488787-31-1

Upstream product

• 5323-87-5 3-Ethoxycyclohex-2-en-1-one 
• 67-64-1 acetone 

Downstream Products

• 488787-32-2 6-[(1-methyl-1-triethylsilyloxy)ethyl]-3-ethoxy-2-cyclohexen-1-one 
• 67119-85-1 (+/-)-4-(1-hydroxy-1-methylethyl)cyclohex-2-enone 

Relevant academic research and scientific papers

Umpolung Strategy for Arene C?H Etherification Leading to Functionalized Chromanes Enabled by I(III) N-Ligated Hypervalent Iodine Reagents

The direct formation of aryl C?O bonds via the intramolecular dehydrogenative coupling of a C?H bond and a pendant alcohol represents a powerful synthetic transformation. Herein, we report a method for intramolecular arene C?H etherification via an umpoled alcohol cyclization mediated by an I(III) N-HVI reagent. This approach provides access to functionalized chromane scaffolds from primary, secondary and tertiary alcohols via a cascade cyclization-iodonium salt formation, the latter providing a versatile functional handle for downstream derivatization. Computational studies support initial formation of an umpoled O-intermediate via I(III) ligand exchange, followed by competitive direct and spirocyclization/1,2-shift pathways. (Figure presented.).

Cannabidiol derivative as well as preparation method and medical application thereof

The invention relates to a cannabidiol derivative and application thereof in medicine, in particular to a pyrimidine derivative as shown in a general formula (I), or a stereoisomer, a solvate, a metabolite, a pharmaceutically acceptable salt or a co-crystal thereof, with definition of each substituent in the general formula (I) being the same as that in the specification.

Cannabidiol derivative as well as preparation method and medical application thereof

The invention relates to a cannabidiol derivative and application thereof in medicine, in particular to a pyrimidine derivative as shown in a general formula (I), or a stereoisomer, a solvate, a metabolite, a prodrug, a pharmaceutically acceptable salt or a co-crystal thereof, and definition of each substituent in the general formula (I) is the same as that in the specification.

Synthesis of tetrahydrocannabinols based on an indirect 1,4-addition strategy

The synthetic procedure presented for the preparation of the title compounds requires 1,4-addition of bulky cuprates to cyclohexenones and subsequent reaction with electrophiles. However, the enolates generated by BF3·OEt2-assistance suffer from lack of nucleophilicity. To circumvent this problem, we developed an indirect method consisting of the following three steps: (1) iodination of the cyclohexenones at the α position; (2) BF3·OEt2-assisted 1,4-addition of cuprates (Ar2Cu(CN)-Li2, Ar = aryl) followed by quenching the enolates with water; (3) reaction of the α-iodo-β-arylcylohexanones thus formed with EtMgBr to generate magnesium enolates. The enolates thus generated in this way showed a high reactivity toward ClP(O)(OEt)2 to furnish enol phosphates. The aforementioned procedure was also applied to a synthesis of optically active Δ9-tetrahydrocannabinol. In addition, a naphthalene analogue of the latter compound was also synthesized in a similar way.