28290-23-5

Basic information

• Product Name: (-)-α-selinene
• CAS NO: 28290-23-5
• Molecular Weight: 204.356
• Mol File: 28290-23-5.mol
• Article Data: 6

Chemical Properties

• CAS DataBase Reference: (-)-α-selinene(CAS DataBase Reference)
• NIST Chemistry Reference: (-)-α-selinene(28290-23-5)
• EPA Substance Registry System: (-)-α-selinene(28290-23-5)

Safety Data

• Hazardous Substances Data: 28290-23-5(Hazardous Substances Data)

Upstream product

• 115562-82-8 3,9-dimethyl-11-(methylethenyl)-1,3,9-decatriene 
• 83093-43-0 (1S,4aS,7R,8aS)-7-(1,2-Dihydroxy-1-methyl-ethyl)-1,4a-dimethyl-octahydro-naphthalen-2-one 
• 473-16-5 (+)-α-eudesmol 
• 92803-54-8 C₂₂H₃₄N₂O₄S 
• 92803-57-1 Toluene-4-sulfonic acid 2-((2R,4aR,8aR)-4a,8-dimethyl-1,2,3,4,4a,5,6,8a-octahydro-naphthalen-2-yl)-2-hydroxy-propyl ester 
• 80322-01-6 2-((2R,4aR,8aR)-4a,8-Dimethyl-1,2,3,4,4a,5,6,8a-octahydro-naphthalen-2-yl)-propane-1,2-diol 
• 117212-69-8 3-Isopropenyl-5,8a-dimethyl-3,4,4a,7,8,8a-hexahydro-2H-naphthalen-1-one 
• 1779-49-3 Methyltriphenylphosphonium bromide 
• 78719-76-3 1-((2R,4aR,8aR)-4a,8-Dimethyl-1,2,3,4,4a,5,6,8a-octahydro-naphthalen-2-yl)-ethanone 
• 138089-74-4 3-ethoxy-5-methyl-6-(3-methyl-2-butenyl)-2-cyclohexen-1-one 
• 138089-76-6 2-(4-ethoxy-6-methyl-2-oxo-3-cyclohexenyl)acetaldehyde 
• 138089-84-6 1,5-dimethyl-8-(1-methylethenyl)-4-(phenylseleno)bicyclo<4.4.0>decan-3-one 
• 138089-82-4 5-methyl-8-(1-methylethenyl)-4-(phenylseleno)bicyclo<4.4.0>dec-1-en-3-one 
• 138089-78-8 3-ethoxy-5-methyl-6-<3-methyl-4-(trimethylsilyl)-2-butenyl>-2-cyclohexen-1-one 

Relevant articles and documents

Total Synthesis of rac-Sesquiterpenoid AE 1

rac-Sesquiterpenoid AE 1 (rac-1) can be obtained in an 11-step sequence starting from 5-methylresorcinol (2).The key compound 9 is synthesized by the use of a diastereoselective dienone cyclization with the allylic silane 8.Subsequent transformation of 9 leads to rac-1. Key Words: Sesquiterpenoid AE 1 / Dienone cyclization / Allylsilane

TOTAL SYNTHESIS OF RACEMIC SELINA-3,7(11)-DIENE, α-SELINENE AND α-EUDESMOL

Three natural products of the eudesmane family, selina-3,7(11)-diene, α-selinene and α-eudesmol, have been synthesized using a common strategy.The key steps involved in the strategy include the direct deprotonation/alkylation of isoprenyl sulfone and the intramolecular Diels-Alder reaction.

A NEW ROUTE FOR THE CONVERSION OF CARVONE INTO EUDESMANE SESQUITERPENES

The β-hydroxy-α-phenylsulfenyl ketone 2, derived from S-(+)-carvone, was treated with 2 equivalents of the Wittig-Horner phosphine oxide derivative 6 followed by excess methyl iodide to give a ca. 2:3 mixture of the E and Z α-phenylsulfenyl ketones 3a and 3b.The mixture of sulfides was oxidized to the corresponding sulfoxides 3c,d with m-chloroperbenzoic acid.When this mixture refluxed in benzene, elimination of phenylsulfinic acid occured and the intermediate E diene derivative 4a underwent an intramolecular Diels-Alder reaction to give the trans-octalone 5a, the cis-octalone 5c, and another product believed to be the trans-octalone 5b in a 60:28:12 ratio.The Z diene derivative 4b was recovered under these reaction conditions.Wolff-Kishner reduction of the octalone mixture gave (-)-α-selinene (10) as the major product along with the cis-octalin 11 and other unidentified minor products.When the Z diene derivative 4b was heated in toluene at 150 deg C for 48 h, a mixture of octalones having the same composition as that produced above was obtained.Likewise, when the 2:3 mixture of sulfoxides 3c and 3d was heated in toluene at 150 deg C, the same mixture of octalones was produced.Apparently, at the higher temperature, the Z diene derivative 4b isomerized to the E isomer 4a which ultimately underwent the intramolecular Diels-Alder reaction.