182743-63-1

Usage

Uses

Used in Pharmaceutical Production:
2,3-Pentadien-1-ol, 4-(4-methoxyphenyl)is utilized as a key intermediate in the synthesis of various pharmaceuticals. Its unique structural features and reactivity contribute to the development of new drug candidates with potential therapeutic applications.
Used in Flavoring Industry:
2,3-Pentadien-1-ol, 4-(4-methoxyphenyl)is also employed in the creation of flavorings, where its chemical properties can be harnessed to produce distinct and desirable tastes in food and beverage products.
Used in Organic Synthesis:
2,3-Pentadien-1-ol, 4-(4-methoxyphenyl)serves as a versatile building block in organic synthesis, allowing chemists to construct a wide range of complex chemical compounds for various applications.
Used in Medicinal Chemistry and Drug Discovery:
Due to its structural features, 2,3-Pentadien-1-ol, 4-(4-methoxyphenyl)may have potential applications in the field of medicinal chemistry, where it could be used in the design and discovery of new drugs with improved efficacy and safety profiles.

Upstream product

• 182743-62-0 4-methoxy-4-(4-methoxyphenyl)pent-2-yn-1-ol 
• 1712-69-2 1-isopropenyl-4-methoxybenzene 
• 182743-61-9 3-methoxy-3-(4-methoxyphenyl)but-1-yne 
• 15960-71-1 rac-2-(4-methoxyphenyl)but-3-yn-2-ol 
• 155096-11-0 4-(4-methoxyphenyl)-2,3-pentadienoic acid ethyl ester 

Downstream Products

• 182743-64-2 Acetic acid 4-(4-methoxy-phenyl)-penta-2,3-dienyl ester 

Relevant academic research and scientific papers

The Aminium Salt and Photoinduced Electron Transfer Initiated Diels-Alder Cycloaddition of Electron-Rich Allenes: Evidence for a Stepwise Mechanism and the Importance of Steric and Electronic Effects for the Reactivity of Distonic Radical Cation Intermediates

Several novel electron-rich arylallenes have been synthesized, characterized, and used as dienophiles in the radical-cation-catalyzed cycloaddition with 1,2,3,4,5-pentamethylcyclopentadiene, which affords, in most cases, the Diels-Alder products in 5 min at 0 deg C with a high peri-, chemo-, facial, and stereoselectivity.In line with oxidation-potential considerations it is concluded that the electron-transfer-induced reaction proceeds along a pathway by cycloaddition of the diene radical cation to a neutral allene with a rather short chain length.The low cycloaddition yields from some of the allenes are interpreted as evidence for a stepwise mechanism involving distonic radical cations as key intermediates.We discuss the tendency of the distonic radical cations to undergo ring closure to the Diels-Alder-product radical cations in terms of enthalpy considerations, which, we suggest, offer a novel criterion for the design of stepwise radical cation reactions. - Keywords: allenes; cycloadditions; Diels-Alder reactions; mechanistic studies; radical cations

Cation Radical Catalyzed Diels-Alder Reaction of Electron-Rich Allenes

The cation radical catalyzed cycloaddition of electron-rich arylallenes 1a-e with 1,2,3,4,5-pentamethylcyclopentadiene (2a) afforded the Diels-Alder products 3 and 4 at 0 deg C in 5 min with a high chemoselectivity, facial selectivity, and stereoselectivity.From the results of various mechanistic tests, it is inferred that the electron transfer induced reaction proceeds via a pathway by cycloaddition of the diene cation radical to a neutral allene 1 exhibiting a rather short chain length.However, with electron-withdrawing substituents at the remote end of the allene functionality, the cycloaddition is only a minor reaction path.With diarylallene 1f and diene 2a or 2b, no cycloaddition but formation of products 7 and d1-7 occured.It is concluded that distonic cation radicals may be intermediates in a stepwise formal Diels-Alder reaction induced by electron transfer.