10130-91-3Relevant academic research and scientific papers
Facile synthesis of c/s-2-alkyl-3-trialkylsilyloxycycloalkanones via the non-aldol aldol rearrangement of 2,3-epoxycycloalkanols
Jung, Michael E.,Allen, Damian A.
supporting information; experimental part, p. 2039 - 2041 (2009/04/18)
Silyl triflate-promoted rearrangement of c/s-2,3-epoxycycloalkanols A, prepared by epoxidation of the cyclic allylic alcohol and then sllylatlon, afforded good yields (～70-75%) of the c/s-2-alkyl-3-silyloxycycloalkanones B, presumably via the intermediates C and D, even with quite large α-substituents, e.g., terf-butyl. Finally, it has been shown that the stereochemistry of the epoxy alcohol is crucial as one would expect from the mechanism.
Amber-woody scent: Alcohols with divergent structure present common olfactory characteristics and sharp enantiomer differentiation
Margot, Christian,Simmons, Dana P.,Reichlin, Daniel,Skuy, David
, p. 2662 - 2684 (2007/10/03)
Only one out of the four possible trans isomers of the important perfumery alcohol Norlimbanol (1) possesses a very strong amber-woody smell, the isomer 1A with (1′ R,3S,6'S) absolute configuration. Its enantiomer 1B is almost odorless and devoid of amber-woody character, whereas the diastereoisomers 1C and 1D are considerably weaker and perceptible only by the most-sensitive persons. The same is true for a whole series of perceptual analogs of 1, including β-alkoxy alcohols. These ethers belong to two structural classes: [(2,2,6-trimethylcyclohexyl)oxy]- (see 3, 4, and 16) or {[2-(tert-butyl)cyclohexyl]oxy)alkan-2-ol derivatives (see 19 and 20; Table). A superimposition model allowing for good overlap of the respective hydroxylated side chains offers a tentative explanation for the shared perceptual characteristics of the two classes (Fig. 5). The lipophilic cyclohexane moieties present only a minimal overlap in this model, suggesting that quite larger molecules might possess the same smell. (S)-Configured β-alkoxy alcohols can conveniently be obtained on a larger scale by enantioselective reduction of the corresponding ketones (Scheme 9).
Oxidation of α-Substituted Cyclohexanols by Nitric Acid
Smith, John R. Lindsay,Thomas, C. Barry,Whittaker, Mark
, p. 2191 - 2194 (2007/10/02)
The influence of α-substituents on the oxidative cleavage of cyclohexanol by nitric acid in the presence of copper(II) and vanadium(V) ions has been investigated.Following the initial oxidation to give the cyclohexanone, further reaction, leading to ring opening of the ketone, requires at least one α-hydrogen.Thus 2,2,6,6-tetramethylcyclohexanol is converted to the corresponding ketone whilst 2,2,6-trimethylcyclohexanol is oxidised to a mixture of dicarboxylic acids.The mechanisms of the oxidations are discussed and enolisation is shown to be the key to oxidative cleavage.For ketones that can give two alternative enols, reaction occurs predominantly via the more stable tautomer.
208. Diastereoselektivitaet der Geruchswahrnehmung von Alkoholen der Iononreihe
Schulte-Elte, Karl H.,Giersch, Wolfgang,Winter, Beat,Pamingle, Herve,Ohloff, Guenther
, p. 1961 - 1985 (2007/10/02)
The characteristic odor of the diastereoisomers 1 and 2 of 1-(2,2,6-trimethylcyclohexyl)-3-hexanol is configuration dependent, the trans-alcohol 1 being identified as the sensorily active component.Structure modifications of model 1/2, for example substitution on C(2), C(13), and C(14) (ionon numbering) by CH3 groups, introduction of double bonds in the 3- or 4-position, and isosteric substitution of C(7) by an O-atom, leads to analogues revealing an unequivocal relation between stereochemistry and odor.The specific odor of alcohol 1 is generally released when all substituents are in an equatorial position; the resulting analogy with the molecular size and shape of odoriferous steroids suggests that the release of the particular scent can be correlated with a steroid-resembling receptor event.
