1502-37-0

Usage

Uses

Used in Perfumery and Flavoring Industry:
(E)-9-Cycloheptadecen-1-one is used as a key ingredient in the manufacturing of perfumes and flavorings. Its distinct sweet, floral scent makes it a valuable addition to the fragrance industry, enhancing the aroma of various products.
Used in Cosmetics and Personal Care Products:
In the cosmetics and personal care sector, (E)-9-Cycloheptadecen-1-one is utilized as a fragrance ingredient. Its pleasant odor contributes to the overall sensory experience of these products, making them more appealing to consumers.
Used in Pharmaceutical Applications:
(E)-9-Cycloheptadecen-1-one also holds potential in the pharmaceutical industry. Its unique chemical structure may offer opportunities for the development of new drugs or therapeutic agents, although further research is required to explore these possibilities.
Used as a Flavoring Agent in Food Products:
(E)-9-Cycloheptadecen-1-one is employed as a flavoring agent in the food industry, where it can be used to enhance the taste and aroma of various products, contributing to a more enjoyable consumer experience.

Upstream product

• 135618-36-9 nonadeca-1,18-dien-10-one 
• 13038-21-6 non-8-en-1-ol 
• 156918-61-5 8-nonene-1-mesylate 
• 74244-64-7 cycloheptadec-9-en-1-one 
• 17344-59-1 (E)/(Z)-cycloheptadec-9-en-1-ol 
• 213207-73-9 10-iodo-1-decene 
• 1351586-51-0 nonadeca-1,18-dien-10-ol 
• 1540-84-7 9,26-pentatriacontadien-18-one 
• 75722-67-7 (E/Z)-17-oxo-cycloheptadec-8-enecarboxylic acid ethyl ester 
• 3100-36-5 (E/Z)-cyclohexa-dec-8-enone 
• 504-54-1 (9Z,26Z)-pentatriaconta-9,26-dien-18-one 

Downstream Products

• 17344-59-1 E-cycloheptadec-9-enol 
• 3661-77-6 cycloheptadecanone 
• 101034-26-8 cycloheptadecanone-(2,4-dinitro-phenylhydrazone) 
• 4429-77-0 cycloheptadecanol 

Relevant academic research and scientific papers

A highly efficient synthesis of civetone

A highly efficient synthesis of civetone has been performed by joining two crucial reactions; (a) Ti-Claisen condensation and (b) intramolecular olefin metathesis using Grubbs' reagent. This synthesis includes not only a stepwise method (A) but also a one-pot method (B). (C) 2000 Elsevier Science Ltd.

Continuous Flow Z-Stereoselective Olefin Metathesis: Development and Applications in the Synthesis of Pheromones and Macrocyclic Odorant Molecules**

The first continuous flow Z-selective olefin metathesis process is reported. Key to realizing this process was the adequate choice of stereoselective catalysts combined with the design of an appropriate continuous reactor setup. The designed continuous process permits various self-, cross- and macro-ring-closing-metathesis reactions, delivering products in high selectivity and short residence times. This technique is exemplified by direct application to the preparation of a range of pheromones and macrocyclic odorant molecules and culminates in a telescoped Z-selective cross-metathesis/ Dieckmann cyclisation sequence to access (Z)-Civetone, incorporating a serial array of continually stirred tank reactors.

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.

Olefin Metathesis in Confined Geometries: A Biomimetic Approach toward Selective Macrocyclization

