19926-46-6Relevant articles and documents
1,n-rearrangement of allylic alcohols promoted by hot water: Application to the synthesis of navenone B, a polyene natural product
Li, Pei-Fang,Wang, Heng-Lu,Qu, Jin
, p. 3955 - 3962 (2014/05/20)
It was reported for the first time that hot water as a mildly acidic catalyst efficiently promoted 1,n-rearrangement (n = 3, 5, 7, 9) of allylic alcohols. In some cases, the rearrangement reactions joined isolated C-C double or triple bonds to generate conjugated polyene or enyne structure motifs. We used the 1,3-rearrangement reaction of an allylic alcohol in hot water as part of an attractive new strategy for construction of the polyene natural product navenone B by iterative use of a Grignard reaction, a 1,3-rearrangement of the resulting allylic alcohol, and subsequent oxidation of the rearranged product.
Discovery of orally efficacious melanin-concentrating hormone receptor-1 antagonists as antiobesity agents. Synthesis, SAR, and biological evaluation of bicyclo[3.1.0]hexyl ureas
McBriar, Mark D.,Guzik, Henry,Shapiro, Sherry,Paruchova, Jaroslava,Xu, Ruo,Palani, Anandan,Clader, John W.,Cox, Kathleen,Greenlee, William J.,Hawes, Brian E.,Kowalski, Timothy J.,O'Neill, Kim,Spar, Brian D.,Weig, Blair,Weston, Daniel J.,Farley, Constance,Cook, John
, p. 2294 - 2310 (2007/10/03)
Melanin-concentrating hormone (MCH) is a cyclic, nonadecapeptide expressed in the CNS of all vertebrates that regulates feeding behavior and energy homeostasis via interaction with the central melanocortin system. Regulation of this interaction results in
Formation of 1-Phenyl-2,3-dioxabicycloheptane in the Reaction of 1,3-Dibromo-4-phenylcyclopentane with Hydrogen Peroxide in the Presence of Silver Trifluoroacetate
Takahashi, Kimio,Shiro, Motoo,Kishi, Morio
, p. 3098 - 3104 (2007/10/02)
Reaction of 1,3-dibromo-4-phenylcyclopentane (23), prepared from 4-hydroxycyclopent-2-en-1-one (10) in a stereocontrolled manner, or its stereoisomer 24 with anhydrous hydrogen peroxide in the presence of silver trifluoroacetate in ether gave 1-phenyl-2,3-dioxabicycloheptane (25) mainly as a rearranged product.The expected 5-phenyl-2,3-dioxabicycloheptane (8) and phenylcyclopentenyl hydroperoxides 26 and 27 were also formed in this reaction.An authentic sample of endoperoxide 8 was prepared by using peroxide transfer reaction between bis(tri-n-butyltin)peroxide and bistriflate of cis-diol 35.The stereochemistry of the endoperoxide 8 and related compounds in this series was confirmed by correlation with the data from X-ray crystallographic analysis of the diacetate of diol 21 obtained from endoperoxide 8 by stannous chloride reduction.