1725-04-8

Usage

Synthesis Reference(s)

Journal of the American Chemical Society, 103, p. 5183, 1981 DOI: 10.1021/ja00407a039Tetrahedron Letters, 22, p. 1737, 1981 DOI: 10.1016/S0040-4039(01)90426-5

InChI:InChI=1/C13H24O2/c14-13-11-9-7-5-3-1-2-4-6-8-10-12-15-13/h1-12H2

Upstream product

• 78812-92-7 N-Benzoyl-N-(13-hydroxy-tridecanoyl)-benzamide 
• 4884-18-8 6,7,13,14,20,21-hexaoxatrispiro[4.2.4⁸.2.4¹⁵.2⁵]henicosane 
• 133123-01-0 Acrylic acid 10-iodo-decyl ester 
• 89611-21-2 13-Hydroxy-tridecanoic acid (Z)-2-dimethylcarbamoyl-1-methyl-vinyl ester 

Downstream Products

• 918876-23-0 15-(benzyloxy)-3-methylpentadec-1-en-3-ol 
• 918876-33-2 2-(12-(benzyloxy)dodecyl)-6-methoxy-2,5,7,8-tetramethyl-3,4-dihydro-2H-chromene 
• 918876-11-6 12-(6-(benzyloxy)-2,5,7,8-tetramethyl-3,4-dihydro-2H-chromen-6-yl)dodecan-1-ol 
• 918876-25-2 2-(12-(benzyloxy)dodecyl)-2,5,7,8-tetramethyl-3,4-dihydro-2H-chromen-6-ol 
• 918876-29-6 2-(12-(benzyloxy)dodecyl)-2,5,7,8-tetramethyl-3,4-dihydro-2H-chromen-6-yl acetate 
• 918876-14-9 dibenzyl 12-(6-hydroxy-2,5,7,8-tetramethyl-3,4-dihydro-2H-chromen-6-yl)dodecyl phosphate 
• 918876-12-7 dibenzyl 12-(6-(benzyloxy)-2,5,7,8-tetramethyl-3,4-dihydro-2H-chromen-6-yl)dodecyl phosphate 
• 918876-15-0 dibenzyl 2-(dibenzyl 12-dodecyl phosphate)-2,5,7,8-tetramethyl-3,4-dihydro-2H-chromen-6-yl phosphate 
• 13362-52-2 1,13-tridecanediol 
• 112-70-9 tridecan-1-ol 

Relevant academic research and scientific papers

Flow Chemistry under Extreme Conditions: Synthesis of Macrocycles with Musklike Olfactoric Properties

Starting from small cyclic ketones, continuous flow synthesis is used to produce medium-sized rings and macrocycles that are relevant for the fragrance industry. Triperoxides are important intermediates in this process and are pyrolyzed at temperatures above 250 °C. The synthesis is carried out in two continuously operated flow reactors connected by a membrane-operated separator. The practicality of flow chemistry is impressively demonstrated in this work by the use of hazardous reagent mixtures (30% H2O2, 65% HNO3) and the pyrolysis of no less problematic peroxides. All new macrocycles were tested for their olfactory properties in relation to musk.

A New Synthetic Method of Macrocyclic Lactones from ω-Iodoalkylacrylates

When the photostimulated cyclization reaction of ω-iodoalkylacrylates was performed in the presence of metal hydride complexes such as sodium cyanoborohydride (NaBH3CN), sodium borohydride (NaBH4) and potassium borohydride (KBH4), the corresponding macrocyclic lactones were produced.The use of NaBH3CN led to the highest yield of lactones.

LACTONISIERUNG VON MAKROLID-SECOSAEUREN MIT "PUSH-PULL ACETYLENEN"

A highly efficient method for the macrolactonization of seco-acids is described.Seco-acids are converted into stable enolesters 3 by the acetylene 1, which are cyclized under proton or Lewis acid catalysis.This new method has been successfully applied to the lactonization of the 7-epi-brefeldin A seco-acids 8a, b.

ACTIVATED CARBOXYLATES FROM THE PHOTOOXYGENATION OF OXAZOLES. APPLICATION TO THE SYNTHESIS OF RECIFEIOLIDE AND OTHER MACROCYCLIC LACTONES.

The oxazole system may serve as a protecting group for the carboxyl function.The carboxylate is generated under mild conditions of photooxygenation in high yield in the form of the reactive triamide.This reaction has been applied to the synthesis of macrocyclic lactones.