24247-53-8

Usage

InChI:InChI=1/C4H5BrO/c1-2-4(5)3-6/h2-3H,1H3/b4-2-

Upstream product

• 50553-14-5 2,3-dibromo-butyraldehyde 
• 127-09-3 sodium acetate 
• 98551-14-5 2-bromo-crotonaldehyde diethylacetal 
• 19147-46-7 4,5-dibromo-hex-2-enoic acid 
• 123-73-9 crotonaldehyde 
• 25798-85-0 1,1,3-triethoxy-2-bromo-butane 
• 67-66-3 chloroform 
• 7726-95-6 bromine 
• 10028-15-6 ozone 
• 74322-77-3 trans-1-Morpholinobutadien 
• 83769-15-7 (2-Bromo-3,3-dihydroxy-1-methyl-propyl)-dimethyl-sulfonium; bromide 
• 123-73-9 trans-Crotonaldehyde 
• 98551-14-5 (Z)-2-bromo-1,1-diethoxy-2-butene 
• 15798-64-8 cis-crotonaldehyde 

Downstream Products

• 1453-58-3 3-Methylpyrazole 
• 52467-65-9 (Z)-2-bromobut-2-en-1-ol 
• 19762-47-1 2-bromo-crotonaldehyde-(2,4-dinitro-phenylhydrazone) 
• 2591-86-8 N-Formylpiperidine 
• 105098-71-3 α-piperidinocrotonaldehyde 
• 22039-42-5 1,2-dipiperidino-ethene 
• 114746-02-0 1,2-Dipiperidinoethylen 

Relevant academic research and scientific papers

Synthese regioselective par voie organometallique de vinylsilanes fonctionnels a partir de derives carbonyles α-ethyleniques α-trimethylsilyles

The α-trimethylsilyl conjugated carbonyl derivatives 1 easily react with organometallics 2 (M = Al, Mg, Zn) and allow preparation of functional vinylsilanes 3 or 4, in regioselective manner: R'-CH C(SiMe3)-C(OH)(R')(R) 3; (R')(R)CH-C(SiMe3)C(R')(OSiMe3) 4.

Studies towards total synthesis of antillatoxin: Investigation of the indium-mediated allylation reactions of carbonyl compounds with β-bromocrotylbromide in water

Indium mediates the coupling of β-bromocrotylbromide with carbonyl compounds in saturated ammonium chloride in the presence of lanthanide triflate under sonication to give the corresponding compounds in good yield and moderate to high syn diastereoselecti

Enantioselective NHC-Catalyzed [3+3] Annulation of α-Bromoenals with 2-Aminobenzimidazoles

A chiral carbene-catalyzed [3+3] annulation of α-bromoenals with 2-aminobenzimidazoles providing pyrimido[1,2-a]benzimidazoles has been described. This protocol features a broad scope and good functional group tolerance. Biological studies indicated that the formed pyrimido[1,2-a]benzimidazole exhibited moderate cytotoxic activity against tumor cells.

Catalytic Enantioselective [2+2] Cycloaddition of α-Halo Acroleins: Construction of Cyclobutanes Containing Two Tetrasubstituted Stereocenters

A catalytic enantioselective formal [2+2] cycloaddition between α-halo acroleins and electronically diverse arylalkenes is described. In the presence of (S)-oxazaborolidinium cation as the catalyst, densely functionalized cyclobutanes containing two vicin

Reactions of α-haloacroleins with azides: Highly regioselective synthesis of formyl triazoles

A general metal-free route to 1,4-disubstituted and 1,4,5-trisubstituted 1,2,3-triazoles was developed. α-Haloacroleins reacted with organic azides in a DMSO/H2O mixture solvent at room temperature to produce 1,4-disubstituted triazoles (up to 99%) with exclusive regioselectivities. This protocol is convenient and scalable with a broad substrate scope including aliphatic and aromatic azides. The resulting triazoles exhibited an aldehyde group at the C4 position and demonstrated synthetic utilizations. One 1,2,3-triazole compound containing diastereotopic protons was also identified.

N-Heterocyclic Carbene-Catalyzed β-Indolylation of α-Bromoenals with Indoles

An unprecedented example of NHC-catalyzed β-indolylation of α-bromoenals with indoles has been developed. This concise protocol features several advantages (mild reaction conditions, broad substrate scope) and constructs synthetically useful building blocks, namely β-biaryl methylene esters. Notably, the β-biaryl methylene-type fragment is widely found in natural products or pharmaceuticals. (Figure presented.).

N-Heterocyclic Carbene-Catalyzed Enantioselective β-Amination of α-Bromoenals Enabled by a Proton-Shuttling Strategy

An unprecedented enantioselective NHC-catalyzed β-amination of α-bromoenals with o-benzodiamines was developed by utilizing a proton-shuttling strategy. This formal [4+3] annulation protocol yielded the corresponding 1,5-benzodiazepines in high yields with excellent enantioselectivities. The obtained optically active 1,5-benzodiazepines as building blocks and pharmacophores should be useful in the synthesis of other valuable molecules or in drug discovery.

Sequential O-Arylation/Lanthanide(III)-Catalyzed [3,3]-Sigmatropic Rearrangement of Bromo-Substituted Allylic Alcohols

Lanthanide(III)-catalyzed aryl-Claisen rearrangement of substrates bearing halo-substituted allyl groups, specifically 2-bromoallyl aryl ethers, afford ortho -2-bromoallylphenols. Aryl ether substrates were synthesized from brominated allylic alcohols via Mitsunobu reaction, Cu(II)-catalyzed arylation using potassium aryltrifluoroborate salts, or S N Ar reaction. Aryl-Claisen rearrangements proceeded in moderate to excellent yields using Eu(III) catalysis. The alkenylbromide functionality remains intact, illustrating the compatibility of synthetically important alkenylhalides during C-O/C-C σ-bond migration processes. Subsequent derivatization of the ortho -2-bromoallylphenol products through O-alkylation or C-arylation/alkenylation via Suzuki-Miyaura cross-coupling demonstrate the potential to access densely-functionalized molecules.

Syntheses of strychnine, norfluorocurarine, dehydrodesacetylretuline, and valparicine enabled by intramolecular cycloadditions of Zincke aldehydes

A full account of the development of the base-mediated intramolecular Diels-Alder cycloadditions of tryptamine-derived Zincke aldehydes is described. This important complexity-generating transformation provides the tetracyclic core of many indole monoterpene alkaloids in only three steps from commercially available starting materials and played a key role in short syntheses of norfluorocurarine (five steps), dehydrodesacetylretuline (six steps), valparicine (seven steps), and strychnine (six steps). Reasonable mechanistic possibilities for this reaction, a surprisingly facile dimerization of the products, and an unexpected cycloreversion to regenerate Zincke aldehydes under specific conditions are also discussed.

Enantioselective Diels-Alder reaction of α-(acylthio)acroleins: A new entry to sulfur-containing chiral quaternary carbons

A catalytic and enantioselective Diels-Alder reaction of α-(carbamoylthio)acroleins induced by an organoammonium salt of chiral triamine is described. α-(Carbamoylthio)acroleins are designed and synthesized as new sulfur-containing dienophiles for the fir