17957-87-8

Basic information

• Product Name: (6R)-9-methyl-3-oxabicyclo[4.3.0]nonan-4-one
• Synonyms: (6R)-9-methyl-3-oxabicyclo[4.3.0]nonan-4-one;(4aR)-4,4aα,5,6,7,7aα-Hexahydro-7β-methylcyclopenta[c]pyran-3(1H)-one
• CAS NO: 17957-87-8
• Molecular Formula: C9H14O2
• Molecular Weight: 154.21
• Mol File: 17957-87-8.mol

Chemical Properties

• Boiling Point: 265.2°Cat760mmHg
• Flash Point: 105.1°C
• Appearance: /
• Density: 1.04g/cm³
• Vapor Pressure: 0.00926mmHg at 25°C
• Refractive Index: 1.47
• CAS DataBase Reference: (6R)-9-methyl-3-oxabicyclo[4.3.0]nonan-4-one(CAS DataBase Reference)
• NIST Chemistry Reference: (6R)-9-methyl-3-oxabicyclo[4.3.0]nonan-4-one(17957-87-8)
• EPA Substance Registry System: (6R)-9-methyl-3-oxabicyclo[4.3.0]nonan-4-one(17957-87-8)

Safety Data

• Hazardous Substances Data: 17957-87-8(Hazardous Substances Data)

Usage

Uses

Used in Organic Synthesis:
(6R)-9-methyl-3-oxabicyclo[4.3.0]nonan-4-one is used as an intermediate in the synthesis of various organic compounds. Its unique structure and reactivity make it a valuable building block for creating a wide range of molecules with different properties and applications.
Used as a Flavoring Agent:
In the food and beverage industry, (6R)-9-methyl-3-oxabicyclo[4.3.0]nonan-4-one is used as a flavoring agent. Its distinct chemical structure contributes to the development of specific flavors and scents, enhancing the overall sensory experience of various products.
Used in Medicinal Chemistry and Pharmaceutical Research:
(6R)-9-methyl-3-oxabicyclo[4.3.0]nonan-4-one holds potential in medicinal chemistry and pharmaceutical research. Its unique structure and reactivity make it a promising candidate for the development of new drugs and therapeutic agents. Researchers can leverage its properties to design and synthesize novel compounds with potential applications in treating various diseases and medical conditions.

InChI:InChI=1/C9H14O2/c1-6-2-3-7-4-9(10)11-5-8(6)7/h6-8H,2-5H2,1H3/t6-,7-,8-/m1/s1

Upstream product

• 158512-67-5 (7R,7aR)-7-Methyl-5,6,7,7a-tetrahydro-1H-cyclopenta[c]pyran-3-one 
• 92751-90-1 (1S,4aR,7S,7aS)-1-Hydroxy-7-methyl-1,4a,5,6,7,7a-hexahydro-cyclopenta[c]pyran-4-carboxylic acid 
• 89502-68-1 (4aS,7S,7aR)-7-Methyl-1,3,4,4a,7,7a-hexahydro-cyclopenta[c]pyran-3-ol 
• 77523-28-5 (4aS,4bS)-2b-Methyl-hexahydro-cyclopropa[cd]pentalen-2-one 
• 4166-63-6 1-methylbicyclo[2.2.2]oct-5-ene-2-one 
• 7424-85-3 ethyl 3-methyl-2-oxocyclopentanecarboxylate 
• 28839-89-6 (1S,2S,3S,6S,7R,9S)-9-Methyl-4-oxa-tricyclo[4.2.1.0^3,7]nonan-2-ol 
• 89502-66-9 (1R,4R,5S,6R)-5-Hydroxymethyl-6-methyl-bicyclo[2.2.1]heptan-2-one 
• 89502-74-9 (1R,3R,6R,7S,9R)-9-Methyl-4-oxa-tricyclo[4.2.1.0^3,7]nonan-2-one 
• 193467-10-6 ((1R,2S,3R,4S)-3-Dimethoxymethyl-bicyclo[2.2.1]hept-5-en-2-yl)-methanol 
• 193558-27-9 (1R,2R,3R,6R,7S,9S)-9-Benzyloxymethyl-4-oxa-tricyclo[4.2.1.0^3,7]nonan-2-ol 
• 193467-11-7 (1R,2R,3R,6S,7S,9S)-9-Dimethoxymethyl-4-oxa-tricyclo[4.2.1.0^3,7]nonan-2-ol 
• 96243-78-6 (1R,3R,6R,7S,9S)-9-Methyl-4-oxa-tricyclo[4.2.1.0^3,7]nonan-2-one 
• 89502-68-1 (4aS,7R,7aR)-7-Methyl-1,3,4,4a,7,7a-hexahydro-cyclopenta[c]pyran-3-ol 

Downstream Products

• 485-43-8 (+/-)-Isoiridomyrmecin 
• 485-43-8 (+/-)-iridomyrmecin 
• 485-43-8 isoiridomyrmecin, iridomyrmecin 
• 60419-55-8 (+/-)-teucriumlactone C 

Relevant articles and documents

Catalyst-controlled inverse-electron-demand hetero-Diels-Alder reactions in the enantio- and diastereoselective synthesis of iridoid natural products

(Matrix presented) Iridoid natural products 1-4 are accessed stereoselectively by means of tridentate (Schiff base)Cr(III)-catalyzed hetero-Diels-Alder reactions between ethyl vinyl ether and enantioenriched 5-methyl-1-cyclopentene-1-carboxaldehyde. An efficient route to the aldehyde from citronellal is afforded by the ring-closing metathesis reaction.

