30820-22-5

Usage

Uses

Used in Agricultural and Forestry Industries:
GRANDLURE I is used as a monitoring tool for detecting the presence of beetle populations in these industries. Its ability to attract both male and female beetles helps in assessing the extent of infestation and the effectiveness of pest control measures.
GRANDLURE I is also used as a pest control agent to manage beetle populations in agricultural and forestry settings. By attracting beetles to a specific location, it facilitates targeted pest control interventions, reducing the need for broad-spectrum pesticides and minimizing the environmental impact.
In Integrated Pest Management (IPM) Programs:
GRANDLURE I is used as a component of integrated pest management programs, where it serves as a key tool for monitoring beetle populations and guiding pest control strategies. Its effectiveness in attracting both male and female beetles makes it a valuable addition to a comprehensive IPM approach, which combines biological, cultural, and chemical control methods to manage pests in an environmentally sustainable manner.

InChI:InChI=1/C10H18O/c1-8(2)9-4-5-10(9,3)6-7-11/h9,11H,1,4-7H2,2-3H3/t9-,10+/m0/s1

Upstream product

• 20763-19-3 (methoxymethylene)triphenylphosphorane 
• 56102-13-7 2-[(1S,2R)-2-(2-Benzenesulfinyl-1-methyl-ethyl)-1-methyl-cyclobutyl]-ethanol 
• 55760-16-2 2-isopropenyl-1-methyl-1-cyclobutaneacetic acid 
• 63623-52-9 ((1S,2S)-2-Isopropenyl-1-methyl-cyclobutyl)-acetaldehyde 
• 125404-41-3 2-Isopropenyl-1-<2-(p-methoxyphenoxy)ethyl>-1-methylcyclobutane 
• 99766-55-9 trans-methyl-2-acetyl-1-methylcyclobutane carboxylate 
• 99766-56-0 trans-2-isopropenyl-1-methylcyclobutyl methanol 
• 70645-38-4 (1S,2R)-2-Isopropenyl-1-methyl-cyclobutanecarboxylic acid methyl ester 
• 136296-94-1 2-(2-Iodo-1-methylethyl)-1-<2-(p-methoxyphenoxy)ethyl>-1-methylcyclobutane 
• 53171-65-6 trans-2-isopropenyl-1-methylcyclobutyl acetonitrile 
• 56102-12-6 1-(1'-Hydroxyeth-2'-yl)-1-methyl-(1'-phenylthioprop-2'-yl)cyclobutan 
• 63049-27-4 1-Methyl-1-(2'-oxoethyl)-2-(1'-phenylthioprop-2'-yl)cyclobutan 
• 56102-08-0 (4R,5R)-5-(1-Methyl-2-phenylsulfanyl-ethyl)-spiro[3.3]heptan-1-one 

Relevant academic research and scientific papers

Catalytic enantioselective synthesis of benzocyclobutenols and cyclobutanolsviaa sequential reduction/C-H functionalization

We report here a sequential enantioselective reduction/C-H functionalization to install contiguous stereogenic carbon centers of benzocyclobutenols and cyclobutanols. This strategy features a practical enantioselective reduction of a ketone and a diastereospecific iridium-catalyzed C-H silylation. Further transformations have been explored, including controllable regioselective ring-opening reactions. In addition, this strategy has been utilized for the synthesis of three natural products, phyllostoxin (proposed structure), grandisol and fragranol.

Ring-Expansion Induced 1,2-Metalate Rearrangements: Highly Diastereoselective Synthesis of Cyclobutyl Boronic Esters

The broad synthetic utility of organoboron compounds stems from their ready ability to undergo 1,2-migrations. Normally, such shifts are induced by α-leaving groups or by reactions of alkenyl boronates with electrophiles. Herein, we present a new strategy to induce 1,2-metalate rearrangements, via ring expansion of vinylcyclopropyl boronate complexes activated by electrophiles. This leads to a cyclopropane-stabilized carbocation, which triggers ring expansion and concomitant 1,2-metalate rearrangement. This novel process delivers medicinally relevant 1,2-substituted cyclobutyl boronic esters with high levels of diastereoselectivity. A wide range of organolithiums and Grignard reagents, electrophiles, and vinylcyclopropyl boronic esters can be used. The methodology was applied to a short, stereoselective synthesis of (±)-grandisol. Computational studies indicate that the reaction proceeds via a nonclassical carbocation followed by anti-1,2-migration.

