7796-73-8

Basic information

• Product Name: 3,3-DIMETHYL-4-PENTENOIC ACID
• Synonyms: 3,3-DIMETHYLPENT-4-ENOIC ACID;3,3-DIMETHYL-4-PENTENOIC ACID;AKOS 365
• CAS NO: 7796-73-8
• Molecular Formula: C₇H₁₂O₂
• Molecular Weight: 128.17
• Mol File: 7796-73-8.mol
• Article Data: 22

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 3,3-DIMETHYL-4-PENTENOIC ACID(CAS DataBase Reference)
• NIST Chemistry Reference: 3,3-DIMETHYL-4-PENTENOIC ACID(7796-73-8)
• EPA Substance Registry System: 3,3-DIMETHYL-4-PENTENOIC ACID(7796-73-8)

Safety Data

• Hazardous Substances Data: 7796-73-8(Hazardous Substances Data)

Usage

Description

3,3-Dimethyl-4-pentenoic acid is a chemical compound characterized by its molecular formula C7H12O2. It is a colorless liquid with a distinctive fruity odor, and is primarily produced through chemical synthesis rather than being commonly found in nature. 3,3-DIMETHYL-4-PENTENOIC ACID is recognized for its low toxicity and is generally regarded as safe for use in various applications, including food and cosmetic products.

Uses

Used in Food and Beverage Industry:
3,3-Dimethyl-4-pentenoic acid is utilized as a flavoring agent, imparting a fruity aroma and taste to food and beverage products. Its unique scent and flavor profile make it a valuable ingredient in enhancing the sensory experience of various consumables.
Used in Perfumery:
In the perfume industry, 3,3-Dimethyl-4-pentenoic acid serves as a key component in creating complex and appealing fragrances. Its fruity odor contributes to the development of scents that can be used in a wide range of perfumes, colognes, and other olfactory products.
Used as a Chemical Intermediate:
3,3-Dimethyl-4-pentenoic acid also plays a crucial role as a chemical intermediate in the synthesis of other compounds. Its chemical properties make it a versatile building block for the production of various chemical substances, contributing to the development of new materials and products across different industries.

Upstream product

• 556-82-1 3-methyl-2-buten-1-ol 
• 802294-64-0 propionic acid 
• 78-39-7 Triethyl orthoacetate 
• 758-66-7 diethyl 2-(2-methylbut-3-en-2-yl)malonate 
• 21079-27-6 diethyl 2-(1,1-dimethyl-2-propynyl)malonate 
• 7796-72-7 ethyl 3,3-dimethylpent-4-enoate 
• 62535-33-5 1-diazo-5-methyl-hex-4-en-2-one 
• 63721-05-1 methyl 3,3-dimethyl-4-penteneoate 
• 6802-75-1 diethyl isopropylidenemalonate 

Downstream Products

• 81310-19-2 (2R,5R)-3,3-Dimethyl-7-oxo-1-aza-bicyclo[3.2.0]heptane-2-carbaldehyde 
• 81310-20-5 (2R,5R)-3,3-Dimethyl-7-oxo-1-aza-bicyclo[3.2.0]heptane-2-carboxylic acid benzyl ester 
• 81310-22-7 2,2,4a,7,7-Pentamethyl-1,2,3,4,4a,5,6,7-octahydro-[1,8]naphthyridine; compound with (2R,5R)-3,3-dimethyl-7-oxo-1-aza-bicyclo[3.2.0]heptane-2-carboxylic acid 
• 1427450-05-2 5-(fluoromethyl)-4,4-dimethyl-1-phenylpyrrolidin-2-one 
• 121190-28-1 3,3-dimethyl-pent-4-enoic acid phenylamide 
• 1268994-81-5 N-(6,6,7,7,8,8,9,9,10,10,11,11,11-tridecafluoro-3,3-dimethyl-undecyl)-benzenamine 

Relevant articles and documents

Extended Hydrogen Bond Networks for Effective Proton-Coupled Electron Transfer (PCET) Reactions: The Unexpected Role of Thiophenol and Its Acidic Channel in Photocatalytic Hydroamidations

Preorganization and aggregation in photoredox catalysis can significantly affect reactivities or selectivities but are often neglected in synthetic and mechanistic studies, since the averaging effect of flexible ensembles can effectively hide the key activation signatures. In addition, aggregation effects are often overlooked due to highly diluted samples used in many UV studies. One prominent example is Knowles's acceleration effect of thiophenol in proton-coupled electron transfer mediated hydroamidations, for which mainly radical properties were discussed. Here, cooperative reactivity enhancements of thiophenol/disulfide mixtures reveal the importance of H-bond networks. For the first time an in-depth NMR spectroscopic aggregation and H-bond analysis of donor and acceptor combined with MD simulations was performed revealing that thiophenol acts also as an acid. The formed phosphate-H+-phosphate dimers provide an extended H-bond network with amides allowing a productive regeneration of the photocatalyst to become effective. The radical and acidic properties of PhSH were substituted by Ph2S2 and phosphoric acid. This provides a handle for optimization of radical and ionic channels and yields accelerations up to 1 order of magnitude under synthetic conditions. Reaction profiles with different light intensities unveil photogenerated amidyl radical reservoirs lasting over minutes, substantiating the positive effect of the H-bond network prior to radical cyclization. We expect the presented concepts of effective activation via H-bond networks and the reactivity improvement via the separation of ionic and radical channels to be generally applicable in photoredox catalysis. In addition, this study shows that control of aggregates and ensembles will be a key to future photocatalysis.

Synthesis of 5-[(Pentafluorosulfanyl)methyl]-γ-butyrolactones via a Silver-Promoted Intramolecular Cyclization Reaction

The synthesis of 5-[(pentafluorosulfanyl)methyl]-γ-butyrolactones bearing different substituents at position 3 or 4 is reported. A silver-promoted intramolecular cyclization of substituted 4-chloro-5-(pentafluorosulfanyl)pentanoic acids allows the preparation of the substituted SF5-containing γ-butyrolactones in up to 96 % yield.

Rapid Access to Thiolactone Derivatives through Radical-Mediated Acyl Thiol-Ene and Acyl Thiol-Yne Cyclization

A new synthetic approach to thiolactones that employs an efficient acyl thiol-ene (ATE) or acyl thiol-yne (ATY) cyclization to convert unsaturated thiocarboxylic acid derivatives into thiolactones under very mild conditions is described. The high overall yields, fast kinetics, high diastereoselectivity, excellent regiocontrol, and broad substrate scope of these reaction processes render this a very useful approach for diversity-oriented synthesis and drug discovery efforts. A detailed computational rationale is provided for the observed regiocontrol.