147600-17-7

Usage

Uses

Used in Organic Synthesis:
(R)-2-HYDROXY-3-METHYL-3-BUTENENITRILE is used as an intermediate in the production of various pharmaceuticals and agrochemicals, playing a crucial role in the synthesis of these compounds.
Used in Pharmaceutical Research:
In the pharmaceutical industry, (R)-2-HYDROXY-3-METHYL-3-BUTENENITRILE is used as a building block in the synthesis of complex organic molecules, contributing to the development of new drugs and therapeutic agents.
Used in Chiral Ligand Preparation:
(R)-2-HYDROXY-3-METHYL-3-BUTENENITRILE is also employed in the preparation of chiral ligands, which are essential in asymmetric catalysis and the synthesis of enantiomerically pure compounds.
Used in Biological Activity and Pharmacological Property Studies:
Furthermore, (R)-2-HYDROXY-3-METHYL-3-BUTENENITRILE has been studied for its potential biological activities and pharmacological properties, indicating its importance in the field of chemistry and pharmaceutical research.

Upstream product

• 78-85-3 2-methylpropenal 
• 7677-24-9 trimethylsilyl cyanide 
• 143-33-9 sodium cyanide 
• 74-90-8 hydrogen cyanide 

Downstream Products

• 4450-34-4 4-chloro-3-methyl-2-butenenitrile 
• 123810-33-3 2-chloro-3-methyl-3-butenenitrile 

Relevant academic research and scientific papers

α-Pinene-type chiral Schiff bases as tridentate ligands in asymmetric addition reactions

A group of tridentate Schiff bases derived from (+)-α-pinene were synthesized. The steric effects in the transition state, the importance of π-π stacking interactions as well as the electronic effects of aryl aldehydes according to Hammett constant values in the enantioselective addition of Et2Zn to aldehydes with the use of Schiff bases as chiral ligands are described. Also, a variety of aldehydes were cyanated using a catalyst prepared in situ from titanium tetraisopropoxide and chiral Schiff bases. The influence of a conjugated double-bond in the cyanation substrates on enantioselectivity was observed. The chemical structures of the chiral Schiff base-titanium alkoxide complexes are discussed based on their 1H and 13C NMR spectra. 3D models of the Zn2-complex catalyst and Ti-complex catalyst containing α-pinane-type Schiff bases based on X-ray diffraction experiments are postulated. The models presented were consistent with the reported chirality of the addition product and observed ee.

Exploration of the molecular origin of the azinomycin epoxide: Timing of the biosynthesis revealed

(Equation Presented) Streptomyces sahachiroi whole cell feeding experiments, utilizing putative precursors labeled with stable isotopes, established that the epoxide unit of the DNA cross-linked agents, azinomycin A and B, proceeds via a valine-dependent pathway and that hydroxylation and dehydration precedes formation of the terminal epoxide. Sodium 3-methyl-2-oxobutenoate, formed through a transimination reaction, was shown to be the penultimate precursor incorporated into the azinomycin epoxide.

Salicylaldehyde Schiff bases derived from 2-ferrocenyl-2-amino alcohols. Part 1: New chiral ligands for the titanium-catalyzed enantioselective cyanation of aldehydes

The condensation of a set of diversely substituted (S)-2-amino-2-ferrocenyl ethanol derivatives 1a-e with the salicylaldehydes 5A-C resulted in the generation of a small library of new chiral Schiff base-ligands, whose titanium isopropoxide complexes have

Titanium and ruthenium binaphthyl Schiff base complexes as catalysts for asymmetric trimethylsilylcyanation of aldehydes

