73925-68-5

Basic information

• Product Name: (-)-(4R,5S,6S)-4,5-Epoxy-4,5-dihydro-α-ionon
• Synonyms: (-)-(4R,5S,6S)-4,5-Epoxy-4,5-dihydro-α-ionon
• CAS NO: 73925-68-5
• Molecular Weight: 208.301
• Mol File: 73925-68-5.mol
• Article Data: 10

Chemical Properties

• CAS DataBase Reference: (-)-(4R,5S,6S)-4,5-Epoxy-4,5-dihydro-α-ionon(CAS DataBase Reference)
• NIST Chemistry Reference: (-)-(4R,5S,6S)-4,5-Epoxy-4,5-dihydro-α-ionon(73925-68-5)
• EPA Substance Registry System: (-)-(4R,5S,6S)-4,5-Epoxy-4,5-dihydro-α-ionon(73925-68-5)

Safety Data

• Hazardous Substances Data: 73925-68-5(Hazardous Substances Data)

Upstream product

• 127-41-3 alpha-ionone 
• 190059-33-7 (E)-4-(1,3,3-Trimethyl-7-oxa-bicyclo[4.1.0]hept-2-yl)-but-3-en-2-one 
• 14398-36-8 (3E)-4-[(S)-2,6,6-trimethylcyclohex-2-enyl]but-3-en-2-one 

Downstream Products

• 14398-36-8 (3E)-4-[(S)-2,6,6-trimethylcyclohex-2-enyl]but-3-en-2-one 
• 55955-46-9 (+/-)-4t-(2c-hydroxy-2t,6,6-trimethyl-cyclohex-r-yl)-but-3-en-2-one 
• 112379-22-3 4-<3-(1-Methoxy-2-bromoethoxy)-2,6,6-trimethylcyclohex-1-yl>-2-butanone 
• 112379-22-3 4-<3-(1-Methoxy-2-bromoethoxy)-2,6,6-trimethylcyclohex-1-yl>-2-butanone 
• 112379-29-0 4-(3-Ethenoxy-2,6,6-trimethylcyclohexen-1-yl)-2-butanone 
• 112893-58-0 4-<3-(1-Ethoxy-2-bromoethoxy)-2,6,6-trimethylcyclohexen-1-yl>-but-3-en-2-one 
• 112893-56-8 4-<3-(1-Ethoxy-2-bromoethoxy)-2,6,6-trimethyl-cyclohexen-1-yl>-2-butanone 
• 108886-20-0 Camphansaeure-<2-hydroxy-2,4,4-trimethyl-3-(3-oxobut-1-enyl)cyclohexyl>ester 
• 73925-69-6 (-)-(1'S)-2',3'-dihydro-2'-hydroxy-α-ionone 
• 73892-47-4 (+)-(R)-4-Acetoxy-β-ionon 

Relevant articles and documents

MnO2/TBHP: A Versatile and User-Friendly Combination of Reagents for the Oxidation of Allylic and Benzylic Methylene Functional Groups

In the presence of activated MnO2, tert-butyl hydroperoxide (TBHP) in CH2Cl2 is able to oxidize the allylic and benzylic methylene groups of different classes of compounds. I describe a one-pot oxidation protocol based on two sequential steps. In the first step, carried out at low temperature, MnO2 catalyses the oxidation of the methylene group. This is followed by a second step where reaction temperature is increased, allowing MnO2 both to catalyse the decomposition of unreacted TBHP and to oxidize allylic alcohols that could possibly be formed. The proposed oxidation procedure is generally applicable, although its efficiency, regioselectivity, and chemoselectivity are strongly dependent on the structure of the substrate. A simple and user-friendly synthetic procedure for the oxidation of allylic and benzylic methylene groups to the corresponding conjugated carbonyl derivatives is described. The proposed oxidation protocol is based on the combined use of MnO2 and tert-butyl hydroperoxide, and is generally applicable.

Total Synthesis of (+)-Granatumine A and Related Bislactone Limonoid Alkaloids via a Pyran to Pyridine Interconversion

We report the first total synthesis of (+)-granatumine A, a limonoid alkaloid with PTP1B inhibitory activity, in ten steps. Over the course of this study, two key methodological advances were made: a cost-effective procedure for ketone α,β-dehydrogenation using allyl-Pd catalysis, and a Pd-catalyzed protocol to convert epoxyketones to 1,3-diketones. The central tetrasubstituted pyridine is formed by a convergent Knoevenagel condensation and carbonyl-selective electrocyclization cascade, which was followed by a direct transformation of a 2H-pyran to a pyridine. These studies have led to the structural revision of two members of this family.

Lipase-mediated synthesis of the enantiomeric forms of 4,5-epoxy4,5-dihydro-α-ionone, and 5,6-epoxy-5,6-dihydro-β-ionone. A new direct access to enantiopure (R)-, and (5)-α-ionone

Stereoselective lipase-mediated esterifications of epoxy-a-ionpl 5, and epoxy-ionol 9 afTorded suitable precursors of the enantiomers of the corresponding oxidised derivatives epoxy-u-ionone 3, and epoxy-ionone 4. An interesting development of this work is the easy conversion of enantiopure 3a, and 3b into highly valuable enantiopure (5)-, and (R)-ionone (1a, and Ib) via a mild deoxygenation reaction.