4459-57-8

Upstream product

• 52914-66-6 2-methyl-1-cyclopentadecanone 
• 57-10-3 1-hexadecylcarboxylic acid 
• 82166-53-8 4-(trimethylsilyl)pent-4-en-2-ol 
• 452962-43-5 4-trimethylsilanyl-pent-4-en-2-one 
• 874583-95-6 15-hydroxy-hexadecanoic acid 6-(3-hydroxymethyl-but-3-enyl)-pyridin-2-yl ester 
• 7664-93-9 sulfuric acid 
• 182062-30-2 16-Methyl-oxacyclohexadec-13-yn-2-one 
• 87227-40-5 (E)-16-Methyl-oxacyclohexadec-3-en-2-one 
• 874583-93-4 15-triethylsilanyloxy-hexadecanoic acid 6-[3-(tert-butyl-dimethyl-silanyloxymethyl)-but-3-enyl]-pyridin-2-yl ester 
• 86911-21-9 16-Methyl-13-nitro-oxacyclohexadecan-2-one 
• 57785-39-4 12-oxo-15-hexadecanolide 

Relevant academic research and scientific papers

Synthesis of (±)-recifeiolide and its homologs via acetylenic lactones

The title compounds (7c,d) have been prepared by the Z to E isomerization (NaNO2, HNO3) of the corresponding Z-lactones (6c,d), which are stereoselectively available (H2, Lindlar cat.) from the acetylenic lactones 4a-d, prepared earlier from cycloalkanones.

A New Synthesis of Medium Ring and Macrocyclic Acetylenic Lactones from Oxabicycloalkenones via their Tosylhydrazones

Tosylhydrazones 4a-d of vinylogous lactones 1a-d on treatment with N-bromosuccinimide, under strictly controlled conditions, give the title acetylenic compounds 5a-d in 65-90percent yield.

Removable Silyl Group as a "masked Proton" in Oxy-2-oxonia(azonia)-Cope Rearrangement: Applications in Stereoselective Total Synthesis of Natural Macrolides

In the presence of a Lewis acid, trimethylsilyl-substituted β,γ-unsaturated ketones and aldehydes (imines) undergo nucleophilic addition to produce zwitterionic intermediates, followed by oxy-2-oxonia(azonia)-Cope rearrangements to give homoallylic esters (amides). In the case of TMS-containing 2-vinylcycloalkanones, the process results in ring-enlargement, providing 10- to 16-membered lactones. This protocol was applied to the total synthesis of (R)-phoracantholide I.

FRAGRANCE COMPOSITION

A novel musk-based fragrance having an excellent musky fragrance is provided. Also provided is a fragrance composition containing, as an active ingredient, a macrocyclic lactone compound represented by the following formula (1): wherein A represents an ethylene group or an ethenylene group; and when A is an ethylene group, R represents an alkyl group having 3 carbon atoms, and n represents an integer from 1 to 6, while when A is an ethenylene group, R represents an alkyl group having 1 to 3 carbon atoms, and n represents an integer from 1 to 6.

Studies on the transesterification and macrolactonization of 2-pyridyl esters by intramolecular N-alkylation or metal ion coordination

In a process analogous to use of the Mukaiyama reagent, ω-hydroxyalkyl 2-pyridyl ester derivatives were converted into lactones by N-alkylation or the coordination of copper(II) inflate and transacylation of the resultant electrophilic ω-hydroxyalkanecao boxypyridinium salts. Georg Thieme Verlag Stuttgart.

Regioselective Conversion of Nonactivated CH Bonds, VI - Selective ω- to (ω-2)-Chlorination of Fatty Acids by Way of Adsorption on Alumina

Fatty acids 4-7 can be chlorinated with high selectivity in the (ω-2)- to ω-position.For that purpose the acid is adsorbed on alumina and allowed to react with gaseous chlorine or t-BuOCl at 20 and -35 deg C.The resulting chloroalkanoic acids 10-13 can be converted into macrocyclic lactones 14-17 by treatment with DBU. Key Words: Fatty acids / Chlorination, selective / Lactones

The stereoselective alkylation and conformational analysis of 15-hexadecanolide

15-Hexadecanolide can be alkylated with 80% stereoselectivity. The stereochemistry of the major product was proven by chemical correlation with the alkylation products of cyclopentadecanone. A simple model using [4444] conformation of cyclohexadecane is proposed to rationalize these results along with molecular mechanics calculations.