15210-25-0

Usage

Uses

Used in Fragrance Industry:
2,3,4,5,6,7,8,9,10,11,12,13-Dodecahydro-1H-cyclopenta[12]annulen-1-one is used as a fragrance ingredient for its musky odor. It is commonly found in perfumes, colognes, and other personal care products, adding a distinct scent profile to these products.
Used in Flavor Industry:
In addition to its use in fragrances, 2,3,4,5,6,7,8,9,10,11,12,13-dodecahydro-1H-cyclopenta[12]annulen-1-one is also utilized in the flavor industry. Its unique properties contribute to the taste and aroma of various food and beverage products.
Used in Organic Synthesis:
2,3,4,5,6,7,8,9,10,11,12,13-Dodecahydro-1H-cyclopenta[12]annulen-1-one is used in the synthesis of other organic compounds. Its chemical properties make it a valuable building block for creating a wide range of chemical products, further expanding its industrial applications.

Upstream product

• 67220-92-2 1-(3.3-Dichlorpropenyl)cyclododecanol 
• 88868-56-8 1-ethynyl-2-methylene-cyclododecyl acetate 
• 52815-18-6 (2,2-Dichloro-spiro[2.11]tetradec-1-yl)-methanol 
• 1129-90-4 cyclododecyne 
• 124-38-9 carbon dioxide 
• 97-93-8 triethylaluminum 
• 541-41-3 chloroformic acid ethyl ester 
• 105-58-8 Diethyl carbonate 
• 1501-82-2 cyclododecene 
• 814-68-6 acryloyl chloride 
• 92007-34-6 (6E,10E)-1,1-Dichloro-3a,4,5,8,9,12,13,13a-octahydro-1H,3H-cyclopentacyclododecen-2-one 
• 92007-33-5 cis-14,14-dichlrobicyclo<10.2.0>tetradeca-trans,trans-4,8-dien-13-one 
• 92007-35-7 (6E,10E)-3-Chloro-1,4,5,8,9,12,13,13a-octahydro-cyclopentacyclododecen-2-one 
• 706-31-0 (1E,5E,9Z)-cyclododeca-1,5,9-triene 

Downstream Products

• 672-78-6 methyl p-toluene sulfinate 
• 80-48-8 methyl p-toluene sulfonate 
• 14224-80-7 cyclopentadec-4-yn-1-one 
• 502-72-7 cyclopentadecanone 

Relevant academic research and scientific papers

Reinvestigation of the Nazarov cyclization of 1-(3-hydroxypropynyl)cyclododecan-1-ol to bicyclo[10.3.0]pentadec-1(12)-en-13-one

Reinvestigation of the acid-catalyzed cyclization of 1-(3-hydroxypropynyl)cyclododecan-1-ol under the conditions of the Nazarov reaction demonstrated that this conversion yields two isomeric bicyclic ketones, namely, bicyclo[10.3.0]pentadec-1(12)-en-13-one and bicyclo[10.3.0]pentadec-1-en-3-one. The latter compound is thermodynamically less stable.

Cycloalumination of cycloalkynes with triethylaluminum catalyzed by zirconium complexes

Cycloalumination of cycloalkynes with triethylaluminum in the presence of zirconium complexes was performed for the first time, and new bicyclic aluminacyclopentenes were obtained in 74-94% yield. Pleiades Publishing, Ltd., 2012.

An efficient one-pot method for the synthesis of mono- and biscyclopentenones via zirconium-catalyzed cycloalumination of cyclic alkynes and diynes

Mono- and bisaluminacyclopentenes obtained via zirconium-catalyzed cycloalumination with Et3Al and cyclic alkynes or diynes can be converted into the corresponding mono- and biscyclopentenones by treatment with CO2, ClCOOEt, or CO(OE

Cyclopentadecanone preparation method

The invention provides a cyclopentadecanone preparation method. The method includes that cyclododecene and acryloyl chloride are subjected to reaction to obtain a ketene intermediate shown as a formula (II), the intermediate and a sulfuryl hydrazine compound are subjected to reaction to obtain a hydrazone intermediate shown as a formula (III), and the hydrazone intermediate is subjected to ring opening and hydrogenation to obtain a cyclopentadecanone product shown as a formula (V). Compared with a traditional cyclopentadecanone synthesis route, the method mainly has advantages of low cost andeasiness in acquisition of starting materials, the ketene intermediate shown as the formula (II) is obtained by high-selectivity reaction of cyclododecene and acryloyl chloride, and the integral synthesis route is simple and short in step, high in total yield and applicable to cyclopentadecanone industrial production.

Electroorganic Chemistry. 140. Electroreductively Intra- and Intermolecular Couplings of Ketones with Nitriles

Electroreduction of γ- and δ-cyano ketones in i-PrOH with Sn cathode gave α-hydroxy ketones and their dehydroxylated ketones as the intramolecularly coupled products.Guaiazulene, (-)-valeranone, polyquinanes, dihydrojasmone, methyl dihydrojasmonate, and rosaprostol have been synthesized by utilizing this electroreductive intramolecular coupling of γ- and δ-cyano ketones in one of the key steps.Similarly, electroreduction of a mixture of ketone and nitrile gave the corresponding intermolecularly coupled product.The product obtained by the electroreductive intermolecular coupling of (+)-dihydrocarvone with acetonitrile has been found to be the precursor of an effective chiral ligand for the enantioselective addition of diethylzinc to aldehydes.

An Electrochemical Variant in the Syntheses of Exaltone and Muscone: Anodic Fragmentation of α,β-Unsaturated Tosylhydrazones

Ring enlargement of bicyclopentadec-1(12)-en-13-one p-toluenesulfonylhydrazone into cyclopentadec-4-yn-1-one was accomplished under mild and controlled anodic oxidation conditions.The mechanism of this fragmentation is reconsidered.

STRATEGY FOR CYCLOPENTENONE ANNULATION OF OLEFINS: A GENERAL PROTOCOL FOR BICYCLOENONE SYNTHESIS

Several bicyclic α-chloro enones obtained through Greene annulation of cyclic olefins are shown to undergo efficient, two step, enone transposition via Luche reduction and aq. formic acid treatment.Application of this methodology to the formal synthesis of exaltone and (+/-)-muscone is described.

2-Cyclopentenones from 1-Ethynyl-2-propenyl Acetates

PdCl2(MeCN)2 catalyzes the cyclization of 1-ethynyl-2-propenyl acetates 1 to 1,4-cyclopentadienyl acetates 2, which are cleaved in situ to 2-cyclopentenones 3.

SYNTHESIS OF 1-(3-HYDROXYPROPYNYL)-1-CYCLODODECANOL AND ITS CYCLIZATION TO BICYCLOPENTADEC-1(12)-EN-13-ONE

Methods were developed for the synthesis of 1-(3-hydroxypropynyl)-1-cyclododecanol from cyclododecanone and propargyl alcohol and from 1-ethynyl-1-cyclododecanol and formaldehyde.Its cyclization to bicyclopentadec-1(12)-en-13-one was investigated.

Cyclopentenone Synthesis from 1,1-Dichloroallyllithium-Ketone Adducts as Well as from Dichlorocarbene-Allyl Alcohol Adducts

Treatment of (3,3-dialkyl-2,2-dichlorocyclopropyl)methanols with hydrobromic acid gives 2-cyclopentenones through postulated intermediates, 3-chlorocyclopentadienyl cations.Another method which should give the same cationic intermediates involves trifluoroacetic acid catalyzed reaction of 3,3-dichloro-1-alken-4-ols.This is found to be particularly useful for cyclopentenone annulation.