Spiro-cyclohexane-(1,2')-indane and -tetralin cpds. - prepd. from bis-carbalkoxyethyl-indane and -tetralin cpds. by Dieckmann reaction, having steroid hormone activity

摘要

New spiro-cyclohexane derivs. are of formula (I). In (I), R1 is a fused-on six-membered carbocyclic ring; R2 and R3 are each H, or form part of a pi -bonding system within the ring, or together form a C-C bond within such a pi-bonding system; R4 and R5 are each H or a monovalent organic gp., or R4+R5 is a divalent organic gp.; R6 is H or a monovalent organic gp.; R7 is H or together with R9 forms a C-C bond; R8 is H or a monovalent organic gp. or together with R9 forms a divalent organic gp.; R9 is H or a monovalent organic gp.; or R7+R9 is a C-C pi-bond, or R8+R9 is a divalent organic gp.; and n is 1 or 2. They are used e.g., to activate oestrogenic cpds. (e.g. stilboestrol), permitting high oestrogenic activity to be obtd. with low doses of oestrogens (this can be useful e.g. in contraceptive or cosmetic prepns.), where redn. of the side-effects of oestrogens is desirable). (I) also have e.g. oestrogenic, anti-oestrogenic, androgenic or anti-androgenic activity. Specific cpds. (I) include spiro3-ethoxycarbonylcyclohexane-1,21-indane -11,4-dione. In an example, this cpd is produced by gradually adding 2,2-bis(2-ethoxycarbonylethyl)-indanone under N2 to a stirred suspension of Na in dry toluene at 100 degrees and refluxing 4 hrs.