20760-12-7

Upstream product

• 525-82-6 FLAVONE 
• 487-26-3 Flavanone 
• 487-25-2 cis-4-hydroxyflavan 
• 90-02-8 salicylaldehyde 
• 103-63-9 1-phenyl-2-bromoethane 
• 1244125-06-1 2-(3,5-bis(trifluoromethyl)phenyl)-4-phenethyl-4H-benzo[d][1,3,2]dioxaborinine 
• 1214-47-7 1-(2-hydroxyphenyl)-3-phenylprop-2-en-1-one 
• 22618-13-9 1-(2-methoxyphenyl)-3-phenylpropan-1-one 
• 118-93-4 o-hydroxyacetophenone 
• 3516-95-8 2'-hydroxy-3-phenylpropiophenone 
• 100-52-7 benzaldehyde 

Downstream Products

• 13524-55-5 trans-3-Phenyl-1-(2-hydroxy-phenyl)-propen-1 
• 179319-84-7 2-(1-methoxy-3-phenyl-propyl)-phenol 
• 3516-95-8 2'-hydroxy-3-phenylpropiophenone 
• 179319-72-3 2-[2-(1-Methoxy-3-phenyl-propyl)-phenoxymethyl]-oxirane 
• 179319-71-2 1-(2-Oxiranylmethoxy-phenyl)-3-phenyl-propan-1-ol 
• 1481-90-9 2-(3-phenylpropyl)phenol 
• 95004-18-5 1-(2-Diethylamino-ethoxy)-2-(3-phenyl-1-hydroxy-propyl)-benzol 
• 73087-55-5 2-ethoxy-4-phenethylchroman 
• 207617-04-7 2-[(R)-3-Phenyl-1-((1R,2R,4R,6R,7R)-1,10,10-trimethyl-3-oxa-tricyclo[5.2.1.0^2,6]dec-4-yloxy)-propyl]-phenol 
• 207220-47-1 2-[(S)-3-Phenyl-1-((1R,2R,4R,6R,7R)-1,10,10-trimethyl-3-oxa-tricyclo[5.2.1.0^2,6]dec-4-yloxy)-propyl]-phenol 

Relevant academic research and scientific papers

Transfer Hydrogenation of Flavanones and ortho-Hydroxychalcones to 1,3-Diarylpropanols Catalyzed by CNN Pincer Ruthenium Complexes

The transfer hydrogenation of flavanones and ortho-hydroxychalcones catalyzed by ruthenium pincer complexes RuCl(CNNPh)(disphosphine) has allowed the synthesis of ortho-hydroxy 1,3-diarypropanols in 80–88 % yield, under mild reaction conditions and short reaction times (1 h) in 2-propanol. The amount of the co-catalyst NaOiPr has been found crucial for the selective reduction of flavanones to ortho-hydroxy 1,3-diarypropanols vs. flavan-4-ols. Preliminary results show that with pincer catalysts bearing (S,R)-Josiphos, flavanone is reduced to the corresponding (S)-alcohol in moderate conversion (36 %) and up to 92 % ee.

Solvent-Controlled Hydrogenation of 2’-Hydroxychalcones: A Simple Solution to the Total Synthesis of Bussealins

A solvent-controlled hydrogenation of 2’-hydroxychalcones to selectively obtain different hydrogenation products is herein reported. Thus, hydrogenation of 2’-hydroxychalcones using EtOH as solvent provided the corresponding 1,3-diarylpropanes in excellent yields. On the contrary, when the hydrogenation was performed in DCM, the corresponding dihydrochalcones were isolated. Switching the reaction solvent to n-BuOH/H2O (1:1), afforded 1,3-diarylpropanols from moderate to good yields. The methodology here reported offers a straightforward, simple and cost-effective method for the preparation of a wide variety of 2’-hydroxy-1,3-diarylpropanes derivatives, and was also applied to the preparation of natural Bussealins C and D. (Figure presented.).

Zirconium-catalyzed Nagata reaction for the synthesis of 2-aryl-1,3,2-aryldioxaborins via a mild three-component condensation of phenols, aldehydes, and boronic acid

An efficient ZrCl4-catalyzed ortho-hydroxyalkylation of phenols with aldehydes promoted by 3,5-bis(trifluoromethyl)phenyl boronic acid, leading to the formation of 2-aryl-1,3,2-aryldioxaborins, was investigated and optimized. The reaction afforded the desired aryldioxaborins in good to excellent yields under mild conditions at room temperature. The electron-deficient boronic acid promoter was essential. Electron-rich phenols react faster, and both alkyl and aryl aldehydes are suitable substrates. The resulting aryldioxaborins can be further elaborated to produce substituted saligenols, 2-ethoxy chromans, and 2-substituted phenols.

Improved Synthesis of the Enantiomers of Propafenone Using Chiral Building Blocks

A short and efficient synthesis of the enantiomers of the antiarrhythmic drug propafenone (1) is described using both (R)-isopropylideneglycerol tosylate and (S)-glycidyl tosylate as chiral building blocks. The key step of the high yield synthesis is the

Structural requirements for activity of propafenone-type modulators in P- glycoprotein-mediated multidrug resistance

The sodium channel blocker propafenone and a series of analogs have been identified as effective modulators of P-glyco-protein-mediated multidrug resistance in human tumor cells. A series of closely related structural homologues showed a highly significant correlation between lipophilicity and pharmacological effect. Reduction of the carbonyl group as well as conversion to a methylether led to a remarkable decrease in activity, whereby lipophilicity lost its predictive character as the main determinant for modulator potency. Similarly, the relative positioning of the acyl- and propanolamine side chains also influences activity, so the distance between carbonyl group and nitrogen atom seems important.

Intramolecular Alkylation of Phenols. Part 5. A Regiospecific Anionic Ring Closure of Phenols via Quinone Methides

The bis-magnesium salts of the triols (6a) and (6h) cyclise when heated in benzene with high ortho-regiospecificity to the corresponding bis-phenols (7) and (8).The triols (6k) and (6o) under the same conditions cyclise with high para-regiospecificity to the corresponding bis-phenols (7) and (8).Both (6a) and (6h) cyclise via o-quinone methides, and (6k) and (6o) via p-quinone methides.Results from the use of, inter alia, 18-crown-6, indicate that the high ortho-regiospecificity of the cyclisation of (6a) and (6h) is due to intramolecular Mg(II) bridging of the intermediate o-quinone methides.The high para-regiospecificity of cyclisation of (6k) and (6o) is due to steric hindrance towards o-cyclisation of the intermediate p-quinone methides presented by the Mg(II) cation.The unexpected facility with which (6a) and (6k) undergo ring closure is discussed.