103130-93-4

Upstream product

• 56671-82-0 3-Iodocyclohex-2-enone 
• 55791-06-5 benzyl mesylate 
• 100-52-7 benzaldehyde 
• 100-39-0 benzyl bromide 
• 163332-59-0 (3-Methoxy-cyclohex-1-enesulfonyl)-benzene 
• 5323-87-5 3-Ethoxycyclohex-2-en-1-one 
• 1589-82-8 phenylmagnesium bromide 
• 504-02-9 1,3-cylohexanedione 
• 108-86-1 bromobenzene 
• 1193-18-6 3-methylcyclohexen-2-one 
• 229638-74-8 5-benzyl-bicyclo[3.1.0]hexan-1-ol 
• 930-68-7 cyclohexenone 
• 6921-34-2 benzylmagnesium chloride 
• 119826-71-0 3-(2-bromobenzyl)cyclohex-2-en-1-one 

Downstream Products

• 69849-60-1 3-benzyl-3-methylcyclohexan-1-one 
• 201021-74-1 3-benzyl-3-formylmethylcyclohexene 
• 388601-34-1 3-Benzyl-3-carboxymethylcyclohexene 
• 201021-73-0 C₂₁H₂₄O₂S 
• 1227936-32-4 (rac)-3-benzyl-3-phenylcyclohexanone 
• 1312208-23-3 (+)-(S)-3-benzyl-3-(nitromethyl)cyclohexan-1-one 
• 1352139-36-6 C₂₁H₂₁NO₃ 
• 201021-72-9 3-benzylcyclohex-2-en-1-ol 
• 1266384-80-8 C₁₃H₁₆O 
• 1266384-89-7 C₂₀H₂₃NO₂S 
• 1266384-88-6 C₂₀H₂₃NO₂S 

Relevant academic research and scientific papers

Two methods for the preparation of 2-cyclohexenones from resin-bound 1,3-cyclohexanedione

The addition of organolithium or Grignard reagents to viny]ogous ester resin 1 followed by mild hydrolysis of product resins 2 provides 3-alkyl-2-cyclohexenones in high purity (>95%). Alternatively, conversion of 1 to vinyl triflate resin 4 followed by palladium-mediated couplings with aryl boronic acids and hydrolysis furnishes 3-ary]-2-cyclohexenones in lower yield, but exceptional purity.

Synthesis of chiral seven-membered β-substituted lactams: Via Rh-catalyzed asymmetric hydrogenation

Rh/bisphosphine-thiourea ligand (ZhaoPhos)-catalyzed asymmetric hydrogenation of seven-membered β-substituted α,β-unsaturated lactams was successfully developed to prepare various chiral seven-membered β-substituted lactams with good to excellent results (up to >99% conversion, 99% yield, and >99% ee).

Synthesis of 3-substituted 2-cyclohexenones through umpoled functionalization

A new protocol to obtain 3-substituted 2-cyclohexenones, was developed by reversing the chemical reactivity of 2-cyclohexenone. One-pot synthesis of 3-substituted 2-cyclohexenones can be achieved by treatment of 3-phenylthiosilyl enol ether with a mixture of t-BuLi/HMPA that allows hydrogen-selective exchange in presence of reactive electrophiles such as aldehydes, ketones and alkyl halides. This affords the corresponding product in moderate overall yield, after silyl enol ether cleavage and concomitant thiophenol elimination initiated with TBAF.

The cinchona primary amine-catalyzed asymmetric epoxidation and hydroperoxidation of α,β-unsaturated carbonyl compounds with hydrogen peroxide

Using cinchona alkaloid-derived primary amines as catalysts and aqueous hydrogen peroxide as the oxidant, we have developed highly enantioselective Weitz-Scheffer-type epoxidation and hydroperoxidation reactions of α,β-unsaturated carbonyl compounds (up to 99.5:0.5 er). In this article, we present our full studies on this family of reactions, employing acyclic enones, 5-15-membered cyclic enones, and α-branched enals as substrates. In addition to an expanded scope, synthetic applications of the products are presented. We also report detailed mechanistic investigations of the catalytic intermediates, structure-activity relationships of the cinchona amine catalyst, and rationalization of the absolute stereoselectivity by NMR spectroscopic studies and DFT calculations.

Catalytic asymmetric epoxidation of cyclic enones

A highly enantioselective epoxidation of cyclic enones with hydrogen peroxide has been developed that is catalyzed by chiral primary amine salts. Copyright

Synthesis and evaluation of spirobenzazepines as potent vasopressin receptor antagonists

A novel series of spirobenzazepines was synthesized and evaluated for V1a and V2 receptor antagonist activity. Compounds 8b, 8i, and 8k have shown selective V1a receptor antagonist activity. Compounds 8p and 8q were shown to be dual V1a/V2 receptor antagonists.

CYCLOPENTENE DERIVATIVES USEFUL AS ANTAGONISTS OF THE MOTILIN RECEPTOR

The compounds of formula I are useful in treating gastrointestinal disorders associated with antagonizing the motilin receptor disorders. The compounds compete with erythromycin and motilin for the motilin receptor. In addition the compounds are antagonists of the contractile smooth muscle response to those ligands.

Preparation of 2,3-epoxycycloalkanones from bicyclo[n.1.0]Alkan-1-ols

Copper- or iron-catalyzed oxidative rearrangement of bicyclo[n.1.0]alkan-1-ols yields 3-hydroperoxycycloalkanones and/or bicyclic peroxyhemiketals, which are transformed into 2,3-epoxycycloalkanones by treatment with a base.

Chemo-enzymatic preparation of optically active endo- bicyclo[4.1.0]heptan-2-ols

Resolutions of endo-bicyclo[4.1.O]heptan-2-ols were achieved by acylation in the presence of lipase from Candida antarctica (Novozym). The (1S,2R,6R) enantiomers reacted faster and the enantiomeric ratios were between 60 and 800 for the 6-substituted bicycloalkanols.

Regioselective arylation on the γ-position of α, β-unsaturated carbonyl compounds with aryl bromides by palladium catalysis

Arylation of 2-substituted 2-alkenals and 3-substituted 2-cyclohexen- and 2-cyclopenten-1-ones can effectively and regioselectively proceed at their γ-position by treatment with aryl bromides in the presence of a palladium catalyst and a base.