6283-04-1

Usage

InChI:InChI=1/C11H15NO/c1-2-11(13)12-9-8-10-6-4-3-5-7-10/h3-7H,2,8-9H2,1H3,(H,12,13)

Upstream product

• 802294-64-0 propionic acid 
• 64-04-0 phenethylamine 
• 5818-15-5 d'hydrazide de l'acide propionique 
• 79-03-8 propionyl chloride 
• 140-29-4 phenylacetonitrile 
• 4799-68-2 3-benzyloxypropan-1-ol 
• 122-63-4 benzyl proprionate 
• 105-37-3 Ethyl propionate 
• 105-38-4 vinyl propionate 
• 1943-82-4 phenethyl isocyanate 
• 999-75-7 ethylzinc iodide 
• 123-62-6 propionic acid anhydride 
• 156-28-5 2-phenylethylamine hydrochloride 

Downstream Products

• 41173-70-0 1-ethyl-3,4-dihydro-isoquinoline 
• 104178-96-3 N-propyl-2-phenylethylamine hydrochloride 
• 7661-60-1 1-ethyl-isoquinoline 
• 250266-58-1 C₁₁H₁₄N₂O₃ 
• 27906-91-8 N-propyl-2-phenylethylamine 

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.

Rhodium-Catalyzed Addition of Organozinc Iodides to Carbon-11 Isocyanates

Amides were prepared using rhodium-catalyzed coupling of organozinc iodides and carbon-11 (11C, t1/2 = 20.4 min) isocyanates. Nonradioactive isocyanates and sp3 or sp2 organozinc iodides generated amides in yields of 13%-87%. Incorporation of cyclotron-produced [11C]CO2 into 11C-amide products proceeded in yields of 5%-99%. The synthetic utility of the methodology was demonstrated through the isolation of [11C]N-(4-fluorophenyl)-4-methoxybenzamide ([11C]6g) with a molar activity of 267 GBq μmol-1 and 12% radiochemical yield in 21 min from the beginning of synthesis.

Flow-based enzymatic synthesis of melatonin and other high value tryptamine derivatives: A five-minute intensified process

To increase the uptake of biocatalytic processes by industry, it is essential to demonstrate the reliability of enzyme-based methodologies directly applied to the production of high value products. Here, a unique, efficient, and sustainable enzymatic platform for the multi-gram synthesis of melatonin, projected to generate around 1.5 billion U.S. dollars worldwide by 2021, and its analogues was developed. The system exploits the covalent immobilization of MsAcT (transferase from Mycobacterium smegmatis) onto agarose beads increasing the robustness and longevity of the immobilized biocatalyst. The fully-automated process deriving from the integration between biocatalysis and flow chemistry is designed to maximize the overall yields (58-92%) and reduce reaction times (5 min), overcoming the limitation often associated with bioprocesses and bridging the gap between lab scale and industrial production.

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.).

Production preparation method of p-nitrophenylethylamine hydrochloride

The invention provides a production preparation method of p-nitrophenylethylamine hydrochloride, belongs to the technical field of drug synthesis, and solves the problems that in the prior art the synthetic p-nitrophenylethylamine hydrochloride is low in conversion rate of and is not suitable for large-scale industrial production. Synthesis steps include 1) amino protection, to be more specific, using beta-phenylethylamine as a raw material for reacting with an acyl protecting agent in a solvent to obtain an intermediate 1; 2) nitrating reaction, to be more specific, adding dropwise the intermediate 1 prepared by the step 1) into concentrated sulfuric acid, maintaining reaction temperature at room temperature, slowly adding dropwise concentrated nitric acid, after the completion of the reaction, adding crushed ice, adding an alkaline solution to adjust the pH to alkaline, and filtering to obtain an intermediate 2; and 3) deprotection, to be more specific, adding dropwise hydrochloric acid into the intermediate 2 in a solvent to adjust the pH to acid, heating to reflux, cooling, and precipitating the product p-nitrophenylethylamine hydrochloride. The production preparation method ofthe p-nitrophenylethylamine hydrochloride has low cost and high product yield, and is suitable for large-scale industrial production.

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).

A Titanium(III)-Catalyzed Reductive Umpolung Reaction for the Synthesis of 1,1-Disubstituted Tetrahydroisoquinolines

A catalytic reductive C1-acylation of 3,4-dihydroisoquinolines is presented that gives direct access to 1,1-disubstituted tetrahydroisoquinolines. The reaction is a titanium(III)-catalyzed reductive umpolung process in which nitriles act as effective acylation agents. The method is highly chemo- and regioselective and is demonstrated in 20 examples. It is well-suited for the large-scale synthesis of functionalized tetrahydroisoquinoline products, which is exemplified in the form of a six-step synthesis of (±)-3-demethoxyerythratidinone. (Figure Presented).

Oxidative activation of dihydropyridine amides to reactive acyl donors

Amides of 1,4-dihydropyridine (DHP) are activated by oxidation for acyl transfer to amines, alcohols and thiols. In the reduced form the DHP amide is stable towards reaction with amines at room temperature. However, upon oxidation with DDQ the acyl donor is activated via a proposed pyridinium intermediate. The activated intermediate reacts with various nucleophiles to give amides, esters, and thio-esters in moderate to high yields. This journal is

Tandem synthesis of amides and secondary amines from esters with primary amines under solvent-free conditions

An iridium(III)-catalyzed tandem synthesis of amides and amines from esters under solvent-free conditions is described. A commercially available iridium(III) complex, [Cp*IrCl2]2, with sodium acetate showed the best activity for the synthesis of amides and secondary amines. The amide was formed by ester-amide exchange which generates an alcohol in situ which is subsequently transformed to a secondary amine via hydrogen autotransfer. This synthetic protocol with high atom economy generates water as the sole by-product and can afford amides and amines from various esters in a one-pot reaction, expanding the synthetic versatility of ester transformations.

Selective catalytic sp3 C-O bond cleavage with C-N bond formation in 3-alkoxy-1-propanols

The ruthenium catalyzed selective sp3 C-O cleavage with amide formation was reported in reactions of 3-alkoxy-1-propanol derivatives and amines. The cleavage only occurs at the C3-O position even with 3-benzyloxy-1-propanol. Based on the experimental results, O-bound and C-bound Ru enolate complexes were proposed as key intermediates for the unique selective sp3 C-O bond cleavage in 3-alkoxy-1-propanols.