73486-92-7

Usage

InChI:InChI=1/C16H20O3/c1-18-14-10-7-13(8-11-14)9-12-16(17)19-15-5-3-2-4-6-15/h7-12,15H,2-6H2,1H3/b12-9+

Upstream product

• 943-89-5 (E)-3-(4-methoxyphenyl)acrylic acid 
• 108-93-0 cyclohexanol 
• 63254-54-6 cyclohexyl diazoacetate 
• 123-11-5 4-methoxy-benzaldehyde 
• 696-62-8 para-iodoanisole 
• 3066-71-5 cyclohexyl acrylate 

Relevant academic research and scientific papers

Sustainable Mizoroki-Heck reaction in water: Remarkably high activity of Pd(OAc)2 immobilized on reversed phase silica gel with the aid of an ionic liquid

Palladium acetate immobilized on reversed phase amorphous silica gel with the aid of an ionic liquid, [bmim]PF6, was highly efficient in the promotion of the Mizoroki-Heck reaction in pure water without a ligand up to the sixth re-use, in 95% average yield with TON and TOF 1,600,000 and 71,000 (h-1), respectively. The Royal Society of Chemistry 2005.

MYOGLOBIN-BASED CATALYSTS FOR CARBENE TRANSFER REACTIONS

Methods are provided for carrying out carbene transfer transformations such as olefin cyclopropanation reactions, carbene heteroatom-H insertion reactions (heteroatom = N, S, Si), sigmatropic rearrangement reactions, and aldehyde olefination reactions with high efficiency and selectivity by using a novel class of myoglobin-based biocatalysts. These methods are useful for the synthesis of a variety of organic compounds which contain one or more new carbon-carbon or carbon-heteroatom (N, S, or Si) bond. The methods can be applied for conducting these transformations in vitro (i.e., using the biocatalyst in isolated form) and in vivo (i.e., using the biocatalyst in a whole cell system).

Myoglobin-catalyzed olefination of aldehydes

The olefination of aldehydes constitutes a most valuable and widely adopted strategy for constructing carbon-carbon double bonds in organic chemistry. While various synthetic methods have been made available for this purpose, no biocatalysts are known to mediate this transformation. Reported herein is that engineered myoglobin variants can catalyze the olefination of aldehydes in the presence of α-diazoesters with high catalytic efficiency (up to 4,900 turnovers) and excellent Ediastereoselectivity (92-99.9 % de). This transformation could be applied to the olefination of a variety of substituted benzaldehydes and heteroaromatic aldehydes, also in combination with different alkyl α-diazoacetate reagents. This work provides a first example of biocatalytic aldehyde olefination and extends the spectrum of synthetically valuable chemical transformations accessible using metalloprotein-based catalysts.

Immobilization of Pd(OAc)2 in ionic liquid on silica: Application to sustainable Mizoroki-Heck reaction

(Equation Presented) Palladium acetate was supported on amorphous silica with the aid of an ionic liquid, [bmim]PF6. The immobilized catalyst was highly efficient in promoting the Mizoroki-Heck reaction without a ligand in n-dodecane for at least six reuses, in 89-98% yields. The TON and TOF reached 68 400 and 8000, respectively.