127471-65-2

Upstream product

• 15356-60-2 (1S,2R,5S)-(+)-menthol 
• 79-03-8 propionyl chloride 
• 802294-64-0 propionic acid 
• 123-62-6 propionic acid anhydride 
• 15356-70-4 menthol 
• 89-78-1 menthol 
• 105-38-4 vinyl propionate 
• 2216-51-5 (-)-menthol 
• 74-85-1 ethene 
• 201230-82-2 carbon monoxide 

Downstream Products

• 68326-56-7 (R)-1-[(4-methylphenyl)sulfinyl]butan-2-one 
• 119244-66-5 l-menthyl (trimethylsilyl)propanoate 
• 112297-86-6 l-menthyl 2-methyl-2-(trimethylsilyl)-4-phenylbutyrate 
• 112297-82-2 l-menthyl 2-methyl-2-(trimethylsilyl)-4-phenylbutyrate 
• 112297-84-4 l-menthyl 2-methyl-2-(trimethylsilyl)-3-phenylpropionate 
• 112297-80-0 l-menthyl 2-methyl-2-(trimethylsilyl)-3-phenylpropionate 
• 112297-85-5 l-menthyl 2,5-dimethyl-2-(trimethylsilyl)-4-hexanoate 
• 112297-81-1 l-menthyl 2,5-dimethyl-2-(trimethylsilyl)-4-hexanoate 
• 112297-87-7 l-menthyl 2-methyl-2-(trimethylsilyl)heptanoate 
• 112297-83-3 l-menthyl 2-methyl-2-(trimethylsilyl)heptanoate 
• 61597-98-6 (1R,2S,5R)-menthyl (S)-(-)-lactate 
• 17162-29-7 (-)-menthyl lactate 

Relevant academic research and scientific papers

Second Generation Total Synthesis of (–)-Preussochromone D

An improved enantioselective synthesis of the natural product (–)-preussochromone D (3) and first insights into a possible route to the trans-preussochromones E and F are described. Starting from commercially available 5-hydroxy-4H-chromen-4-one, two ster

Characterization and structure basis of Pseudomonas alcaligenes lipase's enantiopreference towards d,l-menthyl propionate

In this >work, a lipase from Pseudomonas alcaligenes CGMCC4405 (PaL) was cloned and expressed. It was very attractive that the recombinant PaL exhibited excellent enantioselectivity (E > 200) in the resolution of racemic d,l-menthyl propionate to produce l-menthol. The structure basis of enantiopreference is a fundamental scientific problem which needs to be resolved. In our research, molecular dynamic simulation (MD) research was employed to research the different binding modes of d and l-menthyl propionate. The results showed that when bound with slow-reacting enantiomer (d-menthyl propionate), the steric requirements of the large substituent (isopropyl) of the d-menthyl propionate force a rotation of the imidazole ring of catalytic residue His271 and further pushed the active site His271 away from its proper orientation. Moreover, the average distance between alcohol oxygen (O alc) and HNEε of catalytic His271 increased to 3.7 A, which was too far to form an essential hydrogen bond and further prevented efficient catalysis of slow enantiomer. This correlation of the distance between alcohol oxygen (Oalc) and H NEε of catalytic His271 and the enantioselectivity was also confirmed by the result of site-directed mutagenesis.

Palladium-Catalyzed Direct Dicarbonylation of Amines with Ethylene to Imides

The selective and effective conversion of low-cost and simple bulk chemicals into high value-added products through catalytic strategy has a wide range of practical significance. Here, a palladium-catalyzed method for the direct and efficient dicarbonylation of amines with basic industrial feedstock ethylene to imide has been developed. Moderate to excellent yields of the desired imides can be produced from readily available amines in a straightforward manner.

Preparation method of

The preparation method comprises the following steps 1-11: Wherein. ROH (Formula X) is a chiral alcohol and the like, PG is a hydroxy protecting group, a compound of Formula VI and a compound of Formula V are the chiral auxiliary of the present invention. To the invention, the chiral auxiliary base ROH compound and the chiral alcohol X (Formula VI) are used for preparing the chiral auxiliary base-type compound of formula V IV and the compound of Formula XI, and the compound of formula IV can be prepared through three-step simple operation steps of chiral auxiliary base. Be applicable to industrial production.

