21293-04-9

Usage

Uses

Used in Fragrance and Flavor Industry:
(5E,7Z)-5,7-Dodecadiene is used as a key component in the creation of various fragrances and flavors due to its characteristic odor. Its unique scent profile contributes to the development of diverse and complex aromas in the fragrance and flavor market.
Used in Pharmaceutical Industry:
(5E,7Z)-5,7-Dodecadiene serves as a precursor in the manufacturing of pharmaceuticals. Its chemical structure allows for further modification and synthesis of various medicinal compounds, making it an essential building block in the development of new drugs.
Used in Agrochemical Industry:
(5E,7Z)-5,7-Dodecadiene is also utilized in the synthesis of agrochemicals, which are chemicals specifically designed to benefit agriculture. (5E,7Z)-5,7-Dodecadiene's role as a precursor enables the production of various agrochemicals that can be used in pest control, crop protection, and other agricultural applications.
Used in Polymer and Plastics Industry:
(5E,7Z)-5,7-Dodecadiene is a valuable intermediate in the production of polymers, plastics, and other industrial materials. Its long-chain hydrocarbon structure makes it suitable for use in the synthesis of polymers with specific properties, which can be tailored for various applications in the plastics and materials industry.

InChI:InChI=1/C12H22/c1-3-5-7-9-11-12-10-8-6-4-2/h9-12H,3-8H2,1-2H3

Upstream product

• 1035808-44-6 (E)-5,6,7-dodecatriene 
• 693-02-7 hex-1-yne 
• 16644-98-7 (E)-1-iodohexene 
• 87240-93-5 trans-2,5-dibutyl-3-sulfolene 
• 1120-29-2 5,7-dodecadiyne 
• 16538-47-9 (Z)-1-iodohex-1-ene 
• 1119-67-1 1-iodo-1-hexyne 
• 87240-86-6 2-butyl-2,5-dihydrothiophene 1,1-dioxide 
• 113858-30-3 (5Z,7Z)-6-Bromo-dodeca-5,7-diene 

Relevant academic research and scientific papers

Reductive coupling of alkynes by oxobis(diethyldithiocarbamato)molybdenum(IV)-sodium borohydride

The reductive coupling of terminal alkynes and the intramolecular cyclization of diynes by oxobis(diethyldithiocarbamato)molybdenum(IV) in the presence of sodium borohydride are reported. The reaction leads to a mixture of products resulting primarily from 'head to tail' coupling of the alkynes. 1,7-Octadiyne undergoes cyclization to afford cycloheptene-3-ylidene in 45% yield. The product distribution appears to be controlled by steric factors associated with the alkyne-molybdenum intermediate.

Ni-catalyzed Si-B addition to 1,3-dienes: Disproportionation in lieu of silaboration

Upon attempted silaboration of acyclic 1- and 1,4-substituted 1,3-dienes, a new disproportionation reaction was discovered, yielding 1:1 mixtures of allylsilanes and dienylboranes. It was demonstrated that, as a key step in this new catalytic process, hyd

ORGANIC SYNTHESIS USING HALOBORATION REACTION. PART 9. A DIRECT AND SELECTIVE SYNTHESIS OF (Z,Z)-1-BROMO-1,3-DIENES AND (E,Z)-1,3-DIENES BY THE HYDROBORATION-BROMOBORATION SEQUENCE OF TWO ALKYNES

1-Alkenyldibromoboranes readily obtainable by the hydroboration of first alkynes with dibromoborane-dimethyl sulfide followed by treatment with tribromoborane, react without any difficulty with second 1-alkynes as bromoborating agents to give (1-alkenyl)(2-bromo-1-alkeny)-bromoboranes (5).The reaction of 5 with iodine in the presence of potassium acetate provides (Z,Z)-1-bromo-1,3-dienes (6), specifically, which are readily converted into the corresponding (E,Z)-1,3-dienes (7) by treatment with t-butyllithium and methanol.

STEREOSELECTIVE SYNTHESIS OF (E)-, (E,Z)- AND (E,E)-CONJUGATED DIENES VIA ALKYLATION OF 3-SULFOLENES AS KEY STEP

Stereoselective method for synthesizing (E)-, (E,Z)- and (E,E)-conjugated dienes via alkylation of 3-sulfolenes as key step is developed.Sex pheromones with (E)- and (E,E)-conjugated diene structures are synthesized with exclusively high stereoselectivity by applying the method.

