CAS Numberp-: 502-87-43D model (JSmol)o-: Interactive image · p-: Interactive imageChEBIo-: CHEBI:52409 · p-: CHEBI:52406
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- Quinone methides are conjugated organic compounds that contain a cyclohexadiene with a carbonyl and an exocyclic methylidene or extended alkene unit1. They are similar to quinones, but with one oxygen replaced by a carbon1. They can be ortho or para oriented1. They are common in natural products and biological processes2. They have remarkable chemical reactivity as versatile acceptors for 1,6-addition reactions2. They can exist in neutral or zwitterionic forms2.Learn more:✕This summary was generated using AI based on multiple online sources. To view the original source information, use the "Learn more" links.A quinone methide is a type of conjugated organic compound that contain a cyclohexadiene with a carbonyl and an exocyclic methylidene or extended alkene unit. It is analogous to a quinone, but having one of the double bonded oxygens replaced with a carbon. The carbonyl and methylidene are usually oriented either ortho or para to each other.en.wikipedia.org/wiki/Quinone_methide
para -Quinone methides (p -QMs; Fig. 1, type A) are ubiquitous structural motifs present in a wide variety of biologically active natural products. 1p -QMs also play numerous roles in biological processes, such as lignin biosynthesis, 2 adrenergic receptors, 3 enzyme inhibition, 4 and DNA alkylation 5 and cross-linking. 6 Owing to their unique structural assembly comprising reactive carbonyl and olefinic moieties, p -QMs...
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Quinone - Wikipedia
• Quinone methide – where one O is replaced by C
• Xylylene – where both O's are replaced by C's
• Quinone imine – where one O is replaced by N, illustrated by NAPQI
• Quinone diimine – where both O's are replaced by N's, illustrated by the antiseptic ambazoneWikipedia · Text under CC-BY-SA license- Estimated Reading Time: 7 mins
The Generation and Reactions of Quinone Methides - PMC
WEBJan 1, 2011 · Introduction. The 1,2- and 1,4 quinone methides are formally neutral molecules. However, the zwitterionic aromatic valence bond resonance structures ( Scheme 1) make an important contribution to their structure.
- Author: Maria M. Toteva, John P. Richard
- DOI: 10.1016/B978-0-12-386047-7.00002-3
- Publish Year: 2011
- Published: 2011/01/01
- Studies of Quinone methide wikipedia
Mild map to quinone methides | Nature Chemistry
WEBMar 23, 2020 · For over a century, quinone methides (QMs) have been described in organic chemistry as highly reactive intermediates, reacting willingly as Michael-acceptors or dienes in cycloadditions. They...
Quinone methides and indole imine methides as intermediates in …
WEBJun 6, 2022 · Quinone methides (QMs) are versatile intermediates in organic synthesis, materials chemistry (for example, polymer synthesis) and biological processes (for example, lignin biosynthesis and DNA...
Quinone Methide Function in Organic Synthesis - Medium
WEBMar 30, 2024 · Quinone methide is primarily used by organic chemists and researchers focused on synthetic chemistry, pharmaceuticals, and materials science. Exploring the Function of Quinone Methide in Organic ...
Chemoselective oxidative generation of ortho-quinone …
WEBArticle. Published: 23 March 2020. Chemoselective oxidative generation of ortho -quinone methides and tandem transformations. Muhammet Uyanik, Kohei Nishioka, Ryutaro Kondo & Kazuaki Ishihara....
Applications of ortho-Quinone Methide Intermediates …
WEBOct 16, 2011 · Abstract. Ortho -quinone methides are important synthetic intermediates and widely implicated in biological processes. In this Synopsis, recent advances concerning the synthesis and utility of these …
The Emergence of Quinone Methides in Asymmetric …
WEBJun 9, 2015 · Quinone methides (QMs) are highly reactive compounds that have been defined as “elusive” intermediates, or even as a “synthetic enigma” in organic chemistry. Indeed, there were just a handful of …
Category:Quinone methides - Wikipedia
WEBPages in category "Quinone methides" The following 4 pages are in this category, out of 4 total. This list may not reflect recent changes. Quinone methide; C. Celastrol; K. Kendomycin; T. Taxodone This page was last edited on 31 December 2018, at 21:29 (UTC). Text is available under the ...
The Domestication of ortho -Quinone Methides - ACS Publications
WEBAn ortho-quinone methide (o-QM) is a highly reactive chemical motif harnessed by nature for a variety of purposes. Given its extraordinary reactivity and biological importance, it is surprising how few applications within organic synthesis exist.
