6288-14-8

Usage

Chemical class

Acetate esters

Derivative

Acetic acid

Common uses

Synthesis of pharmaceutical drugs, building block in organic chemistry

Potential use

Pharmaceutical research and drug development

Also known as

2-acetoxy-1-phenylethan-1-one

Applications

Production of flavors and fragrances, manufacturing of plastics and polymers

Versatility

Diverse industrial and scientific uses

Upstream product

• 64-17-5 ethanol 
• 1003855-72-8 (S)-2-(toluene-sulfonyl-⁽⁴⁾-oxy)-propionic acid anilide 
• 127-08-2 potassium acetate 
• 62-53-3 aniline 
• 535-17-1 (S)-2-acetoxypropionic acid 
• 535-17-1 2-acetoxypropionic acid 
• 21262-52-2 2-chloro-N-phenylpropanamide 
• 127-09-3 sodium acetate 
• 38939-83-2 2-acetoxypropionyl chloride 
• 36394-75-9 (S)-2-acetoxypropanoyl chloride 
• 103-71-9 phenyl isocyanate 

Downstream Products

• 106942-22-7 lactanilide 
• 64-19-7 acetic acid 

Relevant academic research and scientific papers

Design, synthesis, and evaluation of novel inhibitors for wild-type human serine racemase

Most of the endogenous free D-serine (about 90%) in the brain is produced by serine racemase (SR). D-Serine in the brain is involved in neurodegenerative disorders and epileptic states as an endogenous co-agonist of the NMDA-type glutamate receptor. Thus, SR inhibitors are expected to be novel therapeutic candidates for the treatment of these disorders. In this study, we solved the crystal structure of wild-type SR, and tried to identify a new inhibitor of SR by in silico screening using the structural information. As a result, we identified two hit compounds by their in vitro evaluations using wild-type SR. Based on the structure of the more potent hit compound 1, we synthesized 15 derivatives and evaluated their inhibitory activities against wild-type SR. Among them, the compound 9C showed relatively high inhibitory potency for wild-type SR. Compound 9C was a more potent inhibitor than compound 24, which was synthesized by our group based upon the structural information of the mutant-type SR.

Reduction of 2-chloro-N-phenylpropanamide and 2-methyl-N-phenylaziridine with lithium aluminium hydride

The reduction of 2-chloro-N-phenylpropanamide with LiAlH4 has been re-examined. In contrast to previous findings, we obtain in almost equal quantities two amines from this reaction, namely N-propylaniline and the rearranged product N-isopropylaniline. 2-Methyl-N-phenylaziridine is an intermediate in the reduction and can be isolated from reactions with less LiAlH4. Reduction of 2-methyl-N-phenylaziridine itself proceeds non-regioselectively to provide a mixture of propyl- and isopropylanilines. Formation of the amines by reduction of the aziridine is much slower than formation by reduction of the 2-chloropropanamide, which indicates that Lewis acid catalysis (by aluminium chlorohydrides) facilitates the reduction of the aziridine. In addition, Lewis acid catalysis increases the relative yield of the propylamine product. The reduction of 2-chloro-N-phenylpropanamide furnishes 2-phenylamino-1-propanol as a by-product, rather than the previously proposed 1-phenylamino-2-propanol. The Royal Society of Chemistry.

Preparation and use of (S)-O-acetyllactyl chloride (Mosandl's reagent) as a chiral derivatizing agent

(S)-O-Acetyllactyl chloride is used as a versatile chiral derivatizing agent for the chromatographic determination of the enantiomeric excesses of alcohols or amines. However, some precautions must be taken to avoid its racemization during preparation and use. In addition, the racemic counterpart of this reagent can be used to determine the best analytical separation conditions.