The synthesis of macrocycles is severely impeded by concomitant oligomer formation. Here, we present a biomimetic approach that utilizes spatial confinement to increase macrocyclization selectivity in the ring-closing metathesis of various dienes at elevated substrate concentration up to 25 mM using an olefin metathesis catalyst selectively immobilized inside ordered mesoporous silicas with defined pore diameters. By this approach, the ratio between macro(mono)cyclization (MMC) product and all undesired oligomerization products (O) resulting from acyclic diene metathesis polymerization was increased from 0.55, corresponding to 35% MMC product obtained with the homogeneous catalyst, up to 1.49, corresponding to 60% MMC product. A correlation between the MMC/O ratio and the substrate-to-pore-size ratio was successfully established. Modification of the inner pore surface with dimethoxydimethylsilane allowed fine-tuning the effective pore size and reversing surface polarity, which resulted in a further increase of the MMC/O ratio up to 2.2, corresponding to >68% MMC product. Molecular-level simulations in model pore geometries help to rationalize the complex interplay between spatial confinement, specific (substrate and product) interaction with the pore surface, and diffusive transport. These effects can be synergistically adjusted for optimum selectivity by suitable surface modification.

METHOD OF CYCLIC COMPOUNDS PRODUCTION IN OLEFINE METATHESIS REACTION AND USE OF RUTHENIUM CATALYSTS IN PRODUCTION OF CYCLIC OLEFINS IN OLEFINE METATHESIS REACTION

The invention relates to a method for the preparation of cyclic compounds in the metathesis of olefins from acyclic dienes comprising terminal and/or non-terminal C=C double bonds; the invention also relates to the use of homogeneous ruthenium complexes and homogeneous ruthenium complexes deposited on a solid support as catalysts and/or pre-catalysts for the preparation of cyclic olefins in olefin metathesis reactions. Formula (I)

Fluorinated Musk Fragrances: The CF2Group as a Conformational Bias Influencing the Odour of Civetone and (R)-Muscone

The difluoromethylene (CF2) group has a strong tendency to adopt corner over edge locations in aliphatic macrocycles. In this study, the CF2group has been introduced into musk relevant macrocyclic ketones. Nine civetone and five muscone analogues have been prepared by synthesis for structure and odour comparisons. X-ray studies indeed show that the CF2groups influence ring structure and they give some insight into the preferred ring conformations, triggering a musk odour as determined in a professional perfumery environment. The historical conformational model of Bersuker and co-workers for musk fragrance generally holds, and structures that become distorted from this consensus, by the particular placement of the CF2groups, lose their musk fragrance and become less pleasant.

Stereoselective access to Z and e macrocycles by ruthenium-catalyzed Z-selective ring-closing metathesis and ethenolysis

The first report of Z-selective macrocyclizations using a ruthenium-based metathesis catalyst is described. The selectivity for Z macrocycles is consistently high for a diverse set of substrates with a variety of functional groups and ring sizes. The same catalyst was also employed for the Z-selective ethenolysis of a mixture of E and Z macrocycles, providing the pure E isomer. Notably, an ethylene pressure of only 1 atm was required. These methodologies were successfully applied to the construction of several olfactory macrocycles as well as the formal total synthesis of the cytotoxic alkaloid motuporamine C.

(Z)-8-CYCLOHEPTADECENE-1-ONE USED AS A PERFUME

The invention relates to (Z)-8-cycloheptadecene-1-one which is used as a perfume, in addition to mixture of perfume or aroma substances comprising (Z)-8-cycloheptadecene-1-one and one or more additional perfume or aroma substances.

Novel ruthenium(II)2 carboxylates as catalysts for alkene metathesis

The reactions of [Ru(=CHR)Cl2(PCy3)2] (1: R = Ph; 1a: R = -CH=CPh2) with silver salts of carboxylic acids afforded new dimeric complexes of the general formula [Ru2(=CHR)2(R′CO2)2 (μ-R′CO2)2(PCy3)2 (-H2O)] (2: R = Ph, R′ = CF3; 3: R = Ph, R′ = C2F5; 4: R = -CH=CPh2, R′ = CF3; 5: R = Ph, R′ = C6F5; 6: R = -CH=CPh2, R′ = C6F5; 7: R = -CH=CPh2, R′ = CCl3) in good yields. With R′ = CF3, C2F5 or CCl3 these complexes are active catalysts for metathesis of acyclic alkenes, including unsaturated fatty acid esters, as well as for ring closing metathesis. The reactivity of these complexes with bases and weak donor solvents has been studied and their half-life times in several media were determined.