A frustrated-Lewis-pair approach to catalytic reduction of alkynes to cis-alkenes

Frustrated Lewis pairs are compounds containing both Lewis acidic and Lewis basic moieties, where the formation of an adduct is prevented by steric hindrance. They are therefore highly reactive, and have been shown to be capable of heterolysis of molecular hydrogen, a property that has led to their use in hydrogenation reactions of polarized multiple bonds. Here, we describe a general approach to the hydrogenation of alkynes to cis-alkenes under mild conditions using the unique ansa-aminohydroborane as a catalyst. Our approach combines several reactions as the elementary steps of the catalytic cycle: hydroboration (substrate binding), heterolytic hydrogen splitting (typical frustrated-Lewis-pair reactivity) and facile intramolecular protodeborylation (product release). The mechanism is verified by experimental and computational studies.

Catalytic homocoupling of aryl, alkenyl, and alkynyl halides with Ni(II)-complexes and zirconocene dichloride

A new catalytic system (cat. (H)2Phen(Me)2· NiCl2 or (MeO)2Dipyr(H)2·NiCl 2, cat. Zr(cp)2Cl2, 2 equiv Mn, and 2 equiv LiCl) has been developed to facilitate the homocoupling of a wide range of aryl, alkenyl, and alkynyl halides.

HIGHLY STEREOSELECTIVE SYNTHESES OF CONJUGATED E,E- AND E,Z-DIENES, E-ENYNES AND E-1,2,3-BUTATRIENES VIA ALKENYLBORANE DERIVATIVES

A highly selective and potentially general methodology for the synthesis of conjugated E,E- and E,Z-dienes, E-enynes, and E-1,2,3-butatrienes via hydroboration of alkynes is reported.The observed stereoselectivity was >98-99percent.

REDUCTIVE DIMERIZATION OF VINYL HALIDES IN AN Ni/Pb/Al THREE METAL REDOX SYSTEM. A FACILE ACCESS TO TERPHENYL DERIVATIVES

A novel three metal redox system, NiCl2(bpy)/PbBr2/Al, is found to be potent in the reductive coupling of vinyl halides, affording 1,4-biaryl-1,3-butadienes, precursors of terphenyl derivatives.

Configurational Instability of α-Alkenyl and α-Alkynyl Vinyllithiums. Syntheses of Stereodefined 2-Alkyl-1-en-3-ynes

Metal-halogen exchange of either (Z)-enynyl bromides or (Z)-dienyl bromides by sec-BuLi produces vinyllithiums that are configurationally stable only at temperatures below -120 deg C and -78 deg C, respectively.Allylation of (Z)-enynylalanates with allyl bromide or methylation of (Z)-enynyl bromides with CH3MgI and Fe(acac)3 catalyst furnishes the corresponding 2-alkyl-1-en-3-ynes.

Stereoselective Synthesis of (E)-, (E,Z)-, and (E,E)-Conjugated Dienes via Alkylation of 3-Sulfolenes as the Key Step

A new stereoselective method is presented for synthesizing (E)-, (E,Z)-, and (E,E)-conjugated dienes via alkylation of 3-sulfolenes as the key step.Direct alkylation of 3-sulfolene at the 2-position proceeds with good yields when labile sulfolene α-carbanion is generated in the presence of alkyl iodides in THF-HMPA solution at -78 deg C.Alkylation of 2-alkyl-3-sulfolenes gives trans-2,5-dialkyl-3-sulfolenes with 100percent regioselectivity and more than 90percent stereoselectivity.Desulfonylation of trans-3,5-disubstituted 3-sulfolenes is examined in detail, and the conditions to give stereoselectively the corresponding (E,Z)-and (E,E)-conjugated dienes are found.Applying the method, three insect pheromones, (E)-9,11-dodecadien-1-yl acetate, a sex pheromone of the red bollworm moth, (E,E)-8,10-dodecadien-1-ol, a sex pheromone of the codling moth, and (E,E)-11,13-hexadecadienal, a sex pheromone of the cabbage webworm, are easily synthesized by starting with 3-sulfolene with nearly 100percent stereoselectivity.Synthesis of cis-3,4,5-trisubstituted cyclohexenes using 2-substituted 3-sulfolenes as the diene synthons is also described.