21964-49-8

Usage

Uses

Used in Chemical Synthesis:
1,13-Tetradecadiene is used as a key intermediate in the synthesis of various biologically active compounds. Its ability to undergo polymerization using aluminum triisobutyl-titanium tetrachloride makes it a valuable component in the production of different chemical products.
Used in Pharmaceutical Industry:
1,13-Tetradecadiene is used as a starting material for the synthesis of naturally occurring, biologically active pyridine alkaloids such as theonelladins C and D, niphatesine C, and xestamine D. These alkaloids have potential applications in the development of new drugs and therapeutic agents.
Used in Surface Modification:
1,13-Tetradecadiene has been grafted to hydrogenated B-doped silicon (100) surfaces, which can be utilized in the development of advanced materials with specific properties for various applications, including electronics and sensors.

InChI:InChI=1/C14H26/c1-3-5-7-9-11-13-14-12-10-8-6-4-2/h3-4H,1-2,5-14H2

Upstream product

• 18719-24-9 oct-7-enoic acid 
• 110-52-1 1,4-dibromo-butane 
• 106-95-6 allyl bromide 
• 4549-32-0 1,8-dibromooctane 
• 82621-68-9 (10R)-10-methyl-1-tridecene 
• 96924-72-0 methyl (R)-5-tosyloxy-3-methylpentanoate 
• 106-98-9 1-butylene 
• 1501-82-2 cyclododecene 
• 592-41-6 1-hexene 
• 505-54-4 thapsic acid 
• 4117-09-3 7-bromo-hept-1-ene 
• 4549-31-9 1,7-dibromoheptane 

Downstream Products

• 502-72-7 cyclopentadecanone 
• 16556-72-2 2-nonylcyclohexanone 
• 19812-64-7 1,14-tetradecanediol 
• 74-85-1 ethene 
• 69227-94-7 1,2-Epoxy-11-tetradecene 
• 135346-28-0 3-propyl-1,13-tetradecadiene 
• 106694-77-3 (5Z,15Z)-5,15-icosadiene 
• 81500-71-2 (Z)-5,16-heptadecadiene 
• 135346-29-1 (Z)-3-propyl-1,12-heptadecadiene 
• 134359-57-2 2-((E)-14-Phenyl-tetradec-2-enyl)-malonic acid diethyl ester 
• 21390-07-8 1,3-dimethoxy-5-<14'-(3'',5''-dimethoxyphenyl)tetradecyl>benzene 
• 112-72-1 1-Tetradecanol 
• 129189-60-2 Δ¹²-tetradecenol 
• 524695-42-9 N-benzyl-4-methyl-N-(14-pyridin-3-yl-tetradec-2-enyl)-benzenesulfonamide 

Relevant academic research and scientific papers

Cyclododecene cometathesis with hexene-1 on the MoCl5/SiO2-Me4Sn catalytic system

The stereochemistry of the cometathesis of cyclododecene (CDD) with hexene-1 in the presence of the MoCl5/SiO2-Me4Sn heterogeneous catalytic system has been studied. It has been established that CDD is the mixture of cis- (Z) and trans- (E) stereoisomers with the ratio of 30/70, respectively. It has been shown that the reactivity of the E-stereoisomer of CDD in the reaction of cometathesis is higher when compared to the Z-stereoisomer. Thus, when the conversion of CDD is 92%, the ratio E/Z = 6: 94, i.e., the amount of the E-stereoisomer decreases from 70 to 7%, while the amount of the Z-stereoisomer increases from 30 to 93%, respectively.

Enzymatic Oxidative Tandem Decarboxylation of Dioic Acids to Terminal Dienes

The biocatalytic oxidative tandem decarboxylation of C7–C18dicarboxylic acids to terminal C5–C16dienes was catalyzed by the P450 monooxygenase OleT with conversions up to 29 % for 1,11-dodecadiene (0.49 g L–1). The sequential nature of the cascade was proven by the fact that decarboxylation of intermediate C6–C11ω-alkenoic acids and heptanedioic acid exclusively gave nonconjugated 1,4-pentadiene; scale-up allowed the isolation of 1,15-hexadecadiene and 1,11-dodecadiene; the system represents a short and green route to terminal dienes from renewable dicarboxylic acids.