A highly stereocontrolled formal total synthesis of (±)- and of (-)-grandisol by 1,4-conjugated addition of organocopper reagents to cyclobutylidene derivatives

Starting from suitable cyclopropanes, a formal total synthesis of racemic grandisol and of the enantiopure (-)-grandisol is presented. The racemic synthesis of the grandisol precursor was accomplished in five steps. The synthesis of the chiral non-racemic precursor (1S,2S,2′R)-cis of this pheromone was realized in 10 steps, with an overall yield of 45%, using the enantiopure cyclobutanone (R,S), previously obtained by ring expansion of an optically pure oxaspiropentane. The key stereodefining step was the addition of lithium dimethylcuprate to a chiral α,β-unsaturated cyclobutylidene carbonyl derivative.

Stereospecific palladium(0)-catalyzed reduction of 2-cyclobutylidenepropyl esters. A versatile preparation of diastereomeric monoterpenoids: (±)-fragranol and (±)-grandisol

Mixtures of (E and Z)-2-cyclobutylidenepropyl sulfonates, readily available from α,α-disubstituted cyclobutanones arising from suitable cyclopropane derivatives ring expansion, underwent regioselective and stereospecific reduction by formate anion to offer, through π-1,1- trimethyleneallylpalladium complexes formed upon treatment with palladium(0), a new and convenient entry to the diastereomeric four-membered ring monoterpenoids (±)-fragranol and (±)-grandisol.

A new stereoselective synthesis of (±)-grandisol based on the remote alkylation protocol

A new stereoselective synthesis of (±)-grandisol (1a) has been developed. The synthesis starts with a simple cyclobutyl derivative to which the methyl group and the 1,2-cis disposed side chains were appended through a remote alkylation protocol.

First total synthesis of the sex pheromone of the oleander scale Aspidiotus nerii: An unusual sesquiterpenic functionalized cyclobutane

The first total synthesis of the sex pheromone of the oleander scale Aspidiotus nerii (5), an economically important polyphagous pest, is described. The synthesis is based on a stereo-controlled and completely regioselective intramolecular exo-cyclization of cis-epoxynitrile 9 to afford cyclobutane alcohol t-10 stereoselectively. Introduction of the unusual 4-methylpent-4-enyl group onto the cyclobutane skeleton was effected through Wittig reaction of aldehyde 17b with the bulky ylide 3,3-(ethylenedioxy)butylidenetriphenyl-phosphorane. This process requires protection of the primary hydroxy group of 10 with a nonbulky protecting agent, like methoxymethyl (MOM) but not tetrahydropyranyl (THP), as confirmed by molecular modelling studies. After selective transformations to manipulate the three acid-sensitive protecting functionalities present, that is, the tert-butyl-dimethylsilyl (TBDMS), ethylene acetal, and MOM groups, compound 5 was obtained in 26.4% overall yield from t-10b. In a different approach, complete cleavage of these protecting groups in 19b furnished keto diol 31, which after regioselective acetylation of the primary alcohol and Wittig reaction afforded acetate 5 in 21.4% overall yield from t-10b. The synthetic material exhibited spectroscopic features identical to those of the natural material and showed remarkable biological activity in field tests.

Stereoselective total synthesis of (±)-fragranol by TiCl4 promoted [2 + 2] cycloaddition of allyl-tert-butyldiphenylsilane and methyl methacrylate

A stereoselective total synthesis of the monoterpenoid alcohol (±)-fragranol has been accomplished utilizing a TiCl4 promoted [2 ± 2] cycloaddition of allyl-tert-butyldiphenylsilane and methyl methacrylate as the key step.

Utilization of Selenium-directed Cycloadditions: Concise Synthesis of (+/-)-Fragranol

The reaction of 2-(phenylseleno)prop-1-ene 1 and methyl vinyl ketone 2 in the presence of EtAlCl2 gave the cycloadducts 3a and 3b.A radical substitution of the adducts 3a and 3b with allyltributyltin gave the allylated cyclobutane product, which was transformed into the cyclobutane natural product, (+/-)-fragranol.Stereoselective radical substitution using the ethylene glycol ketals of compounds 3a and 3b was also achieved.

A stereospecific synthesis of (±)-grandisol via an intramolecular lactone enolate alkylation: A remarkable regiodivergence in C- vs O-alkylation

(±)-Grandisol (1) has been synthesized in a stereospecific manner by an intramalecular lactone enolate alkylation route featuring remarkable conaol over C- vs O-alkylation.

Practical Preparation of Bicyclohept-3-en-6-ones and its Utilisation in Stereoselective Total Synthesis of Grandisol and Lineatin via a Versatile Intermediate.

New and efficient stereoselective total syntheses have been devised for racemic grandisol and lineatin, two important components of pheromonic blends.They are based on the utilisation of 1,4-dimethylbicyclohept-3-en-6-one as a pivotal intermediate.This compound, as well as other bicyclohept-3-en-6-ones, are now easily available by a practical bicyclization of the corresponding 3-hydroxy-6-alkenoic acids.