1502-37-0

Basic information

• Product Name: (E)-9-Cycloheptadecen-1-one
• Synonyms: (E)-9-Cycloheptadecen-1-one;trans-Civetone
• CAS NO: 1502-37-0
• Molecular Formula: C₁₇H₃₀O
• Molecular Weight: 0
• Mol File: 1502-37-0.mol
• Article Data: 9

Chemical Properties

• Appearance: /
• CAS DataBase Reference: (E)-9-Cycloheptadecen-1-one(CAS DataBase Reference)
• NIST Chemistry Reference: (E)-9-Cycloheptadecen-1-one(1502-37-0)
• EPA Substance Registry System: (E)-9-Cycloheptadecen-1-one(1502-37-0)

Safety Data

• Hazardous Substances Data: 1502-37-0(Hazardous Substances Data)

Usage

General Description

(E)-9-Cycloheptadecen-1-one, also known as heneicos-9-en-1-one, is a chemical compound belonging to the class of organic compounds known as ketones. It is a colorless liquid with a slightly sweet, floral odor, and is found in various plant species. The compound is used in the manufacturing of various products such as perfumes, flavorings, and other chemicals. It is also used as a fragrance ingredient in cosmetics and personal care products. Additionally, (E)-9-Cycloheptadecen-1-one has potential applications in the field of pharmaceuticals and as a flavoring agent in food products.

Upstream product

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

Downstream Products

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

Relevant articles and documents

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.

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.

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.