5732-81-0

Basic information

• Product Name: hexahydro-6,6,6a-trimethyl-2H-cyclopenta[b]furan-2-one
• Synonyms: hexahydro-6,6,6a-trimethyl-2H-cyclopenta[b]furan-2-one;3,3a,4,5,6,6a-Hexahydro-6,6,6a-trimethyl-2H-cyclopenta[b]furan-2-one
• CAS NO: 5732-81-0
• Molecular Formula: C₁₀H₁₆O₂
• Molecular Weight: 168.23284
• EINECS: 227-240-0
• Mol File: 5732-81-0.mol

Chemical Properties

• Boiling Point: 242.1°C at 760 mmHg
• Flash Point: 93.4°C
• Appearance: /
• Density: 1.027g/cm³
• Vapor Pressure: 0.0347mmHg at 25°C
• Refractive Index: 1.474
• CAS DataBase Reference: hexahydro-6,6,6a-trimethyl-2H-cyclopenta[b]furan-2-one(CAS DataBase Reference)
• NIST Chemistry Reference: hexahydro-6,6,6a-trimethyl-2H-cyclopenta[b]furan-2-one(5732-81-0)
• EPA Substance Registry System: hexahydro-6,6,6a-trimethyl-2H-cyclopenta[b]furan-2-one(5732-81-0)

Safety Data

• Hazardous Substances Data: 5732-81-0(Hazardous Substances Data)

Usage

InChI:InChI=1/C10H16O2/c1-9(2)5-4-7-6-8(11)12-10(7,9)3/h7H,4-6H2,1-3H3

Upstream product

• 1126-91-6 1,8,8-trimethyl-2-oxabicyclo[3.2.1]octan-3-one 
• 13559-66-5 (+/-)-camphor oxime 
• 736109-58-3 1,7,7-trimethyl-bicyclo[2.2.1]heptan-2-one 
• 1727-75-9 (2,3,3-trimethyl-cyclopent-1-enyl)-acetic acid 
• 25435-53-4 (2,2,3-Trimethyl-cyclopent-3-enyl)-acetic acid 
• 1727-76-0 β-campholenonitrile 

Downstream Products

• 73090-03-6 1-<(2,3,3-Trimethyl-2-hydroxycyclopentyl)methyl>cyclohexanol 
• 2565-75-5 1-(toluene-4-sulfonyloxy)-2-(2,3,3-trimethyl-cyclopent-1-enyl)-ethane 

Relevant articles and documents

Synthesis and Reactions of β-Camphole Compounds

In contrast to the well known α-campholenic (B) and fencholenic compounds (C) little is known about β-campholenic derivatives (A) because of their difficult accessibility. β-Campholenic compounds (A) can be obtained: (1) by Baeyer-Villiger oxidation of camphor via lactone 7 and β-dihydrocampholenic lactone (5); (2) by Beckmann fragmentation of camphor oxime via α-(2) and β-campholenic nitril (3) and the lactone 5; and (3) by acid catalysed rearrangement of α-campholenic derivatives (B, 17a, b).The β-analogous brahmanol (14) can be synthesized by the reaction of the β-campholenic bromide (11) with methyl diethyl malonate or by r earrangement of brahmanol.

Selective anodic oxidation of camphor

Camphor (1) was anodically oxidized at Pb/PbO2 and Pt in 1M H2SO4 (50 Vol.% MeCN). 1,2-campholide (4) as the main product was obtained with material yields up to 96% and current efficiencies up to 39% at the PbO2 anode. The most important side products were oxygen and 1,8,8-trimethyl-2-oxa-bicyclo[3.3.0]octan-3-one (5). A quantitative conversion of 4 to 5 is possible in strong acids. The effects of current densities and concentrations were studied in detail.

INSECT GROWTH REGULATORS. PART XV. SYNTHESES OF JUVENOIDS WITH THE 2,3,3-TRIMETHYL-1-CYCLOPENTENE SYSTEM

New analogs of insect juvenile hormone were obtained by a multi-step synthesis starting from β-campholenenitrile (2).The Grignard reaction and the Claisen rearrangement by the orthoacetate method were applied for building and elongating an aliphatic chain.All compounds obtained are characterized by the presence of trans-disubstituted double bonds in the β-position in relation to the cyclopentane ring.

One-Step Annelation. A Convenient Method for the Preparation of Diols, Spirolactones, and Spiroethers from Lactones

1-(ω-Hydroxyalkyl)cyclopentanols and -cyclohexanols were prepared in one step in high yields from butane-1,4-diyl- and pentane-1,5-diylmagnesium dibromides and lactones in tetrahydrofuran.This method was found to be general and applicable to lactones of any size (β, γ, δ, and ε) and structure whether aliphatic, aromatic, bicyclic, or spirocyclic.Evidently important steric hindrance close to the carbonyl group prevents annelation and attack on the second nucleophilic center of the Grignard reagent.Furthermore, in the case of oxetan-2-one one obtains, in additionto the corresponding diol, products resulting from scission of the C-O bond.The diols by appropriate transformation afford new routes to spirolactones and spiroethers.