Periplanone B

{{Chembox

| Verifiedfields = changed

| Watchedfields = changed

| verifiedrevid = 464199257

| ImageFile = Periplanone B.png

| ImageFile2 = Periplanone B ball-and-stick.png

| ImageSize = 200px

| IUPACName = (5E)-1β,2β:10,14-Diepoxygermacra-4(15),5-dien-9-one

| SystematicName = (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

| 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|correct|CAS}}

| CASNo = 61228-92-0

| UNII_Ref = {{fdacite|correct|FDA}}

| UNII = 8HV41M9E86

| 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 =

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|Section3={{Chembox Hazards

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Periplanone B is a pheromone produced by the female American cockroach,{{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 | pmid = 24264316 | s2cid = 30323914 |display-authors=etal}} Periplaneta americana. It is a sexual attractant to male cockroaches, especially at short ranges.{{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 |pmid=24420472 |s2cid=21794952 }}

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.{{cite book |title= Classics in Total Synthesis|last= Nicolaou|first= K. C.|author-link=K. C. Nicolaou |author2=E. J. Sorensen|year= 1996|publisher= VCH|location= Weinheim, Germany|isbn= 3-527-29284-5|page=[https://archive.org/details/classicstotalmet00kcni/page/n236 211]|url=https://archive.org/details/classicstotalmet00kcni|url-access= limited}}

References