Highly Productive and Enantioselective Enzyme Catalysis under Continuous Supported Liquid–Liquid Conditions Using a Hybrid Monolithic Bioreactor

Enzyme-containing ionic liquids (ILs) were immobilized in cellulose-2.5-acetate microbeads particles embedded in a porous monolithic polyurethane matrix. This bioreactor was used under continuous liquid-liquid conditions by dissolving the substrates in a nonpolar organic phase immiscible with the ILs, thereby creating a biphasic system. Lipases (candida antarctica lipase B, CALB, candida rugosa lipase, CRL) were used to catalyze the enantioselective transesterification of racemic (R,S)-1-phenylethanol with vinyl butyrate and vinyl acetate, the esterification of (+/-)-2-isopropyl-5-methylcyclohexanol with propionic anhydride and the amidation of (R,S)-1-phenylethylamine with ethyl methoxyacetate. With this unique setup, very high productivities, that is, turnover numbers (TONs) up to 5.1×106 and space-time yields (STYs) up to 28 g product L?1 h?1, exceeding the corresponding values for batch-type reactions by a factor of 3100 and 40, respectively, were achieved while maintaining or even enhancing enantioselectivity compared to batch reactions via kinetic resolution. To our best knowledge, this is the first continuously operated bioreactor using supported liquid-liquid conditions that shows these features in the synthesis of chiral esters and amides.

An extremely efficient and green method for the acylation of secondary alcohols, phenols and naphthols with a deep eutectic solvent as the catalyst

The typical deep eutectic solvent [CholineCl][ZnCl2]3, easily prepared from choline chloride and zinc chloride, is green and useful for the acylation of secondary alcohols, phenols, and naphthols with acid anhydrides. Its efficiency allows the acylation of sterically hindered secondary alcohols and acid anhydrides to proceed in high yield under mild condition. The catalyst is cheap, easy to handle, conveniently synthesized in a single step, and recyclable for several times without significant loss of catalytic activity.

Synthesis, antimicrobial evaluation, and QSAR analysis of 2-isopropyl-5-methylcyclohexanol derivatives

A series of 2-isopropyl-5-methylcyclohexanol derivatives were synthesized and evaluated for their antibacterial activity against Gram-positive Staphylococcus aureus and Bacillus subtilis and Gram-negative Escherichia coli and in vitro antifungal activity against Candida albicans and Aspergillus niger. The results of antimicrobial activity demonstrated that the compounds 10, 20, and 21 were the most active ones among the synthesized compounds. The QSAR studies revealed the importance of dipole moment (μ), total energy (Te), and topological parameters (κ1 and κ3) in describing the antimicrobial activity of 2-isopropyl-5-methylcyclohexanol derivatives. Springer Science+Business Media, LLC 2011.

Homobenzotetramisole: An effective catalyst for kinetic resolution of aryl-cycloalkanols

Homobenzotetramisole (HBTM), a ring-expanded analogue of the previously reported catalyst BTM, displays higher catalytic activity and a different structure-selectivity profile. It displays good enantioselectivities in kinetic resolution of secondary benzylic alcohols but is particularly effective for 2-aryl-substituted cycloalkanols.

pH memory of immobilized lipase for (±)-menthol resolution in ionic liquid

Magnetic DEAE-GMA-EDMA microspheres were prepared via suspension polymerization and used for the immobilization of Candida rugosa lipase by ion exchange. The effect of pH values on the immobilization of lipase was investigated. Resolution of (±)-menthol in the hydrophobic ionic liquid 1-butyl-3-methylimidazolium hexafluorophosphate was performed by immobilized lipase-catalyzed enantioselective esterification with propionic anhydride as acyl donor. The effects of pH condition at lipase immobilization on the conversion and enantioselectivity were investigated. As a result, pH memory of the immobilized lipase for catalyzing (±)-menthol resolution in the ionic liquid was observed. Better conversion and the best enantioselectivity were obtained with the immobilized lipase prepared at pH 5.0. Under the condition, (-)-menthyl propionate with enantiomeric excess of >90% was obtained. Moreover, the enantioselectivity of the immobilized lipase decreased gradually with increasing pH value.

Erbium(III) chloride: A very active acylation catalyst

Erbium(iii) chloride is a powerful catalyst for the acylation of alcohols and phenols. The reaction works well for a large variety of simple and functionalized substrates by using different kinds of acidic anhydrides (Ac 2O, (EtCO)2O, (PriCO)2O, (Bu tCO)2O, and (CF3CO)2), without isomerization of chiral centres. Moreover, the catalyst can be easily recycled and reused without significant loss of activity. CSIRO 2007.