38401-84-2

Usage

Uses

Used in Insect Control:
2-Ethyl-1,6-dioxaspiro[4.4]nonane is used as an insect pheromone in the insecticide industry. It is a natural product secreted by Bark Beetle species to attract females. By mimicking the pheromone, it can be utilized in pest control strategies to trap and control the population of these insects, reducing the need for chemical insecticides and promoting environmentally friendly pest management practices.

Synthesis Reference(s)

The Journal of Organic Chemistry, 47, p. 3140, 1982 DOI: 10.1021/jo00137a020Synthetic Communications, 13, p. 1235, 1983 DOI: 10.1080/00397918308063739

InChI:InChI=1/C9H16O2/c1-2-8-4-6-9(11-8)5-3-7-10-9/h8H,2-7H2,1H3

Upstream product

• 13888-01-2 3-ethyltetrahydrofuran-2-one 
• 129102-66-5 C₃H₆CeCl₂O^(1-)*Ce⁽³⁺⁾*2Cl^(1-) 
• 69978-25-2 1-(α-furyl)pentan-3-ol 
• 92362-26-0 2-(1-phenylselenoethyl)-1,6-dioxaspiro<4.4>nonane 
• 116842-32-1 Methyl 7-Nitro-4-oxononanoate 
• 116467-39-1 Methyl 4,4-(Ethylenedioxy)-7-nitrononanoate 
• 81540-30-9 1-(α-tetrahydrofuryl)-2-carboethoxypentan-3-one 
• 81540-29-6 1-(α-tetrahydrofuryl)pentan-3-one 
• 98-01-1 furfural 
• 4469-83-4 1-(α-tetrahydrofuryl)pentan-3-ol 
• 1192-30-9 tetrahydrofurfuryl bromide 
• 695-06-7 hexan-4-olide 
• 4469-84-5 1,7-nonanediol 
• 546-67-8 lead(IV) tetraacetate 

Downstream Products

• 69744-43-0 (2R,5S)-2-ethyl-1,6-dioxaspiro<4.4>nonane 
• 70427-58-6 (2S,5S)-2-ethyl-1,6-dioxaspiro<4.4>nonane 
• 70427-57-5 (2S,5R)-2-ethyl-1,6-dioxaspiro<4.4>nonane 
• 69744-44-1 (2R,5R)-2-ethyl-1,6-dioxaspiro<4.4>nonane 

Relevant academic research and scientific papers

A Method for the Synthesis of Ketones and Spiroketals via Desulfurization of Thienylethers

Starting from substituted methoxythiophenes 1 ketones and spiroketals can be synthesized in one step by desulfurization with partial hydrogenation.The bark beetle pheromone chalcogran 2a and the wasp anti aggression pheromone 2b were prepared by this method.

A CONVERGENT SCHEME FOR THE SYNTHESIS OF SPIROKETALS AND THE SYNTHESIS OF (+)-CHALCOGRAN

The hetero-Diels-Alder condensation between furanoid and pyranoid exocyclic vinyl ethers establishes the spiroketal system and subsequent oxidative ring contraction leads to l.6-dioxaspiroalkane carboxylic acids.The latter are useful subunits for polyether antibiotic synthesis.

Ammonium-salt-tagged IMesAuCl complexes and their application in gold-catalyzed cycloisomerization reactions in water

The total synthesis and characterization of ammonium-salt-tagged IMesAuCl complexes is described. Moreover, we have demonstrated their catalytic activity and recyclability in cycloisomerization reactions of allenic and acetylenic alcohols in water. The water-soluble gold catalysts can be stabilized by the addition of LiCl.

Consecutive reactions with sulfoximines: Straightforward synthesis of substituted 5,5-spiroketals

An efficient synthesis of 5,5-spiroketals (i.e., 1,6-dioxa-spiro[4.4]nonane derivatives) is described from 2-(sulfonimidoyl-methylene)tetrahydrofurans involving a consecutive epoxide opening/oxa-Michael spiroketalization sequence. This methodology was applied to the very direct synthesis of chalcogran, a beetle pheromone. Georg Thieme Verlag Stuttgart ? New York.

Alkynyltrifluoroborates as versatile tools in organic synthesis: A new route to spiroketals

(Chemical Equation Presented) A simple and efficient two-step approach to spiroketals is described. Key steps include the preparation of functionalized hydroxyl α-alkynones by ring-opening reactions of lactones with lithium alkynyltrifluoroborates followed by a palladium-catalyzed hydrogenation/ spirocyclization of the prespiroketal intermediate.

Exo and endohormones. XX. Synthesis of racemic 2-ethyl-1,6-dioxaspiro[4,4]nonane, the aggregation pheromone of pityogenes chalcographus (Coleoptera, Scolytidae)

The synthesis of a diastereoisomeric mixture of 2-etyl-1,6-dioxaspiro[4,4]nonane (chalcograne) a main component of the aggregation pheromone of the spruce bark beetle Pityogenes chalcographus (Coleoptera, Scolytidae), a serious pest in European forests, by 1,7-nonanediol cyclization using Pb(OAc)4 is given below. The side products of spirocyclization were identified by GC/MS.

Dihydro- and Tetrahydrofuran Building Blocks from 1,4:3,6-Dianhydrohexitols. 2. Synthesis of Acetal, Alcohol, Diol, Epoxide, Hydrocarbon, and Lactone Pheromones

The potential of building blocks 1-3 for synthesis of enantiopure substances is illustrated by their transformation to various insect pheromones featuring functionalities specified in the title.A convenient synthesis of building block 3 from sorbitol is described.

Synthesis of spiroacetal pheromones via metalated hydrazones

The synthesis of simple alkyl substituted spiroacetals by α,α'-alkylation of metalated acetone dimethylhydrazone with appropriate electrophiles and subsequent acid catalyzed cleavage and ring closure of the products is described.

Conversion of Polyfunctional Nitroalkanes into Carbonyl Compounds Synthesis of the Pheromone Chalcogran and of Key Building Blocks for the Macrolides Pyrenophorin and Vermiculine

Starting from nitroalkane adducts of the general structure 3, several versions of the Nef reaction are performed.The reagent combination H2O2/K2CO3 turned out to be the most useful in liberating the carbonyl group because of toleration of acid-sensitive functionalities.Other methods provide the acetal 5, diketone 7, γ-lactones 8 and 9, or the chlorinated nitro compound 13, respectively.Cyclization of the highly functionalized diketone 18 gives cyclopentenone derivative 19.Trifunctional and tetrafunctional intermediates 12 and 17 can be transformed into 20 and 21 by reduction and silylation.These compounds are known or conceivable precursors for the antibiotic macrolides pyrenophorin and vermiculine, respectively.Nitroalkane 22 affords within a few simple steps the aggregation pheromone chalcogran 24.The synthetic paths are discussed with regard to efficiency and flexibility.