33447-72-2

Usage

Uses

Used in Organic Synthesis:
(R)-3-Buten-2-ol is used as a solvent in organic synthesis for facilitating chemical reactions. Its ability to dissolve a wide range of compounds makes it a versatile component in the synthesis of various organic compounds.
Used in Chemical Production:
(R)-3-Buten-2-ol serves as a precursor for the production of other chemicals. Its role in the synthesis of different chemical entities highlights its importance in the chemical industry.
Used in Flavoring and Fragrance Industry:
In the food and beverage industry, (R)-3-Buten-2-ol is used as a flavoring agent and fragrance. Its distinctive odor and compatibility with various ingredients make it a valuable addition to enhance the sensory experience of food and drink products.
Used in Research and Industrial Applications:
(R)-3-Buten-2-ol is synthesized from various starting materials and is commonly used in research and industrial applications. Its presence in these fields underscores its significance in scientific exploration and the development of new technologies and products.

InChI:InChI=1/C4H8O/c1-3-4(2)5/h3-5H,1H2,2H3/t4-/m1/s1

Upstream product

• 598-32-3 2-hydroxy-3-butene 
• 33447-73-3 phthalic acid mono-(1-methyl-allyl ester) 
• 78-94-4 methyl vinyl ketone 
• 925669-95-0 2,3-cis-epoxybutane 
• 65001-62-9 3-buten-2-yl benzoate 
• 844641-16-3 (S)-threonyl-(S)-phenylglycine 

Downstream Products

• 115692-63-2 (R)-(+)-2-(trans-but-2-enyl)-2-methylcyclohexanone 
• 440356-62-7 (3aS,4R,6aS)-1,4-dimethyltetrahydro-3H,6H-furo[3,4-c]isoxazol-6-one 
• 440356-62-7 (3aR,4R,6aR)-1,4-dimethyltetrahydro-3H,6H-furo[3,4-c]isoxazol-6-one 
• 70218-44-9 (R)-N-(but-3-en-2-yl)benzamide 
• 1307285-89-7 (-)-(R)-but-3-en-2-yl 6-(hept-6-en-1-yl)-2,4-dimethoxybenzoate 

Relevant academic research and scientific papers

An Asymmetric Transformation of Symmetrical Epoxides to Both Enantimers of Allylic Alcohols by Chiral Lithium Amides

Both enantiomers of several optically active allylic alcohols are obtained from cyclic and acyclic symmetrical epoxides by using chiral lithium amides, i.e., lithium cyclohexylmethylamide or lithium (S)-2-pyrrolidide, as bases.

Resolution of allylic alcohols via Copper(I) complexes with a chiral diamine

By using the Corey diamine 1,2-diphenyl-N,N'-bis[(2,4,6- trimethylphenyl)methyl]-1,2-diaminoethane, Copper(I) olefin complexes are prepared. When the olefin is a racemic allylic alcohol, selective coordination of one enantiomer is observed. Cleavage with aqueous HCl or NaCN allows a two-steps resolution affording excellent enantiomeric excess.

Are Highly Stable Covalent Organic Frameworks the Key to Universal Chiral Stationary Phases for Liquid and Gas Chromatographic Separations?

High-performance liquid chromatography (HPLC) and gas chromatography (GC) over chiral stationary phases (CSPs) represent the most popular and highly applicable technology in the field of chiral separation, but there are currently no CSPs that can be used for both liquid and gas chromatography simultaneously. We demonstrate here that two olefin-linked covalent organic frameworks (COFs) featuring chiral crown ether groups can be general CSPs for extensive separation not only in GC but also in normal-phase and reversed-phase HPLC. Both COFs have the same 2D layered porous structure but channels of different sizes and display high stability under different chemical environments including water, organic solvents, acids, and bases. Chiral crown ethers are periodically aligned within the COF channels, allowing for enantioselective recognition of guest molecules through intermolecular interactions. The COF-packed HPLC and GC columns show excellent complementarity and each affords high resolution, selectivity, and durability for the separation of a wide range of racemic compounds, including amino acids, esters, lactones, amides, alcohols, aldehydes, ketones, and drugs. The resolution performances are comparable to and the versatility is superior to those of the most widely used commercial chiral columns, showing promises for practical applications. This work thus advances COFs with high stability as potential universal CSPs for chromatography that are otherwise hard or impossible to produce.

