2430-93-5

Upstream product

• 72175-11-2 (Z)-3-decenoic acid methyl ester 
• 60053-24-9 penta-3,4-dienoic acid 
• 693-25-4 n-pentylmagnesium bromide 
• 68676-85-7 3-Decenal 
• 30361-33-2 (2E,4E)-deca-2,4-dienoic acid 
• 124-13-0 Octanal 
• 141-82-2 malonic acid 
• 111-66-0 oct-1-ene 
• 108-24-7 acetic anhydride 
• 64-19-7 acetic acid 
• 544-48-9 (2E,4E)-Deca-2,4-dienoic acid 
• 625-38-7 but-3-enoic acid 
• 96227-88-2 (Z)-1,4-dihydroxydec-2-ene 
• 111-71-7 heptanal 

Downstream Products

• 111-71-7 heptanal 
• 66-25-1 hexanal 
• 2518-53-8 hexyl-5 (5H) furannone-2 
• 1262032-24-5 (E)-N-tosyl-3-decenamide 
• 62936-12-3 dodec-5E-en-1-ol 
• 10339-60-3 trans-3-decen-1-ol 
• 39944-81-5 ethyl (4Z)-undec-4-enoate 
• 49580-59-8 (Z)-4-undecenoic acid 

Relevant academic research and scientific papers

Stereoselective Ring-Opening of gem-Difluorocyclopropanes: An Entry to Stereo-defined (E,E)- and (E,Z)-Conjugated Fluorodienes

The ring-opening of gem-difluorocyclopropyl acetaldehydes producing selectively (E,E)- and (E,Z)-conjugated fluorodienals is described. Two stereo-divergent methods are presented to access both stereoisomers from a common precursor, in high yield and selectivity. The mechanistic aspect of these transformations is discussed.

A Chiral Electrophilic Selenium Catalyst for Highly Enantioselective Oxidative Cyclization

Chiral electrophilic selenium catalysts have been applied to catalytic asymmetric transformations of alkenes over the past two decades. However, highly enantioselective reactions with a broad substrate scope have not yet been developed. We report the first successful example of this reaction employing a catalyst based on a rigid indanol scaffold, which can be easily synthesized from a commercially available indanone. The reaction efficiently converts β,γ-unsaturated carboxylic acids into various enantioenriched γ-butenolides under mild conditions.

Taming the carboxyl group for directed carbometalation: Observations on the use of anions, dianions and ester enolates

Carboxylate anions, dianions and ester enolates provide simultaneous protection and activation for directed carbometalation reactions. Advantage can be taken of the bis-carbanionic character of the intermediate for further controlled C-C bond forming reac

Merging domino and redox chemistry: Stereoselective access to di- and trisubstituted β,γ-unsaturated acids and esters

Merging is the game! The coupling of a domino reaction and an internal neutral redox reaction constitutes an excellent manifold for the stereoselective synthesis of di- and trisubstituted olefins featuring a malonate unit, an ester, or a free carboxylic acid as substituents at the allylic position (see scheme; MW=microwave). The reaction utilizes simple starting materials (propargyl vinyl ethers), methanol or water as solvents, and a very simple and bench-friendly protocol. Copyright

Method for regio- and stereoselective synthesis of (E)-Β,γ- unsaturated acids from aldehydes under solvent-free conditions

Synthesis of (E)-β,-γunsaturated acids from aldehydes with malonic acid has been explored under solvent-free conditions. The modified Knoevenagel condensation reaction with N-methyl morpholine (NMM) as catalyst exhibits highly β,-γ regioselectivity and exclusively E-stereoselectivity. A mechanism accounting for both regio- and stereoselectivity has been proposed and preliminarily studied. Copyright Taylor & Francis Group, LLC.

Metabolism of deuterated erythro-dihydroxy fatty acids in Saccharomyces cerevisiae: Enantioselective formation and characterization of hydroxylactones

