64330-04-7

Upstream product

• 127-08-2 potassium acetate 
• 100-52-7 benzaldehyde 
• 1113-68-4 N-methyldiacetamide 
• 96013-60-4 N-methyl-N-tosylcinnamamide 
• 96-30-0 chloroacetylmethylamide 
• 141544-06-1 4-Methyl-6-oxo-2-phenyl-cyclohex-4-ene-1,3-dicarboxylic acid bis-methylamide 
• 4360-47-8 cinnamonitrile 
• 333-27-7 methyl trifluoromethanesulfonate 
• 1885-38-7 cinnamic nitrile 
• 84738-96-5 C₂H₇AlClN 
• 4192-77-2 ethyl cinnamate 
• 67-66-3 chloroform 
• 7664-93-9 sulfuric acid 
• 7664-41-7 ammonia 

Downstream Products

• 140-10-3 (E)-3-phenylacrylic acid 
• 940-43-2 N-methyl-3-phenylpropanamide 
• 60960-88-5 (E)-N-methylcinnamylamine 
• 119163-39-2 (2S,3R)-3-Phenyl-oxirane-2-carboxylic acid methylamide 
• 486413-41-6 (2R,3S)-3-phenyloxirane-2-carboxylic acid methylamide 
• 1279129-49-5 C₁₈H₁₉NO 
• 1279129-44-0 C₁₄H₁₉NO 
• 1279129-45-1 C₁₆H₂₃NO 
• 1279129-38-2 C₁₃H₁₇NO 
• 1279129-43-9 C₁₂H₁₅NO 

Relevant academic research and scientific papers

A novel method for the synthesis of α,β-unsaturated amides mediated by Samarium diiodide

Promoted by Samarium diiodide (SmI2), α,β-unsaturated amides were formed from nitrogenanions (formed in situ by the reduction of nitro compounds) and αβ-unsaturated esters. This reaction contrasts with the conjugate addition between amines and α,β-unsaturated esters promoted by samarium triiodide (SmI3) and provides an alternative attractive way to obtain α,β-unsaturated amides using SmI 2.

Organocatalytic Trans Semireduction of Primary and Secondary Propiolamides: Substrate Scope and Mechanistic Studies

We report a chemoselective, phosphine-catalyzed semireduction of primary and secondary propiolamides. In the presence of stoichiometric pinacolborane and catalytic n-tributylphosphine, a variety of propiolamides were successfully converted to the corresponding acrylamides in excellent yield with (E)-stereoselectivity. The reaction condition is tolerant of various functional groups including alkene, alkyne, ketone, or ester. Deuterium labeling studies established that the hydride from activated pinacolborane is added to the α-carbon and the proton on the amide nitrogen is abstracted by the ?-carbon to furnish the (E)-acrylamides. DFT calculations revealed a clear energetic driving force for the (E)- over the (Z)-isomer. (Figure presented.).

Manganese Catalyzed Enantioselective Epoxidation of α,β-Unsaturated Amides with H2O2

Herewith, we report the enantioselective epoxidation of electron-deficient cis- and trans-α,β-unsaturated amides with the environmentally benign oxidant H2O2. The catalysts - manganese complexes with bis-amino-bis-pyridine and structurally related ligands - exhibit reasonably high efficiency (up to 100 TON) and excellent chemo- and enantioselectivity (up to 100% and 99% ee, respectively). Crucially, the cis-enamides epoxidation enantioselectivity and yield are dramatically enhanced by the presence of NH-moiety, which effect can be explained by the hydrogen bonding interaction between the cis-enamide substrate and the manganese based oxygen transferring species. (Figure presented.).

Catalytic, transition-metal-free semireduction of propiolamide derivatives: Scope and mechanistic investigation

We report a transition-metal-free trans-selective semireduction of alkynes with pinacolborane and catalytic potassium tert-butoxide. A variety of 3-substituted primary and secondary propiolamides, including an analog of FK866, a potent nicotinamide mononucleotide adenyltransferase (NMNAT) inhibitor, are reduced to the corresponding (E)-3-substituted acrylamide derivatives in up to 99% yield with >99:1 E/Z selectivity. Mechanistic studies suggest that an activated Lewis acid-base complex transfers a hydride to the α-carbon followed by rapid protonation in a trans fashion.

