Chamigrene

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title: "Chamigrene" type: doc version: 1 created: 2026-02-28 author: "Wikipedia contributors" status: active scope: public tags: ["sesquiterpenes", "spiro-compounds"] topic_path: "general/sesquiterpenes" source: "https://en.wikipedia.org/wiki/Chamigrene" license: "CC BY-SA 4.0" wikipedia_page_id: 0 wikipedia_revision_id: 0

| Name = (−)-β-Chamigrene | ImageFile = (-)-beta-chamigrene.svg | ImageSize = | ImageAlt = | IUPACName = (R)-11-Methylene-3,7,7-trimethylspiro[5.5]undec-2-ene | OtherNames = | Section1 = {{Chembox Identifiers | CASNo = 18431-82-8 | CASNo_Ref = | ChEBI = 10359 | ChemSpiderID = 390805 | KEGG = C09637 | PubChem = 442353 | SMILES = CC1(C)[C@@]2(C(=C)CCC1)CCC(C)=CC2 | InChI = 1S/C15H24/c1-12-7-10-15(11-8-12)13(2)6-5-9-14(15,3)4/h7H,2,5-6,8-11H2,1,3-4H3/t15-/m1/s1 | InChIKey = WLNGPDPILFYWKF-OAHLLOKOSA-N | Section2 = {{Chembox Properties | C=15|H=24 | Appearance = | Density = | MeltingPt = | BoilingPt = | Solubility = }} | Section3 = {{Chembox Hazards | MainHazards = | FlashPt = | Autoignition = }}

(−)-β-Chamigrene is the parent compound of subclass of sesquiterpenes found in various marine and terrestrial plants. The stereoisomer (−)-β-chamigrene is the most common in nature.

Chamigrenes (chamigrene-related compounds) are characterized by a spiro[5.5]undecane core with an all-carbon quaternary stereocenter at the junction of the spirocycle.{{cite journal | journal = Tetrahedron | volume = 66 | issue = 26 | date = 2010 | pages = 4668–4686 | title = A general enantioselective route to the chamigrene natural product family | author = David E. White, Ian C. Stewart, Brinton A. Seashore-Ludlow, Robert H. Grubbs, and Brian M.Stoltz | doi=10.1016/j.tet.2010.04.128 | pmid = 20798895 | pmc = 2925317 }}

References

References

  1. {{Aldrich

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sesquiterpenesspiro-compounds