123163-72-4

Basic information

• Product Name: perplanone D
• Synonyms: perplanone D;(2S,Z,E)-9-Isopropyl-2-methyl-6-methylenecyclodecadien-3,7-one
• CAS NO: 123163-72-4
• Molecular Formula: C15H22O
• Molecular Weight: 216.32
• Mol File: 123163-72-4.mol
• Article Data: 3

Chemical Properties

• Boiling Point: 329.5°Cat760mmHg
• Flash Point: 146.9°C
• Appearance: /
• Density: 0.93g/cm³
• Vapor Pressure: 0.000177mmHg at 25°C
• Refractive Index: 1.5
• CAS DataBase Reference: perplanone D(CAS DataBase Reference)
• NIST Chemistry Reference: perplanone D(123163-72-4)
• EPA Substance Registry System: perplanone D(123163-72-4)

Safety Data

• Hazardous Substances Data: 123163-72-4(Hazardous Substances Data)

Usage

InChI:InChI=1/C15H20O/c1-11(2)14-9-8-12(3)6-5-7-13(4)15(16)10-14/h5,7-9,11,14H,3-4,6,10H2,1-2H3/b7-5-,9-8-/t14-/m0/s1

Upstream product

• 159989-91-0 (3Z,7E)-(1S,2S,9S)-9-Isopropyl-2-methyl-6-methylene-cyclodeca-3,7-diene-1,2-diol 
• 159846-98-7 (E)-(S)-5-[2-(tert-Butyl-diphenyl-silanyloxy)-ethyl]-6-methyl-hept-3-en-2-one 
• 159846-97-6 (S)-5-[2-(tert-Butyl-diphenyl-silanyloxy)-ethyl]-6-methyl-heptan-2-one 
• 159847-05-9 (2Z,6E)-(1S,8S,10R)-8-Isopropyl-1-methyl-5-methylene-11-oxa-bicyclo[8.1.0]undeca-2,6-diene 
• 1027561-94-9 (4E,8Z)-(S)-3-Isopropyl-6-methylene-10-oxo-undeca-4,8-dienal 
• 499-94-5 (S)-carvomenthene 
• 115514-36-8 (S)-3-isopropyl-6-oxo-heptanal 
• 5989-54-8 (-)-(S)-limonene 
• 191287-29-3 Acetic acid (E)-(1S,3S)-3-isopropyl-6,10-dimethylene-9-oxo-cyclodec-4-enyl ester 
• 189359-16-8 (E)-(7S,9S)-9-Hydroxy-7-isopropyl-4,10-dimethylene-cyclodec-5-enone 
• 81968-62-9 (1R,7S,E)-7-isopropyl-4,10-dimethylenecyclodec-5-enol 
• 23986-74-5 germacrene D 
• 191287-32-8 (3Z,7E)-(1S,9S)-9-Isopropyl-2,6-dimethylene-cyclodeca-3,7-dienol 

Relevant articles and documents

Total synthesis of (-)-periplanones C and D. Their pheromonal activities against three Periplaneta species

Total synthesis of(-)-periplanones C [(-)-PC; 1] and D [(-)-PD; 2] was achieved starting from (-)-germacrene D via 7 and 8 steps, respectively, according to the similar route on syntheses of racemic PC and PD. The 1H NMR and GC mass spectra of 2 unambiguously determined the structure of the natural sample of PD which was isolated from Periplaneta fuliginosa. Bioassay of synthetic samples of 1 and 2 was carried oat against males of P. fuliginosa, P. americana, and P. japonica. 10-9 g of 1 elicited significant response in males of P. americana and P. japonica. 10-10 g of 2 elicited strong response in P. fuliginosa males, whereas it showed significantly weak response against males of P. americana and P. japonica. Almost same degree of activities was observed between 1 and 2 against males of P. americana and P. japonica at 10-10 g dose.

Periplanone Total Synthesis via Intramolecular Pinacol Coupling

We have carried out an enantioselective synthesis of (-)-periplanone C by a route involving titanium-induced, intramolecular pinacol coupling reaction of 1,10 keto aldehyde as the key step.The coupling occurs with predictable stereochemistry to give a mix