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

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

• 35322-42-0 12-hydroxydodecan-2-one 
• 38460-95-6 undec-10-enoyl chloride 
• 75-24-1 trimethylaluminum 
• 16834-14-3 dimethylthallium(III) chloride 
• 75-47-8 iodoform 
• 36219-78-0 10-oxo-undecanal 
• 18815-73-1 methylzinc iodide 
• 75-16-1 methylmagnesium bromide 
• 112-38-9 10-undecenoic acid 
• 74-88-4 methyl iodide 
• 102613-04-7 N-methyl-N-methoxyundec-10-enamide 
• 104634-45-9 dodeca-11-ene-1-yne 
• 5876-87-9 1,11-dodecadiene 
• 7647-10-1 palladium(II) chloride 

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.

Comparison of Aroma Character Impact Volatiles of Thummong Leaves (Litsea petiolata Hook. f.), Mangdana Water Beetle (Lethocerus indicus), and a Commercial Product as Flavoring Agents in Thai Traditional Cooking

Thummong (Litsea petiolata Hook. f.) is a tree native to southern Thailand. The leaves of this tree are highly aromatic and used to flavor Thai dishes in place of the traditional water beetle Mangdana (Lethocerus indicus) for religious and cultural reasons. Total and aroma-active volatiles from both flavoring materials were compared using gas chromatography-olfactory (GC-O) and gas chromatography-mass spectrometry (GC-MS). The volatiles from Thummong leaves and the Mangdana water beetle were collected and concentrated using headspace solid-phase microextraction. A total of 23 and 25 aroma-active volatiles were identified in Thummong leaves and Mangdana, respectively. The major aroma-active volatiles in Thummong leaves consisted of 7 aldehydes, 5 ketones, and 3 esters. In contrast, the aroma-active volatiles in the water beetle consisted of 11 aldehydes, 3 esters, and 2 ketones. Both had (E)-2-nonenal as the most intense aroma-active volatile. The water beetle character impact volatile (E)-2-hexenyl acetate was absent in the leaves, but its aroma character was mimicked by 11-dodecen-2-one in the leaves, which was absent in the beetle. In addition, a commercial Mangdana flavoring was examined using GC-O and GC-MS and found to contain only a single aroma-active volatile, hexyl acetate. All three flavoring sources exhibited similar aroma characteristics but were produced from profoundly different aroma-active volatiles.

Cyclopropanation of Terminal Alkenes through Sequential Atom-Transfer Radical Addition/1,3-Elimination

An operationally simple method to affect an atom-transfer radical addition of commercially available ICH2Bpin to terminal alkenes has been developed. The intermediate iodide can be transformed in a one-pot process into the corresponding cyclopropane upon treatment with a fluoride source. This method is highly selective for the cyclopropanation of unactivated terminal alkenes over non-terminal alkenes and electron-deficient alkenes. Due to the mildness of the procedure, a wide range of functional groups such as esters, amides, alcohols, ketones, and vinylic cyclopropanes are well tolerated.

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.

Versatile methodology to hydrate alkynes, in the presence of a wide variety of functional groups, with mercury(II) p-toluensulfonamidate, under catalytic, mild, and neutral conditions

A method to generate carbonylic compounds from alkynes under mild and neutral conditions, with excellent functional group compatibility and good yields, is described. Hydration takes place under catalytic conditions by using 0.1 to 0.2 equivalents of the easily available and inexpensive mercury(II) p-toluensulfonamidate in a hydroalcoholic solution. After use, the catalyst is rendered inert and/or recycled. Supplemental materials are available for this article. Go to the publisher's online edition of Synthetic Communications to view the free supplemental file.

Mild chemo-selective hydration of terminal alkynes catalysed by AgSbF 6

The chemo-selective hydration of a wide range of non-activated terminal alkynes catalysed by AgSbF6 under mild conditions is reported.

A new synthetic method for methyl ketones from carboxylic acids using metallic strontium and methyl iodide

Carboxylic acids reacted with metallic strontium and methyl iodide to give methyl ketones preferentially in moderate to good yields. Copyright

Oxidation of alcohols with catalytic amounts of IBX

Herein we present a catalytic IBX-based method for the oxidation of alcohols. Using this system a variety of benzylic alcohols were transformed to aldehydes in good yields whereas secondary alcohols were easily converted to ketones. Primary aliphatic alcohols were oxidised to the corresponding carboxylic acids. 2-lodobenzoic acid can also be used instead of IBX. Georg Thieme Verlag Stuttgart.

A dehydrohalogenation methodology for synthesizing terminal olefins under mild conditions

A new methodology for preparing terminal olefins in good yield by dehydrohalogenation of primary alkyl iodide with tetrabutylammonium fluoride in dimethyl sulfoxide at room temperature is presented. Optimization of the mild reaction conditions and assays on various alkyl iodides are described. Georg Thieme Verlag Stuttgart.