1128-32-1Relevant academic research and scientific papers
Difluoromethylthiolation of Phenols and Related Compounds with a HF2CSO2Na/Ph2PCl/Me3SiCl System
Huang, Zhongyan,Matsubara, Okiya,Jia, Shichong,Tokunaga, Etsuko,Shibata, Norio
, p. 934 - 937 (2017/02/26)
A novel HF2CSO2Na/Ph2PCl/Me3SiCl system is disclosed for the late-stage direct difluoromethylthiolation of Csp2 and Csp3 nucleophiles. Difluoromethylthiolation of phenols and naphthols proceeded nicely under this system to regioselectively provide corresponding SCF2H compounds in good yields. Other substrates such as indoles, pyrroles, pyrazoles, enamines, ketones, and β-keto esters were also transformed to corresponding SCF2H products in good yields. The late-stage direct difluoromethylthiolation of a number of natural products and pharmaceutically attractive molecules was also achieved.
Radical-scavenging polyphenols: New strategies for their synthesis
Bovicelli, Paolo
, p. 1703 - 1710 (2008/03/11)
New strategies for the synthesis of polyphenols, compounds with antioxidant properties contained in every kind of plants, are discussed. Syntheses of different classes of polyphenols, namely ubiquinones, present in many natural systems in which electron-transfer mechanisms are involved, hydroxytyrosol, one of the main components of the phenol fraction in olives, and flavonoids, widespread in the plant kingdom, were approached by simple and environmentally sustainable methods.
New convenient synthesis of iridol. An approach to the synthesis of ubiquinones
Bovicelli, Paolo,Antonioletti, Roberto,Barontini, Maurizio,Borioni, Giorgio,Bernini, Roberta,Mincione, Enrico
, p. 1255 - 1257 (2007/10/03)
A strategy for the synthesis of ubiquinones, in which iridol is the key intermediate, has been developed, together with a new convenient synthesis of iridol (2,3-dimethoxy-5-methylphenol) starting from the easily available 4-methylphenol and using mild conditions and friendly and high-yielding reactions.
Phenyl ethers from cultured lichen mycobionts of Graphis scripta var. serpentina and G. rikuzensis.
Takenaka, Yukiko,Tanahashi, Takao,Nagakura, Naotaka,Hamada, Nobuo
, p. 794 - 797 (2007/10/03)
Spore-derived mycobionts of the lichen Graphis scripta var. serpentina and G. rikuzensis were cultivated on a malt-yeast extract medium supplemented with 10% sucrose and their metabolites were investigated. 3,3'-Dihydroxy-5,5'-dimethyldiphenyl ether was isolated from the cultures of the mycobionts of G. scripta var. serpentina, while a new phenyl ether, rikuzenol, along with two known diphenyl ethers, violaceol-I and violaceol-II, were isolated from those of G. rikuzensis. The structure of the new compound was determined by spectroscopic methods. Violaceol-I was chemically synthesized and interconversion between violaceol-I and violaceol-II was proven.
Synthesis of crown ethers related to ubiquinones
Merz,Rauschel
, p. 797 - 802 (2007/10/02)
Crown ethers in which the two methoxy groups of ubiquinone-0 (2,3-dimethoxy-5-methyl-1,4-benzoquinone) are replaced by oligoethylene glycol bridges have been obtained in five straightforward steps in 35-40% overall yield from 5-methylpyrogallol. A Fremy salt oxidation of a phenolic precursor is used in the final step. The further elaboration of crown ether analogues of ubiquinone-2 was achieved by enol geranylation of cyclopentadiene adducts of the former quinones and subsequent retro-Diels-Alder reaction. The Claisen rearrangement of 2,2-dimethoxy-5-methylphenyl allyl ethers and related crown ethers affords ortho- and para-allyl-substituted phenols (3:1) that are oxidized to give bisnorubiquinone derivatives and their ortho-quinone isomers. All new compounds are characterized by high resolution NMR and mass spectrometry.
Ubiquinones and Related Compounds, XXXV. On Peracid Oxidation of 1-(Methoxy)-2,3-dimethoxy-5-methylbenzene
Morimoto, Hiroshi,Hayashi, Nobuyoshi,Kawakami, Takeo
, p. 1963 - 1966 (2007/10/02)
The mechanism of the peracid oxidation of 1,2,3-trimethoxy-5-methylbenzene leading to 2,3-dimethoxy-5-methyl-1,4-benzoquinones has been investigated using 18O.The oxygen at the 1-position in the benzoquinone obtained originates from the oxidizing agent.
