Periplanone B

Last updated
Periplanone B
Periplanone B.png
Periplanone B ball-and-stick.png
Names
IUPAC name
(5E)-1β,2β:10,14-Diepoxygermacra-4(15),5-dien-9-one
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
Identifiers
3D model (JSmol)
ChemSpider
PubChem CID
UNII
  • InChI=1S/C15H20O3/c1-9(2)11-5-4-10(3)6-12-14(18-12)15(8-17-15)13(16)7-11/h4-5,9,11-12,14H,3,6-8H2,1-2H3/b5-4+/t11-,12+,14+,15-/m0/s1 Yes check.svgY
    Key: KVFSFBCTIZBPRK-KGDVWTLMSA-N Yes check.svgY
  • InChI=1/C15H20O3/c1-9(2)11-5-4-10(3)6-12-14(18-12)15(8-17-15)13(16)7-11/h4-5,9,11-12,14H,3,6-8H2,1-2H3/b5-4+/t11-,12+,14+,15-/m0/s1
    Key: KVFSFBCTIZBPRK-KGDVWTLMBF
  • O=C2[C@]1(OC1)[C@@H]3O[C@@H]3CC(\C=C\[C@H](C(C)C)C2)=C
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).
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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. The stereochemical configuration and first total synthesis were reported by W. Clark Still's group at Columbia University in 1979. [3]

References

  1. ↑ Okada, K; et al. (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. Bibcode:1990JCEco..16.2605O. doi:10.1007/BF00988072. PMID   24264316. S2CID   30323914.
  2. ↑ Chow, YF; Wang, SF (1981). "Attraction responses of the American cockroach to synthetic periplanone-B". Journal of Chemical Ecology. 7 (2): 265–272. Bibcode:1981JCEco...7..265C. doi:10.1007/BF00995749. PMID   24420472. S2CID   21794952.
  3. ↑ Nicolaou, K. C.; E. J. Sorensen (1996). Classics in Total Synthesis . Weinheim, Germany: VCH. p.  211. ISBN   3-527-29284-5.


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