19958-66-8Relevant academic research and scientific papers
Structure-Odor Correlations in Homologous Series of Mercapto Furans and Mercapto Thiophenes Synthesized by Changing the Structural Motifs of the Key Coffee Odorant Furan-2-ylmethanethiol
Schoenauer, Sebastian,Schieberle, Peter
, p. 4189 - 4199 (2018/05/01)
Furan-2-ylmethanethiol (2-furfurylthiol; 2-FFT, 1) is long-known as a key odorant in roast and ground coffee and was also previously identified in a wide range of thermally treated foods such as meat, bread, and roasted sesame seeds. Its unique coffee-like odor quality elicited at very low concentrations, and the fact that only a very few compounds showing a similar structure have previously been described in foods make 1 a suitable candidate for structure-odor activity studies. To gain insight into the structural features needed to evoke a coffee-like odor at low concentrations, 46 heterocyclic mercaptans and thio ethers were synthesized, 32 of them for the first time, and their odor qualities and odor thresholds were determined. A movement of the mercapto group to the 3-position kept the coffee-like aroma but led to an increase in odor threshold. A separation of the thiol group from the furan ring by an elongation of the carbon side chain caused a loss of the coffee-like odor and also led to an increase in odor thresholds, especially for ω-(furan-2-yl)alkane-1-thiols with six or seven carbon atoms in the side chain. A displacement of the furan ring by a thiophene ring had no significant influence on the odor properties of most of the compounds studied, but the newly synthesized longer-chain 1-(furan-2-yl)- and 1-(thiophene-2-yl)alkane-1-thiols elicited interesting passion fruit-like scents. In total, only 4 out of the 46 compounds also showed a coffee-like odor quality like 1, but none showed a lower odor threshold. Besides the odor attributes, also retention indices, mass spectra, and NMR data of the synthesized compounds were elaborated, which are helpful in possible future identification of these compounds in trace levels in foods or other materials.
Using water, light, air and spirulina to access a wide variety of polyoxygenated compounds
Noutsias, Dimitris,Alexopoulou, Ioanna,Montagnon, Tamsyn,Vassilikogiannakis, Georgios
supporting information; experimental part, p. 601 - 604 (2012/04/23)
A new set of completely green methods utilising air, light, water and spirulina to transform readily accessible furan substrates into a diverse range of synthetically useful polyoxygenated motifs commonly found in natural products is presented herein. The Royal Society of Chemistry 2012.
A rapid condensation between lysophosphorylcholine and fatty acids with an easily separable amine base
Acharya, Hukum P.,Kobayashi, Yuichi
, p. 2015 - 2018 (2007/10/03)
With 2,6-Cl2C6H3COCl and 1-methylimidazole, the title condensation completed at room temperature within 12 hours, which is shorter time than that with the standard DCC/DMAP system. Use of easily separable 1-methylimidazole from the crude product by chromatography is an additional advantage of the present reagent system. Georg Thieme Verlag Stuttgart.
Novel bioactive phospholipids: Practical total syntheses of products from the oxidation of arachidonic and linoleic esters of 2-lysophosphatidylcholine
Sun, Mingjiang,Deng, Yijun,Batyreva, Eugenia,Sha, Wei,Salomon, Robert G.
, p. 3575 - 3584 (2007/10/03)
Total syntheses of nine novel phospholipids were accomplished to facilitate the identification and biological testing of compounds that are generated upon oxidative cleavage of arachidonate and linoleate esters of 2-lysophosphatidylcholine, the two most abundant polyunsaturated phospholipids in low-density lipoprotein. An efficient general synthesis exploiting 2-lithiofuran as a 4-oxo-2butenoyl carbanion equivalent provided phospholipids containing γ-keto-α,β-unsaturated carbonyl functional arrays. By exploiting facile cis-trans isomerizations, two commercially available cis alkenes, (2Z)-2-butene-1,4-diol and 2,5-dihydrofuran, could be employed as starting materials for preparing the Horner-Wadsworth-Emmons reagent 4-(diethoxyphosphoryl)-2E-butenal, a valuable building block for the synthesis of 2,4-dienals. The reagent was exploited in a total synthesis of 13-oxotridec-9E,11E-dienoic acid, confirming the identity of this product that is generated upon autoxidation of linoleic acid and by decomposition of 13-hydroperoxy-9,11-octadecadienoate (13HPODE), especially in the presence of redox active transition metal ions, cytochrome p-450, or hydroperoxide lyase.
A synthesis of oxolenes and furans via oxacyclopentylidene chromium and molybdenum complexes
Schmidt, Bernd,Kocienski, Philip,Reid, Gillian
, p. 1617 - 1630 (2007/10/03)
An easy and convenient preparation of substituted oxolenes and furans by metal-assisted cyclization of alkynols using labile pentacarbonylchromium and pentacarbonylmolybdenum complexes is described.
A Palladium Mediated Spiroketal Synthesis
Elsley, David A.,MacLeod, Donald,Miller, John A.,Quayle, Peter,Davies, Gareth M.
, p. 409 - 412 (2007/10/02)
The synthesis of a variety of spiroketal-containing systems is outlined, utilising a palladium catalysed coupling reaction in the pivotal carbon-carbon bond forming step.
Allenol ether intermediates in the synthesis of 1,7-dioxaspiro [5.5]undec-4-enes and 1,6-dioxaspiro[4.5]dec-3-enes
Kocienski,Whitby
, p. 1029 - 1038 (2007/10/02)
Sequential dialkylation of methoxyallene via the corresponding lithium derivatives gives 1,3-dialkylated methoxyallenes which undergo acid-catalysed ring closure to 1,7-dioxaspiro[5.5]undec-4-enes. Similarly, cyclic allenol ethers (2-vinylidenetetrahydropyrans) generated by rearrangement of 2-alkynyltetrahydropyrans cyclise on treatment with acid to give 1,6-dioxaspiro[4.5]dec-3-enes.
Intramolecular Cycloaddition of Allylium-2-olates (Oxyallyls) to the Furan Nucleus: Synthesis of Oxy-bridged Octahydro-azulenes and -benzocycloheptenes
Foehlisch, Baldur,Herter, Rolf
, p. 2580 - 2596 (2007/10/02)
The Grignard reagents prepared from the 2-(ω-chloroalkyl)furans 3b, c can be acylated with the anhydrides or chlorides of chloroacetic, dichloroacetic, and α-chloropropionic acid to form the ω-furyl-substituted α-chloro ketones 1a-d.Treatment of 1 with the lithium perchlorate/triethylamine reagent affords the octahydroepoxyazulenones 2a-c and -1H-benzocycloheptenone 2d, respectively.In the case of 2b and c the exo-connection at C-8a, i.e. trans-anellation of the carbocyclic rings, is preferred.
