64590-81-4

Usage

General Description

2-Propenoic acid, 2-(acetylamino)-3-phenyl-, methyl ester, (E)-, commonly known as methyl 2-(acetylamino)-3-phenylacrylate, is an organic compound with the chemical formula C13H13NO3. It is a clear, colorless liquid with a fruity odor and is commonly used in the production of pharmaceuticals, fragrances, and various other organic compounds. The compound is also known for its use in the synthesis of various pharmaceuticals and as a reagent in organic chemistry. It is important to handle this chemical with care, as it can be harmful if ingested, inhaled, or comes into contact with the skin or eyes.

Upstream product

• 186581-53-3 diazomethane 
• 64590-80-3 (E)-α-(N-acylamino)cinnamic acid 
• 55065-02-6 2-(N-acetylamino)cinnamic acid 
• 77-78-1 dimethyl sulfate 
• 55065-02-6 N-acetamido cinnamic acid 
• 1438888-27-7 C₁₇H₁₈NO₆P 
• 100-52-7 benzaldehyde 

Downstream Products

• 3618-96-0 (S)-N-acetylphenylalanine 
• 21156-62-7 (R)-N-acetylphenylalanine methyl ester 
• 72234-47-0 methyl 4-phenyl-1,2,5-thiadiazole-3-carboxylate 
• 2577-90-4 methyl (2S)-2-amino-3-phenylpropanoate 

Relevant academic research and scientific papers

Stereoselective Synthesis of (E)-α,β-dehydroamino acid esters

Dehydroamino acid (Dhaa) is recognized as a useful tool or substrate for amino acid and peptide research. Although the stereoselective synthesis of the thermodynamically more stable Z-Dhaa has been well examined and established, the stereoselective synthesis of E-Dhaa has still remained to be a challenging synthetic task. In this paper, a stereoselective synthesis of E-Dhaa esters using a new (α-diphenylphosphono)glycine is described. The characteristic aspects of the new method are summarized as follows: (i) metal additives play an important role in the promotion of E-stereoselectivities. (ii) the use of NaI was effected for the synthesis of E-Dhaas bearing an aryl substituent and an amino functionality, (iii) MgBr2·OEt2 and ZnCl 2 contributed to improve the E-stereoselective synthesis of E-Dhaas bearing an alkyl substituent and an oxygen functionality, (iv) various protecting and functional groups were compatible under the reaction conditions, and (v) N-Cbz, Boc, and acyl-α-(diphenylphosphono)glycines were served for the stereoselective olefination reaction to provide the corresponding E-Dhaas. A variety of (E)-dehydroamino acid esters were stereoselectively synthesized by using (diphenylphosphono)glycinate. The stereoselectivity was influenced by metal additives. Various (E)-dehydroamino acid esters were prepared by the condensation reaction of the new phosphonates with easily available aldehydes by choosing the appropriate reaction conditions.

Mechanism of asymmetric hydrogenation of α-(acylamino)acrylic esters catalyzed by BINAP-ruthenium(II) diacetate

The mechanism of asymmetric hydrogenation of α-(acylamino)acrylic esters with Ru(CH3COO)2-[(S)-binap] (BINAP = 2,2′-bis(diphenylphosphino)-1,1′-binaphthyl), giving the S saturated products in > 90% ee, has been investigated by means