6071-81-4

Usage

Uses

Used in Pharmaceutical Synthesis:
3-hydroxypent-4-enenitrile is used as an intermediate in the pharmaceutical industry for the synthesis of various drugs. Its presence of both hydroxyl and nitrile groups allows for a wide range of chemical reactions, enabling the creation of diverse medicinal compounds.
Used in Organic Compounds Synthesis:
In the field of organic chemistry, 3-hydroxypent-4-enenitrile serves as a key intermediate for the synthesis of other organic compounds. Its functional groups facilitate multiple reaction pathways, contributing to the development of new chemical entities with potential applications in various sectors.
Used in Polymer Production:
3-hydroxypent-4-enenitrile is utilized as a precursor in the production of polymers. Its structural attributes make it suitable for incorporation into polymer chains, potentially enhancing the properties of the resulting polymers and expanding their range of applications.
Used in Industrial Product Manufacturing:
3-hydroxypent-4-enenitrile also finds use as a precursor in the manufacturing of various industrial products. Its versatility and reactivity in chemical processes make it a valuable component in the development of new materials and technologies.

InChI:InChI=1/C5H7NO/c1-2-5(7)3-4-6/h2,5,7H,1,3H2/t5-/m1/s1

Upstream product

• 24928-94-7 3-acetoxy-pent-4-enenitrile 
• 930-22-3 epoxybutene 
• 143-33-9 sodium cyanide 
• 27451-36-1 (RS)-3-hydroxypent-4-enenitrile 
• 15939-26-1 (S)-3-Hydroxy-penten-⁽⁴⁾-thionsaeureamid 

Relevant academic research and scientific papers

Rhodium-Catalyzed Enantioselective Intermolecular Hydroalkoxylation of Allenes and Alkynes with Alcohols: Synthesis of Branched Allylic Ethers

Regio- and enantioselective additions of alcohols to either terminal allenes or internal alkynes provides access to allylic ethers by using a RhI/diphenyl phosphate catalytic system. This method provides an atom-economic way to obtain chiral aliphatic and aryl allylic ethers in moderate to good yield with good to excellent enantioselectivities.

Substrate evaluation of rhodococcus erythropolis SET1, a nitrile hydrolysing bacterium, demonstrating dual activity strongly dependent on nitrile sub-structure

Assessment of Rhodococcus erythropolis SET1, a novel nitrile hydrolysing bacterial isolate, has been undertaken with 34 nitriles, 33 chiral and 1 prochiral. These substrates consist primarily of β-hydroxy nitriles with varying alkyl and aryl groups at the β position and containing in several compounds different substituents α to the nitrile. In the case of β-hydroxy nitriles without substitution at the α position, acids were the major products obtained, along with recovered nitrile after biotransformation, as a result of suspected nitrilase activity of the isolate. Unexpectedly, amides were found to be the major hydrolysis product when the β-hydroxy nitriles possessed a vinyl group at this position. To probe this behaviour further, additional related substrates were evaluated containing electron-withdrawing groups at the α position, and amide was also observed upon biotransformation in the presence of SET1. Therefore this novel isolate has also demonstrated NHase activity with nitriles that appears to be substrate-dependent.

Enantioselective ring opening of epoxides with cyanide catalysed by halohydrin dehalogenases: A new approach to non-racemic β-hydroxy nitriles

Halohydrin dehalogenases (HheA, HheB and HheC) were found to efficiently catalyse a carbon-carbon bond forming reaction between terminal aliphatic epoxides and cyanide, yielding β-hydroxy nitriles. With all three enzymes nucleophilic ring opening of epoxi

Thiacrown Ether Technology in Lipase-Catalyzed Reaction: Scope and Limitation for Preparing Optically Active 3-Hydroxyalkanenitriles and Application to Insect Pheromone Synthesis

Both reaction rate and enantioselectivity in Pseudomonas cepacia lipase (PCL)-catalyzed hydrolysis of 3-hydroxyalkanenitrile acetates were significantly changed by the addition of catalytic amounts of thiacrown ether (1,4,8,11-tetrathiacyclotetradecane). Although the reaction rate of various nitriles was accelerated, the enantioselectivity greatly depended on the nature of the substrate. Among 10 substrates tested, thiacrown ether offered highest enantioselectivity in PCL-catalyzed hydrolysis of 1-(cyanomehtyl)propyl acetate. Forty or more times this crown ether, molarity based on the enzyme, was required to attain an acceptably high reaction rate and enantioselectivity. Applying this technology, we succeeded in synthesizing the optically pure attractant pheromone of ant Myrmica scabrinodis (A), (R)-3-octanol and its antipode of (S)-isomer in good overall yields.