16339-76-7

Usage

Chemical composition

A long-chain hydrocarbon molecule with a bromine atom attached to the 13th carbon atom.

Classification

Alkene, containing a double bond between the 1st and 2nd carbon atoms.

Usage

Building block in the synthesis of various organic compounds, including fatty alcohols, surfactants, and polymers.

Industrial applications

Valuable intermediate for the production of diverse industrial and consumer goods.

Research applications

Used in organic chemistry research and as a reagent in the preparation of complex organic molecules.

Upstream product

• 16339-75-6 12-tridecenyl alcohol 
• 4101-68-2 1,10-dibromodecane 
• 1730-25-2 allylmagnesium bromide 
• 10035-10-6 hydrogen bromide 
• 558-13-4 carbon tetrabromide 
• 603-35-0 triphenylphosphine 
• 51887-25-3 tridec-2-yn-1-ol 
• 18202-11-4 tridec-12-yn-1-ol 
• 4549-32-0 1,8-dibromooctane 
• 1119-51-3 bromopentene 
• 34164-50-6 4-penten-1-ylmagnesium bromide 
• 36247-32-2 1,8-bis(p-toluenesulfonyloxy)octane 
• 15886-83-6 octane-1,14-diol dimesylate 
• 629-41-4 1,8-Octanediol 

Downstream Products

• 24607-08-7 avocadene 
• 81662-61-5 (2S,4R)-16-Heptadecene-1,2,4-triol 4-p-nitrobenzoate 
• 81662-60-4 (2S,4S)-16-Heptadecene-1,2,4-triol 4-p-nitrobenzoate 
• 81662-58-0 4-Nitro-benzoic acid (S)-1-((S)-2,2-dimethyl-[1,3]dioxolan-4-ylmethyl)-tetradec-13-enyl ester 
• 81662-59-1 4-Nitro-benzoic acid (R)-1-((S)-2,2-dimethyl-[1,3]dioxolan-4-ylmethyl)-tetradec-13-enyl ester 
• 81662-62-6 (2S,4S)-16-Heptadecene-1,2,4-triol 4-p-nitrobenzoate 1-pivalate 
• 81662-63-7 (2S,4R)-16-Heptadecene-1,2,4-triol 4-p-nitrobenzoate 1-pivalate 
• 81662-64-8 (2R,4S)-16-Heptadecene-1,2,4-triol 2-benzoate 4-p-nitrobenzoate 1-pivalate 
• 81662-65-9 (2R,4R)-16-Heptadecene-1,2,4-triol 2-benzoate 4-p-nitrobenzoate 1-pivalate 
• 1050216-97-1 3-(undec-10-yn-1-oxy)-5-(tridec-12-en-1-oxy)benzyl alcohol 
• 1404497-38-6 (2S, 4R)-2,4-dihydroxyheptadec-16-enyl 4-methylbenzene sulfonate 
• 1404497-41-1 (3S,5R)-5-(12-tridecenyl)-tetrahydrofuran-3-ol 
• 82909-47-5 13-Tetradecyn-1-oic acid 

Relevant academic research and scientific papers

An Efficient Synthesis of 3-Alkylpyridine Alkaloids Enables Their Biological Evaluation

3-Alkylpyridine alkaloids (3-APAs) isolated from the arctic sponge Haliclona viscosa are a promising group of bioactive marine alkaloids. However, due to limited bioavailability, investigations of their bioactivity have been hampered. Additionally, synthesis of a common intermediate requires the use of protecting groups and harsh conditions. In this work, we developed a simple and concise two-step route to nine different natural and synthetic haliclocyclins. These compounds displayed modest antibiotic activity against several Gram-positive bacterial strains.

Synthesis of 13C-labelled cutin and suberin monomeric dicarboxylic acids of the general formula HO213C-(CH2)n-13CO2H (n = 10, 12, 14, 16, 18, 20, 22, 24, 26, 28)

13C-labeled dicarboxylic acids HO213C-(CH2)n-13CO2H (n = 10, 12, 14, 16, 18, 20, 22, 24, 26, 28) have been synthesized as internal standards for LC-MS and GC-MS analysis of cutin and suberin monomer degradation by soil-based microorganisms. Different synthetic strategies had to be applied depending on the chain length of the respective synthetic target and because of economic considerations. 13C-labels were introduced by nucleophilic substitution of a suitable leaving group with labelled potassium cyanide and subsequent hydrolysis of the nitriles to produce the corresponding dicarboxylic acids. All new compounds are characterized by GC/MS, IR, and NMR methods as well as by elemental analysis.

