166978-00-3

Upstream product

• 67159-79-9 3,3-dimethyl-6-nitro-indan-1-one 
• 7403-42-1 4-Methyl-4-phenyl-2-pentanone 
• 71-43-2 benzene 
• 67159-81-3 5-Amino-1,1-dimethyl-indan-3-one 
• 638-10-8 ethyl 3-methylbut-2-enoate 
• 71597-85-8 (p-hydroxyphenyl)boronic acid 
• 1010-48-6 3-methyl-3-phenylbutanoic acid 
• 26465-81-6 3,3-dimethylindan-1-one 

Downstream Products

• 1133-54-6 6-methoxy-3,3-dimethylindan-1-one 
• 166978-69-4 methyl 4-(1,1-dimethyl-3-oxo-indan-5-yloxymethyl)benzoate 

Relevant academic research and scientific papers

Synthesis of β,β-disubstituted indanones via the Pd-catalyzed tandem conjugate addition/cyclization reaction of arylboronic acids with α,β-unsaturated esters

Under Pd catalysis with a newly synthesized electron-deficient heterocycle, 2-(4,5-dihydroimidazol-2-yl)- pyrimidine (as the ligand), the reaction of α,β-unsaturated esters with arylboronic acids afforded a wide range of 3,3-disubstituted indan-1-ones bearing a quaternary carbon in high yields. Mechanistic studies revealed that the reaction involves a tandem conjugate addition/1,4-Pd shift followed by a cyclization.

Retinoid-like compounds

The present invention relates to a compound of formula I STR1 or a nontoxic pharmaceutically acceptable salt, physiologically hydrolyzable ester or solvate thereof, in whichX is --O--CO--, --NH--CO--, --CS--NH--, --CO--O--, --CO--NH--, --COS--, --SCO--, --SCH 2 --, --CH 2 --CH 2 --, --C C--, --CH 2 --NH--, --COCH 2 --, --NHCS--, --CH 2 S--, --CH 2 O--, --OCH 2 --, --NHCH 2 -- or --CR 5 CR 6 --;R m and R k are independently hydrogen, halogen, C 1-6 alkyl, hydroxy, C 1-6 alkyloxy or nitro;n is zero or one;R 4 is --(CH 2) t --Y, C 1-6 alkyl, or C 3-6 cycloalkyl;R 1 is --CO 2 Z, C 1-6 alkyl, CH 2 OH, --CONHR y, or CHO;R 2 and R 3 are independently hydrogen or C 1-6 alkyl;R a and R b are independently hydrogen or C 1-6 alkyl; but when n is one, R a and R b together can form a radical of the formula STR2 Y is naphthyl or phenyl, both radicals can be optionally substituted with one to three same or different C 1-6 alkyl or halogen;Z is hydrogen or C 1-6 alkyl;R 5, R 6 and R y are independently hydrogen or C 1-6 alkyl; andt is zero to six.

Retinoid-like compounds

The present invention relates to a compound of formula STR1 or a nontoxic pharmaceutically acceptable salt, physiologically hydrolyzable ester or solvate thereof, in which X is --O--CO--, --NH--CO--, --CS--NH--, --CO--O--, --CO--NH--, --COS--, --SCO--, --SCH2 --, --CH2 --CH2 --, --C C--, --CH2 --NH--, --COCH2 --, --NHCS--, --CH2 S--, --CH2 O--, --OCH2 --, --NHCH2 -- or --CR5 =CR6 --; Rm and Rk are independently hydrogen, halogen, C1-6 alkyl, hydroxy, C1-6 alkyloxy or nitro; n is zero or one; R4 is --(CH2)t --Y, C1-6 alkyl, or C3-6 cycloalkyl; R1 is --CO2 Z, C1-6 alkyl, CH2 OH, --CONHRy, or CHO; R2 and R3 are independently hydrogen or C1-6 alkyl; Ra and Rb are independently hydrogen or C1-6 alkyl; but when n is one, Ra and Rb together can form a radical of the formula STR2 Y is naphthyl or phenyl, both radicals can be optionally substituted with one to three same or different C1-6 alkyl or halogen; Z is hydrogen or C1-6 alkyl; R5, R6 and Ry are independently hydrogen or C1-6 alkyl; and t is zero to six.

Steric Effects. A Study of a Rationally Designed System

The principles for the rational design of systems suitable for the study of steric effects are defined.A suitable molecular framework was synthesized and a study of internal rotaition by dynamic NMR spectroscopy (DNMR) 0f 33 derivatives, differing principally in the nature of the molecular fragment (X), showed the following. (i) For 1 (Y = Me; X = halogen) the rotaition barriers (ΔG excit.) increase smoothly and monotonically with the van der Waals radius of X (rx), which permits the estimation of effective rx for fragments of lower symmetry. (ii) The rotational barriers are the sum of additive contributions, designated interference values (IH-X), which can be used to predict the rotational barriers in 2,2'-disubstituted biphenyls. (iii) A simple geometrical parameter, apparent overlap (r*), which is related to the distortion of the framework in the transition state, is proposed and found to have an excellent linear correlation with the barrier to rotation in 2,2'-disubstituted biphenyls. (iv) This correlation can be used for a semiquantitative estimation of rotational barriers in biaryls and other systems.