112709-47-4

Basic information

• Product Name: (3S,6S,7E,11Z)-6-(1-methylethyl)-9-methylidene-1-oxaspiro[2.9]dodeca-7,11-dien-4-one
• Synonyms: 112709-47-4; Periplanone A
• CAS NO: 112709-47-4
• Molecular Formula: C₁₅H₂₀O₂
• Molecular Weight: 232.3181
• Mol File: 112709-47-4.mol
• Article Data: 4

Chemical Properties

• Boiling Point: 355.684°C at 760 mmHg
• Flash Point: 151.451°C
• Density: 1.032g/cm³
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.521
• CAS DataBase Reference: (3S,6S,7E,11Z)-6-(1-methylethyl)-9-methylidene-1-oxaspiro[2.9]dodeca-7,11-dien-4-one(CAS DataBase Reference)
• NIST Chemistry Reference: (3S,6S,7E,11Z)-6-(1-methylethyl)-9-methylidene-1-oxaspiro[2.9]dodeca-7,11-dien-4-one(112709-47-4)
• EPA Substance Registry System: (3S,6S,7E,11Z)-6-(1-methylethyl)-9-methylidene-1-oxaspiro[2.9]dodeca-7,11-dien-4-one(112709-47-4)

Safety Data

• Hazardous Substances Data: 112709-47-4(Hazardous Substances Data)

Upstream product

• 2181-42-2 trimethylsulphonium iodide 
• 113666-35-6 (2S,4S,5E,9R,10R)-2-t-butyldimethylsilyloxy-9,10-epoxy-7-methylene-4-(1-methylethyl)-5-cyclodecene-1-one 
• 593-71-5 Chloroiodomethane 
• 70552-79-3 (2Z,6E,8S)-10-t-butyldimethylsilyloxy-8-isopropyl-5-methylene-2,6-cyclodecadien-1-one 
• 113581-00-3 germacrone 
• 120913-03-3 C₂₄H₃₂N₂O₄S 
• 120913-02-2 Acetic acid (E)-(1R,3R)-3-isopropyl-6,10-dimethylene-9-oxo-cyclodec-4-enyl ester 
• 116363-89-4 (3Z,7E)-(1S,9S)-9-Isopropyl-2,6-dimethylene-cyclodeca-3,7-dienol 
• 105990-54-3 C₂₀H₃₄O₂Si 
• 111917-96-5 tert-Butyl-((3Z,7E)-9-isopropyl-2,6-dimethylene-cyclodeca-3,7-dienyloxy)-dimethyl-silane 
• 111917-97-6 (+/-)-Periplanon D₁ 

Downstream Products

• 69239-67-4 Persoon's periplanone-A 

Relevant articles and documents

X-Ray Crystallographic and NOE Studies on the Conformation of Periplanones and their Analogues

The structure of periplanone-A was established by X-ray crystallographic analysis.In comparison of the X-ray and 1H NMR data with those of periplanone-B, it was shown that periplanone-A and -B adopt essentially the same conformation.The epoxy epimer of periplanone-A has 104-times lower biological activity than periplanone-A, and NMR analysis indicated that the molecule exists in a mixture of different conformers.The conformation of the regioisomer, in which the carbonyl and epoxy groups are transposed, was analysed by X-ray crystallography and 1H NMR spectroscopy.It is highly biologically active, and the conformation of the germacranoid skeleton was shown to be almost identical with that of periplanone-A.Simplified analogues and germacrene-D had relatively lower activity.NOE Experiments on these compounds suggested the conformational resemblance of their germacranoid skeletons with those of periplanone-A and -B.

Short step-synthesis and biological activity of Hauptmann's periplanone A and its stereoisomer

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