30820-22-5

Basic information

• Product Name: GRANDLURE I
• Synonyms: cis-cyclobutaneethano;cyclobutaneethanol,;GRANDLURE I;cis-1-Methyl-2-(1-methylethenyl)-cyclobutaneethanol
• CAS NO: 30820-22-5
• Molecular Formula: C₁₀H₁₈O
• Molecular Weight: 154.25
• Mol File: 30820-22-5.mol
• Article Data: 19

Chemical Properties

• Boiling Point: 209.9±9.0℃ (760 Torr)
• Flash Point: 78.5±15.0℃
• Appearance: /
• Density: 0.907±0.06 g/cm3 (20 ºC 760 Torr)
• Vapor Pressure: 0.0453mmHg at 25°C
• Refractive Index: 1.468
• PKA: 15.14±0.10(Predicted)
• CAS DataBase Reference: GRANDLURE I(CAS DataBase Reference)
• NIST Chemistry Reference: GRANDLURE I(30820-22-5)
• EPA Substance Registry System: GRANDLURE I(30820-22-5)

Safety Data

• Hazardous Substances Data: 30820-22-5(Hazardous Substances Data)

Usage

General Description

"GRANDLURE I" is a powerful insect attractant containing the pheromone grandlure and a food attractant. The pheromone component of this chemical is released by female beetles to attract males for mating purposes, making it highly effective in attracting both males and females of certain beetle species. The food attractant component further enhances its effectiveness by drawing in beetles looking for a food source. This combination makes "GRANDLURE I" an ideal tool for monitoring and controlling beetle populations in agricultural and forestry settings. Its ability to lure both male and female beetles makes it a versatile and highly valuable chemical for pest management.

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 
• 249930-46-9 (1S,2S)-2-Formyl-1-methyl-cyclobutanecarboxylic acid methyl ester 

Relevant articles and documents

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.

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.

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.