期刊
JOURNAL OF ORGANIC CHEMISTRY
卷 84, 期 13, 页码 8487-8496出版社
AMER CHEMICAL SOC
DOI: 10.1021/acs.joc.9b00719
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资金
- Enamine Ldt.
- Ministry of Education and Science of Ukraine [19BF037-03]
An efficient approach to synthesis of previously unavailable 2-substituted difluorocyclobutane building blocks was developed and applied on a multigram scale. The key step of the synthetic sequence included deoxofluorination of O-protected 2-(hydroxylmethyl)cyclobutanone. Dissociation constants (pK(a)) and log P values for 2,2-difluorocyclobutaneamine and 2,2-difluorocyclobutanecarboxylic acid or their derivatives were measured and compared with the values obtained for the corresponding 3,3-difluorocyclobutane derivatives and nonfluorinated counterparts. Three-dimensional structures of 2,2- and 3,3-difluorocyclobutanamines were compared using exit vector plot analysis of X-ray crystallographic data.
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