Flow-photochemical synthesis of the functionalized benzobicyclo[3.2.1]octadiene skeleton

Ratković, Ana; Marinić, Željko; Škorić, Irena

doi:10.1016/j.molstruc.2018.05.027

Cited by 9 publications

(10 citation statements)

References 47 publications

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“…As can be quickly gleaned a substantial quantity of fragrance materials are manufactured annually. However, some of the listed components are also themselves used to produce other ingredients; for example, myrcene (506) is used for the preparation of linalool (10), geraniol (343), nerol, and 4-(4-Hydroxy-4-methylpentyl)cyclohex-3-ene-1carbaldehyde (lyral, International Flavors & Fragrance, IFF). a These prices and volumes are estimated.…”

Section: Fragrance Chemistrymentioning

confidence: 99%

“…Recently, continuous-flow DA cycloadditions have been performed on myrcene (506), which is an acyclic monoterpene widely used as a building block in the F&F industry [427]. The authors wanted to prepare a new potential surfactant using myrcene (506) and acrylic acid (507). The DA adduct 508 obtained was scaled up from the batch to flow systems.…”

Section: Cycloaddition Reactionsmentioning

confidence: 99%

“…Scheme 117: Continuous-flow DA reaction developed in a plater flow reactor for the preparation of the adduct 508 from myrcene (506).…”

Section: Cycloaddition Reactionsmentioning

confidence: 99%

See 2 more Smart Citations

A comprehensive review of flow chemistry techniques tailored to the flavours and fragrances industries

Gambacorta¹,

Sharley²,

Baxendale³

2021

Beilstein J. Org. Chem.

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Due to their intrinsic physical properties, which includes being able to perform as volatile liquids at room and biological temperatures, fragrance ingredients/intermediates make ideal candidates for continuous-flow manufacturing. This review highlights the potential crossover between a multibillion dollar industry and the flourishing sub-field of flow chemistry evolving within the discipline of organic synthesis. This is illustrated through selected examples of industrially important transformations specific to the fragrances and flavours industry and by highlighting the advantages of conducting these transformations by using a flow approach. This review is designed to be a compendium of techniques and apparatus already published in the chemical and engineering literature which would constitute a known solution or inspiration for commonly encountered procedures in the manufacture of fragrance and flavour chemicals.

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Section: Fragrance Chemistrymentioning

confidence: 99%

Section: Cycloaddition Reactionsmentioning

confidence: 99%

See 1 more Smart Citation

A comprehensive review of flow chemistry techniques tailored to the flavours and fragrances industries

Gambacorta¹,

Sharley²,

Baxendale³

2021

Beilstein J. Org. Chem.

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“…Recently we prepared photoproducts, shown in Figure 1 , and probed the cholinesterase inhibition [ 27 , 28 ]. Compounds endo - 1 and endo - 2 were the most potent inhibitors of AChE (IC 50 = 17.5 µM) and BChE (IC 50 = 8.8 µM), respectively, among the tested compounds.…”

Section: Introductionmentioning

confidence: 99%

Benzobicyclo[3.2.1]octene Derivatives as a New Class of Cholinesterase Inhibitors

et al. 2020

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A library of amine, oxime, ether, epoxy and acyl derivatives of the benzobicyclo[3.2.1]octene were synthesized and evaluated as inhibitors of both human acetylcholinesterase (AChE) and butyrylcholinesterase (BChE). The majority of the tested compounds exhibited higher selectivity for BChE. Structural adjustment for AChE seems to have been achieved by acylation, and the furan ring opening of furo-benzobicyclo[3.2.1]octadiene results for compound 51 with the highest AChE affinity (IC50 = 8.3 µM). Interestingly, its analogue, an oxime ether with a benzobicyclo[3.2.1]-skeleton, compound 32 was one of the most potent BChE inhibitors in this study (IC50 = 31 µM), but not as potent as endo-43, an ether derivative of the benzobicyclo[3.2.1]octene with an additional phenyl substituent (IC50 = 17 µM). Therefore, we identified several cholinesterase inhibitors with a potential for further development as potential drugs for the treatment of neurodegenerative diseases.

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“…From their viewpoint, it was very important to consider the structure of the natural terpene, α-pinene (Scheme 1), as a compound having the bicyclo(3.1.1)hexene structure, very similar to the structure of photoproducts obtained by a cycloaddition reaction in very good yields. Recently, these yields have even been improved by the utilization of the flow-photochemical methodology [36]. The manganese(III) complexes of the cationic 5,10,15,20-tetrakis(1-methyl-4-pyridinium)porphyrin (Mn(III)TMPyP 5+ ) and the anionic 5,10,15,20-tetrakis(4-sulfonatophenyl)porphyrin (Mn(III)TSPP 3− ) along with the anionic free base were used in the experiments (Figure 2).…”

mentioning

confidence: 99%

Photocatalytic Oxygenation by Water-Soluble Metalloporphyrins as a Pathway to Functionalized Polycycles

Šagud

Škorić

2018

International Journal of Photoenergy

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Photocatalytic processes are present in natural biochemical pathways as well as in the organic synthetic ones. This minireview will cover the field of photocatalysis that uses both the free-base and specially metallated porphyrins as catalysts. While free-base porphyrins are valuable sensitizers to output singlet oxygen, metalloporphyrins are even more adjustable as photocatalysts because of their coordination capacity, generating a wider range of oxidation reactions. They can be applied in autooxidation reactions, hydroxylations, or direct oxygen transfer producing epoxides. This review will mainly focus on how manganese and some iron porphyrins can be utilized for the functionalization of compounds that have a polycyclic skeleton in their structure. These kinds of compounds are notoriously taxing to obtain and difficult to further functionalize by conventional organic synthetic methods. We have focused on photocatalytic oxygenation reactions in mild conditions with the use of water-soluble porphyrins, as this has been proven to be a good tool for these transformations. In the photocatalytic reactions of some polycyclic heteroaromatic compounds, new polycyclic epoxides, enediones, ketones, alcohols, and/or hydroperoxides are yielded, depending on the catalyst applied. The application of anionic and cationic Mn(III) porphyrins under different reaction parameters results in different reaction pathways generating a vast number of photocatalytic products. Recently, Co and Ni complexes have been also photophysically investigated and confirmed as potential photocatalysts for the functionalization of organic substrates.

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Flow-photochemical synthesis of the functionalized benzobicyclo[3.2.1]octadiene skeleton

Cited by 9 publications

References 47 publications

A comprehensive review of flow chemistry techniques tailored to the flavours and fragrances industries

A comprehensive review of flow chemistry techniques tailored to the flavours and fragrances industries

Benzobicyclo[3.2.1]octene Derivatives as a New Class of Cholinesterase Inhibitors

Photocatalytic Oxygenation by Water-Soluble Metalloporphyrins as a Pathway to Functionalized Polycycles

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