1-(2-Benzyl-1,5-dimethyl-6,7,8-trioxabicyclo[3.2.1]octan-2-yl)ethan-1-ol DOI Creative Commons
Peter S. Radulov, Ivan A. Yaremenko, Alexander O. Terent’ev

et al.

Molbank, Journal Year: 2022, Volume and Issue: 2023(1), P. M1532 - M1532

Published: Dec. 23, 2022

The title compound, 1-(2-Benzyl-1,5-dimethyl-6,7,8-trioxabicyclo[3.2.1]octan-2-yl)ethan-1-ol, was synthesized for the first time by selective reduction in keto ozonide under action of strong reducing agent LiAlH4. product characterized NMR, IR, HRMS, and elemental analysis.

Language: Английский

Hydrodealkenylative C(sp3)–C(sp2) Bond Fragmentation Using Isayama–Mukaiyama Peroxidation DOI

Jeremy H. Dworkin,

Zhuoxi M. Chen,

Kathleen C. Cheasty

et al.

Journal of the American Chemical Society, Journal Year: 2025, Volume and Issue: unknown

Published: April 15, 2025

Advancements in radical capture strategies have expanded the range of products accessible from alkenes through dealkenylative synthesis. These methods, however, are still limited, as they rely on ozonolysis to generate key peroxide intermediates alkenes. Ozonolysis has several limitations. It is not compatible with containing electron-rich aromatics. also inapplicable certain alkene substitution patterns context Additionally, it struggles sterically hindered alkenes, internal nucleophiles and electrophiles, allylic alcohols. In this paper, using Isayama-Mukaiyama peroxidation (IMP), we address limitations rescue previously inaccessible substrates broaden applicability functionalization. particular, apply IMP hydrodealkenylation describe a novel hydrogenation condition─employing catalytic [FeIII], benzenethiol, γ-terpinene refluxing methanol─to resolve β-scission issues associated IMP-generated alkyl silylperoxides.

Language: Английский

Citations

1
Photocatalytic Sulfonyl Peroxidation of Alkenes via Deamination of N-Sulfonyl Ketimines DOI
Yuting Feng, Shujun Chen, Leiyang Lv

et al.

Organic Letters, Journal Year: 2024, Volume and Issue: 26(9), P. 1920 - 1925

Published: Feb. 22, 2024

A photocatalytic three-component sulfonyl peroxidation of alkenes with N-sulfonyl ketimines and tert-butyl hydroperoxide is reported. The reaction takes place via the photoinduced EnT process, which allows efficient synthesis a variety β-peroxyl sulfones under mild conditions in absence transition metal catalyst. downstream derivatizations peroxides were also performed. Furthermore, utility this protocol was manifested by 11β-HSD1 inhibitor antiprostate cancer drug bicalutamide.

Language: Английский

Citations

6
An overview on the antimalarial activity of 1,2,4‐trioxanes, 1,2,4‐trioxolanes and 1,2,4,5‐tetraoxanes DOI

Monika Shukla,

Komal Rathi,

Mohammad Hassam

et al.

Medicinal Research Reviews, Journal Year: 2023, Volume and Issue: 44(1), P. 66 - 137

Published: May 24, 2023

Abstract The demand for novel, fast‐acting, and effective antimalarial medications is increasing exponentially. Multidrug resistant forms of malarial parasites, which are rapidly spreading, pose a serious threat to global health. Drug resistance has been addressed using variety strategies, such as targeted therapies, the hybrid drug idea, development advanced analogues pre‐existing drugs, model strains control mechanisms. Additionally, discovering new potent drugs grows due prolonged life cycle conventional therapy brought on by emergence ongoing changes in existing therapies. 1,2,4‐trioxane ring system artemisinin (ART) most significant endoperoxide structural scaffold thought be key pharmacophoric moiety required pharmacodynamic potential endoperoxide‐based antimalarials. Several derivatives have also found treatments multidrug‐resistant strain this area. Many 1,2,4‐trioxanes, 1,2,4‐trioxolanes, 1,2,4,5‐tetraoxanes synthesised result, many these shown promise activity both vivo vitro against Plasmodium parasites. As consequence, efforts develop functionally straight‐forward, less expensive, vastly more synthetic pathway trioxanes continue. This study aims give thorough examination biological properties mode action compounds derived from 1,2,4‐trioxane‐based functional scaffolds. present 1,2,4‐trioxane, 1,2,4‐trioxolane, 1,2,4,5‐tetraoxane dimers with potentially will highlighted systematic review (January 1963–December 2022).

Language: Английский

Citations

9
Investigation of the thermal hazard and decomposition mechanism of 1,1-di(tert-butylperoxy) cyclohexane by experiment and DFT simulation DOI
Nan Liang Chen,

Hang Yao,

Xinyi Liu

et al.

