3088-44-6

Usage

Uses

Used in Pharmaceutical Industry:
3-allyloxypropionitrile is used as a key intermediate in the synthesis of biologically active compounds due to its unique reactivity. This allows for the creation of a wide range of pharmaceutical products with potential therapeutic applications.
Used in Organic Synthesis:
Beyond its pharmaceutical applications, 3-allyloxypropionitrile also serves as an intermediate in the production of other chemicals, contributing to the broader field of organic synthesis and the development of new chemical entities.
Safety Considerations:
It is important to handle 3-allyloxypropionitrile with care, as it is considered harmful if ingested, inhaled, or absorbed through the skin. Additionally, it may cause irritation to the eyes and skin, necessitating proper safety measures during its use and manipulation.

InChI:InChI=1/C6H9NO/c1-2-5-8-6-3-4-7/h2H,1,3,5-6H2

Upstream product

• 107-18-6 allyl alcohol 
• 107-13-1 acrylonitrile 
• 20907-32-8 sodium allyloxide 

Downstream Products

• 22577-15-7 3-(allyloxy)propionic acid 
• 55629-55-5 3-<3-(Methylphenylsilyl)-propoxy>-propionitril 
• 55629-61-3 3-[3-(Ethyl-phenyl-silanyl)-propoxy]-propionitrile 
• 55629-56-6 3-[3-(Benzyl-methyl-silanyl)-propoxy]-propionitrile 
• 55629-63-5 3-<3-(Diphenylsilyl)-propoxy>-propionitril 
• 55629-59-9 3-{3-[Methyl-((E)-styryl)-silanyl]-propoxy}-propionitrile 
• 55629-57-7 3-[3-(Methyl-phenethyl-silanyl)-propoxy]-propionitrile 
• 55629-58-8 3-{3-[Methyl-(3-phenyl-propyl)-silanyl]-propoxy}-propionitrile 
• 127764-29-8 3-(3-triphenylstannyl-propoxy)-propionitrile 
• 55629-65-7 Acetic acid 3-{[3-(2-cyano-ethoxy)-propyl]-methyl-phenethyl-silanyl}-propyl ester 

Relevant academic research and scientific papers

Electron-rich triarylphosphines as nucleophilic catalysts for oxa-Michael reactions

Electron-rich triarylphosphines, namely 4-(methoxyphenyl)diphenylphosphine (MMTPP) and tris(4-trimethoxyphenyl)phosphine (TMTPP), outperform commonly used triphenylphosphine (TPP) in catalyzing oxa-Michael additions. A matrix consisting of three differently strong Michael acceptors and four alcohols of varying acidity was used to assess the activity of the three catalysts. All test reactions were performed with 1 mol % catalyst loading, under solvent-free conditions and at room temperature. The results reveal a decisive superiority of TMTPP for converting poor and intermediate Michael acceptors such as acrylamide and acrylonitrile and for converting less acidic alcohols like isopropanol. With stronger Michael acceptors and more acidic alcohols, the impact of the more electron-rich catalysts is less pronounced. The experimental activity trend was rationalized by calculating the Michael acceptor affinities of all phosphine-Michael acceptor combinations. Besides this parameter, the acidity of the alcohol has a strong impact on the reaction speed. The oxidation stability of the phosphines was also evaluated and the most electron-rich TMTPP was found to be only slightly more sensitive to oxidation than TPP. Finally, the catalysts were employed in the oxa- Michael polymerization of 2-hydroxyethyl acrylate. With TMTPP polymers characterized by number average molar masses of about 1200 g/mol at room temperature are accessible. Polymerizations carried out at 80°C resulted in macromolecules containing a considerable share of Rauhut-Currier-type repeat units and consequently lower molar masses were obtained.

Preparation method of 3-allyl acrylonitrile

The invention discloses a preparation method of 3-allyl acrylonitrile. The preparation method comprises the following steps: S1, alkalizing materials; S2, performing synthesis reaction; and S3, performing rectification under reduced pressure to obtain the 3-allyl acrylonitrile. The invention provides the preparation method of the 3-allyl acrylonitrile, which is mild in reaction condition, safe, high in synthesis efficiency, low in preparation cost and high in purity of 3-allyl acrylonitrile.

An Enantioselective Cross-Dehydrogenative Coupling Catalysis Approach to Substituted Tetrahydropyrans

An enantioselective cross-dehydrogenative coupling (CDC) reaction to access tetrahydropyrans has been developed. This process combines in situ Lewis acid activation of a nucleophile in concert with the oxidative formation of a transient oxocarbenium electrophile, leading to a productive and highly enantioselective CDC. These advances represent one of the first successful applications of CDC for the enantioselective couplings of unfunctionalized ethers. This system provides efficient access to valuable tetrahydropyran motifs found in many natural products and bioactive small molecules.

A Titanium(III)-Catalyzed Reductive Umpolung Reaction for the Synthesis of 1,1-Disubstituted Tetrahydroisoquinolines

A catalytic reductive C1-acylation of 3,4-dihydroisoquinolines is presented that gives direct access to 1,1-disubstituted tetrahydroisoquinolines. The reaction is a titanium(III)-catalyzed reductive umpolung process in which nitriles act as effective acylation agents. The method is highly chemo- and regioselective and is demonstrated in 20 examples. It is well-suited for the large-scale synthesis of functionalized tetrahydroisoquinoline products, which is exemplified in the form of a six-step synthesis of (±)-3-demethoxyerythratidinone. (Figure Presented).

Preparation of 3-(n-alkenoxy)propanoic acids

3-(n-Alkenoxy)propanoic acids have been prepared by reaction of alkenols with tert-butyl acrylate (catalyzed by Triton B or n-butyl lithium) followed by cleavage of the tert-butyl group by CF3COOH or KO2.