and after the addition is complete, reaction is performed for 40 to 80 minutes at room temperature; excess amount of carbon dioxide is introduced, and heated to 50 DEG C-70 DEG C for reaction for 1 to 3 hours to obtain a reaction solution; (2) the reaction solution is poured into a cooled saturated ammonium chloride aqueous solution, an organic layer is separated by extraction and layering, the organic layer is dried, filtered and concentrated to obtain crude 3-butynoic acid; (3) the crude 3-butynoic acid is recrystallized with methyl tert-butyl ether, and filtered to obtain a crystal, and then the crystal is dried to obtain pure 3-butynoic acid. No water is produced in the preparation of the 3-butynoic acid final product, the 3-butynoic acid purification process is simplified, and the 3-butynoic acid final product is less in impurities and high in purity.

Enantioselective halogenative semi-pinacol rearrangement: Extension of substrate scope and mechanistic investigations

The present Full Paper article discloses a survey of our recent results obtained in the context of the enantioselective halogenation-initiated semi-pinacol rearrangement. Commencing with the fluorination/semi-pinacol reaction first and moving to the heavier halogens (bromine and iodine) second, the scope and limitations of the halogenative phase-transfer methodology will be discussed and compared. An extension of the fluorination/semi-pinacol reaction to the ring-expansion of five-membered allylic cyclopentanols will be also described, as well as some preliminary results on substrates prone to desymmetrization will be given. Finally, the present manuscript will culminate with a detailed mechanistic investigation of the canonical fluorination/semi-pinacol reaction. Our mechanistic discussion will be based on in situ reaction progress monitoring, complemented with substituent effect, kinetic isotopic effect and non-linear behaviour studies.

Catalytic Enantioselective Allenoate-Alkene [2 + 2] Cycloadditions

Catalytic enantioselective [2 + 2] cycloadditions between allenoates and alkenes is disclosed. The method functions well for a variety of alkenes, and the products are generated with excellent levels of enantioselectivity. One of the most significant aspe

ALLENAMIDE AS AN ORTHOGONAL HANDLE FOR SELECTIVE MODIFICATION OF CYSTEINE IN PEPTIDES AND PROTEINS

There is provided a compound of formula I, having the structure: wherein R1 to R5 have the meanings given in the description.