140935-01-9

Upstream product

• 107-14-2 chloroacetonitrile 
• 621-82-9 Cinnamic acid 
• 372-09-8 cyanoacetic acid 
• 75-05-8 acetonitrile 
• 107-16-4 glycolonitrile 
• 102-92-1 Cinnamoyl chloride 
• 50-00-0 formaldehyd 
• 143-33-9 sodium cyanide 
• 140-10-3 (E)-3-phenylacrylic acid 

Downstream Products

• 1259319-87-3 (E)-1-hydroxy-7-phenylhept-6-ene-2,5-dione 
• 3538-69-0 (E)-3-phenylacryloylhydrazide 
• 1569087-33-7 C₁₃H₁₅NO₂ 
• 3538-69-0 3-phenylacrylic acid hydrazide 

Relevant academic research and scientific papers

EXPANDING THE CHEMICAL SUBSTRATES FOR GENETIC CODE REPROGRAMMING TO INCLUDE LONG CHAIN CARBON AND CYCLIC AMINO ACIDS

Disclosed are methods, systems, components, and compositions for synthesis of sequence defined polymers. The methods, systems, components, and compositions may be utilized for incorporating novel substrates that include non-standard amino acid monomers an

Preparation method of cyanomethyl ester

The invention discloses a preparation method of cyanomethyl ester. In the presence of an oxidizing agent, a carboxylic acid compound and cyanoacetic acid are used as reactants, iodide is used as a catalyst, and sodium acetate is used as alkali, so as to p

Cyanoacetic Acid as a Masked Electrophile: Transition-Metal-Free Cyanomethylation of Amines and Carboxylic Acids

Using cyanoacetic acid as a masked electrophile, a new cyanomethylation reaction of amines and carboxylic acids was developed, producing a variety of α-aminonitriles and cyanomethyl esters with good yields and excellent functionality tolerance. This protocol features simple manipulation, inexpensive reagents, and a wide substrate scope. Iodoacetonitrile was generated in situ from the iodination-decarboxylation of cyanoacetic acid in this transformation.

Titanium-mediated addition of grignard reagents to acyl cyanohydrins: Aminocyclopropane versus 1,4-diketone formation

The 1,2-dianion reactivity of the reagent generated from EtMgBr and titanium isopropoxide was illustrated when N-acyl cyanohydrins were used as substrates (>20 examples), giving both aminocyclopropane derivatives and 1,4-dicarbonyl compounds. When the reaction was performed in diethyl ether, 5-hydroxy-1,4-diketones were the main product. Under specific conditions (use of tetrahydrofuran and a bulky carboxylic moiety), the cyclopropane derivatives were obtained in good yields. The observed dichotomy may be explained by a ring-opening of the five-membered titanacycle intermediate followed by a nonselective acyl addition. The 1,2-dianion reactivity of the reagent generated from EtMgBr and Ti(OiPr)4 was illustrated when N-acyl cyanohydrins were used as substrates (>20 examples). When the reaction was performed in diethyl ether, 1,4-diketones were mainly isolated. Under certain conditions, cyclopropane derivatives were also obtained in good yields. A mechanism rationalizing this dichotomy is presented. Copyright

Titanium-mediated synthesis of 1,4-diketones from grignard reagents and acyl cyanohydrins

Double duty: In the presence of titanium isopropoxide, Grignard reagents were found to react with acyl cyanohydrins to give substituted 5-hydroxy-1,4-diketones (see scheme). This new reaction involves a formal addition of a 1,2-dianion equivalent to both the ester and nitrile moieties.

Cyanomethyl esters: Useful protection for carboxylic acids

The alkylation of carboxylate salts with chloroacetonitrile yields cyanomethyl esters. Deprotection of the carboxyl group is most readily performed by stirring with an aqueous solution of sodium sulfide.