Investigations on the catalytic behaviour of titanium complexes formed in situ from Ti(OPri)4 and a variety of Schiff bases, mainly the binaphthyl derivatives 2,2′-bis(3-R1-5-R 2-2-hydroxybenzylideneamino)-1,1′-binaphthyl, toward the asymmetric trimethylsilylcyanation of some aromatic and aliphatic aldehydes demonstrated that the titanium complex of the binaphthyl Schiff base with R1 = R2 = But is one of the best catalysts for such a process, with an enantiomeric excess (e.e.) as high as 96% obtained for m-tolualdehyde. Crystal structure determination of a nitrosylruthenium complex, [RuII(L)(NO)Cl] (L is the dianion of the binaphthyl Schiff base with R1 = R2 = Cl), revealed that the complex assumes a cis-β configuration with the binaphthyl moiety having a dihedral angle of 70.2°. After treatment with AgPF6, the ruthenium complex also exhibited a good catalytic property for the trimethylsilylcyanation of benzaldehyde albeit with a lower e.e. (24%). The Royal Society of Chemistry 1999.

Asymmetric Carbon-Carbon Bond Forming Reactions Catalyzed by Chiral Schiff Base-Titanium Alkoxide Complexes

The enantioselective addition of trimethylsilyl cyanide to a variety of aldehydes proceeded by the aid of a catalyst prepared in situ from titanium tetraisopropoxide and chiral Schiff bases and gave the corresponding cyanohydrins in high optical yield (up to 96percent e.e.).A remarkable rate enhancement was brought about by the addition of the Schiff base to the titanium alkoxide mediated silylcyanation of aldehydes.This catalyst system also promoted the highly enantioselective reaction of diketene with aldehydes, which led to the formation of optically active 5-hydroxy-3-oxoesters.

Enantioselective Trimethylsilylcyanation of Some Aldehydes Catalyzed by Chiral Schiff Base-Titanium Alkoxide Complexes

A variety of aldehydes (aromatic, heteroaromatic, α,β-unsaturated, and nonconjugate aliphatic aldehydes) has been trimethylsilylcyanated in highly enantiomeric excess (ee) with a catalyst prepared in situ from titanium tetraisopropoxide and chiral Schiff bases.A remarkable rate enhancement was brought about by the addition of the Schiff base into the titanium alkoxide mediated silylcyanation of aldehydes.The chemical structure of chiral Schiff base-titanium alkoxide complexes is discussed based on their 13C NMR spectra, field desorption (FD) mass spectra, and molecular weights.

A Facile Synthesis of Optically Active γ-Cyanoallylic Alcohols Using Asymmetric Hydrocyanation of α,β-Alkenyl Aldehydes Followed by Stereospecific Sigmatroopic Chirality Transfer of the Cyanohydrin Acetates

Optically active γ-cyanoallylic alcohols were synthesised by using asymmetric hydrocyanation of α,β-alkenyl aldehydes catalyzed by peptide-titanium complex to give α-cyanoallylic alcohols (cyanohydrins) with high optical yields followed by palladium compl

Three-Carbon Annelations. Regiocontrolled Reactivity of Trimethylsilyl- and Ethoxyethyl-Protected Cyanohydrins. Versatile Homoenolate and Acyl Anion Equivalents

The trimethylsilyl- (2) and ethoxyethyl- (4) protected cyanohydrins of α,β-unsaturated aldehydes are utilized as three-carbon annelation reagents.Metalated reagent 2 displays exclusive α reactivity with aldehydes and ketones at -78 deg C.Metalated reagent 4 displays exclusive α reactivity at -78 deg C and exclusive γ reactivity at 0 deg C.Reagent 4 thus allows for complete regiocontrol in its addition to aldehydes and ketones which permits selective addition of either a homoenolate or an acyl anion equivalent.Metalation of the α product 11 at -78 deg C with subsequent warming to 0 deg C produces exclusively the γ product, confirming the reversible nature of the addition to the carbonyl.The derived α '-trimethylsiloxy enones 17 (R3=Me3Si), α '-hydroxy enones 17 (R3=H), α '-acetoxyenones 17 (R3=Ac), and γ-lactones 10 are useful cyclopentenone precursors.Treatment of 17 with p-TsOH in toluene at reflux produces cyclopentenones.The reaction proceeds via the postulated intermediacy of a pentadienyl cation 15 which undergoes in situ electrocyclic ring closure.