Syntheses and palladium, platinum, and borane adducts of symmetrical trialkylphosphines with three terminal vinyl groups, P((CH2) mCH=CH2)3

Reactions of Br(CH2)mCH=CH2 with Mg powder and then PCl3 (0.33 equiv.) afford P((CH2)m-CH=CH 2)3 (1; m = a, 4; b, 5; c, 6; d, 7; e, 8; f, 9; 52-87 %). Reactions of 1a-c, e with PdX2(COD) (X = Cl, Br) give trans-PdX 2(P((CH2)mCH=CH2)3) 2 (35-92 %). Reactions of 1b-e with PtCl2 in benzene give mainly trans-PtCl2(P((CH2)mCH=CH 2)3)2 (trans-5b-e; 52-75 %), whereas those with K2PtCl4 in water give mainly cis-5b-e (33-70 %). The reaction of equimolar quantities of 1c and H3B.S(CH3) 2 gives the 1 : 1 adduct H3B·P((CH 2)6CH=CH2)3 (85 %). In none of these transformations are by-products derived from the C=C linkages observed.

Linear and branched olefin production from cyclic olefin feedstocks

Ring opening cross metathesis of secondary non-cyclic hydrocarbons with cyclic unsaturated hydrocarbons having 8 carbon atoms or more to produce corresponding unsaturated product hydrocarbons having more than 8 carbon atoms.

Semivolatile and volatile compounds in combustion of polyethylene

The evolution of semivolatile and volatile compounds in the combustion of polyethylene (PE) was studied at different operating conditions in a horizontal quartz reactor. Four combustion runs at 500 and 850°C with two different sample mass/air flow ratios and two pyrolytic runs at the same temperatures were carried out. Thermal behavior of different compounds was analyzed and the data obtained were compared with those of literature. It was observed that α,ω-olefins, α-olefins and n-paraffins were formed from the pyrolytic decomposition at low temperatures. On the other hand, oxygenated compounds such as aldehydes were also formed in the presence of oxygen. High yields were obtained of carbon oxides and light hydrocarbons, too. At high temperatures, the formation of polycyclic aromatic hydrocarbons (PAHs) took place. These compounds are harmful and their presence in the combustion processes is related with the evolution of pyrolytic puffs inside the combustion chamber with a poor mixture of semivolatile compounds evolved with oxygen. Altogether, the yields of more than 200 compounds were determined. The collection of the semivolatile compounds was carried out with XAD-2 adsorbent and were analyzed by GC-MS, whereas volatile compounds and gases were collected in a Tedlar bag and analyzed by GC with thermal conductivity and flame ionization detectors.

SYNTHESIS OF THE TWO ENANTIOMERS OF THE SEX PHEROMONE OF DIABROTICA UNDECIMPUNCTATA HOWARDI AND OF CHIRAL PRECURSORS OF OTHER PHEROMONES STARTING FROM ENENTIOMERICALLY PURE METHYL HYDROGEN (R)-3-METHYLGLUTARATE

Readily available methyl hydrogen (R)-3-methylglutarate (2) is a useful chiral building block for the synthesis of several biologically active compounds.Enantiomerically pure (R)-2 has been employed to synthesize stereospecifically each of the two enantiomers, 1a and 1b, of 10-methyl-2-tridecanone,the sex pheromone of the southern corn rootworm, Diabrotica undecimpunctata howardi Barber.Compound (R)-2 has been also used to prepare 99percent optically pure (R)-3-methyl-1-pentanol (6) and enantiomerically pure (R)-5-methyl-i-tricosyne (7).These compounds are useful building blocks suitable for the further elaboration to other chiral insect pheromones.