1690-73-9

Usage

Physical state

Clear, colorless liquid The compound appears as a transparent and colorless liquid, which indicates its visual characteristics.

Odor

Distinct, slightly sweet The compound has a noticeable and mildly pleasant aroma, which can be described as slightly sweet.

Uses

Intermediate in pharmaceuticals and agrochemicals production The compound is commonly utilized as an intermediate substance in the manufacturing of various pharmaceuticals and agrochemicals.

Synthesis

Organic compound synthesis It is also used as a starting material or building block in the synthesis of other organic compounds.

Hazardous nature

Potentially hazardous substance The compound is considered to have potential hazards, which necessitates careful handling.

Health risks

Skin and eye irritation Contact with the compound may cause irritation to the skin and eyes.

Additional hazards

Harmful if inhaled or ingested The compound may have harmful effects on one's health if it is breathed in or swallowed.

Upstream product

• 50-00-0 formaldehyd 
• 931-20-4 1-methylpiperidin-2-one 
• 944276-44-2 3-(hydroxymethyl)-1-methylpiperidine-2-one 
• 21576-27-2 ethyl 1-methyl-2-oxopiperidine-3-carboxylate 
• 201230-82-2 carbon monoxide 

Downstream Products

• 50586-03-3 C₁₇H₂₁NO₅ 
• 50586-04-4 5-(Benzyloxycarbonyl-methyl-amino)-2-methylene-pentanoic acid 

Relevant academic research and scientific papers

The reaction of α- and ω-methylenelactams with nitrones. Influence of electronic and geometric factors on the stereoselectivity of their 1,3-dipolar cycloaddition

Various four to six-membered ring α- and ω-methylenelactams 1-5 were reacted with nitrones 6 and afforded good yields of spiroadducts 7-12 through a regiospecific [3 + 2] cycloaddition. Owing to the creation of at least two new asymmetric centres, mixtures of diastereoisomers were usually obtained whose structures were established by two-dimensional NOESY experiments or X-ray crystallography. Among the dipolarophiles, 3-methyleneazetidin-2-ones 1 yielded adducts with a very high stereoselectivity. A similar behaviour was also observed with α-benzoylnitrone 6a as a 1,3-dipole. Electronic and geometric interactions of the reagents 1-5 and 6 in the course of the cycloaddition process were discussed in order to account for the experimental stereochemical outcomes.

Radical carbonylation of ω-alkynylamines leading to α-methylene lactams. Synthetic scope and the mechanistic insights

Tin hydride mediated radical carbonylation and cyclization reaction was investigated using a variety of ω-alkynyl amines as substrates. In this reaction α-methylene and α-stannylmethylene lactams having five to eight membered rings were obtained as princi

Novel spiroheterocycles by aziridination of α-methylene-γ- and -δ-lactams

New potentially bioactive α-spiroaziridino-γ- and -δ-lactams have been prepared by treatment of α-methylene-γ- and -δ-lactams with ethyl N-([(4-nitrophenyl)sulfonyl]oxy)-carbamate (NsONHCO2Et) in the presence of CaO. These compounds, through reductive aziridine ring opening, can be intermediates for the synthesis of α- and β-aminolactams, which are useful as conformational constraints in peptides. The above procedure has been successfully extended to one α-methyleneoxindole to obtain a new spirooxindole derivative, a potential precursor of natural alkaloids. Wiley-VCH Verlag GmbH & Co. KGaA, 2007.

Synthesis of lactams by radical substitution reaction of α,β-unsaturated acyl radicals at amine nitrogen

(Chemical Equation Presented) Substitution at nitrogen by α,β-unsaturated acyl radicals took place accompanied by elimination of an α-phenethyl radical. This reaction led to the development of a new carbonylative annulation method for five- to seven-membe