573-94-4

Basic information

• Product Name: (4S,4aβ,7aβ)-4β,7β-Dimethyloctahydrocyclopenta[c]pyran-3-one
• Synonyms: (4S)-4,4aβ,5,6,7,7aβ-Hexahydro-4β,7β-dimethylcyclopenta[c]pyran-3(1H)-one;(4S,4aβ,7aβ)-4β,7β-Dimethyloctahydrocyclopenta[c]pyran-3-one;Isoiridomyrmecin;Isoiridomyrmercin;Isoirridomyrmercin;Cyclopenta(C)pyran-3(1H)-one, hexahydro-4,7-dimethyl-, (4S-(4-alpha,4A-alpha,7-alpha,7A-alpha))-
• CAS NO: 573-94-4
• Molecular Formula: C10H16O2
• Molecular Weight: 168.234
• Mol File: 573-94-4.mol
• Article Data: 26

Chemical Properties

• Boiling Point: 270.5°Cat760mmHg
• Flash Point: 107.7°C
• Appearance: /
• Density: 1g/cm³
• Vapor Pressure: 0.0068mmHg at 25°C
• Refractive Index: 1.46
• CAS DataBase Reference: (4S,4aβ,7aβ)-4β,7β-Dimethyloctahydrocyclopenta[c]pyran-3-one(CAS DataBase Reference)
• NIST Chemistry Reference: (4S,4aβ,7aβ)-4β,7β-Dimethyloctahydrocyclopenta[c]pyran-3-one(573-94-4)
• EPA Substance Registry System: (4S,4aβ,7aβ)-4β,7β-Dimethyloctahydrocyclopenta[c]pyran-3-one(573-94-4)

Safety Data

• Hazardous Substances Data: 573-94-4(Hazardous Substances Data)

Usage

InChI:InChI=1/C10H16O2/c1-6-3-4-8-7(2)10(11)12-5-9(6)8/h6-9H,3-5H2,1-2H3/t6-,7+,8+,9+/m1/s1

Upstream product

• 107485-97-2 δ-iridodiol 
• 60419-55-8 (+)-teucriumlactone 
• 131726-13-1 (4aR,7S,7aR)-Hexahydro-7-methylcyclopenta[c]pyran-3-one 
• 74-88-4 methyl iodide 
• 261511-35-7 (2S)-[(1S,4S,5R)-4-Benzyloxymethyl-4-methylcyclopent-2-en-1-yl]propanoic acid 
• 883997-14-6 ethyl (4S,5S)-5,6-isopropylidene-4-methylhexanoate 
• 883997-13-5 ethyl (4S,5S,2E)-5,6-isopropylidene-4-methylhexanoate 
• 883997-25-9 methyl (2E,6S,7S)-7,8-dihydroxy-2,6-dimethyl-2-octenoate 
• 883997-27-1 methyl (2E,6S,7S)-8-tert-butyldimethylsiloxy-7-hydroxy-2,6-dimethyl-2-octenoate 
• 883997-32-8 methyl (2E,6S,7S)-8-tert-butyldimethylsiloxy-2,6-dimethyl-7-[(phenoxythiocarbonyl)oxy]-2-octenoate 
• 74243-88-2 (βS,4S)-β,2,3-trimethyl-1,3-dioxolane-4-ethanol 
• 144938-82-9 (1S,4R)-(+)-4-(Hydroxymethyl)cyclopent-2-enol 
• 261511-33-5 (3S,3aS,4R,6aS)-4-Benzyloxymethyl-3,3a,4,6a-tetrahydro-3-methylcyclopenta[b]furan-2-one 
• 261511-22-2 (1S)-cis-4-Benzyloxymethylcyclopent-2-en-1-ol 

Downstream Products

• 485-43-8 (+/-)-Isoiridomyrmecin 
• 485-43-8 isoiridomyrmecin 
• 485-43-8 iridomyrmecin 

Relevant articles and documents

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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.

Biorational synthesis of iridomyrmecin diastereomers from catnip oil

4S,4aS,7S,7aR; 4R,4aS,7S,7aR; 4S,4aS,7S,7aS, and 4R,4aS,7S,7aS diastereomers of iridomyrmecin have been prepared in 5 steps from 4aS,7S,7aR and 4aS,7S,7aS-nepetalactones, major components of catnip oil. 4S,4aS,7S,7aR and 4R,4aS,7S,7aR-iridomyrmecin have b