66465-65-4

Upstream product

• 35044-57-6 ethyl 2,6,6-trimethyl-2,4-cyclohexadiene-1-carboxylate 
• 127996-38-7 2,3-epoxy-2,6,6-trimethyl-cyclohexanecarboxylic acid ethyl ester 

Downstream Products

• 96850-03-2 ethyl 2-(bromomethyl)-6,6-dimethyl-3-oxocyclohex-1-ene-1-carboxylate 
• 96850-02-1 ethyl 2,6,6-trimethyl-3-oxocyclohex-1-ene-1-carboxylate 
• 96850-01-0 ethyl 4-bromo-3-oxo-2,6,6-trimethylcyclohex-1-ene-1-carboxylate 

Relevant academic research and scientific papers

Process for preparing seed germinating stimulants

Processes for preparing compounds which exhibit seed germinating activity are disclosed. An ester of acetoacetic acid is condensed with a ketone to produce a substituted cyclohexenone which is reacted with a thiol to get a dithioketal which is then desulfurized to produce an ester of a substituted cyclohex-2-ene-1-carboxylic acid which exhibits seed germinating activity. The same compound can be produced by a different process which reacts the substituted cyclohexenone with a reducing agent. An exemplary reducing agent would be an organosilane and a Lewis acid.

A New Synthetic Route to (+/-)-Strigol

A new more facile synthetic route to strigol, a potent weed seed germination stimulant, utilizes as starting material ethyl 4-oxo-2,6,6-trimethylcyclohex-2-ene-1-carboxylate (2), obtained by the condensation of mesityl oxide and ethyl acetoacetate.Compound 2 was converted in six steps in 38percent overall yield to the previously reported strigol intermediate, 1,4-dioxo-7,7-dimethyl-4,5,6,7-tetrahydro-2-indanacetic acid (11).The new approach is based upon inexpensive starting materials and reagents and is suitable for large-scale production.The key features of the synthesis include reduction of enone 2 to olefin 5 with triethylsilane and boron trifluoride etherate and a one-pot conversion of ethyl 2-(bromomethyl)-6,6-dimethyl-3-oxocyclohex-1-ene-1-carboxylate (10) to the diketo acid 11.