Chemistry:Periplanone B
From HandWiki
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| Names | |
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| IUPAC name
(5E)-1β,2β:10,14-Diepoxygermacra-4(15),5-dien-9-one
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| Systematic IUPAC name
(1R,2R,5S,6E,10R)-8-Methylidene-5-(propan-2-yl)-11-oxaspiro[bicyclo[8.1.0]undecane-2,2′-oxiran]-6-en-3-one | |
| Other names
(1Z,5E)-1,10(14)-Diepoxy-4(15),5-germacradiene-9-one
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| Identifiers | |
3D model (JSmol)
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| Properties | |
| C15H20O3 | |
| Molar mass | 248.322 g·mol−1 |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). | |
 verify (what is   ?)
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| Infobox references | |
Tracking categories (test):
Periplanone B is a pheromone produced by the female American cockroach,[1] Periplaneta americana. It is a sexual attractant to male cockroaches, especially at short ranges.[2]
History
The activity of this pheromone was first described in 1952, but it was not until 25 years later that Persoons et al. reported the gross structure of periplanones A and B.[3] The stereochemical configuration and first total synthesis were reported by W. Clark Still's group at Columbia University in 1979.[4]
References
- ↑ Okada, K (September 1990). "Behavioral responses of male Periplaneta americana L. to female sex pheromone components, periplanone-A and periplanone-B". Journal of Chemical Ecology 16 (9): 2605–2614. doi:10.1007/BF00988072. PMID 24264316. Bibcode: 1990JCEco..16.2605O.
- ↑ Chow, YF; Wang, SF (1981). "Attraction responses of the American cockroach to synthetic periplanone-B". Journal of Chemical Ecology 7 (2): 265–272. doi:10.1007/BF00995749. PMID 24420472. Bibcode: 1981JCEco...7..265C.
- ↑ Wood, William F. (1982). "The Sex Pheromone of the Gypsy Moth and the American Cockroach". Journal of Chemical Education 59 (1): 35–36. doi:10.1021/ed059p35. Bibcode: 1982JChEd..59...35W.
- ↑ Nicolaou, K. C.; E. J. Sorensen (1996). Classics in Total Synthesis. Weinheim, Germany: VCH. p. 211. ISBN 3-527-29284-5. https://archive.org/details/classicstotalmet00kcni.
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