62065-26-3

Basic information

• Product Name: pentalenene
• Synonyms: pentalenene;(1S,8aS)-1,2,3,3aβ,5aα,6,7,8-Octahydro-1β,4,7,7-tetramethylcyclopenta[c]pentalene;(1S,8aS)-1β,4,7,7-Tetramethyl-1,2,3,3aβ,5aα,6,7,8-octahydrocyclopenta[c]pentalene;(1alpha,3Aalpha,5abeta,8ar*)-1,2,3,3A,5A,6,7,8-octahydro-1,4,7,7-tetramethylcyclopenta(C)pentalene
• CAS NO: 62065-26-3
• Molecular Formula: C15H24
• Molecular Weight: 204.35106
• Mol File: 62065-26-3.mol
• Article Data: 6

Chemical Properties

• Boiling Point: 262.5°C at 760 mmHg
• Flash Point: 110.2°C
• Appearance: /
• Density: 0.94g/cm³
• Vapor Pressure: 0.0177mmHg at 25°C
• Refractive Index: 1.515
• CAS DataBase Reference: pentalenene(CAS DataBase Reference)
• NIST Chemistry Reference: pentalenene(62065-26-3)
• EPA Substance Registry System: pentalenene(62065-26-3)

Safety Data

• Hazardous Substances Data: 62065-26-3(Hazardous Substances Data)

Usage

InChI:InChI=1/C15H24/c1-10-7-12-8-14(3,4)9-15(12)11(2)5-6-13(10)15/h7,11-13H,5-6,8-9H2,1-4H3/t11-,12-,13+,15-/m1/s1

Upstream product

• 17123-68-1 4,4-dimethylhept-6-en-2-one 
• 105230-70-4 7,7-dimethylbicyclo<3.3.0>-2-octen-3-one 
• 83110-20-7 (1S,2S,6S,8R,9R)-1,4,4-Trimethyl-12-oxa-tricyclo[7.2.1.0^2,6]dodecan-8-ol 
• 83110-21-8 (1S,2S,6S,8R,9R)-8-Bromo-1,4,4-trimethyl-12-oxa-tricyclo[7.2.1.0^2,6]dodecane 
• 83110-19-4 (1S,2S,6S,9R)-1,4,4-Trimethyl-12-oxa-tricyclo[7.2.1.0^2,6]dodecan-8-one 
• 69753-92-0 (1S,2S,6S,9R)-1,4,4-Trimethyl-8-methylene-12-oxa-tricyclo[7.2.1.0^2,6]dodecane 
• 83110-23-0 (Z)-(3aR,4R,9aS)-2,2,4-Trimethyl-2,3,3a,4,5,6,9,9a-octahydro-1H-cyclopentacycloocten-4-ol 
• 917-64-6 methyl magnesium iodide 
• 83110-27-4 2,10,10-Trimethyltricyclo<6.3.0.0^1.5>undecan-6-one 
• 372-97-4 farnesyl pyrophosphate 
• 1449248-38-7 C₁₅H₂₄O 
• 94904-15-1 (3aR,4S,5S,5aS,8R,8aS)-2,2,5,8-tetramethyldecahydrocyclopentapentalen-4-ol 
• 1449248-37-6 (E)-2,2,5-trimethyl-4-vinylidenenedec-8-enal 
• 1449248-40-1 (R,E)-2,2,5-trimethyl-4-vinylidenedec-8-en-1-ol 

Relevant articles and documents

Mechanistic Similarities of Sesquiterpene Cyclases PenA, Omp6/7, and BcBOT2 Are Unraveled by an Unnatural fPP-Ether Derivative

The sesquiterpene cyclases pentalenene synthase (PenA) and two Δ6-protoilludene synthases Omp6 and Omp7 convert a FPP ether into several new tetrahydrofurano terpenoids, one of which is also formed as the main product by the sesquiterpene cyclase BcBOT2. Thus, PenA, Omp6/7, and BcBOT2 follow closely related catalytic pathways and induce similar folding of their diphosphate substrates despite low levels of amino acid sequence similarity. Some of the new terpenoids show pronounced olfactoric properties.

An asymmetric total synthesis of (+)-pentalenene

A stereoselective total synthesis of (+)-pentalenene was achieved through the tandem cycloaddition reaction of the allenyl diazo substrate prepared from (+)-citronellal. The initial intramolecular [2+3] cycloaddition reaction between the diazo functionality and the allenyl group produced the trimethylenemethane (TMM) intermediate after immediate loss of nitrogen molecule from the cycloaddition intermediate. Subsequent [2+3] cycloaddition of the TMM with olefin produced the angularly fused triquinane structure stereoselectively.

Asymmetric Total Synthesis of (+)-Pentalenene via Chiral Sulfinylallyl Anions. Hydrolytic Ring Closure of Enol Thioether Ketones

-