Epoxides of fatty acids are hydrolyzed by epoxide hydrolases (EHs) into dihydroxy fatty acids which are of particular interest in the mammalian leukotriene pathway. In the present report, the analysis of the configuration of dihydroxy fatty acids via their respective hydroxylactones is described. In addition, the biotransformation of (±)-erythro-7,8- and -3,4-dihydroxy fatty acids in the yeast Saccharomyces cerevisiae was characterized by GC/EI-MS analysis. Biotransformation of chemically synthesized (±)-erythro-7,8- dihydroxy(7,8-2H2)tetradecanoic acid ((±)-erythro- 1) in the yeast S. cerevisiae resulted in the formation of 5,6-dihydroxy(5,6- 2H2)dodecanoic acid (6), which was lactonized into (5S,6R)-6-hydroxy(5,6-2H2)dodecano-5-lactone ((5S,6R)-4) with 86% ee and into erythro-5-hydroxy(5,6-2H2)dodecano-6- lactone (erythro-8). Additionally, the α-ketols 7-hydroxy-8-oxo(7- 2H1)tetradecanoic acid (9a) and 8-hydroxy-7-oxo(8- 2H1)tetradecanoic acid (9b) were detected as intermediates. Further metabolism of 6 led to 3,4-dihydroxy(3,4- 2H2)decanoic acid (2) which was lactonized into 3-hydroxy(3,4-2H2)decano-4-lactone (5) with (3R,4S)-5=88% ee. Chemical synthesis and incubation of (±)-erythro-3,4-dihydroxy(3,4- 2H2)decanoic acid ((±)-erythro-2) in yeast led to (3S,4R)-5 with 10% ee. No decano-4-lactone was formed from the precursors 1 or 2 by yeast. The enantiomers (3S,4R)- and (3R,4S)-3,4-dihydroxy(3- 2H1)nonanoic acid ((3S,4R)- and (3R,4S)-3) were chemically synthesized and comparably degraded by yeast without formation of nonano-4-lactone. The major products of the transformation of (3S,4R)- and (3R,4S)-3 were (3S,4R)- and (3R,4S)-3-hydroxy(3-2H 1)nonano-4-lactones ((3S,4R)- and (3R,4S)-7), respectively. The enantiomers of the hydroxylactones 4, 5, and 7 were chemically synthesized and their GC-elution sequence on Lipodex E chiral phase was determined.

Sequential cross-metathesis/cyclopropanation: short syntheses of (+/-)-cascarillic acid and (+/-)-grenadamide

The total synthesis of (+/-)-cascarillic acid has been achieved by a sequential cross-metathesis/Simmons-Smith cyclopropanation between, respectively, 1-octene with an appropriate unsaturated carboxylic acid. In parallel, a direct access to grenadamide was developed from 1-nonene with a readily available unsaturated amide. In both cases, the chemical yields were high (up to 98%) and the E/Z ratio was near 80/20. The synthesis of a dibromocyclopropane analogue has also been considered.

A new synthesis of β,γ-alkenyl carboxylic acids from α,β-alkenyl carboxylic acid chlorides and α,β-alkenyl aldehydes with one-carbon elongation

Reaction of the lithium α-sulfinyl carbanion of chloromethyl phenyl sulfoxide with α,β-alkenyl carboxylic acid chlorides gave γ,δ-alkenyl α-chloro-β-keto sulfoxides in variable yields. The keto sulfoxides were also synthesized from α,β-alkenyl aldehydes in two steps in good overall yields: addition of the lithium α-sulfinyl carbanion of chloromethyl phenyl sulfoxide to α,β-alkenyl aldehydes followed by oxidation of the adducts with 2,3-dichloro-5,6-dicyano-1,4-benzoquinone or Dess-Martin periodinane. These products were treated in sequence with potassium hydride, tert-butyllithium, and 5% aqueous sodium hydroxide, in one flask to give β,γ-alkenyl carboxylic acids with one-carbon elongation in good yields. The procedure offers a new method for synthesizing β,γ-alkenyl carboxylic acids from α,β-alkenyl carboxylic acid chlorides and α,β-alkenyl aldehydes with one-carbon elongation.

SiO2 catalysed expedient synthesis of [E]-3-alkenoic acids in dry media

Aliphatic aldehydes with α-hydrogens and malonic acid undergo decarboxylative condensation on the surface of SiO2 when subjected to microwave irradiation generating βγ-unsaturated acids in high yields.

Improvement on the synthesis of (E)-alk-3-enoic acids

(E)-Alk-3-enoic acids have been prepared in high yield (85-90%) and excellent stereoselectivity (98-99%) by a modified Knoevenagel condensation of a straight carbon chain aldehyde with malonic acid, in dimethyl sulfoxide (DMSO) or dimethylformamide (DMF) at 100°C, in the presence of piperidinium acetate as catalyst. Condensation of the aldehyde with a monoester of malonic acid, under the above conditions, gave the corresponding ester of (E)-alk-3-enoic acid in high yield (76-82%) and good stereoselectivity (90-92%). Condensation of the aldehyde with cyanoacetic acid gave the β,γ-unsaturated nitrile in moderate yield (35-40%) without stereoselectivity.