3760-14-3

Usage

Uses

Used in Pharmaceutical Industry:
1,5-DIMETHYL-1,5-CYCLOOCTADIENE is used as a building block for the synthesis of various pharmaceuticals, contributing to the development of new drugs and medicines. Its versatility in organic reactions allows for the creation of a wide range of pharmaceutical compounds.
Used in Agrochemical Industry:
In the agrochemical sector, 1,5-DIMETHYL-1,5-CYCLOOCTADIENE is utilized as a precursor in the synthesis of agrochemicals, aiding in the production of pesticides, herbicides, and other agricultural chemicals to enhance crop protection and yield.
Used in Fragrance Industry:
1,5-DIMETHYL-1,5-CYCLOOCTADIENE is employed as a component in the creation of fragrances, leveraging its synthetic capabilities to produce a variety of scent compounds used in perfumes, cosmetics, and other scented products.
Used in Coordination Chemistry:
As a ligand, 1,5-DIMETHYL-1,5-CYCLOOCTADIENE is used in coordination chemistry to form stable complexes with transition metals. This application is crucial for various research and industrial processes that require metal complexes for catalysis, sensing, or other functional applications.

InChI:InChI=1/C10H16/c1-9-5-3-7-10(2)8-4-6-9/h5,8H,3-4,6-7H2,1-2H3/b9-5-,10-8-

Upstream product

• 14296-80-1 1,2-dimethylenecyclobutane 
• 78-79-5 isoprene 
• 123-35-3 7-methyl-3-methene-1,6-octadiene 
• 158834-31-2 1,5-dibromo-1,5-cyclooctadiene 

Downstream Products

• 21328-57-4 1,5-Dimethylcyclooctan 

Relevant academic research and scientific papers

Producing cyclic fuels from conjugated diene

A method for making a fuel includes reacting a conjugated diene or a mixture of conjugated dienes with a catalyst selected from the group consisting of a low valent iron catalyst stabilized with a pyridineimine ligand, an iron precatalyst coordinated to the pyridineimine ligand that is activated with a reducing agent, a low oxidation state Fe complex stabilized with a pyridineimine ligand and a coordinating ligand, and combinations thereof, thereby forming a substituted cyclooctadiene. The substituted cyclooctadiene is then hydrogenated, thereby forming cyclooctane fuel.

[4 + 4]-cycloaddition of isoprene for the production of high-performance bio-based jet fuel

Isoprene was efficiently converted to 1,6-dimethyl-1,5-cyclooctadiene (DMCOD) by selective [4 + 4]-cycloaddition with a catalyst formed by in situ reduction of [(MePI)FeCl(μ-Cl)]2 (MePI = [2-(2,6-(CH3)2-C6H3-NC(CH3))-C4H5N]). DMCOD was isolated in 92% yield, at the preparative scale, with a catalyst loading of 0.025 mol%, and a TON of 3680. Catalytic hydrogenation of DMCOD yielded 1,4-dimethylcyclooctane (DMCO). The cyclic structure and ring strain of DMCO afforded gravimetric and volumetric net heats of combustion 2.4 and 9.2% higher, respectively, than conventional jet fuel. In addition, the presence of methyl branches at two sites resulted in a-20 °C kinematic viscosity of 4.17 mm2 s-1, 48% lower than the maximum allowed value for conventional jet fuel. The ability to derive isoprene and related alcohols readily from abundant biomass sources, coupled with the highly efficient [Fe]-catalyzed [4 + 4]-cycloaddition described herein, suggests that this process holds great promise for the economical production of high-performance, bio-based jet fuel blendstocks.

Regio- and Diastereoselective Iron-Catalyzed [4+4]-Cycloaddition of 1,3-Dienes

A family of single-component iron precatalysts for the [4+4]-cyclodimerization and intermolecular cross-[4+4]-cycloaddition of monosubstituted 1,3-dienes is described. Cyclooctadiene products were obtained with high regioselectivity, and catalyst-controlled access to either cis- or trans-diastereomers was achieved using 4-substituted diene substrates. Reactions conducted either with single-component precatalysts or with iron dihalide complexes activated in situ proved compatible with common organic functional groups and were applied on multigram scale (up to >100 g). Catalytically relevant, S = 1 iron complexes bearing 2-(imino)pyridine ligands, (RPI)FeL2 (RPI = [2-(2,6-R2-C6H3-Na-CMe)-C5H4N] where R = iPr or Me, L2 = bis-olefin), were characterized by single-crystal X-ray diffraction, M??bauer spectroscopy, magnetic measurements, and DFT calculations. The structural and spectroscopic parameters are consistent with an electronic structure description comprised of a high spin iron(I) center (SFe = 3/2) engaged in antiferromagnetically coupling with a ligand radical anion (SPI = -1/2). Mechanistic studies conducted with these single-component precatalysts, including kinetic analyses, 12C/13C isotope effect measurements, and in situ M??bauer spectroscopy, support a mechanism involving oxidative cyclization of two dienes that determines regio- and diastereoselectivity. Topographic steric maps derived from crystallographic data provided insights into the basis for the catalyst control through stereoselective oxidative cyclization and subsequent, stereospecific allyl-isomerization and C-C bond-forming reductive elimination.

Chirality control of tropos diphenylmethane-derived phosphoramidites by chiral dienes: Its application to asymmetric Michael addition

The Rh complex of tropos diphenylmethane-derived phosphoramidite could be chirally controlled to adopt single chiral conformation upon addition of a chiral diene. In the asymmetric Michael addition of α-cyanocarboxylates catalyzed by the Rh complexes, the

METHOD FOR PRODUCING TRIMETHYLCYCLODODECATRIENE

The invention relates to the production of trimethylcyclododecatriene in a continuous or discontinuous method, by the trimerisation of isoprene in the presence of a catalyst system and a solvent. The raw trimethylcyclododecatriene obtained can be isolated by distillation. The dimethylcyclooctadiene formed as a by-product can also be isolated from the raw product.