74769-16-7Relevant academic research and scientific papers
Cyclohexanones by Rh-mediated intramolecular C-H insertion
Taber, Douglass F.,Paquette, Craig M.,Gu, Peiming,Tian, Weiwei
, p. 9772 - 9780 (2013/10/22)
Some long chain α-aryl α-diazo ketones under Rh catalysis cyclize efficiently to the corresponding cyclohexanones. This is in marked contrast to the cyclizations of α-diazo β-ketoesters, which consistently deliver cyclopentanone products.
Acyclic analogues of 2-(4-phenylpiperidino)cyclohexanol (vesamicol): Conformationally mobile inhibitors of vesicular acetylcholine transport
Efange,Michelson,Dutta,Parsons
, p. 2638 - 2643 (2007/10/02)
Several 1,3-disubstituted propan-2-ols and one α,β-disubstituted ethanol (11i) were synthesized and evaluated as potential acyclic mimics of the vesicular acetylcholine transport inhibitor 2-(4-phenylpiperidinyl)cyclohexanol (1, vesamicol, AH5183). Analogues containing the 4-phenylpiperidyl fragment (11a, 11b) were more potent than those containing the 4-phenylpiperazyl moiety (11e, 11f). Substitution at the second terminal carbon of the propyl (or ethyl) fragment with simple lipophilic aryl substituents yielded potent inhibitors of vesicular acetylcholine storage, including (-)-11a and d-11i, which are equipotent with vesamicol. However, the activity of analogues containing bicyclic aryl groups was susceptible to aryl substitution patterns (11g vs 11h), indicating a definite receptor site topography. In addition, the inhibitory activity of these acyclic analogues was enantioselective, exhibiting a preference, similar to the parent vesamicol, for the levorotatory isomer [(-)-11a vs (+)-11a]. Therefore, the simple lipophilic acyclic vicinal amino alcohols may successfully mimic the biological activity of vesamicol.
Friedel-Crafts Cyclialkylations of Some Epoxides
Taylor, Stephen K.,Hockerman, Gregory H.,Karrick, Gregory L.,Lyle, Stephen B.,Schramm, Scott B.
, p. 2449 - 2452 (2007/10/02)
Several arylalkyl epoxides (1-9) were investigated for cyclialkylation reactions.Cyclialkylation to form six-membered rings was observed (up to 91 percent isolated yields) at secondary but not at primary epoxide positions.Cyclialkylation was not observed with 4-phenyl-1,2-epoxybutane, but a m-methoxy substituent did promote ring closure to the primary position in moderate yield.Cyclialkylation to seven-membered rings occurred at a secondary position in reasonable yields; less rearrangement occured with the epoxide system than with analogous alkylating agents such as phenylalk yl alcohols.Reduced skeletal rearrangement is characteristic of cyclization reactions that occur with epoxides and suggests that the epoxide serves to moderate electrophilic reactivity.Cyclialkylation to form five-membered rings was not observed with epoxides that were capable of ring-opening at primary or secondary positions.
