529-01-1

Basic information

• Product Name: isopiperitenone
• Synonyms: isopiperitenone;1-Methyl-4-isopropenylcyclohexen-3-one;2-Isopropenyl-5-methyl-5-cyclohexene-1-one;3-Methyl-6-(1-methylethenyl)-2-cyclohexen-1-one;3-Methyl-6-isopropenyl-2-cyclohexene-1-one;p-Mentha-1,8-diene-3-one;(S)-3-Methyl-6-isopropenyl-2-cyclohexen-1-one
• CAS NO: 529-01-1
• Molecular Formula: C₁₀H₁₄O
• Molecular Weight: 150.22
• Mol File: 529-01-1.mol

Chemical Properties

• Boiling Point: 228.9°Cat760mmHg
• Flash Point: 91.1°C
• Appearance: /
• Density: 0.94g/cm³
• Vapor Pressure: 0.0715mmHg at 25°C
• Refractive Index: 1.481
• CAS DataBase Reference: isopiperitenone(CAS DataBase Reference)
• NIST Chemistry Reference: isopiperitenone(529-01-1)
• EPA Substance Registry System: isopiperitenone(529-01-1)

Safety Data

• Hazardous Substances Data: 529-01-1(Hazardous Substances Data)

Usage

InChI:InChI=1/C10H14O/c1-7(2)9-5-4-8(3)6-10(9)11/h6,9H,1,4-5H2,2-3H3/t9-/m0/s1

Upstream product

• 491-05-4 (+)-cis/trans-p-mentha-2,8-dien-1-ol 
• 16750-87-1 (+/-)-filifolon 
• 101221-23-2 1,3,3-trimethyl-2-oxabicyclo<2.2.2>octan-5-one 
• 107514-23-8 7,7-dimethyl-2-methylenebicyclo<3.1.1>heptan-6-one 
• 138-86-3 limonene. 
• 1193-18-6 3-methylcyclohexen-2-one 
• 93176-47-7 1-[4-Methyl-2-(2-phenylselanyl-ethoxy)-cyclohex-3-enyl]-ethanone 
• 5392-40-5 (E/Z)-3,7-dimethyl-2,6-octadienal 
• 5989-27-5 D-limonene 
• 67969-82-8 tetrafluoroboric acid diethyl ether 
• 75197-50-1 C₅H₅Fe(CO)2(CHCH₃CHOC₂H₅)⁽¹⁺⁾*BF₄^(1-) 
• 78070-27-6 lithium cyclohexadienolate 
• 78-79-5 isoprene 
• 58193-39-8 8-chloro-2,6-dimethyl-octa-2,6-dien-4-one 

Downstream Products

• 491-09-8 3-terpinolenone 
• 832721-63-8 2-isopropenyl-5,5-dimethyl-cyclohexanone 
• 51911-80-9 4-isopropyl-1-methyl-3-methylenecyclohexene 

Relevant articles and documents

PROCESS AND COMPOUNDS FOR PREPARATION OF CANNABINOIDS

The invention involves condensation of various derivatives of cyclic alkene alcohols of Formula (II) or Formula (III) where, R1 is alkyl, aryl, alkyl aryl or heterocyclic carbamoyl. R2 is either R1 as mentioned earlier or an acyl group, -C(=O)-R3 where, R3 is selected from a group comprising (subst)C1-C12 alkyl, (subst)aryl, alkyl aryl with olivetol to get (-)-trans-?9-tetrahydrocannabinol (also known as Dronabinol, Formula (I)). The process disclosed provides high purity of dronabinol at crude stage making it easy for purification.

Benzylic and allylic oxidations with bis(trifluoroacetoxyiodo)benzene and tert -butyl hydroperoxide

Oxidation of benzylic and allylic substrates with a bis(trifluoroacetoxyiodo)benzene/tert-butyl hydroperoxide system to the corresponding ,-unsaturated enones was investigated. The scope and reaction mechanism are discussed. Georg Thieme Verlag Stuttgart New York.

