71629-00-0

Basic information

• Product Name: (1R,3aS,5aS)-1,3a,4,5a-tetramethyl-1,2,3,3a,5a,6,7,8-octahydrocyclopenta[c]pentalene
• CAS NO: 71629-00-0
• Molecular Formula: C₁₅H₂₄
• Molecular Weight: 204.3511
• Mol File: 71629-00-0.mol

Chemical Properties

• Boiling Point: 254.9°C at 760 mmHg
• Flash Point: 104.8°C
• Density: 0.95g/cm³
• Vapor Pressure: 0.0269mmHg at 25°C
• Refractive Index: 1.517
• CAS DataBase Reference: (1R,3aS,5aS)-1,3a,4,5a-tetramethyl-1,2,3,3a,5a,6,7,8-octahydrocyclopenta[c]pentalene(CAS DataBase Reference)
• NIST Chemistry Reference: (1R,3aS,5aS)-1,3a,4,5a-tetramethyl-1,2,3,3a,5a,6,7,8-octahydrocyclopenta[c]pentalene(71629-00-0)
• EPA Substance Registry System: (1R,3aS,5aS)-1,3a,4,5a-tetramethyl-1,2,3,3a,5a,6,7,8-octahydrocyclopenta[c]pentalene(71629-00-0)

Safety Data

• Hazardous Substances Data: 71629-00-0(Hazardous Substances Data)

Upstream product

• 325142-49-2 (3S,3aS,5aS,8aS)-4-Benzyloxymethyl-5a-methyl-3,3a,4,5,5a,6,7,8-octahydro-cyclopenta[c]pentalen-3-ol 
• 325142-51-6 4-benzyloxymethyl-3a,5a-dimethyl-4,5,5a,6,7,8-hexahydro-3aH-cyclopenta[c]pentalen-3-one 
• 87372-25-6 (4β,8α)-1α,4β-Dimethyl-9α-carbethoxy-2-methylenetricyclo<6.3.0.0^4,8>undecane 
• 87372-25-6 (4β,8α)-1α,4β-Dimethyl-9β-carbethoxy-2-methylenetricyclo<6.3.0.0^4,8>undecane 
• 71596-72-0 β-epiisocomene 
• 71596-72-0 1,3a,5a-trimethyl-4-methylenedecahydrocyclopenta[c]pentalene 
• 122437-20-1 (5R*,6S*,7S*)-6,7,11,11-tetramethyldispiro<3.0.4.2>undecan-6-ol 
• 72535-12-7 2α,6α,8β-trimethyl-5-methylenetricyclo<6.3.0.0^1,6>undecane 
• 82095-77-0 dehydroisocomene 
• 71718-87-1 1,3,4,7-tetramethyltricyclo<6.3.0.0^4,8>undec-2-en-5-one 
• 76192-89-7 (3α,4α,7α,8aβ)-4,7,8a-trimethyl-2,3,4,5,6,7,8,8a-octahydro-1H-3a,7-methanoazulene-9-one 
• 60416-01-5 3,6a-dimethyl-4,5,6,6a-tetrahydropentalen-2(1H)-one 
• 20643-20-3 3-ethoxy-2-methyl-2-cyclohexen-1-one 
• 84559-11-5 C₁₉H₃₅N₂O₂P 

Relevant articles and documents

Stereocontrolled Total Synthesis of (+/-)-Isocomene and (+/-)-β-Isocomene via Ring Enlargement

A total synthesis of (+/-)-isocomene (1) and (+/-)-β-isocomene (2) employing a chelation-controlled regioselective epoxide-carbonyl rearrangement as the key step has been realized.

Stereoselective total synthesis of the sesquiterpene (±)-β- isocomene

Application of the Lewis acid mediated [3+2] cycloaddition of allyl-tert-butyldiphenylsilane combined with a modified Fleming-Tamao oxidation provides a stereoselective route to the triquinane sesquiterpene (±)-β-isocomene. Georg Thieme Verlag Stuttgart.

Organosilicon-mediated total synthesis of the triquinane sesquiterpenes (±)-β-isocomene and (±)-isocomene

We describe an efficient total synthesis of the sesquiterpenes (±)-β-isocomene and (±)-isocomene using a Lewis acid-promoted [3 + 2] cycloaddition of allyl-tert-butyldiphenylsilane as the key-step.

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.

Sesquiterpene constituents in Petasites hybridus

The essential oil of the rhizomes of Petasites hybridus (Asteraceae) was investigated by gas chromatography, mass spectrometry, 1- and 2-dimensional NMR techniques and chemical correlations. Two new sesquiterpene hydrocarbons, petasitene and pethybrene, c

Enantio- and diastereocontrolled synthesis of an angular triquinane sesquiterpene (+)-arnicenone.

[figure: see text] (+)-Arnicenone, a sesquiterpene of an angular triquinane isolated from Arnica plants, has been synthesized for the first time in an enantiocontrolled manner from a synthetic equivalent of chiral 2-hydroxymethylcyclopentadienone to deter

Intramolecular cationic [5 + 2] cycloaddition reactions promoted by trimethylsilyl triflate in 3.0 M lithium perchlorate-ethyl acetate: Application to a formal total synthesis of (±)-isocomene

Trimethylsilyl triflate is an effective reagent in 3.0 M lithium perchlorate-ethyl acetate for promoting intramolecular cationic [5 + 2] cycloaddition reactions. A formal total synthesis of the angular triquinane isocomene (10) is detailed. Cationic [5 + 2] cycloaddition of quinone monoketal 40 gives rise to tricyclic diketone 35 which is subsequently converted into the known tricyclic ketone 33. Addition of methyl lithium followed by acid-catalyzed rearrangement employing the Pirrung protocol affords (±)-isocomene (10).

Synthesis of tricyclopentanoid sesquiterpenes via rearrangement routes: (±)-modhephene, (±)-epimodhephene and (±)-isocomene

Based on model studies with dispiroundecane 10, dispiroundecane 1 has been synthesized and rearranged to (±)-modhephene 6 and (±)-isocomene 7. The epimeric dispiroundecane 9 yields (±)-epimodhephene 12. A total of thirteen rearrangement products (6, 7, 12, 37, 38, 39, 42, 44, 55, 57, 64, 67) have been isolated from 1 and/or 9, including six unnatural triquinanes. Two of these (55, 57) are formed by unusual 1,3- and 1,4-shifts, respectively. A mechanistic rationale on the basis of force field calculations is given.

Stereocontrolled Synthesis of Isocomene by a Novel Photocycloaddition-Fragmentation Strategy

Isocomene has been synthesized in a stereocontrolled manner by a novel strategy that utilizes a Paterno-Buechi reaction to build complexity and a selective reductive fragmentation to reveal a functionalized diquinane.

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.