33669-76-0

Usage

InChI:InChI=1/C10H20O2/c1-7(2)8-4-5-10(3,12)9(11)6-8/h7-9,11-12H,4-6H2,1-3H3

Upstream product

• 13833-08-4 1-methyl-4-(1-methylethenyl)-cyclohexane-1,2-diol 
• 64-17-5 ethanol 
• 61585-35-1 p-menth-1-ene 
• 1946-00-5 (1RS,2SR,4RS)-p-menth-8-ene-1,2-diol 
• 851520-66-6 (3R)-3-isopropyl-6-methyl-7-oxabicyclo[4.1.0]heptane 
• 5989-27-5 D-limonene 
• 1195-31-9 (+)-p-menth-1-ene 
• 80845-80-3 (R)-(+)-1,2-diformyl-p-menthane 
• 138-86-3 limonene. 
• 1195-92-2 Limonene oxide 

Downstream Products

• 499-70-7 carvomenthone 
• 26238-82-4 3-isopropyl-6-oxo-heptanal 
• 499-70-7 methyl-2 isopropyl-5 cyclohexanone 
• 2102-60-5 (+/-)-3,5-dinitro-benzoic acid-(trans-p-menth-6-en-2-yl ester) 

Relevant academic research and scientific papers

Synthesis of puleganic amides via a catalytically efficient two-step approach

Puleganic amides display interesting insect-repellent properties. A new synthetic route to this type of amide was developed involving an organocatalytic cyclization and metal-catalyzed hydrogenation in a one-pot protocol. An eco-friendly oxidative amination provided the puleganic amides with only one purification step and acceptable yields.

Synthesis and Chiroptical Properties of Some Piperidin-2-ones

The synthesis of optically pure (R)-(+)-4-isopropylpiperidin-2-one, (R)-(+)-4-isopropyl-4-methylpiperidin-2-one, and (R)-(+)-5-methylpiperidin-2-one in high yields from monocyclic terpene precursors are described.The CD spectra of these compounds are reported, and the chiroptical properties of δ-lactams are examined in terms of current theories for the amide chromophore.It is concluded that slight, conformationally induced nonplanarity of the amide chromophore is responsible for signs of the longest wavelenght bands in the CD spectra of these and related compounds.

Spiroannelation via Intramolecular Ketocarbenoid Addition. Stereocontrolled Synthesis of (-)-Acorenone B and (+/-)-α-Chamigrene

The spirobicyclic structures of (+/-)-α-chamigrene (7) and (-)-acorenone B (6) were synthesized by means of a copper-catalyzed, intramolecular cycloaddition of diazo ketones 25 and 47, respectively.The former was prepared from 4-methyl-4-(p-methoxyphenyl)pentanoic acid (8) and the latter was obtained in optically active form from (R)-(+)-limonene (35).Reduction of 26 with lithium in ammonia gave 27, which was transformed to (+/-)-α-chamigrene (7) via olefin 30 and carbinol 32.The tricyclic ketone 53, from 47, was converted via olefin 55 to spiroketone 56.Interoduction of the conjugated olefin afforded (-)-acorenone B (6).Alternatively, 53 was reduced with lithium in ammonia to 54 and this, through a parallel sequence, was taken to (-)-4-epiacorenone B (67).