281193-45-1

Basic information

• Product Name: 6,8-Dioxabicyclo[3.2.1]octane,2-fluoro-1,5-dimethyl-,(1R,2R,5R)-(9CI)
• Synonyms: 6,8-Dioxabicyclo[3.2.1]octane,2-fluoro-1,5-dimethyl-,(1R,2R,5R)-(9CI)
• CAS NO: 281193-45-1
• Molecular Formula: C8H13FO2
• Molecular Weight: 0
• Product Categories: HALIDE
• Mol File: 281193-45-1.mol
• Article Data: 2

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 6,8-Dioxabicyclo[3.2.1]octane,2-fluoro-1,5-dimethyl-,(1R,2R,5R)-(9CI)(CAS DataBase Reference)
• NIST Chemistry Reference: 6,8-Dioxabicyclo[3.2.1]octane,2-fluoro-1,5-dimethyl-,(1R,2R,5R)-(9CI)(281193-45-1)
• EPA Substance Registry System: 6,8-Dioxabicyclo[3.2.1]octane,2-fluoro-1,5-dimethyl-,(1R,2R,5R)-(9CI)(281193-45-1)

Safety Data

• Hazardous Substances Data: 281193-45-1(Hazardous Substances Data)

Upstream product

• 281193-54-2 (1S,2R,5S)-2-Fluoro-5-methyl-1-((R)-toluene-4-sulfinylmethyl)-6,8-dioxa-bicyclo[3.2.1]octane 
• 281193-46-2 (3S,S_S)-1-[(4-methylphenyl)sulfinyl]-3-fluoro-hept-6-en-2-one 
• 390823-85-5 (2R,3S,S_S)-2-{[(4-methylphenyl)sulfinyl]methyl}-3-fluorohept-6-en-1,2-diol 
• 390823-86-6 (1R,2S,5R)-2-Fluoro-5-methyl-1-((S)-toluene-4-sulfinylmethyl)-6,8-dioxa-bicyclo[3.2.1]octane 
• 281193-47-3 (1'S,2R,S_S)-2-{[(4-methylphenyl)sulfinyl]methyl}-2-(1'-fluoro)pent-3'-enyloxirane 
• 281193-51-9 (1R,2S,5R)-2-fluoro-1-{[(4-methylphenyl)sulfenyl]methyl}-5-methyl-6,8-dioxabicyclo[3.2.1]octane 
• 281193-40-6 (3R,S_S)-1-[(4-methylphenyl)sulfinyl]-3-fluoro-hept-6-en-2-one 
• 281193-42-8 (2R,3R,S_S)-2-{[(4-methylphenyl)sulfinyl]methyl}-3-fluorohept-6-en-1,2-diol 
• 281193-43-9 (1R,2R,5R)-2-Fluoro-5-methyl-1-((S)-toluene-4-sulfinylmethyl)-6,8-dioxa-bicyclo[3.2.1]octane 
• 281193-41-7 (1'R,2R,S_S)-2-{[(4-methylphenyl)sulfinyl]methyl}-2-(1'-fluoro)pent-3'-enyloxirane 
• 281193-44-0 (1R,2R,5R)-2-fluoro-1-{[(4-methylphenyl)sulfenyl]methyl}-5-methyl-6,8-dioxabicyclo[3.2.1]octane 

Relevant articles and documents

Stereoselective synthesis of trifluoro- and monofluoro-analogues of frontalin and evaluation of their biological activity

The stereoselective synthesis of both enantiomers of trifluoro frontalin (-)-(1S,5R)- and (+)-(1R,5S)-8, as well as of diastereomeric monofluoro frontalines (-)- (1R,2R,5R)-18 and (-)-(1R,2S,5R)-20, analogues of the bioactive component of the aggregation pheromone of the Scolytidae insect family, has been accomplished starting from (-)-(1R)- and (+)-(1S)-menthyl (S)-toluene-4-sulfinate as a source of chirality and methyl trifluoroacetate or fluoroacetate, respectively, as sources of fluorine. The C-1 stereocenters were installed via stereoselective epoxidation of β-sulfinyl ketones 2 and 13 with diazomethane. The bicyclic core was obtained by totally stereocontrolled and chemoselective tandem Wacker oxidation/intramolecular ketalization of the intermediate unsatured sulfinyl diols 5, 15, and 19. Axially fluorinated (-)-20 elicited a strong electroantennographic response in laboratory tests on females of Dendroctonus micans, whereas equatorially fluorinated (-)-18 and the trifluoroanalogue (-)-8 showed modest responses. Field trials using (-)-20 were not indicative owing to the locally scarce population of D. micans, but it showed some attractiveness for other Coleoptera families.