Synonyms:methylenecyclopropane
97% *data from raw suppliers
METHYLENECYCLOPROPANE 95.00% *data from reagent suppliers
There total 33 articles about Cyclopropylmethyl which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:
Reference yield: 40.0%
Reference yield: 30.0%
Reference yield: 26.0%
2-chloromethyl-3-chloroprop-1-ene
The research explores the use of the cyclopropylmethyl (cPrMe) protecting group as an alternative to conventional methyl groups in the total synthesis of two benzofuran-based natural products: anigopreissin A and the resveratrol–piceatannol hybrid. The study aims to address the limitations of methyl groups, which often require harsh acidic conditions for removal, leading to low yields and undesired products. The cPrMe group was found to be more versatile, stable under various reaction conditions, and easier to remove under different acidic conditions. Key chemicals used in the synthesis include cyclopropylmethyl bromide for protection, BBr3 and BCl3/TBAI for deprotection, and various reagents for constructing the benzofuran scaffold, such as Pd-catalyzed coupling reagents and phosphonate esters. The study concludes that the cPrMe group is a superior protecting group for phenols in the synthesis of these natural products, offering higher yields and greater compatibility with various deprotection conditions.
The research focused on determining the activation energy for the ring-closure reaction of ground state triplet trimethylenemethane (I) to methylenecyclopropane. The purpose was to measure this energy by monitoring the rate of disappearance of the electron spin resonance spectrum over a specific temperature range in frozen solid matrices, using 3-methylenecyclobutanone and methylenecyclopropane as precursors to trimethylenemethane. The study concluded that the activation energy for the ring-closure was significantly lower than the theoretical estimates, with a value of 7 kcal/mole, contrasting with the approximate 20 kcal/mole barrier suggested by theoretical models. The chemicals used in the process included 3-methylenecyclobutanone, methylenecyclopropane, isobutylene, and various solvents such as methylcyclohexane, perfluoromethylcyclohexane, decalin, and tetrahydrofuran for the matrix solutions. The research also involved the synthesis and use of fully deuterated methylenecyclopropane-da to investigate the possibility of a tunneling mechanism in the ring-closure reaction.
The research presents a comprehensive study on the palladium-catalyzed reactions of 3-substituted methylenecyclopropanes (MCPs), focusing on the effects of substituents such as hydroxymethyl or formyl groups on the reaction outcomes. The purpose of the study was to explore the synthetic potential of these MCPs under varying conditions, including the presence or absence of an acid source like acetic acid. The conclusions drawn from the research indicated that Pd-catalyzed reactions of methylenecyclopropylcarbinols (Z)-1 in the presence of acetic acid yielded 2-methylene-but-3-enyl esters 4 in moderate yields, while Pd alone catalyzed the isomerization of (E)-1 to form pent-4-enals 3 in good yields. The reactions of methylenecyclopropanecarbaldehydes (E)-5 and (Z)-5 under Pd catalysis and acetic acid presence resulted in different products, with (E)-5 leading to penta-2,4-dienals 6 and (Z)-5 leading to 2-(3-formylpenta-2,4-dienylidene)cyclopropanecarbaldehydes 7. The study elucidated plausible mechanisms for these transformations based on the results and control experiments. Key chemicals used in the process included Pd(PPh3)4 as the catalyst, AsPh3 as a ligand, and variously substituted MCPs such as methylenecyclopropylcarbinols 1 and methylenecyclopropanecarbaldehydes 5.
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