Tandem Allylboration-Prins Reaction for the Rapid Construction of Substituted Tetrahydropyrans: Application to the Total Synthesis of (-)-Clavosolide A

Tetrahydropyrans are common motifs in natural products and have now been constructed with high stereocontrol through a three-component allylboration-Prins reaction sequence. This methodology has been applied to a concise (13 steps) and efficient (14 % ove

METHOD FOR PRODUCING 3-BUTENE-2-OL

PROBLEM TO BE SOLVED: To provide a method for efficiently producing racemic 3-butene-2-ol having an (S)- or (R)-configuration. SOLUTION: There is provided a method for producing racemic 3-butene-2-ol, wherein an ammonium salt compound represented by the following general formula (1) (wherein, R1, R2 or R3 represents an alkyl group, an aryl group or an aralkyl group; X- represents OH-, HCO3-, CO32-, R4O-, R5CO2-, R6SO3- (R4, R5 or R6 represents an alkyl group, an aryl group or an aralkyl group) and a halide ion; n represents 0.5 when X- is CO32- and n represents 1 when X- is other than CO32-; the carbon atom marked with * is an asymmetric carbon atom) is subjected to Hofmann elimination. COPYRIGHT: (C)2016,JPOandINPIT

Formal synthesis of (R)-(+)-lasiodiplodin

A catalytic approach is reported for the enantioselective synthesis of (R)-(+)-lasiodiplodin methyl ether using asymmetric hetero allylic alkylation as the key step. Georg Thieme Verlag Stuttgart.

Inclusion of aliphatic alcohols in pockets of (S)-threonyl-(S)- phenylglycine using grinding method

Inclusion compounds of a dipeptide, (S)-threonyl-(S)-phenylglycine (Thr-Phg), with several aliphatic alcohols were easily prepared by grinding them in a mortar. Thr-Phg molecules arranged in antiparallel to construct a sheet, and guest alcohols were accommodated in a chiral pocket between the sheets. 3-Butyn-2-ol and 2-butanol were included with moderate enantioselectivity, 57% ee (R) and 49% ee (R), respectively. The role of the hydroxy group of Thr-Phg is not only to construct the unique pocket but also to capture guest alcohols by hydrogen bonding.

The effect of catechin derivatives on the enantioselectivity of lipase-catalyzed hydrolyses of alkynol benzoate esters

Polyphenols, such as (+)-catechin and pyrogallol could be used to enhance stereochemical control in the lipase-catalyzed hydrolysis of alkynol benzoate esters, leading to increased enantioselectivities in the kinetic resolution of alkynols with lipase Amano AH.

Chiral 2,2-Disubstituted Cyclohexanones; Annulation via Claisen Rearrangement Products

The methyl enol ether of 2-methylcyclohexanone reacts regiospecifically with the optical active forms of but-3-yn-2-ol and but-3-en-2-ol. (R)-But-3-yn-2-ol yields an approximately 4:1 mixture of (R)-2-methyl-2-(R-buta-1,2-dienyl)cyclohexanone and the corresponding SR compound.By contrast the but-3-en-2-ol reaction is ca. 96percent enantioselective; (R)-but-3-en-2-ol gives (R)-2-(trans-but-2-enyl)-2-methylcyclohexanone and (S)-but-3-en-2-ol gives the corresponding (S)-cyclohexanone.These Claisen rearrangement products have been transformed into Robinson-type annulated ketones.Cleavage of some highly hindered esters has been carried out efficiently by sodium methylsulphinyl-methanide in dimethyl sulphoxide.

Metal(II) d-Tartarates Catalyzed Asymmetric Ring Opening of Oxiranes with Various Nucleophiles

The asymmetric ring opening of meso-2,3-disubstituted oxiranes with thiols, aniline, and trimethylsilyl azide was studied by the use of metal(II) d-tartarates as heterogeneous chiral Lewis acid catalysts.The enantioselectivity varied widely with the combination of oxirane, nucleophile, and metal(II) d-tartarate, and Zn(II) d-tartarate gave the best enantioselectivity in the respective reactions of 1,2-epoxycyclohexane with 1-butanethiol, aniline, and trimethylsilyl azide to afford the corresponding adducts in 85, 58, and 42 percent ee, respectively.Furthermore, the kinetic resolution of racemic oxiranes with thiols catalyzed by Zn(II) d-tatratate was studied.