169557-36-2

Upstream product

• 75-36-5 acetyl chloride 
• 602-09-5 1,1'-bi-2-naphthol 
• 108-24-7 acetic anhydride 
• 100569-82-2 2,2'-diacetoxy-1,1'-binaphthyl 
• 79044-27-2 (±)-1-(2-hydroxynapthalen-1-yl)napthalen-2-yl acetate 
• 18531-94-7 (R)-1,1'-Bi-2-naphthol 
• 108-05-4 vinyl acetate 
• 64-19-7 acetic acid 
• 135-19-3 β-naphthol 

Relevant academic research and scientific papers

Continuous Flow Preparation of Enantiomerically Pure BINOL(s) by Acylative Kinetic Resolution

A polystyrene-immobilized isothiourea has been applied to the enantioselective acylative kinetic resolution (KR) of monoacylated BINOL(s) with inexpensive isobutyric anhydride in batch and flow. High selectivity values (s=29 at 0 °C) and a remarkable stability of the catalytic system in the operation conditions have been recorded for unsubstituted BINOL. No significant loss of activity/selectivity is recorded after 10 consecutive KR cycles in batch. A continuous flow process has been implemented and operated with a 100 mmol (32.8 g) sample of racemic monoacetylated BINOL in dichloromethane solution in an 84 hours experiment with a packed bed reactor containing 1 g (f=0.37 mmol.g?1) of the functional resin (s=17–21). Residence time can be decreased to 10 min with the same reactor to achieve a conversion of 58% with a selectivity factor s=17 when a more highly functionalized catalyst (f=0.88 mmol.g?1) is used. This translates into a remarkable combined productivity of 5.5 mmolprod ? mmolcat?1 ? h?1.

Rapid Synthesis of Alkenylated BINOL Derivatives via Rh(III)-Catalyzed C-H Bond Activation

Modification of BINOL units has been well examined via Rh-catalyzed C-H activation and functionalization reactions by using ester carbonyls as directing groups and alkenes as coupling partners. The one-pot strategy was an efficient protocol for the rapid synthesis of BINOL derivatives with retention of optical purity.

Base-promoted lipase-catalyzed kinetic resolution of atropisomeric 1,1′-biaryl-2,2′-diols

Herein we report a dramatic acceleration of the lipase-catalyzed kinetic resolution of atropisomeric 1,1′-biaryl-2,2′-diols by the addition of sodium carbonate. This result likely originates from the increased nucleophilicity of the phenolic hydroxyl group toward the acyl-enzyme intermediate. Under these conditions, various substituted C2-symmetric and non-C2-symmetric binaphthols and biphenols were efficiently resolved with ～50% conversion in only 13-30 h with excellent enantioselectivity.

Arthrobacter sp. lipase catalyzed kinetic resolution of BINOL: The effect of substrate immobilization

(S)-1,1′-Binaphthyl-2,2′-diol was prepared in high optical purity (～98%) via Arthrobacter sp. lipase (MTCC No. 5125) catalyzed kinetic resolution. The immobilization of the substrate on a solid inert support significantly improved the enantioselectivity factor (E) by almost sixfolds, i.e. from ～27 to >180. The effect of acyl substituents and co-solvents were also studied.

Efficient acetylation of alcohols and phenols catalyzed by recyclable lithium bis(perfluoroalkylsulfonyl)imide

An efficient acetylation of alcohols and phenols catalyzed by lithium bis(perfluoroalkylsulfonyl)-imide was developed. This acetylation features good yields, mild reaction condtions, and simple workup procedures. Furthermore, the catalyst bearing a long perfluoroalkyl chain is recoverable and readily reusable without losing any activity. Copyright

Efficient routes to racemic and enantiomerically pure (s)-binol diesters

A systematic study for esterification procedures to the synthesis of BINOL diesters is described. Reaction conditions with trifluoracetic acid anhydride (TFAA) and 85% H3PO4 were selected as the best procedure to prepare enantiomeric

Solution-phase synthesis and evaluation of tetraproline chiral stationary phases

A protocol was developed for the solution-phase synthesis of multigram amounts of two 9-fluorenylmethoxycarbonyl (Fmoc)-protected tetraproline peptides. These tetraproline peptides were then attached to amino derivatized silica gel. The replacement of the Fmoc group with the trimethylacetyl group lead to two tetraproline chiral stationary phases (CSPs). A comparison of the chromatographic behavior of these two solution-phase-synthesized tetraproline CSPs with that prepared by stepwise solid-phase synthesis revealed that all three had similar chromatographic performance for resolving 53 model analytes. This suggests that the solution-phase synthesis of oligoprolines, which allows for the specific benefits of good batch reproducibility, selector homogeneity, and possibly low cost, is a feasible alternative to the solid-phase synthesis of oligoproline CSPs. Copyright

Ultrasonic speed and related acoustical parameters of 1,1'-Binaphthalene-2, 2'-diyl diacetate solutions at 308.15 K

The density (ρ), viscosity (η) and ultrasonic speed (U) (2MHz) of chloroform, THF, ethyl alcohol, ethyl acetate, 1,4-dioxane and 1,1'-binaphthalene-2,2'-diyl diacetate (DBNA) solutions have been determined at 308.15 K. Various acoustical parameters namely specific acoustical impedance (Z), adiabatic compressibility (ka), Van der Waals constant (b), intermolecular path length (Lf), internal pressure (π), Rao's molar sound function (R), relaxation time (τ), classical absorption coefficient (α/f2)cl and solvation number (Sn) have been derived from ρ, η and U data and correlated with concentration (C). A fairly good to excellent correlation has been observed between a particular parameter and C. Linear increase of Z, R, b, (α/f2) Cl and τ (except EA) (R2 = 0.90 - 0.999) and linear decrease of ks, π and Lf (R2 = 0.947 - 0.995) with C supported existence of powerful molecular interactions in the solutions and further supported by nonlinear increase of Sn with C. A fairly constant Gibbs free energy of activation has been observed in all the solvent systems studied.

Rational design of BINOL-based diimidazolyl ligands: Homochiral channel-like mono-component organic frameworks by hydrogen-bond-directed self-assembly

We have developed a synthetic strategy to selectively incorporate the imidazole ring into the 1,1′-bi-2-naphthol (BINOL) skeleton at the different position. The resulting conformationally rigid BINOL-based diimidazolyl ligands bearing both hydrogen-bond-acceptors and -donators can self-assemble into homochiral channel-like mono-component organic frameworks via intermolecular O-H...N hydrogen bonds between the phenolic hydroxyl group and the N2 or N4 atom of the imidazole ring.

N,N'-Diiodo-N,N'-1,2-ethanediylbis(p-toluenesulfonamide) as an efficient catalyst for acetylation of alcohols, phenols, amines, and thiols under solvent-free conditions

N,N'-Diiodo-N,N'-1,2-ethanediylbis(p-toluenesulfonamide) (NIBTS) is a highly efficient catalyst for the acetylation of alcohols, phenols, amines, and thiols under solvent-free conditions. Primary, secondary, tertiary alcohols; phenols; amines; and thiols can be easily acetylated in good to excellent yields at 80 C. Copyright Taylor & Francis Group, LLC.