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词条 Cedrene
释义

  1. See also

  2. References

{{Chembox
| 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

  • Cedrol, another component of cedar oil

References

1. ^{{Aldrich|id=22133|name=(−)-α-Cedrene|accessdate=8 July 2012}}
2. ^{{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}}
{{hydrocarbon-stub}}

1 : Sesquiterpenes

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