65372-78-3

Basic information

• Product Name: Berkheyaradulene
• Synonyms: Berkheyaradulene;(1S,8aS)-1,2,3,3a,5a,6,7,8-Octahydro-1β,3aβ,4,5aα-tetramethylcyclopenta[c]pentalene
• CAS NO: 65372-78-3
• Molecular Formula: C15H24
• Molecular Weight: 204.35
• Mol File: 65372-78-3.mol
• Article Data: 9

Chemical Properties

• Boiling Point: 254.9±7.0 °C(Predicted)
• Appearance: /
• Density: 0.95±0.1 g/cm3(Predicted)
• CAS DataBase Reference: Berkheyaradulene(CAS DataBase Reference)
• NIST Chemistry Reference: Berkheyaradulene(65372-78-3)
• EPA Substance Registry System: Berkheyaradulene(65372-78-3)

Safety Data

• Hazardous Substances Data: 65372-78-3(Hazardous Substances Data)

Upstream product

• 71596-72-0 decahydro-1,3a,5a-trimethyl-4-methylene-cyclopenta[c]pentalene 
• 136655-32-8 (5S,6R,7R)-6,7,11,11-Tetramethyl-dispiro[3.0.4.2]undecan-6-ol 
• 87372-22-3 (4β,8α)-1α,4β-Dimethyl-9-carbethoxytricyclo<6.3.0.0^4,8>undec-9-en-2-one 
• 87372-24-5 (4β,8α)-1α,4β-Dimethyl-9β-carbethoxytricyclo<6.3.0.0^4,8>undecan-2-one 
• 87372-25-6 (4β,8α)-1α,4β-Dimethyl-9β-carbethoxy-2-methylenetricyclo<6.3.0.0^4,8>undecane 
• 71596-72-0 β-epiisocomene 
• 71596-71-9 C₂₁H₂₉NO₂Se 
• 87372-25-6 (4β,8α)-1α,4β-Dimethyl-9α-carbethoxy-2-methylenetricyclo<6.3.0.0^4,8>undecane 
• 325142-44-7 C₂₇H₃₃BrO₄ 
• 325142-42-5 C₂₂H₃₀BrNO₄ 
• 325142-43-6 C₂₀H₂₇BrO₄ 
• 325142-48-1 4-Nitro-benzoic acid (3S,3aS,5aS,8aS)-4-benzyloxymethyl-5a-methyl-3,3a,4,5,5a,6,7,8-octahydro-cyclopenta[c]pentalen-3-yl ester 
• 325142-45-8 C₂₅H₃₀O₃ 
• 325142-41-4 C₂₀H₂₆BrNO₃ 

Relevant articles and documents

PHLOROGLUCINOL DERIVATIVES AND OTHER CONSTITUENTS FROM SOUTH AFRICAN HELICHRYSUM SPECIES

Key Word Index - Helichrysum species; Compositae; phloroglucinol derivatives; chromanes; benzofuranes; α-pyrone derivatives; diterpenes; geranyl linalol derivatives; isocomene derivative. The investigation of 11 South African Helichrysum species afforded in addition to known compounds 26 further phloroglucinol derivatives, nine diterpenes, a derivative of isocomene and an α-pyrone derivative.The structures were elucidated by highfield NMR spectroscopy and a few chemical transformations.Furthermore the structures of several phloroglucinol derivatives were established by synthesis.The chemotaxonomy is discussed.

SESQUITERPENE HYDROCARBONS FROM THE ROOTS OF OTANTHUS MARITIMUS

Key Word Index - Otanthus maritimus; Anthemideae; Compositae; sesquiterpenes.

Molecular rearrangements of (-)-modhephene and (-)-isocomene to a (-)-triquinane

The preparation and further rearrangement of (-)-modhephene (1) to a (-)-triquinane 5 has been assessed through acid catalysis. The rearrangement involved protonation, 1,2 σ-bond and methyl shifts, and deprotonation. Monitored experiments by 1H NMR spectroscopy suggested the intermediate (-)-isocomene (3), which was further evidenced when a sample of natural (-)-3 undergoes acid-catalyzed conversion to the (-)-triquinane 5. In addition, deuterated (-)-modhephene (1-d) labeled stereospecifically at the 14β geminal methyl group at C4 was synthesized, through the corresponding chiral deuterated primary alcohol, in 5 steps, starting from natural (-)-14-hydroxymodhephene (8), and rearranged under acid catalysis to elucidate the stereochemical factors that control the methyl shift at this position. The final deuterium-labeled (-)-triquinane, 5-d, obtained from [14- 2H1]-1-d was established to have deuterium in the methyl group at C5 by 13C NMR spectroscopy. This stereoselective methyl migration is in accordance with the molecular orbital demand formulated by the quantum chemical calculations performed in the present study.

Stereospecific Rearrangements in Tricyclopentanoid Sesquiterpenes: The Absolute Configuration of (-)-Isocomene, (-)-β-Isocomene, and (-)-Silphinene

The determination of the absolute configuration of (-)-isocomene ((-)-9), (-)-β-isocomene ((-)-3), and (-)-silphinene ((-)-15) by correlation with (-)-modhephene ((-)-(3aR,4R,6aS)-4) via stereospecific rearrangements is described.