Topic
Cyclopropanone
About: Cyclopropanone is a research topic. Over the lifetime, 310 publications have been published within this topic receiving 3657 citations.
Papers published on a yearly basis
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Papers
TL;DR: In this article, the same carbon by an electron donating group and an adjacent multiple bond, cyclopropanes provide building blocks of unprecedented synthetic potential, and they are readily available along different routes involving: Cyclopropanone hemiacetals, oxaspiropentanes, alkylidenecyclopropane, 1-heterosubstituted lithiocycloprostanes, α-enone silyl enol ethers, 1,3-dichloroacetone and 1-hydroxycyclopropylcarb
Abstract: Substituted on the same carbon by an electron donating group and an adjacent multiple bond, cyclopropanes provide building blocks of unprecedented synthetic potential. They are readily available along different routes involving: cyclopropanone hemiacetals, oxaspiropentanes, alkylidenecyclopropanes, 1-heterosubstituted lithiocyclopropanes, α-enone silyl enol ethers, 1,3-dichloroacetone and 1-hydroxycyclopropylcarbonyl derivatives as main sources.
77 citations
71 citations
TL;DR: This paper showed that readily prepared lithium naphthalenide (2) at -70° is capable of the rapid reductive lithiation of cyclopropanone dithioketals (1) to sulfur-stabilized cyclophropyllithiums (4),1 ketene phenylthio-acetals (8), 1,1,3-tris(phenylthion)alkene (11) to the lithio derivative (12) of an α,β-unsaturated thioacetal.
63 citations
TL;DR: It is suggested that a conventional hydrogen abstraction/hydroxyl recombination mechanism at C-H bonds in 1-4 leads to nonrearranged carbinolamine intermediates and thereby to "ordinary" N-dealkylation products including cyclopropanone hydrate.
Abstract: The suicide substrate activity of N-benzyl-N-cyclopropylamine (1) and N-benzyl-N-(1‘-methylcyclopropyl)amine (2) toward cytochrome P450 and other enzymes has been explained by a mechanism involving single electron transfer (SET) oxidation, followed by ring-opening of the aminium radical cation (protonated aminyl radical) and reaction with the P450 active site. Although the SET oxidation of N-cyclopropyl-N-methylaniline (3) by horseradish peroxidase leads exclusively to ring-opened (non-cyclopropyl) products, P450 oxidation of 3 leads to formation of cyclopropanone hydrate and no ring-opened products, and 3 does not inactivate P450. To help reconcile these discrepant behaviors we have determined the complete metabolic fate of 1 with P450 in vitro. 3-Hydroxypropionaldehyde (3HP), the presumptive “signature metabolite” for SET oxidation of a cyclopropylamine, was observed for the first time in 57% yield, along with cyclopropanone hydrate (34%), cyclopropylamine (9%), benzaldehyde (6%), benzyl alcohol (12%), ...
62 citations
Related Topics (5)
Performance Metrics
| Year | Papers |
|---|---|
| 2021 | 3 |
| 2020 | 5 |
| 2019 | 3 |
| 2018 | 2 |
| 2017 | 3 |
| 2016 | 4 |