3187-28-8Relevant academic research and scientific papers
One-Pot Conversions of (Silylmethyl)cyclopropanes to Homoallylic Alcohols and 1,4-Diols Based on Haloborane-Induced Ring Opening
Ryu, Ilhyong,Hirai, Akira,Suzuki, Haruhisa,Sonoda, Noboru,Murai, Shinji
, p. 1409 - 1410 (2007/10/02)
The reactions of (silylmethyl)cyclopropanes with haloboranes, such as BBr3 and BHBr2, result in desilylative ring opening to give homoallylboranes and boracyclopentanes, respectively.Coupled with subsequent oxidation procedure, these reactions provide ready access to homoallylic alcohols and 1,4-diols.
Spiro[4,5] and spiro[4,6] carboxylic acids: Cyclic analogues of valproic acid. Synthesis and anticonvulsant evaluation
Scott,Moore,Zalucky,Nicholson,Lee,Hinko
, p. 413 - 417 (2007/10/02)
Spiro[4,5]decane-2-carboxylic acid, spiro[4,5]decane-2,2-dicarboxylic acid, spiro[4,6]undecane-2-carboxylic acid (12b), spiro[4,6]undecane-2,2-dicarboxylic acid, and spiro[4,6]undecane-2-acetic acid were synthesized by an improved method and evaluated for anticonvulsant activity. These analogues were synthesized to evaluate the role of the carboxylic acid group as an essential substituent in valproic acid (di-n-propylacetic acid, 1). Carbocyclic spiranes are known to resist metabolic alteration so that any activity elicited by these compounds would be due to the carboxylic acid function and not to any metabolic change. Spiro[4,6]undecane-2-carboxylic acid (12b) was the most active analogue tested and the pentylenetetrazol and picrotoxin evaluations of 12b compared favorably to 1. However, 12b failed to provide adequate protection against maximal electroshock seizures, bicuculline, or strychnine in mice. Possible reasons for these results are discussed.
Composes heterocycliques spiranniques. V. Synthese et etude configurationnelle dans la serie de l'oxa-2 spirodecane
Picard, Philippe,Moulines, Jean,Lecoustre, Max
, p. 65 - 70 (2007/10/02)
The 8-t-butyl-2-oxaspirodecan-3-one, 8-t-butyl-2-oxaspirodecane and its 3-methylated derivatives were synthesized by different routes starting from methyl 4-t-butylcyclohexanecarboxylate, 4-t-butylmethylenecyclohexane and methyl 4-t-butylcyclohexylidenecyanoacetate.The cis (-CH2O axial) and trans (-CH2O equatorial) isomers were isolated by preparative HPLC ; their configurations were established from (1) the known stereoselectivity of the reaction involved in the cis/trans ratio controlling step (2) their proton and 13C nmr spectra.
