76293-69-1

Usage

InChI:InChI=1/C14H24O2/c15-14-12-10-8-6-4-2-1-3-5-7-9-11-13-16-14/h5,7H,1-4,6,8-13H2/b7-5+

Upstream product

• 76293-71-5 pent-4-en-1-yl undec-10-enoate 
• 38460-95-6 undec-10-enoyl chloride 

Relevant academic research and scientific papers

Catalytic performance of ruthenium-supported ionic-liquid catalysts in sustainable synthesis of macrocyclic lactones

Thirteen- to eighteen-membered lactones were synthesized by ring-closing olefin-metathesis reactions of bis-olefins with heterogeneous Grubbs-supported ionic-liquid catalysts (SILCs), in which homogeneous Grubbs catalysts were confined in pores of alumina with the aid of an ionic liquid. The Grubbs-SILCs exhibited higher catalytic performance than their homogeneous counterparts and could be repeatedly recovered by simple filtration and re-used several times.

Highly selective macrocyclic ring-closing metathesis of terminal olefins in non-chlorinated solvents at low dilution

A set of new ruthenium-indenylidene complexes bearing two unsymmetrical unsaturated N-cycloalkyl-NHC ligands were synthesized. These catalysts proved to be highly selective in the macrocyclic ring-closing metathesis performed in non-chlorinated solvents at low dilution (0.01 M). Without the requirement of benzoquinone derivatives to prevent the isomerisation side reactions, this environmentally friendly catalytic process promoted the synthesis of macrocyclic odorant molecules with remarkable >99% purity.

A HIGHLY EFFICIENT SYNTHESIS OF Z-MACROCYCLES USING STEREORETENTIVE, RUTHENIUM-BASED METATHESIS CATALYSTS

A highly efficient, Z-selective ring-closing metathesis system for the formation of macrocycles using a stereoretentive, ruthenium-based catalyst supported by a dithiolate ligand is reported. This catalyst is demonstrated to be remarkably active as observed in initiation experiments showing complete catalyst initiation at - 20°C within 10 min. Using easily accessible diene starting materials bearing a Z-olefin moiety, macrocyclization reactions generated products with significantly higher Z-selectivity in appreciably shorter reaction times, in higher yield, and with much lower catalyst loadings than in previously reported systems. Macrocyclic lactones ranging in size from twelve-mem bered to seventeen-membered rings are synthesized in moderate to high yields (68 - 79% yield) with excellent Z-selectivity (95% - 99% Z).

A Highly Efficient Synthesis of Z-Macrocycles Using Stereoretentive, Ruthenium-Based Metathesis Catalysts

A highly efficient, Z-selective ring-closing metathesis system for the formation of macrocycles using a stereoretentive, ruthenium-based catalyst supported by a dithiolate ligand is reported. The catalyst is remarkably active as observed in initiation experiments showing complete catalyst initiation at ?20 °C within 10 minutes. Macrocyclization reactions generated Z-products from easily accessible diene starting materials bearing a Z-olefin moiety. This approach provides a more efficient and selective route to Z-macrocycles relative to previously reported systems. Reactions were completed within shorter reaction times, and turnover numbers of up to 100 could be achieved. Macrocyclic lactones ranging in size from twelve- to seventeen-membered rings were synthesized in moderate to high yields (67–79 %) with excellent Z-selectivity (95–99 %).

Mesocellular foam-supported catalysts: Enhanced activity and recyclability for ring-closing metathesis

Although ring-closing metathesis (RCM) has been one of the most powerful methodologies for creating cyclic compounds, the pharmaceutical industry has not yet widely adopted this process commercially due to the high costs and leaching problems of homogeneous ruthenium catalysts. To circumvent these problems, we have immobilized the second-generation Hoveyda-Grubbs catalyst effectively onto siliceous mesocellular foam (MCF). The open and interconnected pores of MCF facilitated ligand immobilization and substrate diffusion. We ave observed that the ligand and metal loadings significantly affected the catalytic activity and recyclability. Enhanced recyclability by suppression of ruthenium leaching was achieved by using excess immobilized ligands. The resulting novel heterogenized catalysts demonstrated excellent activity and reusability for the RCM of various types of substrates.

SYNTHESE DE MACROLIDES PAR METATHESE.

Two syntheses of macrolides via olefin metathesis are presented.The first (A) involves preparation of ω-hydroxyacid 6 or 9 by metathesis followed by cyclisation, while the second (B) involves macrocyclic ring closure by metathesis of a ω,ω'diunsaturated ester 12.