135628-86-3

Upstream product

• 135683-65-7 (1S)-1-methylheptyl N,N’-dicyclohexylcarbamimidate 
• 54712-18-4 (R)-2-octyl acetate 
• 5978-70-1 (R)-Octan-2-ol 
• 6169-06-8 (S)-2-Octanol 
• 106760-31-0 (R)(-)-N,N'-dicyclohexyl-O-(1-methylheptyl)-isourea 
• 108-95-2 phenol 

Relevant academic research and scientific papers

Inversion of configuration of alcohols with O-alkyl-N,N'-dicyclohexylisoureas

(S)-(+)-N,N'-Dicyclohexyl-O-(1-methylheptyl)isourea [(S)-2] reacts with acetic acid in cyclohexane to give (R)-(-)-(1-methylheptyl) acetate [(R)-3] with 100% inversion of configuration. Reaction of isourea (R)-2 with phenol proceeds also with inversion of configuration (99.8%) yielding (S)-(+)-(1-methylheptyl) phenyl ether [(S)-4] as the main product; optically active 2- and 4-(1-methylheptyl)phenols [(S)-5] and [(S)-6], respectively, are formed simultaneously. These byproducts, besides others resulting from hydride-shifts, document that the mechanism proceeds via the methylheptyl cation intermediate.