74244-64-7

Basic information

• Product Name: 9-Cycloheptadecen-1-one
• Synonyms: Civettone
• CAS NO: 74244-64-7
• Molecular Formula: C₁₇H₃₀O
• Molecular Weight: 250.42
• Mol File: 74244-64-7.mol

Chemical Properties

• Melting Point: 32.5°C
• Boiling Point: 353.55°C (rough estimate)
• Appearance: /
• Density: 0.9170
• Refractive Index: 1.4830 (estimate)
• CAS DataBase Reference: 9-Cycloheptadecen-1-one(CAS DataBase Reference)
• NIST Chemistry Reference: 9-Cycloheptadecen-1-one(74244-64-7)
• EPA Substance Registry System: 9-Cycloheptadecen-1-one(74244-64-7)

Safety Data

• Hazardous Substances Data: 74244-64-7(Hazardous Substances Data)

Usage

Uses

Used in Fragrance Industry:
9-Cycloheptadecen-1-one is utilized as a fragrance ingredient in perfumes, soaps, and other personal care products. Its woody and cedar-like scent adds depth and complexity to the fragrance compositions, enhancing the overall sensory experience.
Used in Pesticide Industry:
Due to its insecticidal properties, 9-Cycloheptadecen-1-one is employed as a pesticide and insect repellent. It effectively targets and controls various insect pests, protecting crops and reducing the need for chemical pesticides, thus contributing to a more sustainable approach to pest management.
Used in Pharmaceutical Research:
9-Cycloheptadecen-1-one has been studied for its potential anti-inflammatory and anticancer properties. As a result, it is used in pharmaceutical research to explore its therapeutic potential in treating various inflammatory conditions and cancer types. Its ability to modulate biological pathways and exhibit synergistic effects with other drugs makes it a promising candidate for further investigation and development.

Upstream product

• 20701-67-1 9-octadecenedioic acid 
• 17344-59-1 E-cycloheptadec-9-enol 
• 75722-67-7 (E/Z)-17-oxo-cycloheptadec-8-enecarboxylic acid ethyl ester 
• 71-43-2 benzene 
• 80060-75-9 diethyl 19-octadecene-1,18-dioate 
• 6512-99-8 ethyl oleate 
• 13481-97-5 dimethyl 9-octadecen-1,18-dioate 
• 504-54-1 (9Z,26Z)-pentatriaconta-9,26-dien-18-one 

Downstream Products

• 123-99-9 azelaic acid 
• 505-48-6 octane-1,8-dioic acid 
• 3661-77-6 cycloheptadecanone 
• 4429-77-0 cycloheptadecanol 
• 17344-59-1 E-cycloheptadec-9-enol 
• 111-16-0 heptanedioic acid 
• 110-15-6 succinic acid 
• 111-20-6 1,10-decanedioic acid 
• 2424-90-0 heptadecanedioic acid 
• 29263-73-8 9-oxo-heptadecanedioic acid dimethyl ester 
• 1732-09-8 dimethyl subarate 
• 542-46-1 (Z)-civetone 
• 1502-37-0 trans-9-Cycloheptadecen-1-one 

Relevant articles and documents

APPLICATION OF OLEFIN METATHESIS TO ORGANIC SYNTHESIS. SYNTHESES OF CIVETONE AND MACROLIDES

Diethyl 9-octadecene-1,18-dioate was obtained in 87percent yield based on 50percent theoretical conversion by the olefin metathesis reaction catalyzed by WOCl4-Cp2TiMe2.The Dieckmann condensation of this diester using potassium hydride afforded 2-ethoxycarbonylcyclo-9-heptadecenone, which was converted by hydrolysis and decarboxylation to cyclo-9-heptadecenone (civetone) as a mixture of cis and trans isomers (1.3 : 1) in 54percent yield.Also 9-octadecen-18-olide was obtained in 17.9percent by the metathesis of oleyl oleate.

In a Quest for Selectivity Paired with Activity: A Ruthenium Olefin Metathesis Catalyst Bearing an Unsymmetrical Phenanthrene-Based N-Heterocyclic Carbene

Robust, selective, and stable in the presence of ethylene, ruthenium olefin metathesis pre-catalyst, {[3-benzyl-1-(10-phenyl-9-phenanthryl)]-2-imidazolidinylidene}dichloro(o-isopropoxyphenylmethylene)ruthenium(II), Ru-3, bearing an unsymetrical N-heterocyclic carbene (uNHC) ligand, has been synthesized. The initiation rate of Ru-3 was examined by ring-closing metathesis and cross-metathesis reactions with a broad spectrum of olefins, showing an unprecendented selectivity. It was also tested in industrially relevant ethenolysis reactions of olefinic substrates from renewable feedstock with very good yields and selectivities.

At Long Last: Olefin Metathesis Macrocyclization at High Concentration

Macrocyclic lactones, ketones, and ethers can be obtained in the High-Concentration Ring-Closing Metathesis (HC-RCM) reaction in high yield and selectivity at concentrations 40 to 380 times higher than those typically used by organic chemists for similar macrocyclizations. The new method consists of using tailored ruthenium catalysts together with applying vacuum to distill off the macrocyclic product as it is formed by the metathetical backbiting of oligomers. Unlike classical RCM, no large quantities of organic solvents are used, but rather inexpensive nonvolatile diluents, such as natural or synthetic paraffin oils. Moreover, use of a protecting atmosphere or a glovebox is not needed, as the new catalysts are perfectly moisture and air stable. In addition, some other cyclic compounds previously reported as unobtainable by RCM in neat conditions, or in high dilutions even, can be formed with the help of the HC-RCM method.

METHOD FOR PRODUCING MACROCYCLIC KETONES BY MEANS OF DIECKMANN CONDENSATION IN THE GAS PHASE

The invention relates to a method for producing macrocyclic ketones of general formula (I) by direct cyclisation of compounds of general formula (II) in the gas phase on a heterogeneous catalyst. In general formula (I), X represents a monounsaturated or polyunsaturated or saturated C10-C17 alkyl radical which can be optionally substituted by a C1-C6 alkyl radical, and in general formula (II), R1, R2 can respectively be the same or different and represent hydrogen or C1-C6 alkyl, and X has the above-mentioned designation.

METATHESIS REACTIONS OF UNSATURATED ESTERS CATALYZED BY HOMOGENEOUS TUNGSTEN COMPLEXES. SYNTHESES OF CIVETONE AND MACROLIDES

The metathesis reactions of methyl 10-undecenoate, methyl oleate and oleyl acetate have been carried out using WCl6 and WOCl4 as primary catalysts and SnMe4, PbMe4, Cp2TiMe2, and Cp2ZrMe2 as cocatalysts.The catalyst system WOCl4/Cp2TiMe2 was found to be very active for the metathesis of the unsaturated esters and is somewhat better than the system WCl6/SnMe4.Diethyl 9-octadecene-1,18-dioate, obtained by the metathesis of ethyl oleate, was subjected to the Dieckmann cyclization.The cyclized product was decarboxylated to give civetone as a mixture of the cis and trans isomers.Preliminary studies of macrolide synthesis by the intramolecular metathesis of oleyl oleate and 10-undecenyl 10-undecenoate to afford 9-octadecen-18-olide and 10-eicosen-20-olide, respectively, have been carried out.