172104-03-9

Basic information

• Product Name: (6S,7E)-6-hydroxy-10-propyl-3,4,5,6,9,10-hexahydro-2H-oxecin-2-one
• CAS NO: 172104-03-9
• Molecular Formula: C₁₂H₂₀O₃
• Molecular Weight: 212.2854
• Mol File: 172104-03-9.mol
• Article Data: 4

Chemical Properties

• Boiling Point: 376.4°C at 760 mmHg
• Flash Point: 159.9°C
• Density: 1.014g/cm³
• Vapor Pressure: 3.32E-07mmHg at 25°C
• Refractive Index: 1.469
• CAS DataBase Reference: (6S,7E)-6-hydroxy-10-propyl-3,4,5,6,9,10-hexahydro-2H-oxecin-2-one(CAS DataBase Reference)
• NIST Chemistry Reference: (6S,7E)-6-hydroxy-10-propyl-3,4,5,6,9,10-hexahydro-2H-oxecin-2-one(172104-03-9)
• EPA Substance Registry System: (6S,7E)-6-hydroxy-10-propyl-3,4,5,6,9,10-hexahydro-2H-oxecin-2-one(172104-03-9)

Safety Data

• Hazardous Substances Data: 172104-03-9(Hazardous Substances Data)

Upstream product

• 1190042-35-3 (5S)-5-[(4-methoxybenzyl)oxy-]6-heptenoic acid 
• 1190042-34-2 (1R)-1-propyl-3-butenyl (5S)-5-[(4-methoxybenzyl)oxy-]6-heptenoate 
• 3521-91-3 (4R)-hept-1-en-ol 
• 38049-10-4 ethyl 5-oxo-6-heptenoate 
• 478491-17-7 (2E)(5S)-6-(tert-butyldiphenylsilanyloxy)-(4-methoxybenzyloxy)hex-2-enoic acid ethyl ester 
• 139406-51-2 (R)-2-propylethylene oxide 
• 115463-10-0 ethyl (E)-7-(benzyloxy)hept-2-enoate 
• 99016-97-4 (E)-7-(benzyloxy)-2-hepten-1-ol 
• 78999-24-3 5-benzyloxy-1-pentanal 
• 4541-15-5 5-(benzyloxy)-1-pentanol 
• 111-29-5 1 ,5-pentanediol 
• 1374783-94-4 (2S,3R)-2-[4-(benzyloxy)butyl]-3-(chloromethyl)oxirane 

Relevant articles and documents

The first chemoenzymatic total synthesis of the phytotoxic nonenolide putaminoxin and its (5S,6E,9S)-diastereomer

The limitations of an alcohol dehydrogenase regarding the oxidative kinetic resolution of homoallylic alcohol containing alkyl chains were investigated, leading to a valuable building block for the total synthesis of phytotoxic nonenolide putaminoxin. The enzymatic approach towards the enantioenriched homoallylic alcohol was compared to classical, nonenzymatic approaches using asymmetric reagent controlled allyl additions and the obtained building block was used for the total synthesis of putaminoxin and its (5S,6E,9S)-diastereomer. After the spectroscopic analysis of the synthesized compounds, discrepancies were observed to already published data of isolated and synthesized putaminoxin. Therefore, a systematic comparison of NMR data was carried out. The result underlines the necessity of total synthesis for the absolute assignment of configuration.

Novel synthesis of stagonolide-F, putaminoxin and aspinolide-A

Novel synthesis of putaminoxin, stagonolide-F and aspinolide-A have been achieved by utilizing (S) and (R)- malic acid. The key feature of the synthetic strategy includes Horner-Wittig olefination, double bond reduction and Steglich esterification. Olefinic acid for putaminoxin and stagonolide-F was prepared from (S)-malic acid whereas olefinic acid for aspinolide-A was prepared from (R)-malic acid and olefinic alcohols for putaminoxin, stagonolide-F and aspinolide-A were prepared by using Brown's asymmetric allylboration.