39198-04-4

Usage

Physical State

Colorless liquid

Odor

Strong, pungent

Usage

Synthetic aroma compound, flavoring agent in food products, fragrance ingredient in perfumes and personal care products

Chemical Classification

Alpha-chloroketone (contains a carbonyl group bonded to a chlorine atom)

Configuration

(E) configuration (refers to the arrangement of the double bond in the molecule)

Manufacturing

Industrial use

Precautions

Potential health hazards, should be handled with caution.

Upstream product

• 27593-19-7 oct-1-yn-3-one 
• 41309-43-7 (2-bromovinyl)trimethylsilane 
• 142-61-0 Hexanoyl chloride 
• 1066-54-2 trimethylsilylacetylene 

Downstream Products

• 100955-91-7 1-(3-phenyl-isoxazol-5-yl)-hexan-1-one 
• 82297-67-4 (E)-1-(4-methoxyphenyl)oct-1-en-3-one 
• 5394-28-5 2-methyl-6-pentylpyridine 
• 27593-22-2 2-oxo-6-pentyl-2H-pyran-3-carboxylic acid 
• 183872-08-4 3-((E)-3-Hydroxy-oct-1-enyl)-cyclohexanone 
• 21269-27-2 (+/-)-15-epi-11-deoxyprostaglandin E₁ 
• 52487-91-9 1-iodo-3-(p-anisyldiphenylmethoxy)-trans-1-octene 
• 18409-17-1 (E)-oct-2-en-1-ol 
• 2548-87-0 (E)-2-Octenal 
• 104995-81-5 E-(S)-(+)-1-phenyloct-1-en-3-ol 
• 39647-93-3 (S)-(E)-(+)-1-Iodo-1-octen-3-ol 

Relevant academic research and scientific papers

Novel synthetic approach to (S)-coriolic acid

A new synthetic approach to (S)-coriolic acid 1 has been developed, starting from the readily available (E)-1-bromo-2-trimethylsilylethene 4 and trimethylsilylacetylene 5. A simple acylation reaction of 4, followed by a coupling reaction of the halogenoderivative intermediate with 5 in the presence of a Pd(0) catalyst affords the monosilylated ketoenyne 7. After desilylation of 7, enantioselective reduction of the carbonyl group with (S)- BINAL-H leads to the alcohol 2 (e.e.=94%). A subsequent coupling reaction and stereoselective reduction of the triple bond affords the target molecule 1.

Stereoselective Conjugate Addition of Halide Anion to Acetylenic Carbonyl Compounds Promoted by Lanthanoid Reagents

The conjugate addition of halide anion to acetylenic ketones proceeded by the combined use of cerium salts, halotrimethylsilanes and sodium or tetrabutylammonium salts to afford trans-β-halo enones stereoselectively.On the other hand, N,N-diethyl cis-β-haloacrylamides were synthesized from propiolamide.

β-HALOVINYL KETONES: SYNTHESIS FROM ACETYLENIC KETONES

The reaction of terminal acetylenic ketones with NaI or LiBr gave almost exclusively E-β-iodo-or E-β-bromovinyl ketones in trifluoracetic acid, while Z-β-iodo or Z-β-bromovinyl ketones were the major products in acetic acid.Trimethylsilyl iodide and bromide reacted smoothly with acetylenic ketones at -78 deg C to give TMS-allenolates which were readily converted to β-iodo and β-bromovinyl ketones, respectively.