Process Safety and Environmental Protection, Journal Year: 2023, Volume and Issue: 177, P. 1116 - 1128

Published: July 27, 2023

Language: Английский

Citations

9
Oxygen: The Key to Stereoelectronic Control in Chemistry DOI
Igor V. Alabugin, Leah Kuhn

ACS in focus, Journal Year: 2023, Volume and Issue: unknown

Published: April 4, 2023

Although carbon is considered the central element of organic chemistry, broader chemical world has one more star player—oxygen. Billions years evolution have filled your room with oxygen as countless cyanobacteria and plants work on changing our planet. Oxygen everywhere—from geology to biology, from Earth's crust ozone layer. This digital primer aims analyze reactivity through prism chemistry. The key understanding this chemistry lone pairs (i.e., underutilized "idle" electrons that do not directly contribute Lewis structure molecules). By highlighting many roles oxygen, we will illustrate how rises above limitations structures stay neither idle nor "lone" even if they are in "lone pairs" when an atom near a reaction center. introduce important types bonding transcend undergraduate textbooks but likely drive development new reactions future.

Language: Английский

Citations

6
Visible Light-Driven Sandwich-like g-C3N4-Catalyzed Oxidation to Produce Cumene Hydroperoxide DOI
Hongfei Zhu, Jingnan Zhao,

Zongyi Yu

et al.

Industrial & Engineering Chemistry Research, Journal Year: 2023, Volume and Issue: 62(21), P. 8253 - 8268

Published: May 19, 2023

Cumene hydroperoxide (CHP) is an important intermediate for the production of phenol, acetone, propylene oxide, and other raw materials in petrochemical industry. However, due to high reaction temperature pressure, current process industrial CHP has problems potential safety hazards energy consumption. In this work, carbon nitride (g-C3N4) with a unique sandwich structure was discovered as photocatalyst. It efficiently activates molecular oxygen air, oxidizes cumene (CM) prepare CHP, realizes atom economy transformation at room temperature, atmospheric solvent-free conditions. The continuous flow strategy adopted improve gas–liquid mass transfer efficiency reduce phenomenon back-mixing, thereby reducing decomposition products improving product selectivity. conversion rate same that batch reaction, reaching 23%. selectivity increased from 82 92%, residence time shortened 10 h 70 min. catalysts have advantages efficiency, easy availability, environmentally friendly, etc., are recyclable stable. This work provides new establishing green, sustainable, clean, efficient methods preparation peroxides.

Language: Английский

Citations

4
Macrocyclic Organic Peroxides: Constructing Medium and Large Cycles with O-O Bonds DOI Creative Commons
Yana A. Barsegyan, Vera A. Vil’, Alexander O. Terent’ev

et al.

Chemistry, Journal Year: 2024, Volume and Issue: 6(5), P. 1246 - 1270

Published: Oct. 15, 2024

Macrocycles bridge the gap between conventional small molecules and polymers. Drawing inspiration from successful carbon heteroatom-containing macrocycles, peroxide-containing macrocycles are gaining attention for enhanced bioactivity, potential chelating properties, applications in energetic materials. This review presents following strategies construction of cyclic peroxides with 10- to 36-membered frameworks: (1) intramolecular iodocyclization hydroperoxides, (2) intermolecular cyclization hydroperoxides alkyl dihalides or carbonyls, (3) acid-catalyzed rearrangements ozonides 11-membered triperoxides via oxy- peroxycarbenium ions, (4) peroxidation carbonyls targeting macrocyclic peroxides. The specific agents that allow selective medium large cycles also analyzed.

Language: Английский

Citations

1
Bridged 1,2,4-Trioxolanes: SnCl4—Catalyzed Synthesis and an In Vitro Study against S. mansoni DOI Creative Commons
Peter S. Radulov, Ivan A. Yaremenko, Jennifer Keiser

et al.

Molecules, Journal Year: 2023, Volume and Issue: 28(13), P. 4913 - 4913

Published: June 22, 2023

A synthesis of bridged 1,2,4-trioxolanes (bridged ozonides) from 1,5-diketones and hydrogen peroxide catalyzed by SnCl4 was developed. It shown that the ratio target ozonides can be affected application as a catalyst varying solvent. wide range (ozonides) obtained in yields 50 to 84%. The ozonide cycle moderately resistant reduction ester group near alcohol with LiAlH4. were evaluated for their antischistosomal activity. These exhibited very high activity against newly transformed schistosomula adult Schistosoma mansoni.

Language: Английский

Citations

2
Recent advances in the synthesis and antimalarial activity of 1,2,4-trioxanes DOI
Komal Rathi,

Monika Shukla,

Mohammad Hassam

et al.

Bioorganic Chemistry, Journal Year: 2023, Volume and Issue: 143, P. 107043 - 107043

Published: Dec. 19, 2023

Language: Английский

Citations

2
1-(2-Benzyl-1,5-dimethyl-6,7,8-trioxabicyclo[3.2.1]octan-2-yl)ethan-1-ol DOI Creative Commons
Peter S. Radulov, Ivan A. Yaremenko, Alexander O. Terent’ev

et al.

Molbank, Journal Year: 2022, Volume and Issue: 2023(1), P. M1532 - M1532

Published: Dec. 23, 2022

The title compound, 1-(2-Benzyl-1,5-dimethyl-6,7,8-trioxabicyclo[3.2.1]octan-2-yl)ethan-1-ol, was synthesized for the first time by selective reduction in keto ozonide under action of strong reducing agent LiAlH4. product characterized NMR, IR, HRMS, and elemental analysis.

Language: Английский

Citations

0