キノンメチド - Wikipedia
WEBキノンメチド （ 英語: Quinone methide ）は シクロヘキサジエン を含む 共役 な 有機化合物 で、 環 の外側に カルボニル基 と メチレン基 などの 二重結合 を含む アルキル基 をもっている。 キノン に似ているが、キノンでの 炭素-酸素間二重結合 のひとつの 酸素 原子が 炭素 原子に置き換わっている。 カルボニルとメチレンは オルトまたはパラ の配 …
Quinone-Methide Species, A Gateway to Functional Molecular …
WEBSep 2, 2014 · Molecular adaptors based on quinone-methide or a... Quinone-Methide Species, A Gateway to Functional Molecular Systems: From Self-Immolative Dendrimers to Long-Wavelength Fluorescent Dyes | Accounts of Chemical Research
The unexplored potential of quinone methides in chemical biology
WEBJun 15, 2019 · Quinone methides (QMs) are electrophilic reactive intermediates that can be generated from ortho or para methylene substituted phenols by means of thermal, chemical and photochemical activation ( Scheme 1 ).
The generation and reactions of quinone methides - ScienceDirect
WEBJan 1, 2011 · Abstract. The combination of neutral non-aromatic and zwitterionic aromatic contributing valence bond structures confers a distinctive chemical reactivity to quinone methides, which has attracted the interest of a tremendous number of chemist and biochemists. This chapter reviews reactions that generate quinone methides, and the …
WEB7.3.4 Design of a ‘‘Cyclopropyl Quinone Methide” 237 7.3.5 Kinetic Studies of the Mitosene Quinone Methide 243 7.3.6 Cyclopent[b]indole-Based Quinone Methides 250 7.3.7 Prekinamycin-Based Quinone Methides 253 7.4 Conclusions and Future Prospects 260 7.4.1 Quinone Methide O-Protonation 260 7.4.2 Antitumor Agent Design 261
Quinone methide - WikiMili, The Best Wikipedia Reader
WEBA quinone methide is a type of conjugated organic compound that contain a cyclohexadiene with a carbonyl and an exocyclic methylidene or extended alkene unit. It is analogous to a quinone, but having one of the double bonded oxygens replaced with a carbon. The carbonyl and methylidene are usually oriented either ortho or para to each …
ortho -Quinone methide ( o -QM): a highly reactive, ephemeral …
WEBortho-Quinone methides (o-QMs) are short-lived, highly reactive and versatile intermediates in organic synthesis, material chemistry, fine chemicals, and pharmaceuticals.1 The ortho-quinone methide (o-QM) was first suggested by Fries in 1907 and is generally formed by the reaction of phenol with aldehyde in the presence of …
Reaction Mechanisms of Photoinduced Quinone Methide …
WEBNov 26, 2021 · Reaction Mechanisms of Photoinduced Quinone Methide Intermediates Formed via Excited-State Intramolecular Proton Transfer or Water-Assisted Excited-State Proton Transfer of 4- (2-Hydroxyphenyl)pyridine | The Journal of Physical Chemistry Letters. RETURN TO ISSUE PREV Physical Insights in... NEXT.
Troglitazone - Wikipedia
WEBDetailed quantum chemical analysis of the metabolic pathways for troglitazone has shown that quinone reactive metabolite is generated by oxidation of the OH group, but o-quinone methide reactive metabolite is formed by the oxidation of the methyl groups (CH 3 groups) ortho to the OH group of the chromane ring. [28]
Photoactivatable V‐Shaped Bifunctional Quinone …
WEBApr 20, 2022 · Photoactivatable V‐Shaped Bifunctional Quinone Methide Precursors as a New Class of Selective G‐quadruplex Alkylating Agents - Lena - 2022 - Chemistry – A European Journal - Wiley Online Library. …
Bioorthogonal Quinone Methide Decaging Enables Live-Cell …
WEBMay 24, 2024 · By leveraging the bioorthogonal photocatalytic decaging chemistry on quinone methide, CAT-Cell provides a sensitive, tunable, universal, and noninvasive toolbox for unraveling and quantifying the crucial but delicate tumor–immune interactions under live-cell settings.
Variegatic acid - Wikipedia
WEBWhen mushroom tissue containing variegatic acid is exposed to air, the chemical is enzymatically oxidized to blue quinone methide anions, specifically chinonmethid anions. [1] . It is derived from xerocomic acid, which is preceded by atromentic acid and atromentin, and its genetic basis is unknown.