146744-28-7

Upstream product

• 29368-59-0 p-methoxyphenolate 
• 286-20-4 cyclohexane-1,2-epoxide 
• 1122-95-8 sodium 4-methoxyphenolate 
• 286-20-4 cyclohexene oxide 
• 150-76-5 4-methoxy-phenol 

Downstream Products

• 1072-86-2 (1R,2R)-trans-1,2-cyclohexanediol 
• 57794-08-8 (1S,2S)-trans-1,2-Cyclohexanediol 
• 132177-64-1 trans-2-(4-methoxyphenoxy)cyclohexyl 3,5-dinitrobenzoate 

Relevant academic research and scientific papers

Linking BINOL: C2-symmetric ligands for investigations on asymmetric catalysis

The synthesis of new C2-symmetric chiral ligands consisting of two binaphthol units linked by a short bridge is described. These ligands can be used for investigating catalytic asymmetric reactions which utilize BINOL or related ligands as was

Highly regioselective ring opening of oxiranes with phenoxides in the presence of β-cyclodextrin in water

Highly regioselective ring opening of oxiranes to β-hydroxy ethers with phenoxides has been achieved in impressive yields in the presence of β-cyclodextrin as catalyst and water as solvent.

Linked-BINOL: An Approach towards Practical Asymmetric Multifunctional Catalysis

The development and application of a novel linked-1,1′-binaphthol (linked-BINOL) as an approach towards practical asymmetric multifunctional catalysis is described. Linked-BINOL was first designed to increase the stability of a Ga-Li-BINOL complex against

Conformationally controlled intramolecular charge transfer complexes

Trans-1-acceptor-2-donor-substituted cyclohexanes (1), as well as their 4- (or 5-)methyl-substituted homologues (2), have been prepared and are shown to form intramolecular charge-transfer (donor-acceptor) complexes. These weak complexes are turned on and off by the chair-chair interconversion of the cyclohexane ring. The CT absorptions have been measured and the equilibrium constants for the ring reversal have been determined by UV/vis spectroscopy at 298 K, as well as by NMR spectroscopy at two temperatures: at 183 K, by direct comparison of signals due to the two chair conformations, and at 300 K, by comparison of calculated and measured widths of the α-proton signals. The Gibbs free energies assigned to the donor-acceptor interactions range between 0 and -1 kcal mol-1. A crystal structure of one of the complexes (1b) confirms the intramolecular donor-acceptor alignment and interaction. The regioisomers of the methyl-substituted complexes were characterized by NOE interaction between the methyl and an α-proton cis to it.

Catalytic enantioselective meso-epoxide ring opening reaction with phenolic oxygen nucleophile promoted by gallium heterobimetallic multifunctional complexes

The catalytic enantioselective meso-epoxide ring opening reaction with phenolic oxygen nucleophile (4-methoxyphenol) is described for the first time herein. This reaction was first found to be promoted by (R)-GaLB (Ga = gallium, L = lithium, B = (R)-BINOL), giving a variety of epoxide opening products in good to high ee (67-93% ee). However, chemical yield was only modest (yield 31-75%), despite the use of more than 20 mol % GaLB. This was due to the undesired ligand exchange between BINOL and 4-methoxyphenol, which resulted in the decomplexation of GaLB. Application of various known chiral ligands such as 6,6'-bis((triethylsilyl)ethynyl)-BINOL and H8-BINOL were examined, but satisfactory results were not obtained. To overcome this problem a novel linked-BINOL containing coordinative oxygen atom in the linker has been developed. By linking two BINOL units in GaLB, the stability of the Ga-complex was greatly improved. Using 3-10 mol % (R,R)-Ga-Li-linked- BINOL complex, a variety of epoxide opening reactions were found to proceed smoothly, affording products in analogous ee (66-96% ee) and in much higher yield (yield 67-94%) compared to (R)-GaLB. The structure of the LiCl free Ga- Li-linked-BINOL complex was elucidated by X-ray analysis. This is the first X-ray data for an asymmetric catalyst containing gallium. The possible mechanism of the entitled reaction is also discussed, based on the X-ray structure of the Ga-complex.

A Convenient Enantioselective Synthesis of trans-2-Aryloxycyclohexan-1-ols Using Pig Liver Acetone Powder (PLAP) as Biocatalyst

Pig liver acetone powder (PLAP) has been used as a biocatalyst for enantioselective hydrolysis of racemic trans-1-acetoxy-2-aryloxycyclohexanes to produce the resulting (R,R)-2-aryloxycyclohexan-1-ols upto >99percent enantiomeric purities. (R,R)-Selectivity in this hydrolysis of racemic trans-2-aryloxycyclohexyl acetates was explained on the basis of Jones' three dimensional active site-model.

Conformationally Controlled Intramolecular Charge Transfer Complexes

The formation of intramolecular charge transfer complexes between an electron-poor 3,5-dinitrobenzoyl fragment and electron-rich 4-substituted phenoxy fragments can be controlled by restricting the conformation of substituted cyclohexanes containing these