6283-13-2

Upstream product

• 64-04-0 phenethylamine 
• 141-75-3 butyryl chloride 
• 107-92-6 butyric acid 
• 110-69-0 butyraldehyde oxime 
• 123-73-9 crotonaldehyde 
• 623-42-7 butanoic acid methyl ester 
• 109-21-7 butyl butyrate 
• 71-36-3 butan-1-ol 
• 57392-44-6 2,2,2-trichloroethyl butyrate 
• 123-20-6 vinyl n-butyrate 
• 105-54-4 butanoic acid ethyl ester 

Downstream Products

• 23068-45-3 N-Butyl-2-phenylethylamine 
• 7661-37-2 1-propylisoquinoline 

Relevant academic research and scientific papers

Volatiles from the Psychrotolerant Bacterium Chryseobacterium polytrichastri

The flavobacterium Chryseobacterium polytrichastri was investigated for its volatile profile by use of a closed-loop stripping apparatus (CLSA) and subsequent GC-MS analysis. The analyses revealed a rich headspace extract with 71 identified compounds. Compound identification was based on a comparison to library mass spectra for known compounds and on a synthesis of authentic standards for unknowns. Important classes were phenylethyl amides and a series of corresponding imines and pyrroles.

Antagonism of quorum sensing phenotypes by analogs of the marine bacterial secondary metabolite 3-methyl-N-(20-phenylethyl)-butyramide

Quorum sensing (QS) antagonists have been proposed as novel therapeutic agents to combat bacterial infections. We previously reported that the secondary metabolite 3-methyl-N-(20-phenylethyl)-butyramide, produced by a marine bacterium identifie

Facile direct synthesis of amides from trichloroethyl esters using catalytic DBU

A practical method for the direct synthesis of amide compounds is described. Using small quantities of DBU as a catalyst, the direct conversion of 2,2,2-trichloroethyl esters to their corresponding amides was readily achieved. Based on this protocol, various amide compounds were successfully synthesized in high yield, suggesting a promising approach for the practical one-pot aminolysis from 2,2,2-trichloroethyl protected esters.

Biocatalytic N-Acylation of Amines in Water Using an Acyltransferase from Mycobacterium smegmatis

A straightforward one-step biocatalyzed synthesis of different N-acyl amides in water was accomplished using the versatile and chemoselective acyltransferase from Mycobacterium smegmatis (MsAcT). Acetylation of primary arylalkyl amines was achieved with a range of acetyl donors in biphasic systems within 1 hour and at room temperature. Vinyl acetate was the best donor which could be employed in the N-acetylation of a large range of primary amines in excellent yields (85–99%) after just 20 minutes. Other acyl donors (including formyl-, propionyl-, and butyryl-donors) were also efficiently employed in the biocatalytic N-acylation. Finally, the biocatalyst was tested in transamidation reactions using acetamide as acetyl donor in aqueous medium, reaching yields of 60–70%. This work expands the toolbox of preparative methods for the formation of N-acyl amides, describing a biocatalytic approach easy to accomplish under mild conditions in water. (Figure presented.).

Direct Regioselective Synthesis of Tetrazolium Salts by Activation of Secondary Amides under Mild Conditions

Tetrazolium salts are biologically active molecules that have found broad applications in biochemical assays. A regioselective synthesis of tetrazolium salts is described through a formal (3 + 2) cycloaddition. The possibility of employing simple amides and azides as starting material and the mild conditions allow a broad functional group tolerance.

Identification of an Imine Reductase for Asymmetric Reduction of Bulky Dihydroisoquinolines

A new imine reductase from Stackebrandtia nassauensis (SnIR) was identified, which displayed over 25- to 1400-fold greater catalytic efficiency for 1-methyl-3,4-dihydroisoquinoline (1-Me DHIQ) compared to other imine reductases reported. Subsequently, an efficient SnIR-catalyzed process was developed by simply optimizing the amount of cosolvent, and up to 15 g L-1 1-Me DHIQ was converted completely without a feeding strategy. Furthermore, the reaction proceeded well for a panel of dihydroisoquinolines, affording the corresponding tetrahydroisoquinolines (mostly in S-configuration) in good yields (up to 81%) and with moderate to excellent enantioselectivities (up to 99% ee).

Direct Synthesis of Amides by Dehydrogenative Coupling of Amines with either Alcohols or Esters: Manganese Pincer Complex as Catalyst

The first example of base-metal-catalysed synthesis of amides from the coupling of primary amines with either alcohols or esters is reported. The reactions are catalysed by a new manganese pincer complex and generate hydrogen gas as the sole byproduct, thus making the overall process atom-economical and sustainable.

Chemoselective calcium-catalysed direct amidation of carboxylic esters

Unactivated carboxylic esters and primary amines undergo calcium-catalysed direct amide bond formation in excellent yields under homogeneous conditions in toluene. This green and mild reaction proceeds chemoselectively with esters, whereas related carboxylic acids and amides remain unreactive.

Catalytic redox amidations of aldehydes with a polymer-supported peptide-N-heterocyclic carbene multifunctional catalyst

We have prepared an oligomeric histidine-bound N-heterocyclic carbene precursor by coupling a carboxylic acid functionalized 1,2,4-triazolium salt to a peptide using solid-phase peptide synthesis. We have demonstrated that the resulting multifunctional resin-bound catalyst cooperatively facilitates redox amidation reactions of aldehydes and amines, a reaction not catalyzed by N-heterocyclic carbenes alone. Georg Thieme Verlag Stuttgart New York.

Catalytic acylation of amines with aldehydes or aldoximes

The simple nickel salt NiCl2?6H2O catalyzes the coupling of aldoximes with amines to give secondary or tertiary amide products. The aldoxime can be prepared in situ from the corresponding aldehyde. The use of 18O-labeled oximes has allowed insight into the mechanism of this reaction.