22339-23-7

Usage

Synthesis Reference(s)

The Journal of Organic Chemistry, 45, p. 2006, 1980 DOI: 10.1021/jo01298a053Tetrahedron Letters, 13, p. 903, 1972

InChI:InChI=1/C15H22/c1-10(2)13-8-6-12(4)14-7-5-11(3)9-15(13)14/h5,7,9-10,12-13H,6,8H2,1-4H3

Upstream product

• 97329-91-4 (8R,8aS)-5-Isopropyl-3,8-dimethyl-6,7,8,8a-tetrahydro-1H-naphthalen-2-one 
• 144786-61-8 cis-menthonetosylhydrazone 
• 1196-31-2 (1R,4R)-(+)-isomenthone 
• 178900-42-0 (+)-cis-8-hydroxycalamenene 
• 861650-40-0 (5R,8R)-4-Hydroxy-8-isopropyl-5-methyl-5,6,7,8-tetrahydro-naphthalene-2-carboxylic acid methyl ester 
• 874657-05-3 2,15-dihydroxycalamenene 
• 97182-95-1 (1S,4R)-1-Isopropyl-4,7-dimethyl-5-methylsulfanyl-1,2,3,4-tetrahydro-naphthalene 
• 96517-04-3 (8R,8aS)-5-Isopropyl-3,8-dimethyl-1,2,6,7,8,8a-hexahydro-naphthalen-2-ol 
• 861650-18-2 (3R,6R)-6-Isopropyl-3-methyl-cyclohex-1-enecarbaldehyde 

Downstream Products

• 87018-28-8 cadalenequinone mono 2,4-dinitrophenylhydrazone 

Relevant academic research and scientific papers

Sesquiterpene constituents of the liverwort Bazzania trilobata

The sesquiterpene constituents of the liverwort Bazzania trilobata (L.) Gray were investigated. In addition to many known compounds two new sesquiterpene hydrocarbons, (-)-cis-cadina-1(6),4-diene and (+)-trans-dauca- 4(11),8-diene, could be isolated and identified. The structure elucidation was carried out by NMR spectroscopic techniques and chemical conversions.

Aromatic annulation on the p-menthane monoterpenes: Enantiospecific synthesis of the trans and cis isomers of calamenene and 8-hydroxycalamenene

A new enantiospecific route to sesquiterpenes of the calamenene family is described. The synthetic pathway starts from easily available 3-oxygenated-p-menthane monoterpenes and affords the title compounds by a homologation-benzannulation sequence. The trans and cis isomers of the natural compounds calamenene and 8-hydroxycalamenene were obtained in enantiopure form starting from (-)-menthone and (+)-isomenthone, respectively.

Sesquiterpene constituents of the liverwort Calypogeia fissa

Four new sesquiterpenes have been identified as constituents of the liverwort Calypogeia fissa: (+)-10β(H)-muurola-3,7(11)-dien-1-ol, (-)-α- alasken-6β-ol, (-)-α-alasken-8-one and 7,8-dehydro-α-acoradiene. (+)- Cadina-1(10),3,7(11)-triene and (+)-cis-cadina-4,6-dien-11-ol were obtained as reaction products from (+)-10β(H)-muurola-3,7(11)-dien-1-ol.

New Cadinene and Bisabolene Derivatives from the Essential Oil of Pulicaria gnaphalodes

From the essential oil of Pulicaria gnaphalodes growing near Tehran some new cadinene derivatives were isolated.The structures of 1,8-oxidocadin-4-enes (6, 7, epimers at C-10), 1(10),4-cadinadien-8α-ol (1), 4,10(14)-cadinadien- and 4, 10(14)-muuroldaien-8-ols (2-5) could be verified by their 1H- and 13C-NMR spectra.Furthermore, the 8α-epimer 9 of the known α-copaen-8β-ol (10), (Z)-γ-curcumen-12-ol (13a) and the esters (Z)-13b-e could be identified.Key Words: Pulicaria gnaphalodes / Compositae / 1,8-Oxidocadin-4-ene / Cadinadien-8-ols / α-Copaen-8-ol / γ-Curcumen-12-ol

ABSOLUTE STEREOCHEMISTRY OF THE CADINENES FROM EUPATORIUM TRAPEZOIDEUM

Chemical examination of Eupatorium trapezoideum has furnished five cadinenes 1a, 2a, 2b, 4a and 5 and a degraded cadinene 3a whose stereostructures are presented in this paper.The absolute stereochemistry of the major component 1a has been determined by application of Horeau's method as well as chemical correlation studies and has been confirmed by X-ray analysis of 1f thus suggesting that it belongs to the amorphane group.

SYNTHESIS OF ARYL METHYLTHIO ETHERS EMPLOYING α-OXOKETENE DITHIOACETALS

Reaction of α-oxoketene dithioacetals with methallyl magnesium chloride followed by acid treatment affords simple and annulated aryl methylthio ethers.The methylthio substituent can be easily removed with Raney Ni, undergo a Ni catalyzed substitution reac