31930-35-5

Upstream product

• 623-47-2 propynoic acid ethyl ester 
• 1263187-14-9 3-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-acrylic acid ethyl ester 
• 86429-06-3 2-Brom-1-(diphenylboryl)-1-ethencarbonsaeure-ethylester 

Downstream Products

• 27829-72-7 ethyl (E)-hex-2-enoate 
• 54340-72-6 ethyl (E)-2-heptenoate 
• 457628-65-8 (2Z)-3-(3,6-difluoro-2-methoxyphenyl)-2-propen-1-ol 
• 1005796-57-5 benzyl (S,E)-2-(3-ethoxy-3-oxoprop-1-enylcarbamoyl)pyrrolidine-1-carboxylate 
• 39924-40-8 ethyl (2E,4Z)-2,4-undeca-2,4-dienoate 
• 1447908-84-0 (E)-3-bromo-1-phenyl-2-propen-1-ol 
• 28991-15-3 (E)-ethyl 3-(4-methoxyphenoxy)acrylate 
• 38112-60-6 (E)-ethyl tetradec-2-enoate 
• 75814-58-3 (Z)-ethyl tetradec-2-enoate 

Relevant academic research and scientific papers

Aliphatic α-Boryl-α-bromoketones: Synthesis and Reactivity

A protocol for the preparation of α-boryl-α-bromoketones from alkenyl MIDA boronates was developed and applied to functionalized aliphatic derivatives. The reaction sequence included regioselective hydroxybromination of olefin moiety, followed by oxidation of alcohol group with Dess–Martin periodinane. The target trifunctional boronate-containing derivatives were obtained in up to 94 % yield over two steps starting from alkenyl MIDA boronates. In some cases, functional groups present in the substrate participated in the bromohydroxylation step via intramolecular nucleophilic attack at the bromonium cation leading to cyclic products. Additionally, the reactivity of aliphatic α-boryl-α-bromoketones was illustrated by nucleophilic substitution at the α-C atom and heterocyclization reactions.

Boration Reactions with 1-Alkynes

Halodiorganoboranes R2BHal(R = Et, Ph) as well as benzyldihaloboranes PhCH2BHal2 undergo a regiospecific addition to the triple-bond of 1-alkynes ACCR'.The reversible haloboration (1) gives Z-alkenes as the more stable isomers.At elevated temperatures, the irreversible 1,1-organoboration (2) predominates, accompanied by a 1,2-transfer of A, whereas the 1,2-organoboration (3) is observed only as an unimportant side-reaction in a few cases.The cyclisation (4) occurs as a sequence of cis-haloboration and intramolecular aromatic alkenylation in the case of PhCH2BCl2 as borating agent.

Latent Inhibitors. Part 2. Allylic Inhibitors of Alcohol Dehydrogenase

The syntheses of a number of 3-substituted prop-2-en-1-ols and -1-als, required for studying the latent inhibition of horse liver alcohol dehydrogenase (E.C. 1.1.1.1), are described.Substituent were chosen to cover a range of alkoxide, phenolate, thiolate