5956-05-8

Basic information

• Product Name: Acorenone
• Synonyms: (1S,4S,5S)-1-Isopropyl-4,8-dimethylspiro[4.5]deca-8-ene-7-one;Acorenone;(1S,4S,5S)-1,8-Dimethyl-4-isopropylspiro[4.5]dec-8-en-7-one
• CAS NO: 5956-05-8
• Molecular Formula: C15H26O
• Molecular Weight: 0
• Mol File: 5956-05-8.mol
• Article Data: 7

Chemical Properties

• Appearance: /
• CAS DataBase Reference: Acorenone(CAS DataBase Reference)
• NIST Chemistry Reference: Acorenone(5956-05-8)
• EPA Substance Registry System: Acorenone(5956-05-8)

Safety Data

• Hazardous Substances Data: 5956-05-8(Hazardous Substances Data)

Upstream product

• 917-54-4 methyllithium 
• 78-94-4 methyl vinyl ketone 
• 66289-26-7 α-1-Methyl-2-formyl-3-isopropylcyclopentan 
• 58649-46-0 (1R,4S,5S)-1-Isopropyl-4,10,10-trimethyl-8,12-dioxa-dispiro[4.1.5.3]pentadecane 
• 56326-39-7 Spiro-<4,5>-decanon (trans) 
• 6784-16-3 5-methyl-2-isopropylidenecyclopentanone 
• 58649-47-1 2-Isopropyl-5-methyl-1-(3-methyl-pent-4-enyl)-cyclopentanol 
• 6784-18-5 2-isopropyl-5-methylcyclopentanone 
• 51174-45-9 5-chloro-3-methylpent-1-ene 
• 51174-44-8 3-methyl-4-penten-1-ol 
• 56326-41-1 Spiro-<4,5>-decenon (trans) 
• 74-88-4 methyl iodide 
• 39510-28-6 Acetic acid (1S,4R,5R)-1-isopropyl-4,8-dimethyl-spiro[4.5]dec-7-en-7-yl ester 
• 5956-05-8 racem. 4-Epi-acorenon-B 

Downstream Products

• 5956-05-8 4-epi-acorenone 

Relevant articles and documents

Studies on metabolites of mycoparasitic fungi. III. New sesquiterpene alcohol from Trichoderma koningii

A new sesquiterpene alcohol, named tricho-acorenol (1), was isolated from the culture broth of Trichoderma koningii OUDEMANS along with methyl benzoate (2), cyclonerodiol (3), cyclo-(L-Pro-L-Leu) (4), 4-hydroxyphenethyl alcohol (5), uracil (7), and a ceramide (6). The ceramide (6) was identified as (2S,3S,4R)-2-[(2R)-2-hydroxytetracosanoylamino]-1,3,4-octadecanetriol by the use of ion-spray ionization MS (ISI-MS) and comparison of the optical rotation and the 1H-NMR data with those of (2S,3S,4R)-2-[(2R)-2-hydroxytetracosanoylamino]-1,3,4-hexadecanetriol. The structure of tricho-acorenol was elucidated to be (1S,4S,5S,7R)-1-isopropyl-4,8-dimethyl-spiro-[4.5]dec-8-en-7-ol on the basis of chemical and spectroscopic evidence.

Synthetic Studies on Acorane-Alaskane Sesquiterpenes. II. Total Synthesis of (+/-)-Acorenone

The metal-ammonia reduction of the cyclopentabenzofuran derivative (2b) afforded a mixture of 4-epi-β-acorenol (5), a disubstituted olefin (8) as the main product, and a perhydro compound (9).Compound 8 was converted to 5 via the exo-diene (15).Dehydration of 5 afforded the 4-epi-β-acoradiene (6), selective reduction of which gave the monoolefin (7), and then the allylic oxidation of 7 gave (+/-)-acorenone (3) in good yield.Keywords - acorane-alaskane sesquiterpene; acorenone; cyclopentabenzofuran; total synthesis; 4-epi-β-acorenol; 4-epi-α-acorenol; 4-epi-β-acoradiene; metal-ammonia reduction; conjugate reduction; terminal olefin reduction.

Novel Cyclopentabenzofuran Intermediates for the Synthesis of Acorane-Alaskane Sesquiterpenes: Total Synthesis of (+/-)-β-Acorenol and (+/-)-Acorenone

Cyclopentabenzofuran derivatives (5a) and (5b) were synthesized from spirodienone esters (6a) and (6b), respectively, and the utility of these intermediates in acorane-alaskane sesquiterpene synthesis is illustrated by their conversion into (+/-)-β-acorenol (4a) and (+/-)-acorenone (1).