485-43-8

Basic information

• Product Name: (4aα,7aα)-Octahydro-4β,7α-dimethylcyclopenta[c]pyran-3-one
• Synonyms: (+)-Iridomyrmecin;(4aα,7aα)-Octahydro-4β,7α-dimethylcyclopenta[c]pyran-3-one;(4S,4aS,7aR)-4,4a,5,6,7,7a-Hexahydro-4,7α-dimethylcyclopenta[c]pyran-3(1H)-one;Iridomyrmecin;Iridomyrmexin;Irridomyrmercin;Hexahydro-4,7-dimethylcyclopenta[c]pyran-3(1H)-one;Cyclopenta[C]pyran-3(1H)-one, hexahydro-4,7-dimethyl-
• CAS NO: 485-43-8
• Molecular Formula: C10H16O2
• Molecular Weight: 168.23284
• Mol File: 485-43-8.mol
• Article Data: 24

Chemical Properties

• Melting Point: 60-61°
• Boiling Point: bp1.5 104-108°
• Flash Point: 107.7°C
• Appearance: /
• Density: 1g/cm³
• Vapor Pressure: 0.0068mmHg at 25°C
• Refractive Index: nD65 1.4607
• CAS DataBase Reference: (4aα,7aα)-Octahydro-4β,7α-dimethylcyclopenta[c]pyran-3-one(CAS DataBase Reference)
• NIST Chemistry Reference: (4aα,7aα)-Octahydro-4β,7α-dimethylcyclopenta[c]pyran-3-one(485-43-8)
• EPA Substance Registry System: (4aα,7aα)-Octahydro-4β,7α-dimethylcyclopenta[c]pyran-3-one(485-43-8)

Safety Data

• Hazardous Substances Data: 485-43-8(Hazardous Substances Data)

Usage

Chemical Properties

Colorless crystals.characteristic odor, refr index 1.46, optically active. Soluble in ether and fatty alcohols; almost insoluble in water.

Uses

Different sources of media describe the Uses of 485-43-8 differently. You can refer to the following data:
1. Iridomyrmecin (C10H16O2) is one of the few colorless compounds of iridium. It is used to manufacture insecticides.
2. Insecticide, biocide.

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+/m0/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

Preparation method of isoiridomyrmecin

The invention relates to a preparation method of isoiridomyrmecin, which comprises the following steps: (1) by using a compound 1: 4, 7-dimethyl-1, 4a, 5, 6, 7, 7a-hexahydrocyclopentapyran as a raw material, sequentially adding benzyl alcohol, trichloroacetonitrile and a silicon reagent into a solvent for a nucleophilic addition reaction to obtain a compound 2, (2) removing benzyl from the compound 2 and a palladium reagent in the solvent through hydrogen to prepare a compound 3, and (3) sequentially adding N-methyl morpholine oxide, tetrapropylammonium perruthenate and a molecular sieve intothe compound 3 in a solvent, and oxidizing to obtain the isoiridomyrmecin. Compared with the prior art, the method provided by the invention has the advantages of simple operation process, mild reaction conditions, relative environmental friendliness, no use of highly toxic products, high yield and the like, and can be used for large-scale production.

Application of Cp2TiCl-Promoted Radical Cyclization: A Unified Strategy for the Syntheses of Iridoid Monoterpenes

An expedient approach toward the unified total syntheses of (+)-iridomyrmecin, (-)-isoiridomyrmecin, (+)-7-epi-boschnialactone, (+)-teucriumlactone, and (-)-dolichodial in chirally pure forms starting from readily available (+)-β-citronellene is delineated combining step economy and simplicity. Highlights include a Ti(III)-mediated reductive epoxide opening-cyclization for the construction of the core cyclopenta[c]pyran skeleton of the iridoid lactones with complete diastereoselectivity for the newly created bridgehead stereogenic centers. Subsequent transformations facilitate a short access to (+)-teucriumlactone and (-)-dolichodial and formal access to potentially other iridoids.

Stereoselective synthesis of trans-fused iridoid lactones and their identification in the parasitoid wasp Alloxysta victrix, Part II: Iridomyrmecins

Following our earlier approach to the synthesis of dihydronepetalactones, all eight stereoisomers of trans-fused iridomyrmecins were synthesized starting from the enantiomers of limonene. Combined gas chromatography and mass spectrometry including enantioselective gas chromatography revealed that volatiles released by the endohyperparasitoid wasp Alloxysta victrix contain (4S,4aR,7S,7aR)-iridomyrmecin of 95-97% ee and stereochemically pure (4S,4aS,7R,7aS)-iridomyrmecin as a minor component.