142834-85-3

Upstream product

• 115755-56-1 6,7'-di(1-methylcyclohexyl)-spiro(naphthalene-1(2H),2'(1'H)-naphtho<2,1-b>furan)-2-one 
• 84-58-2 2,3-dicyano-5,6-dichloro-p-benzoquinone 

Downstream Products

• 142834-78-4 (Z)-3-{5-(1-Methyl-cyclohexyl)-2-[7-(1-methyl-cyclohexyl)-naphtho[2,1-b]furan-2-yl]-phenyl}-prop-2-en-1-ol 
• 142834-87-5 (Z)-3-{5-(1-Methyl-cyclohexyl)-2-[7-(1-methyl-cyclohexyl)-naphtho[2,1-b]furan-2-yl]-phenyl}-acrylic acid 2,3-dichloro-5,6-dicyano-4-methoxy-phenyl ester 

Relevant academic research and scientific papers

Reduction of DDHQ and TCC esters by NaBH4 - Its specificity in the presence of alkyl/aryl esters

DDHQ/TCC esters 3a-f, 7a-g were prepared either by oxidation of spiroketones 1 with DDQ/o-chloranil or by condensation of acid chloride with DDHQ/TCC. NaBH4 reduction of unsaturated DDHQ 3a-b and TCC 7a-c esters gave the corresponding allylic alcohols in good yield without any observable 1,4-addition products. Reduction of saturated esters 3e,7d, gave the corresponding alcohols. Alkyl esters 5 and 6, methyl benzoate and phenyl benzoate remained unaffected under these reduction conditions. In the reduction of compound 7e containing both alkyl and TCC esters, TCC ester is selectively reduced. Reduction of TCC mono esters 7f-g gave the lactones. The observed facile reduction has been rationalised.

Oxidation of spiroketones with DDQ - Synthesis of tropone derivatives and DDHQ diesters

Oxidation of spiroketones 3a-f with DDQ in dry benzene gave tropone derivatives 4a-f and DDHQ esters 5a-f (cis-cis isomer 6a-f, trans-trans isomer 7a-f). While the aryl substituted spirokeone 17a gave a 2:1 mixture of 19a and the corresponding trans-trans