| 词条 | Periplanone B |
| 释义 |
| Verifiedfields = changed | Watchedfields = changed | verifiedrevid = 464199257 | ImageFile = Periplanone B.png | ImageFile2 = Periplanone B ball-and-stick.png | ImageSize = 200px | IUPACName = (1S, 2S,5S,10S)-(6E)-8-Methylidene-5-propan-2-ylspiro[11-oxabicyclo[8.1.0]undec-6-ene-2,2'-oxirane]-3-one | OtherNames = (1Z,5E)-1,10(14)-Diepoxy-4(15),5-germacradiene-9-one |Section1={{Chembox Identifiers | ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} | ChemSpiderID = 9065530 | 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 | StdInChI_Ref = {{stdinchicite|correct|chemspider}} | StdInChI = 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 | StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} | StdInChIKey = KVFSFBCTIZBPRK-KGDVWTLMSA-N | CASNo_Ref = {{cascite|changed|??}} | CASNo = 61228-92-0 | PubChem = 10890266 | SMILES = O=C2[C@]1(OC1)[C@@H]3O[C@@H]3CC(\\C=C\\[C@H](C(C)C)C2)=C }} |Section2={{Chembox Properties | C=15 | H=20 | O=3 | Appearance = | Density = | MeltingPt = | BoilingPt = | Solubility = }} |Section3={{Chembox Hazards | MainHazards = | FlashPt = | AutoignitionPt = }} }}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] HistoryThe 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] References1. ^{{cite journal | author = Okada, K| title = Behavioral responses of male Periplaneta americana L. to female sex pheromone components, periplanone-A and periplanone-B | journal = Journal of Chemical Ecology | volume = 16 | issue = 9 | pages = 2605–2614 | date = September 1990 | doi = 10.1007/BF00988072 |display-authors=etal}} {{Organic-compound-stub}}2. ^{{cite journal |author1=Chow, YF |author2=Wang, SF | title = Attraction responses of the American cockroach to synthetic periplanone-B | journal = Journal of Chemical Ecology | volume = 7 | issue = 2 | pages = 265–272 | year = 1981 | doi = 10.1007/BF00995749 }} 3. ^{{cite book |title= Classics in Total Synthesis|last= Nicolaou|first= K. C.|authorlink=K. C. Nicolaou |author2=E. J. Sorensen|year= 1996|publisher= VCH|location= Weinheim, Germany|isbn= 3-527-29284-5|page=211|pages= |url= |accessdate= }} 7 : Insect pheromones|Epoxides|Sesquiterpenes|Spiro compounds|Ketones|Alkene derivatives|Oxygen heterocycles |
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