Dealkoxylation ofN-alkoxyamides without an external reductant driven by Pd/Al cooperative catalysis

Lewis acid-assisted palladium-catalysed dealkoxylation ofN-alkoxyamides has been developed. This reaction proceeded smoothly with a range ofN-alkoxyamides in the absence of an external reductant, thereby establishing a convenient and reductant-free protocol. In addition, a gram-scale reaction could be achieved. Preliminary mechanistic investigations indicated that β-hydrogen elimination from a palladium alkoxide intermediate generated an intramolecular hydride source.

Bioactivity and structure–activity relationship of cinnamic acid derivatives and its heteroaromatic ring analogues as potential high-efficient acaricides against Psoroptes cuniculi

A series of cinnamic acid derivatives and its heteroaromatic ring analogues were synthesized and evaluated for acaricidal activity in vitro against Psoroptes cuniculi, a mange mite. Among them, eight compounds showed the higher activity with median lethal concentrations (LC50) of 0.36–1.07 mM (60.4–192.1 μg/mL) and great potential for the development of novel acaricidal agent. Compound 40 showed both the lowest LC50 value of 0.36 mM (60.4 μg/mL) and the smallest median lethal time (LT50) of 2.6 h at 4.5 mM, comparable with ivermectin [LC50 = 0.28 mM (247.4 μg/mL), LT50 = 8.9 h], an acaricidal drug standard. SAR analysis showed that the carbonyl group is crucial for the activity. The type and chain length of the alkoxy in the ester moiety and the steric hindrance near the ester group significantly influence the activity. The esters were more active than the corresponding thiol esters, amides, ketones or acids. Replacement of the phenyl group of cinnamic esters with α-pyridyl or α-furanyl significantly increase the activity. Thus, a series of cinnamic esters and its heteroaromatic ring analogues with excellent acaricidal activity emerged.

Stereoselective olefination and regiospecific vicinal difunctionalization of imines with α-(benzothiazol-2-ylsulfonyl) carbonyl compounds

Depending on their structures, imines are able to undergo either olefination or vicinal difunctionalization with various α-(benzothiazol-2- ylsulfonyl) carbonyl compounds in the absence of external bases. The olefination reaction of aromatic imines with α-(benzothiazol-2-ylsulfonyl) carbonyl compounds proceeds smoothly in tetrahydrofuran at 70 °C to give structurally diverse α,β-unsaturated esters, amides, and ketones in good to excellent yields and with extremely high (E) selectivity. In contrast, the carbon-nitrogen double bonds of cyclic imines and the carbon-carbon double bonds of α,β-unsaturated imines are subjected to regiospecific vicinal difunctionalization with α-(benzothiazol-2-ylsulfonyl) carbonyl compounds under the same reaction conditions to give a variety of benzothiazole derivatives in good to excellent yields. It is noteworthy that the benzothiazole moiety is present in a number of antitumor agents and bioluminescent molecules. In addition, plausible reaction pathways have been proposed to account for these transformations, and these are substantially supported by ESI-MS analysis of the reaction mixtures.

Mild zinc-promoted Horner-Wadsworth-Emmons reactions of diprotic phosphonate reagents

We report the development of a mild protocol for the Horner-Wadsworth- Emmons reaction of diprotic phosphonates that makes use of a zinc triflate promoter in the presence of mild ter-tiary amine bases to produce α,β-unsaturated carboxylic acids and amides. Georg Thieme Verlag Stuttgart.

Efficient Synthesis of Chiral α- and β-Hydroxy Amides: Application to the Synthesis of (R)-Fluoxetine

Four flavors for epoxide openings: The regioselective openings of epoxy amides obtained by asymmetric epoxidation yields all types of aryl- and alkyl-substituted hydroxy amides sometimes counter to the reactivity of the α- and β-positions.

Synthesis and reactions of 2-substituted ethyl N-alkylmalonylhydroxamic acids

Alkylation of O-silylated N-alkylmalonylhydroxamic acids provides a method for the synthesis of 2-substituted N-alkylmalonyl hydroxamic acids. The substituent at C-2 does not materially change the chemistry of the α-lactam intermediates produced from them. They can be converted to unsymmetric ureas and hydantoins in high yields. The addition of unsaturated substituents at C-2 is used to produce cyclic ureas containing medium rings via RCM reactions.