27451-36-1

Usage

Uses

Used in Pharmaceutical and Agrochemical Industries:
1-cyano-2-hydroxy-3-butene is utilized as a key intermediate in the synthesis of various pharmaceuticals and agrochemicals, contributing to the development of new drugs and pesticides.
Used in Asymmetric Synthesis:
1-cyano-2-hydroxy-3-butene is employed in the preparation of chiral aminoalcohol derivatives, which are essential in asymmetric synthesis for creating enantiomerically pure compounds, a critical aspect in the production of many pharmaceuticals.
Synthesis Process:
1-cyano-2-hydroxy-3-butene can be synthesized through the reaction of acrylonitrile with formaldehyde in the presence of a base, providing a practical method for producing this valuable compound.
Safety Considerations:
Given its moderate toxicity, 1-cyano-2-hydroxy-3-butene should be handled with care to ensure the safety of individuals involved in its production and use.

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 

Downstream Products

• 87487-96-5 5-amino-1-pentene-3-ol 
• 6071-81-4 (2S)-1-cyano-2-hydroxy-3-butene 
• 6071-81-4 (R)-3-hydroxy-4-pentenenitrile 
• 38996-05-3 (S)-3-hydroxy-4-pentenoic acid 
• 38996-04-2 (R)-3-hydroxy-4-pentenoic acid 
• 98900-30-2 cis-2-hydroxymethyl-3-hydroxypyrrolidine hydrochloride 
• 126861-76-5 (2R,3R)-3-Hydroxy-2-hydroxymethyl-pyrrolidine-1-carboxylic acid benzyl ester 
• 126861-77-6 (2R,3R)-3-Hydroxy-2-methyl-pyrrolidine-1-carboxylic acid benzyl ester 
• 126861-75-4 N-benzyloxycarbonyl-3-hydroxy-4-pentenylamine 

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.

Degradation of 2-Hydroxybut-3-enylglucosinolate (Progoitrin)

Using a model system consisting of synthesized 2-hydroxybut-3-enylglucosinolate and a purified thioglucoside glucohydrolase preparation from Brassica napus, the effects of ascorbate, of Fe2+ and of Cu2+ were examined on the extent and course of glucosinolate degradation.Ascorbate was found to promote thioglucosidase activity to a considerable extent over the whole of the wide range of concentrations studied (0.024-400 mM), with a maximum (activation factor ca 110) at 1.57 mM ascorbate.Fe2+ slightly suppressed reaction, but caused a significant effect by directing degradation to 1-cyano-2-hydroxybut-3-ene rather than to 5-vinyloxazolidine-2-thione, and at low, catalytic, concentrations.Cu2+ had similar effect, but was a strong inhibitor of the reaction.Key Word Index - Glucosinolates; 2-hydroxybut-3-enylglucosinolate; progoitrin; thioglucoside glucohydrolase.