蜚蠊酮B

蜚蠊酮B
	IUPAC名; (5E)-1β,2β:10,14-Diepoxygermacra-4(15),5-dien-9-one
	系统名; (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
别名	(1Z,5E)-1,10(14)-Diepoxy-4(15),5-germacradiene-9-one
识别
CAS号	61228-92-0
PubChem	10890266
ChemSpider	9065530
SMILES	O=C2[C@]1(OC1)[C@@H]3O[C@@H]3CC(\C=C\[C@H](C(C)C)C2)=C;
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;
InChIKey	KVFSFBCTIZBPRK-KGDVWTLMBF
性质
化学式	C15H20O3
摩尔质量	248.32 g·mol−1
	若非注明，所有数据均出自标准状态（25 ℃，100 kPa）下。

蜚蠊酮B（英語：Periplanone B，PB）是一种由雌性美洲大蠊（学名：Periplaneta americana，俗称蟑螂）产生的信息素^[1]。其是一种性信息素，能吸引一部分品种的雄性蟑螂^[2]。

历史

1952年，由Louis M. Roth和Edwin R. Willis发现了雌性美洲大蠊存在一种信息素能吸引雄性美洲大蠊^[3]。直到25年后，Persoons等人提出美洲大蠊至少存在两种信息素，即蜚蜚蠊酮A和蜚蠊酮B，并提出了蜚赚酮B的结构。蜚蠊酮A则在1986年确定^[4]。直到1979年，蜚蠊酮B的立体构型确定和全合成由哥伦比亚大学的W. Clark Still完成^[5]。

参考文献

^ Okada, K; et al. Behavioral responses of male Periplaneta americana L. to female sex pheromone components, periplanone-A and periplanone-B. Journal of Chemical Ecology. September 1990, 16 (9): 2605–2614. PMID 24264316. S2CID 30323914. doi:10.1007/BF00988072.
^ Chow, YF; Wang, SF. Attraction responses of the American cockroach to synthetic periplanone-B. Journal of Chemical Ecology. 1981, 7 (2): 265–272. PMID 24420472. S2CID 21794952. doi:10.1007/BF00995749.
^ The American Midland Naturalist. A Study of Cockroach Behavior. The American Midland Naturalist. 1952, 47 (1): 66–129. doi:10.2307/2421700.
^ Okada, K., Mori, M., Shimazaki, K. et. al. Behavioral and electroantennogram responses of periplanone analogs. Journal of Chemical Ecology. 1991, 17: 695–706. doi:10.1007/BF00994193.
^ Nicolaou, K. C.; E. J. Sorensen. Classics in Total Synthesis. Weinheim, Germany: VCH. 1996: 211. ISBN 3-527-29284-5.

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[1] Okada, K; et al. Behavioral responses of male Periplaneta americana L. to female sex pheromone components, periplanone-A and periplanone-B. Journal of Chemical Ecology. September 1990, 16 (9): 2605–2614. PMID 24264316. S2CID 30323914. doi:10.1007/BF00988072.

[2] Chow, YF; Wang, SF. Attraction responses of the American cockroach to synthetic periplanone-B. Journal of Chemical Ecology. 1981, 7 (2): 265–272. PMID 24420472. S2CID 21794952. doi:10.1007/BF00995749.

[3] The American Midland Naturalist. A Study of Cockroach Behavior. The American Midland Naturalist. 1952, 47 (1): 66–129. doi:10.2307/2421700.

[4] Okada, K., Mori, M., Shimazaki, K. et. al. Behavioral and electroantennogram responses of periplanone analogs. Journal of Chemical Ecology. 1991, 17: 695–706. doi:10.1007/BF00994193.

[Nicolaou-5] Nicolaou, K. C.; E. J. Sorensen. Classics in Total Synthesis. Weinheim, Germany: VCH. 1996: 211. ISBN 3-527-29284-5.

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