5307-05-1Relevant articles and documents
Synthetic method 4 - alkoxyphenol compounds
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Paragraph 0070-0072, (2021/09/29)
The invention discloses a synthetic method of 4 - alkoxyphenol compounds, and belongs to the field of organic chemical synthesis. The method is as follows: An aryl alkyl ether compound is added to the sealing tube. The catalyst dimerization acetic acid rhodium and the oxidizing agent iodobenzene diethyl ester are added, a solvent trifluoroacetic anhydride is added, and the 4 -alkoxyphenol compound is prepared by heating reaction. To the invention, high regioselectivity direct hydroxylation of the aryl alkyl ether compound is realized, the application range of the substrate is wide, the yield is high, the activity after amplification reaction does not significantly decay, and higher yield is still obtained. The utility model has good practicability and industrial application prospect.
Enantioselective Cleavage of Cyclobutanols Through Ir-Catalyzed C?C Bond Activation: Mechanistic and Synthetic Aspects
Ratsch, Friederike,Strache, Joss Pepe,Schlundt, Waldemar,Neud?rfl, J?rg-Martin,Adler, Andreas,Aziz, Sarwar,Goldfuss, Bernd,Schmalz, Hans-Günther
, p. 4640 - 4652 (2021/02/11)
The Ir-catalyzed conversion of prochiral tert-cyclobutanols to β-methyl-substituted ketones proceeds under comparably mild conditions in toluene (45–110 °C) and is particularly suited for the enantioselective desymmetrization of β-oxy-substituted substrates to give products with a quaternary chirality center with up to 95 % ee using DTBM-SegPhos as a chiral ligand. Deuteration experiments and kinetic isotope effect measurements revealed major mechanistic differences to related RhI-catalyzed transformations. Supported by DFT calculations we propose the initial formation of an IrIII hydride intermediate, which then undergoes a β-C elimination (C?C bond activation) prior to reductive C?H elimination. The computational model also allows the prediction of the stereochemical outcome. The Ir-catalyzed cyclobutanol cleavage is broadly applicable but fails for substrates bearing strongly coordinating groups. The method is of particular value for the stereo-controlled synthesis of substituted chromanes related to the tocopherols and other natural products.
Regioselective synthesis of gentisyl alcohol-type marine natural products
Wang, Hong-Shuang,Li, Hui-Jing,Wang, Long-Fei,Shen, Zhi-Lun,Wu, Yan-Chao
, p. 1891 - 1896 (2018/05/29)
Gentisyl alcohol-type natural products, possessing various important biological properties, have been synthesized from 4-methoxyphenol by using a selective phenol monohydroxymethylation/monochlorination, a CAN oxidation and a sodium dithionite reduction as the key steps. The natural product synthesis is efficient, atom- and step-economical, and requires no protecting groups.