21944-96-7

Basic information

• Product Name: (Z)-undec-5-en-2-one
• Synonyms: (Z)-undec-5-en-2-one
• CAS NO: 21944-96-7
• Molecular Weight: 168.279
• Mol File: 21944-96-7.mol

Chemical Properties

• CAS DataBase Reference: (Z)-undec-5-en-2-one(CAS DataBase Reference)
• NIST Chemistry Reference: (Z)-undec-5-en-2-one(21944-96-7)
• EPA Substance Registry System: (Z)-undec-5-en-2-one(21944-96-7)

Safety Data

• Hazardous Substances Data: 21944-96-7(Hazardous Substances Data)

Upstream product

• 58761-26-5 2,2-Ethanediyldioxyundec-5-yne 
• 13483-31-3 Acetone dimethylhydrazone 
• 25466-54-0 (Z)-1-bromo-2-octene 
• 20039-37-6 dipyridinium dichromate 
• 30390-50-2 (Z)-4-decenal 
• 75-16-1 methylmagnesium bromide 
• 18107-18-1 diazomethyl-trimethyl-silane 
• 39924-57-7 (Z)-1-bromo-1-heptene 
• 104410-62-0 (Z)-3-Nitro-5-undecen-2-one-p-toluenesulfonylhydrazone 
• 92215-45-7 B-(1-Heptynyl)-9-borabicyclo<3.3.1>nonane 
• 104410-61-9 (Z)-3-Nitro-5-undecen-2-one 
• 104410-60-8 (Z)-1-Nitro-3-nonene 
• 136695-81-3 1-bromo-non-3-cis-ene 
• 10340-23-5 (Z)-non-3-en-1-ol 

Relevant articles and documents

DIASTEREOSELECTIVE SYNTHESIS OF (E)-ALKENES AND (E)-1,ω-DIENES STARTING FROM DIASTEREOISOMERIC MIXTURES OF l-BROMO-l-ALKENES : NEW SYNTHESES OF MONOUNSATURATED OR BRIDGED RING-KETAL NATURALLY OCCURRING SUBSTANCES.

The PdCl2(dppf)-catalyzed cross-coupling reaction between diastereoisomeric mixtures of l-bromo-l-alkenes which contain n equiv. of (E)-stereoiomers and n equiv. of Grignard reagents allows to obtain (E)-alkenes or (E)-l,ω-dienes having 95.5-99percent stereoisomeric purity in satisfactory yields.Such compounds are useful precursors to several naturally occurring substances.

Alkenyl Carbonyl Derivatives in Enantioselective Redox Relay Heck Reactions: Accessing α,β-Unsaturated Systems

A highly enantioselective and site-selective Pd-catalyzed arylation of alkenes linked to carbonyl derivatives to yield α,β-unsaturated systems is reported. The high site selectivity is attributed to both a solvent effect and the polarized nature of the carbonyl group, both of which have been analyzed through multidimensional analysis tools. The reaction can be performed in an iterative fashion allowing for a diastereoselective installation of two aryl groups along an alkyl chain.

Use of organoboranes in the synthesis of pheromones: A convenient synthesis of (Z)-6-heneicosen-11-one and (Z)-5-undecen-2-one, pheromones from the Douglas Fir Tussock Moth and the Bontebok, respectively

Treatment of thexylborane with a halomagnesiumdialkylcuprate afforded the corresponding (R-alkyl)thexylborane in favourable yields. A second reaction with a halomagnesiumdialkenylcuprate produced the totally mixed (R-alkyl)(E-alkenyl)thexylborane. Subsequent treatment with sodium cyanide and benzoyl chloride followed by alkaline peroxide yielded an unsaturated ketone. In this way, (Z)-6-heneicosen-11-one, a sex pheromone of the Douglas Fir Tussock Moth, and (Z)-5-undecen-2-one, a pheromone from the pedal gland of the Bontebok, were prepared.

Simple Synthesis of (Z)-12-Nonadecen-9-one, (Z)-13-Icosen-10-one, the Sex Pheromone of Peach Fruit Moth, and (Z)-5-Undecen-2-one, a Biologically Active Molecule from the Pedal Gland of the Bontebok

A simple and convenient synthesis of (Z)-12-nonadecen-9-one, (Z)-13-icosen-10-one, the sex pheromone of the peach fruit moth, and (Z)-undecen-2-one, the pheromone from the pedal gland of the bontebok, is described.These pheromones were readily synthesized using succesive alkylation of acetone dimethylhydrazone in one-pot.

Mild and efficient catalytic method for α-trimethylsilyl ketones

A mild, efficient and convenient method for the synthesis of α-silyl ketones from corresponding aldehydes and trimethylsilyldiazomethane in the presence of a catalytic amount of indium(III) chloride has been developed. ARKAT-USA, Inc.

One-pot regio- and stereoselective cyclization of 1,2,n-triols

A simple and efficient process to cyclize triols containing a 1,2-diol functionality with a pendant hydroxyl group is presented. The one-pot procedure converts the 1,2-diol into an ortho ester in situ, which upon treatment with a Lewis acid generates a cyclic acetoxonium intermediate. This intermediate is subsequently trapped by the pendant hydroxyl group to generate a cyclic ether. The stereochemistry of the 1,2-diol is transferred to the product with complete fidelity (inversion at the site of cyclization), and the reaction proceeds with high regioselectivity. The process is akin to the Lewis acid-catalyzed intramolecular ring-opening of epoxides with hydroxyl groups yielding cyclic ethers of various sizes with regio- and stereochemical control. Copyright

Nickel-catalyzed electrochemical couplings of vinyl halides: Synthetic and stereochemical aspects

Homo- and cross-coupling involving alkenyl halides have been performed efficiently using an electroassisted nickel-complex catalysis. Valuable product such as conjugated dienes, β,γ- or γ,δunsaturated esters, ketones, or nitriles, as well as alkenylated aryl compounds are thus prepared with high yields and high stereoselectivity. Partial isomerization is only observed in a few cases, when the alkenyl halide is involved in a late step of the catalytic cycle. This is the case in the preparation of (Z,Z)-1,3-diene.

Stereoselective alkenylation of activated olefins via nickel-catalyzed electroreductive coupling

The nickel-catalyzed electroreductive conjugate addition of (Z)- or (E)-alkyl halides to electron-deficient olefins in the presence of a sacrificial iron rod as the anode proceeds with complete retention of the stereochemistry of the alkenyl part and affo

NAD(P)+-NAD(P)H Models. 65. Photochemical Reductive Desulfonylation of β-Keto Sulfones with Hantzsch Ester

A new procedure for the reductive desulfonylation of β-keto sulfones is described.The reaction proceeds under a photochemical conditions with the Hantzsch ester in pyridine in the presence of ruthenium(II).Various functional groups are unaffected under the reaction conditions.Application of the procedure to the syntheses of certain natural products is also described.