Model Compounds of Caged Capsaicin:  Design, Synthesis, and Photoreactivity

• Published in: Journal of organic chemistry Vol. 68; no. 23; pp. 9100 - 9104
• Main Authors: Katritzky, Alan R, Xu, Yong-Jiang, Vakulenko, Anatoliy V, Wilcox, Allan L, Bley, Keith R
• Format: Journal Article
• Language: English
• Published: WASHINGTON American Chemical Society 14.11.2003; Amer Chemical Soc
• Subjects: Capsaicin - chemical synthesis; Capsaicin - chemistry; Chemistry; Chemistry, Organic; Exact sciences and technology; Magnetic Resonance Spectroscopy; Models, Chemical; Noncondensed benzenic compounds; Organic chemistry; Photochemistry; Physical Sciences; Preparations and properties; Science & Technology; ANALOGS; NEURONS; RECEPTOR; PHOTOLABILE PROTECTING GROUPS; MECHANISMS; CHEMICAL KINETIC INVESTIGATIONS; RELEASE; DERIVATIVES; Nitro compound; Organic carbonate; Ether; Decomposition; Acetamide; Reaction rate; Design; Reactivity; Ultraviolet irradiation; Photolysis; Benzylic compound; Model compound; Electronic effect; Chemical synthesis
• ISSN: 0022-3263; 1520-6904
• DOI: 10.1021/jo034616t

Molecules were prepared with substituted nitrobenzyl groups covalently bonded to N-(4-hydroxy-3-methoxybenzyl)acetamide (2) by ether or carbonate linkages. These compounds decomposed under irradiation at 363 nm. Those with carbonate linkages decomposed at slower rates than those with ether linkages. Molecules with dimethoxy-substituted benzyl groups decomposed more slowly than monomethoxy-substituted benzyl groups due to the electronic characteristics of the benzylic carbon.