54364-60-2

Usage

Synthesis Reference(s)

Tetrahedron Letters, 24, p. 2513, 1983 DOI: 10.1016/S0040-4039(00)81969-3

InChI:InChI=1/C12H22O/c1-2-3-4-5-6-7-8-9-10-11-12-13/h3-6,13H,2,7-12H2,1H3/b4-3+,6-5-

Upstream product

• 58763-68-1 trans-7-dodecene-9-ynol 
• 871-91-0 oct-7-yn-1-ol 
• 58763-65-8 9-bromo-non-5t-en-3-yne 
• 66471-39-4 nona-4t,6c-dienoic acid ethyl ester 
• 66471-36-1 non-4t-en-6-ynoic acid ethyl ester 
• 54664-99-2 1-hepten-4-yn-3-ol 
• 58763-64-7 non-4t-en-6-yn-1-ol 
• 629-30-1 1,7-heptandiol 
• 34335-17-6 7-(2-tetrahydropyranyloxy)heptanal 
• 81036-11-5 7-(2-tetrahydro-2H-pyranyloxy)heptan-1-ol 
• 66790-17-8 2-dodec-7t-en-9-ynyloxy-tetrahydro-pyran 
• 58763-67-0 12-(1-ethoxy-ethoxy)-dodec-5t-en-3-yne 
• 60222-94-8 9-bromo-non-5-en-3-yne 
• 123042-07-9 [((1E,3Z)-Hexa-1,3-dienyl)sulfanyl]-benzene 

Downstream Products

• 54364-62-4 (7E,9Z)-7,9-dodecadien-1-yl acetate 
• 54364-63-5 (E,Z)-7,9-dodecadienyl acetate 

Relevant academic research and scientific papers

A STEREOSPECIFIC SYNTHESIS OF CONJUGATED (E,Z)-AND (E,E)-ALKADIENES BY THE PALLADIUM-CATALYZED REACTION OF (E)-1-ALKENYLBORONIC ACIDS AND 1-ALKENYL IODIDES

The reaction of (E)-1-alkenylboronic acids with (Z)-or(E)-1-alkenyl iodides in the presence of a catalytic amount of tetrakis(triphenylphosphine)-palladium and sodium hydroxide gave the corresponding conjugated (E,Z)-or (E,E)-alkadienes with high stereospecificity.

Method for preparing trans -7 and cis -9 - dodecadiene acetate

The invention discloses a method for preparing trans -7 and cis -9 - dodecadiene acetate, which comprises (1) adding 1 - 1 dichloroethylene in 2 - butyne tetrahydrofuran solution. The metal palladium compound, cuprous iodide and diisopropylamine undergo a coupling reaction to obtain 1 - chlorine -3 - yne -1 - hexene. (2) 20 °C (ClMgO) Under stirring, at CH. 2 )6 In MgCl, hexamethylphosphoric acid triamide and ferric acetyl acetonate are sequentially added, 1 - chlorine -3 - yne -1 - hexene is added dropwise to obtain the trans 7 - dodecene -9 - alkynol. (3) Zn powder was added to trans 7 - dodecene -9 - alkynol, stirred to obtain trans 7, cis 9 - dodecadienol, acetic anhydride and pyridine were added and stirred to obtain trans -7, cis -9 - dodecadiene acetate. The method provided by the invention is cheap and wide in source; the method has the advantages of short synthesis period, less steps, high yield, good stereoselectivity and simple post-treatment.

Synthesis and field evaluation of synthetic blends of the sex pheromone of crocidosema aporema (lepidoptera: Tortricidae) in soybean

Crocidosema (= Epinotia) aporema (Walsingham) (Lepidoptera: Tortricidae) is a bud borer that feeds on soybean and forage legumes. Its economic importance is restricted to South America, where it can alternate throughout the year between forage and grain legumes. The sex pheromone of C. aporema females is composed of a 15:1 mixture of (7Z,9Z)-dodeca-7,9-dien-1-ol and (7Z,9Z)- dodeca-7,9-dienyl acetate. Aiming at the development of a monitoring tool, it was synthesized both components of the pheromone and evaluated male captures in pheromone traps baited with different blends of synthetic pheromone, in an experimental soybean field in Uruguay. The conjugated dienes were obtained from 2-pentyn-1-ol and 1,7-heptanediol, by oxidation of the former, Wittig coupling and Zn-catalyzed reduction of the triple bond. The 1:1 mixture was the most efficient in capturing males. The pheromone traps were attractive for up to 40 days, even with small septum loads (0.1 mg) and low population levels.

