55012-72-1

Basic information

• Product Name: 5-Hydroxycalamenene
• Synonyms: 5,6,7,8-Tetrahydro-2,5-dimethyl-8-(1-methylethyl)-1-naphthalenol;5-Hydroxycalamenene
• CAS NO: 55012-72-1
• Molecular Formula: C15H22O
• Molecular Weight: 218.33
• Mol File: 55012-72-1.mol
• Article Data: 3

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 5-Hydroxycalamenene(CAS DataBase Reference)
• NIST Chemistry Reference: 5-Hydroxycalamenene(55012-72-1)
• EPA Substance Registry System: 5-Hydroxycalamenene(55012-72-1)

Safety Data

• Hazardous Substances Data: 55012-72-1(Hazardous Substances Data)

Upstream product

• 82054-01-1 3-(2-Methoxy-3-methyl-phenyl)-4-methyl-pent-3-enoic acid ethyl ester 
• 82054-00-0 (Z)-3-(2-Methoxy-3-methyl-phenyl)-4-methyl-pent-2-enoic acid ethyl ester 
• 82053-94-9 5-(2'-methoxy-3'-methylphenyl)-6-methylheptan-3-one 
• 82053-92-7 3-(2'-methoxy-3'-methylphenyl)-4-methylpentanoic acid 
• 82053-90-5 2'-methoxy-3'-methylisobutyrophenone 
• 82053-95-0 5-(2-Methoxy-3-methyl-phenyl)-6-methyl-heptan-3-ol 
• 82053-97-2 5-methoxycalamenene 
• 118304-45-3 1-hydroxy-8-isopropyl-5-methylnaphthalene-2-carbaldehyde 
• 128291-92-9 Toluene-4-sulfonic acid 3-(2-methoxy-3-methyl-phenyl)-4-methyl-pentyl ester 
• 128291-81-6 ethyl 2-cyano-3-(2-methoxy-3-methylphenyl)-4-methylpentanoate 
• 128291-82-7 2-carbamoyl-3-(2-methoxy-3-methylphenyl)-4-methylpentanoic acid 
• 128291-87-2 4-(2-methoxy-3-methylphenyl)-5-methylhexanoic acide 
• 128291-83-8 3-(2-methoxy-3-methylphenyl)-4-methylpentanamide 
• 82053-93-8 3-(2-methoxy-3-methylphenyl)-4-methylpentanoic acid 

Relevant articles and documents

Total synthesis of (±)-cis-5-hydroxycalamenene

A total synthesis of (±)-cis-5-hydroxycalamenene 1 has been achieved from tetralone 5, which in turn was prepared from 5-methoxy-α-tetralone 3. Grignard reaction of compound 5 with isopropylmagnesium chloride, followed by dehydration and aromatization, provided the substituted naphthalene 7 whose conversion to (±)-cis-5-hydroxycalamenene 1 was accomplished by demethylation, formylation, and hydrogenation. Copyright Taylor & Francis Group, LLC.

Studies in Terpenoids: Part LV - Synthesis of 5-Hydroxycalamenene, a Phenolic Sesquiterpene from Bazzania tricrenata

Fries rearrangement of o-cresyl isobutyrate (IV) gives the o-hydroxyketone (V).Dehydration and saponification of the Reformatsky reaction product of the methoxyketone (VI) with ethyl bromoacetate affords the unsaturated acid mixture (VII).The saturated aryl methylpentanoic acid (VIII) derived from VII is reacted with ethyllithium to give the ketone (IX).The secondary alcohol (X) obtained from IX is cyclodehydrated and demethylated in one step to give 5-hydroxycalamenene (I) which is produced stepwise also from X via the methoxytetralin (XI) obtained by PPA treatment.