68676-74-4

Upstream product

• 928-97-2 (E)-3-hexen-1-ol 
• 124-38-9 carbon dioxide 
• 592-41-6 1-hexene 
• 201230-82-2 carbon monoxide 
• 103896-62-4 (E)-diethyl hex-2-en-1-yl phosphate 
• 73881-10-4 (E)-1-bromo-2-hexene 
• 64-18-6 formic acid 
• 928-95-0 (E)-2-Hexen-1-ol 
• 505-57-7 2-hexenal 
• 764-60-3 hex-2-yn-1-ol 
• 2305-21-7 2-hexen-1-ol 
• 928-94-9 (Z)-2-hexen-1-ol 
• 82479-50-3 2-((E)-Hex-2-enyl)-2-hydroxy-indan-1,3-dione 
• 2497-18-9 (E)-2-hexen-1-yl acetate 

Downstream Products

• 57681-53-5 5-propylfuran-2(5H)-one 
• 1262032-23-4 (E)-N-tosyl-3-heptenamide 
• 21662-18-0 trans-2-hexenaldehyde 
• 2108-05-6 trans-3-hepten-1-ol 
• 54340-71-5 (E)-ethyl hept-3-enoate 
• 14369-94-9 ethyl 4-oxoheptanoate 
• 107-92-6 butyric acid 

Relevant academic research and scientific papers

(E)-beta,gamma-alkenyl carboxylic acid derivative and preparation method thereof

The invention discloses an (E)-beta,gamma-alkenyl carboxylic acid derivative and a preparation method thereof. The preparation method disclosed by the invention comprises the following steps: in an organic solvent, under the condition that a nickel catalyst, a dinitrogen ligand, a reducer and an additive exist, carrying out a carboxylation reaction on an allyl alcohol substrate as shown in formula (II) and carbon dioxide. The preparation method disclosed by the invention is high in selectivity, the raw material reagents are easy to get and has high chemical selectivity and region selectivity, and the derivative is high in yield, high in purity, and low in generation cost and is more applicable for industrial production. (Refer to Specification).

Efficient Pd-Catalyzed Regio- and Stereoselective Carboxylation of Allylic Alcohols with Formic Acid

Formic acid is efficiently used as a C1 source to directly carboxylate allylic alcohols in the presence of a low loading of palladium catalyst and acetic anhydride as additive to afford β,γ-unsaturated carboxylic acids with excellent chemo-, regio-, and stereoselectivity. The reaction proceeds through a carbonylation process with in situ-generated carbon monoxide under mild conditions, avoiding the use of high-pressure gaseous CO. A bisphosphine ligand with a large bite angle (4,5-bis{diphenylphosphino}-9,9-dimethylxanthene, Xantphos) was found to be uniquely effective for this transformation. The regio- and stereoconvergence of this reaction is ascribed to the thermodynamically favored isomerization of the allylic electrophile in the presence of the palladium catalyst.

Regioselective Ni-Catalyzed Carboxylation of Allylic and Propargylic Alcohols with Carbon Dioxide

An efficient Ni-catalyzed reductive carboxylation of allylic alcohols with CO2 has been successfully developed, providing linear β,γ-unsaturated carboxylic acids as the sole regioisomer with generally high E/Z stereoselectivity. In addition, the carboxylic acids can be generated from propargylic alcohols via hydrogenation to give allylic alcohol intermediates, followed by carboxylation. A preliminary mechanistic investigation suggests that the hydrogenation step is made possible by a Ni hydride intermediate produced by a hydrogen atom transfer from water.

Ligand-controlled regiodivergent Ni-catalyzed reductive carboxylation of allyl esters with CO2

A novel Ni-catalyzed regiodivergent reductive carboxylation of allyl esters with CO2 has been developed. This mild, user-friendly, and operationally simple method is characterized by an exquisite selectivity profile that is dictated by the ligand backbone.

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

Enantiodivergent and γ-selective asymmetric allylic amination

Double agent: The title reaction using the guanidine catalyst 1 can deliver both enantiomers of the product with excellent enantioselectivity by judicious choice of the double bond geometry of the the β,γ-unsaturated carbonyl compound. Computational studies reveal the possible origin of the inversed enantioselectivity, and the potential for enantiodivergent synthesis chiral amine-containing substrates is attractive. Copyright

Regioselective ring opening and isomerization reactions of 3,4-epoxyesters catalyzed by boron trifluoride

Efficient ring opening of 3,4-epoxyesters with alcohols to produce 4-alkoxy-3-hydroxyesters and their isomerization into 4-ketoesters using boron trifluoride as the catalyst are presented. Both transformations are simple and efficient methods for the synthesis of the above named synthetically useful compounds.

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.

(E)-Selective hydrolysis of (E,Z)-α,β-unsaturated nitriles by the recombinant nitrilase AtNIT1 from Arabidopsis thaliana

From stereoisomeric α,β-unsaturated nitriles (E,Z)-1, the recombinant nitrilase AtNIT1 from Arabidopsis thaliana hydrolyses the (E)-isomers exclusively to the corresponding (E)-carboxylic acids (E)-2 with high specificity. The (E)-selectivity can also be utilised for the preparation of the isomerically pure nitriles (Z)-1. From (E,Z)-2-hydroxycinnamonitrile (E,Z)-3, the otherwise difficult obtainable (Z)-3 was prepared in 66% isolated yield. With β,γ-unsaturated (E,Z)-3-heptenenitrile (E,Z)-4, however, (E)-selectivity was not observed. AtNIT1 exhibits not only diastereoselectivity but also regioselectivity. From a mixture of the four isomers A-D of 3-(2-cyanocyclohex-3-enyl)propenenitrile 6, exclusively isomer D ((E)-cis-6) was hydrolysed to 3-(2-cyanocyclohex-3-enyl)propenoic acid (E)-cis-7, as stated by X-ray crystal structure. Only after complete conversion of D and high enzyme concentrations, isomer C ((E)-trans-6) was hydrolysed to a small extent.

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.