Ozonolysis of alkenes and study of reactions of polyfunctional compounds: LXII. New synthetic route to 7E,9Z-dodecadien-1-yl acetate, pheromone of the leaf roller moth (Lobesia botrana)

Proceeding from the product of the partial ozonolysis of 1,4-cyclohexadiene, methyl 6-oxo-4E-hexenoate, a new synthetic route was developed to 7E,9Z-dodecadienyl acetate, pheromone of the leaf roller moth (Lobesia botrana).

INSECT PHEROMONES AND THEIR ANALOGUES. XLV. SYNTHESIS OF MONO- AND DIENIC COMPONENTS OF INSECT PHEROMONES FROM ISOPROPYL NONA-3E,8-DIENOATE

Non-6E-en-1-ol, dodec-3E-en-1-yl acetate, and dodeca-7E,9Z-dien-1-yl acetate, which are components of sex pheromones of insects of the order Lepidoptera, have been synthesized from the readily accessible isopropyl nona-3E,8-dienoate.

AN EASY ROUTE TO INSECT PHEROMONES WITH A E-Z OR Z-E CONJUGATED DIENE STRUCTURE

Insect pheromones having a conjugated diene system of E-Z or Z-E configuration can be prepared with high stereoselectivity, by means of addition reactions of Z-dialkenyl cuprates to phenylthioacetylene.The alkadienyl sulphides intermediates are then subjected to a cross-coupling reaction with Grignard reagents, in the presence of a Ni(II) complex as a catalysts, leading to the desired pheromones.

THE WITTIG REACTION: COMMENTS ON THE MECHANISM AND APPLICATION AS A TOOL IN THE SYNTHESIS OF CONJUGATED DIENES

For construction, by the Wittig reaction, of conjugated dienes with specific stereochemistry (either Z or E) at the newly formed double bond, without isomerization of the existing ("old") double bond, it is better to react a reactive (nonstabilized) saturated ylide with an α,β-unsaturated aldehyde.The opposite approach, namely, the reaction of a moderate (semi-stabilized) allylic ylide with a saturated aldehyde produces a mixture of geometric isomers, as a result of increased production of the E-configuration at the new double bond, and significant isomerization of the existing double bond.The proposed betaine structure for the intermediate could account only for the two equivalents of Li reaction.In other reactions, the less stable erythro-oxaphosphetane is probably the intermediate, produced by an early anti- or gauche C-C bond formation from the ylide and the carbonyl, from which the Z-double bond is then formed.

Systematic Syntheses and Charactarization of Dodecadien-1-ols with Conjugated Double Bond, Lepidopterous Sex Pheromones

Four geometrical isomers of 5,7-, 6,8-, 7,9- and 8,10-dodecadein-1-ols were systematically synthesized by two routes.One involved the Wittig reaction between (E)-2-alkenal and a phosphorane with an appropriate carbon chain, and yielded a mixture of (E,Z)- and (E,E)-isomers in a ratio of ca. 3:2.The other route comprised of the Wittig reaction of a 2-alkynal and the stereoselective reduction of the triple bond to a (Z)-double bond via hydroboration with dicyclohexylborane to give a mixture of (Z,Z)- and (Z,E)-isomers in a ratio of 6:1 10:1.Both the mixtures were separately chromatographed on a silica gel column impregnated with silver nitrate to give four geometrically pure isomers.With 9,11-diene they were analysed by GC on a capillary column, HPLC, silver nitrate impregnated TLC, and 13C NMR.

STEREOSELECTIVE SYNTHESIS OF (E)-7, (Z)-9 DODECADIEN-1-YL ACETATE

Two convenient synthetic methods for (E)-7, (Z)-9 dodecadien-1-yl acetate, via palladium-copper catalysed reactions of acetylenic intermediates with vinylic halides, are presented.