Total Synthesis and Structural Elucidation of Two Unusual Non-Methylene-Interrupted Fatty Acids in Ovaries of the Limpet Cellana toreuma

In our previous study, unusual odd-numbered dienoic acids with a terminal olefin were found as minor components in ovaries of the Japanese limpet Cellana toreuma, and the synthetic interests have been focused onto their structural confirmation and the inspection into their potential biological activity. Here, we describe an efficient and stereoselective total synthesis of two new unusual dienoic acids, 19:2?7,18 and 21:2?7,20, through a common pathway involving the strategic combination of alkyne-zipper reaction and Lindlar hydrogenation for the construction of their unique carbon chains. In our synthetic study, 2-propyn-1-ol was at first subjected to alkylation and alkyne-zipper reaction to form the two fragments, and the subsequent carbon chain elongation was achieved by the usual coupling reaction to obtain the C-19 and C-21 products bearing an internal acetylenic group. Then, the internal acetylenic group of these products was subjected to Lindlar hydrogenation to form a Z-alkenyl moiety, and the subsequent deprotection of the products was carried out under an acidic condition without isomerization of the internal Z-alkenyl group. Total synthesis of target fatty acids, 19:2?7,18 and 21:2?7,20, was finally accomplished by two-step oxidation of the resulting alcohols into carboxylic acids in a highly chemoselective manner, and the structures of these unusual natural fatty acids were finally elucidated by identifying the GC–MS spectra of the methyl esters of authentic and synthetic fatty acids.

Iodophenyl tagged sphingosine derivatives: Synthesis and preliminary biological evaluation

A facile synthesis of six 4-iodophenyl tagged sphingosine (SP) derivatives bearing alkyl chain lengths from 6 to 13 is described. The key steps for the assembly of these molecules, 5a-f, are Suzuki-Miyaura cross-coupling and cross-metathesis reactions. Th

The thread & cut method: Syntheses of molecular knot precursors

A novel approach to molecular knots is described. This method may allow access to smaller and more complex knots. Two knot precursors, 1a and 1b, are efficiently prepared in overall yields of 9.6% and 8.7%, respectively. The convergent six-step syntheses utilize Frechet-type etherifications, alkyne/azide click cycloadditions, and bis-macrolactonizations. Wiley-VCH Verlag GmbH & Co. KGaA, 2008.

Synthesis of model long-chain ω-alkenyltrichlorosilanes and triethoxysilanes for the formation of self-assembled monolayers

The synthesis of model long-chain hydrocarbons (C13 and C 19) carrying a vinyl group and a trichloro- or a triethoxysilyl group at each end is reported. These compounds are suitable for linkage to a hydroxylated silicon surface and at the other end with vinyl group for further functionalization and multilayer formation.

Olefin substituted long chain compounds

There is disclosed an olefin-substituted compound having the formula:R--(core moiety),wherein R is a straignt chain hydrocarbon having at least one double bond and a carbon chain length of from about 6 to about 18 carbon atoms, wherein multiple double bonds are separated from each other by at least three carbon atoms, wherein the closest double bond to the core moiety is at least five carbon atoms from the core moiety, and wherein the hydrocarbon chain may be substituted by a hydroxyl, halo, keto or dimethylanimo group and/or interrupted by an oxygen atom and salts thereof and pharmaceutical compositions thereof.

Synthesis of Sphingosine Relatives, IX. Synthesis of (2S,3R,4E)-1-O-(β-D-Glucopyranosyl)-N--4-sphingenine. The Structure Proposed for the Esterified Cerebroside in the Epidermis of Guinea Pigs

(2S,3R,4E)-1-O-(β-D-Glucopyranosyl)-N--4-sphingenine (1) was synthesized from D-glucose (A), (2S,3R,4E)-4-sphingenine (sphingosine, B), 24-hydroxytetracosanoic acid (C) and linoleic acid (D).The 1H-NMR spectrum of the synthetic 1 was different from that of the esterified cerebroside which was isolated as a tissue-characteristic compound in the epidermis of foodpad and dorsal skin of guinea pigs.