A Free-Radical and Protecting-Group-Free Approach to (-)-Boschnialactone and γ-Lycorane

The protecting-group-free (PGF) and free-radical-based synthesis of two structurally different natural products, (-)-boschnialactone and γ-lycorane, is reported. The key step in both syntheses is a radical-ionic sequence for construction of the principal structure (a six-membered lactone and a 1,4-dicarbonyl compound, respectively), allowing short and rapid access to these natural products through a PGF route.

Intramolecular Horner-Wadsworth-Emmons reaction in base sensitive substrates: Enantiospecific synthesis of iridoid monoterpene lactones

The cyclopentapyranones (-)-7 and (-)-13, representing the cis-fused 9- carbon core of iridoid lactones, are synthesised from (+)-pulegone.

Total syntheses of several iridolactones and the putative structure of noriridoid scholarein A: An intramolecular Pauson-Khand reaction based one-stop synthetic solution

A simple and general approach towards the total syntheses of several iridolactones such as (±)-boschnialactone, (±)-7-epi-boschnialactone, (±)-teucriumlactone, (±)-iridomyrmecin, (±)-isoboonein, (±)-7-epi-argyol, (±)-scabrol A, (±)-7-epi-scabrol A, and (±)-patriscabrol as well as the putative structure of scholarein A is delineated. The synthetic strategy features a diastereoselective intramolecular Pauson-Khand reaction (IPKR) to construct the iridoid framework followed by some strategic synthetic manipulations to access the targeted monoterpenes including those having diverse oxy-functionalization patterns and with 3-5 contiguous stereogenic centres in a highly stereocontrolled manner. Also, the present endeavour includes the first total synthesis of scabrol A.

Formal synthesis of (±)-hop ether, (±)-isoboonein, and (±)-iridomyrmecin

A general synthesis of (±)-hop ether (5), (±)-isoboonein (6), and (±)-iridomyrmecin (7) from bicyclo[2.2.1]ketone (9) is described. Cyclopentenoid aldehyde (10) and bicyclo[3.2.1]lactone (11) are the key intermediates.

A novel route to iridoids: Enantioselective syntheses of isoiridomyrmecin and α-skytanthine

Enantio- and diastereoselective syntheses of the iridoids (-)-isoiridomyrmecin and (+)-α-skytanthine from a common intermediate (6-bromo-3,3a,6,6a-tetrahydro-2H-cyclopenta[b]furan-2-one) were achieved. Key steps in both syntheses are conjugated nucleophilic substitutions (SN2′ anti-reactions) with C1 zinc cyanocu-prates.

Total synthesis of (±)-boschnialactone and (±)-tetrahydroanhydrodesoxyaucubigenin

A total synthesis of (±)-boschnialactone (1) and (±)-tertahydroanhydrodesoxyaucubigenin (2) is described and trisubstitued cyclopentenoid 3 is a key intermediate.

Preparation of a Promising Cyclobutanone Chiral Building Block: Its Stereochemistry and Utilization

A cyclobutanone possessing a bicyclo[2.2.1]heptene framework {endo-tricyclo[4.2.1.02,5]non-7-en-3-one} has been prepared in both enantiomeric forms employing lipase-mediated kinetic resolution as the key step. To determine the absolute configuration, as well as to demonstrate the synthetic potential, both enantiomers of the cyclobutanone obtained have been transformed enantioconvergently into the key intermediate of the sesquiterpene (+)-β-santalene and the iridoid monoterpene (-)-boschnialactone.

Total Synthesis of (±)-Patriscabrol and (±)-Boschnialactone

A total synthesis of (±)-patriscabrol (1) and (±)-boschnialactone (2) is described. The cyclopentapyranone skeleton is assembled by means of Baeyer-Villiger oxidation of ketol 5.

Syntheses of several cyclopentano-monoterpene lactones using 1,3-dioxin vinylogous ester

Formal syntheses of (±)-boschnialactone (5) and three cyclopentano-monoterpene lactones [i.e., (±)-(iridomyrmecin (6), (±)-isoiridomyrmecin (7), and (±)-allodolicholactone (8)] have been accomplished in the form of the syntheses of 2-(methoxymethyl)-3-methyl-2-cyclopenten-1-one (11) and (±)-(4aα,7α,7aα)-hexahydro-7-methylcyclopenta[c]pyran-3(1H)-one (19), respectively, starting from 6,7-dihyd;ocyclopenta-1,3-dioxin-5(4H)-one (2). A synthesis of (±)-isodehydroiridomyrmecin (9) has also been achieved through a route including direct substitution of the hydroxy group of 2-(tert-butyldimethylsilyloxymethyl)-3- methyl-2-cyclopenten-1-ol (22) with 1-(tert-butyldimethylsilyloxy)-1-methoxyethene (23) as a key step.