Periplanon B

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Structural formula
Structural formula of Periplanone B
General
Surname Periplanon B
other names

(1 S , 2 S , 5 S , 10 S ) - (6 E ) -8-methylidene-5-propan-2-ylspiro [11-oxabicyclo [8.1.0] undec-6-en-2,2'- oxirane] -3-one

Molecular formula C 15 H 20 O 3
Brief description

colorless and odorless solid

External identifiers / databases
CAS number 61228-92-0
PubChem 10890266
Wikidata Q2594205
properties
Molar mass 248.32 g mol −1
Physical state

firmly

density

1.152 g cm −3

safety instructions
GHS hazard labeling
no classification available
As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .

Periplanone B is a sex pheromone of the American cockroach .

American cockroach ( Periplaneta americana )

history

In 1976, the first isolation of Periplanon B on a microgram scale was achieved . The female cockroaches store minimal amounts of less than 1 microgram.

The first total synthesis of the racemate and the determination of the absolute configuration succeeded in 1979 ( W. Clark Still et al.). The total synthesis relied on an anionic Oxy- Cope rearrangement to form the ten-membered ring. Over the years, further total syntheses of the racemate have been published, with ring formation being achieved by means of photocycloaddition .

The first enantioselective synthesis was published in 1990. Periplanon B is synthesized in 18 steps and with a yield of 12%.

Individual evidence

  1. a b EPA: Periplanone B Reregistration Eligibility Decision , accessed March 15, 2015.
  2. H. Hauptmann, G. Mühlbauer, NPC Walker: Synthesis and Crystal Structure of (±) -periplanon B . In: Tetrahedron Letters . tape 27 , no. 12 , 1986, pp. 1315-1318 , doi : 10.1016 / S0040-4039 (00) 84247-1 .
  3. This substance has either not yet been classified with regard to its hazardousness or a reliable and citable source has not yet been found.
  4. Kentaro Okada, Masataka Mori, Kazuko Shimazaki, Tatsuji Chuman: Behavioral responses of male Periplaneta americana L. to female sex pheromone components, periplanone-A and periplanone-B. In: Journal of Chemical Ecology. 16, 1990, pp. 2605-2614, doi : 10.1007 / BF00988072 .
  5. CJ Persoons et al .: Sex pheromones of the American cockroach, Periplaneta americana: A tentative structure of periplanone-B. In: Tetrahedron Letters 17.24 (1976): pp. 2055-2058.
  6. Michael A. Adams, Koji Nakanishi, W. Clark Still, Edward V. Arnold, Jon Clardy, CJ Persoons: Sex pheromone of the American cockroach: absolute configuration of periplanone-B. In: Journal of the American Chemical Society. 101, 1979, pp. 2495-2498, doi : 10.1021 / ja00503a049 .
  7. ^ W. Clark Still: (±) -Periplanone-B. Total synthesis and structure of the sex excitant pheromones of the American cockroach. In: Journal of the American Chemical Society. 101, 1979, pp. 2493-2495, doi : 10.1021 / ja00503a048 .
  8. Stuart L. Schreiber, Conrad Santini: Cyclobutene bridgehead olefin route to the American cockroach sex pheromone, periplanone-B. In: Journal of the American Chemical Society. 106, 1984, pp. 4038-4039, doi : 10.1021 / ja00326a028 .
  9. Takeshi Kitahara, Masataka Mori, Kenji Mori: Total synthesis of (-) - periplanone-B, natural major sex-excitant pheromone of the american cockroach. In: Tetrahedron . 43, 1987, pp. 2689-2699, doi : 10.1016 / S0040-4020 (01) 86874-5 .