5009-33-6

Basic information

• Product Name: dodec-11-en-2-one
• Synonyms: dodec-11-en-2-one;11-Dodecen-2-one;Einecs 225-688-1
• CAS NO: 5009-33-6
• Molecular Formula: C₁₂H₂₂O
• Molecular Weight: 182.30248
• EINECS: 225-688-1
• Mol File: 5009-33-6.mol
• Article Data: 36

Chemical Properties

• Boiling Point: 272.8°C at 760 mmHg
• Flash Point: 97.9°C
• Appearance: /
• Density: 0.833g/cm³
• Vapor Pressure: 0.00597mmHg at 25°C
• Refractive Index: 1.437
• CAS DataBase Reference: dodec-11-en-2-one(CAS DataBase Reference)
• NIST Chemistry Reference: dodec-11-en-2-one(5009-33-6)
• EPA Substance Registry System: dodec-11-en-2-one(5009-33-6)

Safety Data

• Hazardous Substances Data: 5009-33-6(Hazardous Substances Data)

Usage

Synthesis Reference(s)

Synthesis, p. 228, 1988 DOI: 10.1055/s-1988-27522

InChI:InChI=1/C12H22O/c1-3-4-5-6-7-8-9-10-11-12(2)13/h3H,1,4-11H2,2H3

Upstream product

• 75-11-6 diiodomethane 
• 36219-78-0 10-oxo-undecanal 
• 112-45-8 10-Undecenal 
• 18107-18-1 diazomethyl-trimethyl-silane 
• 21951-49-5 dodec-11-en-2-ol 
• 73921-17-2 2,2-Dimethyl-5-undec-10-enoyl-[1,3]dioxane-4,6-dione 
• 117948-98-8 dodec-11-yn-2-one 
• 75-47-8 iodoform 
• 18815-73-1 methylzinc iodide 
• 75-16-1 methylmagnesium bromide 
• 112-38-9 10-undecenoic acid 
• 74-88-4 methyl iodide 
• 295321-69-6 12-iodododecan-2-one 
• 5876-87-9 1,11-dodecadiene 

Downstream Products

• 6175-49-1 dodecan-2-one 
• 2345-12-2 12-oxotridecanoic acid 
• 101713-63-7 1-O-<((2-nitrobenzyl)oxy)carbonyl>-2-O-<(1,1,1-trichloro-2-methyl-11-dodecen-2-yl)carbonyl>-3-O-(tert-butyldimethylsilyl)glycerol 
• 208243-27-0 C₁₉H₂₉⁽²⁾HO₃S 
• 50816-18-7 9-decen-1-yl acetate 

Relevant articles and documents

A general approach to enantiomerically pure methylcarbinols. Asymmetric synthesis of antibiotic (-)-A26771B and the WCR sex pheromone

Either (R) or (S) enantiomerically pure methylcarbinol groups are conveniently produced from monosubstituted alkenes via the Sharpless asymmetric dihydroxylation (AD) reaction. The initial AD product, 1,2- dihydroxyalkane, obtained with predictable absolute configuration and high enantiomeric purity, is converted into 2-acetoxy-1-bromoalkane and then subjected to reductive debromination. These conditions are compatible with a variety of functional groups, including acetal, ester, nitrile, ketone, and silyl ether. The advantages of this method are demonstrated by highly efficient, asymmetric syntheses of enantiomerically pure natural products. All four stereoisomers of the WCR sex pheromone 4 are prepared in six steps form nona-1,8-diene in 10-15% overall yield. Similarly, a highly efficient formal total synthesis of antibiotic (-)-A26771B (5) is accomplished via two alternative approaches. The first one transforms dodec-11-enal into enantiomerically pure 5 in 11 steps and 4.1% overall yield, while the second achieves the same transformation in 12 steps and 6.6% overall yield.

Chemoselective reduction of aldehydes: Via a combination of NaBH4 and acetylacetone

A bench-stable combination of NaBH4-acetylacetone was developed for the efficient chemoselective reduction of aldehydes in the presence of ketones. This method offers a useful synthetic protocol for distinguishing carbonyl reaction sites, and its synthetic utility is reflected by its moisture tolerance and high efficiency in a variety of complex settings.

Aerobic Acetoxyhydroxylation of Alkenes Co-catalyzed by Organic Nitrite and Palladium

An aerobic acetoxyhydroxylation of alkenes cooperatively catalyzed by organic nitrite and palladium at room temperature using clean and cheap air as the sole oxidant has been developed. Various vicinal diols, diacetoxyalkanes, and dihalogenoalkanes have been synthesized. The gram-scale synthesis has also been approached. Vicinal difluorination and dichlorolation products have also been achieved via this reaction.