42832-48-4

Upstream product

• 55287-92-8 (+/-)-tridec-1-en-3-ol 
• 106672-64-4 1-phenylthio-3-tridecanone 
• 112-31-2 caprinaldehyde 
• 106672-59-7 3,4-epoxy-3-phenylsulfinyl-1-phenylthiotridecane 
• 112-44-7 undecylaldehyde 

Downstream Products

• 54844-65-4 (Z)-6-heneicosen-11-one 

Relevant academic research and scientific papers

Influence of the chemical structure on odor qualities and odor thresholds in homologous series of alka-1,5-dien-3-ones, alk-1-en-3-ones, alka-1,5-dien-3-ols, and alk-1-en-3-ols

Odor qualities and odor thresholds in air in homologous series of synthesized alk-1-en-3-ols and alka-1,5-dien-3-ols and their corresponding ketones were evaluated by gas chromatography-olfactometry. In the series of the alk-1-en-3-ols and alk-1-en-3-ones the odor quality changed successively from pungent for the compounds with five carbon atoms via metallic, vegetable-like for the six- and seven-carbon odorants to mushroom-like for the compounds with eight and nine carbon atoms. With further increase in chain length the mushroom-like impression decreased and changed to citrus-like, soapy, or herb-like. In both series, two odor threshold minima were found for the six-carbon and also for the eight- and nine-carbon odorants, respectively. In contrast to this, the odor qualities in the series of the (Z)- and (E)-alka-1,5-dien-3-ols and their corresponding ketones did not change significantly with geranium-like, metallic odors and an increasing mushroom-like odor note with increasing chain length. The lowest thresholds were found for the eight- and nine-carbon (Z)-compounds, respectively.

Influence of the chemical structure on odor qualities and odor thresholds in homologous series of alka-1,5-dien-3-ones, alk-1-en-3-ones, alka-1,5-dien-3-ols, and alk-1-en-3-ols

Odor qualities and odor thresholds in air in homologous series of synthesized alk-1-en-3-ols and alka-1,5-dien-3-ols and their corresponding ketones were evaluated by gas chromatography-olfactometry. In the series of the alk-1-en-3-ols and alk-1-en-3-ones the odor quality changed successively from pungent for the compounds with five carbon atoms via metallic, vegetable-like for the six- and seven-carbon odorants to mushroom-like for the compounds with eight and nine carbon atoms. With further increase in chain length the mushroom-like impression decreased and changed to citrus-like, soapy, or herb-like. In both series, two odor threshold minima were found for the six-carbon and also for the eight- and nine-carbon odorants, respectively. In contrast to this, the odor qualities in the series of the (Z)- and (E)-alka-1,5-dien-3-ols and their corresponding ketones did not change significantly with geranium-like, metallic odors and an increasing mushroom-like odor note with increasing chain length. The lowest thresholds were found for the eight- and nine-carbon (Z)-compounds, respectively.

Ultrasound mediated synthesis of a few naturally occurring compounds

Synthesis of 2-methylheptadecane 1, 14-methylpentadecan-3-one 2, 6-oxo-1-nonanol 3, 5-(Z)-undecenoic acid 4 and 2-tridecanone 5 have been accomplished utilizing zinc-copper couple catalyzed conjugate addition of α,β-unsaturated carbonyl compounds under aqueous sonochemical conditions as the key step.

Synthesis via ultrasound: A very short and convenient synthesis of (Z) and (E)-heneicos-6-en-11-ones

(Z)-Heneicos-6-en-11-one (1) and its E-isomer (2), the sex pheromones of Douglas fir tussock moth, have been synthesised utilising ultrasonic waves.

A Convenient Synthesis of the Peach Fruit Moth Carposina Niponensis Walk. and of the Douglas Fir Tussock Moth Orgya Pseudotsugata Mc.D. Sex Pheromones and Analogs

The (Z)- and (E)-isomers of 7-alken-11-ones with chain lengths of 19, 21 and 23 carbon atoms were synthesized.A procedure based on the reaction of alkenylcopper reagents with vinylketones has been elaborated.

α,β-Epoxy Sulfoxides as Useful Intermediates in Organic Synthesis. IX. A Novel Synthesis of Alkyl Vinyl Ketones and Divinyl Ketones from Carbonyl Compounds and 1-Chloro-3-phenylthiopropyl Phenyl Sulfoxide as a Three-Carbon Homologating Agent

The α,β-epoxy sulfoxides easily derived from carbonyl compounds and 1-chloro-3-phenylthiopropyl phenyl sulfoxide were treated with sodium benzeneselenolate to give β-phenylthio carbonyl compounds in excellent yields.The phenylthio group was oxidized to the sulfinyl group and was then treated with a base to afford alkyl vinyl ketones in quite good yields.This reaction presents a novel method for the preparation of alkyl vinyl ketones from carbonyl compounds by three-carbon homologation.The treatment of α,β-epoxy sulfoxides mentioned above with benzenethiolate gave α,β'-bis(phenylthio) ketones.The elimination of the both thio groups afforded divinyl ketones.

A NOVEL SYNTHESIS OF ALKYL VINYL KETONES AND DIVINYL KETONES FROM CARBONYL COMPOUNDS BY THREE-CARBON HOMOLOGATION

Alkyl vinyl ketones and divinyl ketones are synthesized from carbonyl compounds and 1-chloro-3-phenylthiopropyl phenyl sulfoxide as a three-carbon homologating agent in good overall yileds.

Oxidation of sec-Alcohols to the Corresponding Ketones by Corynebacterium equi

Corinebacterium equi IFO 3730 was found to oxidize a wide variety of sec-alcohols, including alkanols, substituted alkanols, alkenols and cyclic alcohols, in moderate to high yields.Among them, the sec-alcohols which have longer carbon chains were oxidized more smoothly than those with smaller numbers of carbon.Although both enantiomers of unsymmetrically disubstituted carbinols were oxidized, the S form of 2-dodecanol was converted to the corresponding ketone a little faster than the other enantiomer.