词条 | Cedrene |
释义 |
| Name = (−)-α-cedrene | ImageFile = alpha-cedrene skeletal.svg | ImageSize = | ImageAlt = | IUPACName = (1S,2R,5S,7R)-2,6,6,8-tetramethyltricyclo[5.3.1.01,5]undec-8-ene | OtherNames = |Section1={{Chembox Identifiers | CASNo = 469-61-4 | PubChem = 6431015 | ChemSpiderID = 4936353 | SMILES = C[C@@H]1CC[C@@H]2[C@]13CC=C([C@H](C3)C2(C)C)C | InChI = 1/C15H24/c1-10-7-8-15-9-12(10)14(3,4)13(15)6-5-11(15)2/h7,11-13H,5-6,8-9H2,1-4H3/t11-,12+,13+,15+/m1/s1 | InChIKey = IRAQOCYXUMOFCW-OSFYFWSMBF | StdInChI = 1S/C15H24/c1-10-7-8-15-9-12(10)14(3,4)13(15)6-5-11(15)2/h7,11-13H,5-6,8-9H2,1-4H3/t11-,12+,13+,15+/m1/s1 | StdInChIKey = IRAQOCYXUMOFCW-OSFYFWSMSA-N }} |Section2={{Chembox Properties | C=15 | H=24 | Appearance = | Density = 0.932 g/mL at 20 °C[1] | MeltingPt = | BoilingPt = 261–262 °C[1] | Solubility = }} |Section3={{Chembox Hazards | MainHazards = | FlashPt = | AutoignitionPt = }} }}{{Chembox | Name = (+)-β-cedrene | ImageFile = beta-cedrene skeletal.svg | ImageSize = | ImageAlt = | IUPACName = (1S,2R,5S,7R)-2,6,6-trimethyl-8-methylidenetricyclo[5.3.1.0(1,5)]undecane | OtherNames = |Section1={{Chembox Identifiers | CASNo = 546-28-1 | PubChem = 11106485 | ChemSpiderID = 9281621 | SMILES = C[C@@H]1CC[C@@H]2[C@]13CCC(=C)[C@H](C3)C2(C)C | InChI = 1/C15H24/c1-10-7-8-15-9-12(10)14(3,4)13(15)6-5-11(15)2/h11-13H,1,5-9H2,2-4H3/t11-,12+,13+,15+/m1/s1 | InChIKey = DYLPEFGBWGEFBB-OSFYFWSMBA | StdInChI = 1S/C15H24/c1-10-7-8-15-9-12(10)14(3,4)13(15)6-5-11(15)2/h11-13H,1,5-9H2,2-4H3/t11-,12+,13+,15+/m1/s1 | StdInChIKey = DYLPEFGBWGEFBB-OSFYFWSMSA-N }} |Section2={{Chembox Properties | C=15 | H=24 | Appearance = | Density = 0.932 g/mL at 20 °C[2] | MeltingPt = | BoilingPt = 263–264 °C[2] | Solubility = }} |Section3={{Chembox Hazards | MainHazards = | FlashPt = | AutoignitionPt = }} }} Cedrene is a sesquiterpene found in the essential oil of cedar. The two isomers present in the oil are (−)-α-cedrene[3][4] and (+)-β-cedrene,[5] which differ in the position of a double bond. See also
References1. ^1 {{Aldrich|id=22133|name=(−)-α-Cedrene|accessdate=8 July 2012}} {{hydrocarbon-stub}}2. ^1 {{Aldrich|id=22134|name=(+)-β-Cedrene|accessdate=8 July 2012}} 3. ^{{Cite journal | last1 = Lee | first1 = H. Y. | last2 = Lee | first2 = S. | last3 = Kim | first3 = D. | last4 = Kim | first4 = B. K. | last5 = Bahn | first5 = J. S. | last6 = Kim | first6 = S. | doi = 10.1016/S0040-4039(98)01680-3 | title = Total synthesis of α-cedrene: A new strategy utilizing N-Aziridinylimine radical chemistry | journal = Tetrahedron Letters | volume = 39 | issue = 42 | pages = 7713–7716 | year = 1998 | pmid = | pmc = }} 4. ^{{Cite journal | last1 = Takigawa | first1 = H. | last2 = Kubota | first2 = H. | last3 = Sonohara | first3 = H. | last4 = Okuda | first4 = M. | last5 = Tanaka | first5 = S. | last6 = Fujikura | first6 = Y. | last7 = Ito | first7 = S. | title = Novel Allylic Oxidation of alpha-Cedrene to sec-Cedrenol by a Rhodococcus Strain | journal = Applied and Environmental Microbiology | volume = 59 | issue = 5 | pages = 1336–1341 | year = 1993 | pmid = 16348930 | pmc = 182086}} 5. ^{{Cite journal | last1 = Kerr | first1 = W. J. | last2 = McLaughlin | first2 = M. | last3 = Morrison | first3 = A. J. | last4 = Pauson | first4 = P. L. | title = Formal total synthesis of (+/-)-alpha- and beta-cedrene by preparation of cedrone. Construction of the tricyclic carbon skeleton by the use of a highly efficient intramolecular Khand annulation | journal = Organic Letters | volume = 3 | issue = 19 | pages = 2945–2948 | year = 2001 | pmid = 11554814 | doi=10.1021/ol016054a}} 1 : Sesquiterpenes |
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