Allylic oxidations catalyzed by dirhodium caprolactamate via aqueous tert-butyl hydroperoxide: The role of the tert-butylperoxy radical

Dirhodium(II) caprolactamate exhibits optimal efficiency for the production of the tert-butylperoxy radical, which is a selective reagent for hydrogen atom abstraction. These oxidation reactions occur with aqueous tert-butyl hydroperoxide (TBHP) without rapid hydrolysis of the caprolactamate ligands on dirhodium. Allylic oxidations of enones yield the corresponding enedione in moderate to high yields, and applications include allylic oxidations of steroidal enones. Although methylene oxidation to a ketone is more effective, methyl oxidation to a carboxylic acid can also be achieved. The superior efficiency of dirhodium(II) caprolactamate as a catalyst for allylic oxidations by TBHP (mol % of catalyst, % conversion) is described in comparative studies with other metal catalysts that are also reported to be effective for allylic oxidations. That different catalysts produce essentially the same mixture of products with the same relative yields suggests that the catalyst is not involved in product-forming steps. Mechanistic implications arising from studies of allylic oxidation with enones provide new insights into factors that control product formation. A previously undisclosed disproportionation pathway, catalyzed by the tert-butoxy radical, of mixed peroxides for the formation of ketone products via allylic oxidation has been uncovered.

Allylic Oxidations Catalyzed by Dirhodium Catalysts under Aqueous Conditions

The present invention relates to compositions and methods for achieving the efficient allylic oxidation of organic molecules, especially olefins and steroids, under aqueous conditions. The invention concerns the use of dirhodium (II,II) “paddlewheel complexes, and in particular, dirhodium carboximate and tert-butyl hydroperoxide as catalysts for the reaction. The use of aqueous conditions is particularly advantageous in the allylic oxidation of 7-keto steroids, which could not be effectively oxidized using anhydrous methods, and in extending allylic oxidation to enamides and enol ethers.

Compounds, Compositions and methods for insect control

Rapidly acting compositions having vapor phase insecticidal activity comprise natural products or natural product-based materials. Further, these materials are non-petroleum based, are typically 100% biodegradable, and typically do not persist in the environment, unlike traditional pesticides. The compositions kill susceptible insects on contact in seconds, even the notoriously hardy peripleneta species. The compositions also kill insects behind cracks and crevices and when sprayed onto absorbent surfaces such as wood and plasterboard, where traditional contact insecticides work poorly or not at all. New methods of testing insecticides can be used to quantify these effects.

Oxoammonium resins as metal-free, highly reactive, versatile polymeric oxidation reagents

Polymer-supported oxidation of alcohols was conducted very efficiently by employing oxoammonium salts, the reactive intermediates in TEMPO oxidations (TEMPO = 2,2,6,6-tetramethylpiperidinoxyl). These highly reactive salts (see scheme; X = Br, C1) could be prepared and isolated on the polymeric support, and were used for the conversion of single compounds as well as of complex mixtures of alcohols.

Synthesis of dioxochromium(VI) complexes, potential oxidation catalysts

Some new chromium(VI) complexes have been synthesised using a number of tridentate and tetradentate ligands.Catalytic behaviour of one representative dioxochromium complex has been investigated in various oxidation reactions using 70percent t-butylhydroperoxide as oxidant.

Cetyltrimethylammonium chlorochromate (CTACC)-t-butyl hydroperoxide (TBHP): A convenient oxidation reagent

An efficient chromium (VI) catalyst cetyltrimethylammonium chlorochromate (CTACC) in combination with t-butyl hydroperoxide (TBHP) effects excellently the epoxidation of olefins, oxidation of secondary alcohols to carbonyl compounds and various allylic and benzylic oxidations.Some successful stoichiometric oxidations of olefins have been studied.

TOTAL SYNTHESIS OF VARIOUS ELEMANOLIDES

Starting with a suitable substituted divinyl cyclohexanone, eleven naturally occurring 12.8-elemanolides bearing exo-methylene or methyl groups at C-11 and differing in substitution as well as in relative configuration, have been synthesized in racemic form.An approach to elemanolides with additional oxygen functionalities is principally possible by modification of the basic concept.Methods for the oxidative generation of terpenoid exo-methylene lactone and furan units are exemplified by synthesis of menthofuran and the p-menthenolides from isopulegols.