21016-46-6

Usage

Uses

Used in Pharmaceutical and Agrochemical Synthesis:
2,4-DIMETHYL-2-PENTENOIC ACID is used as a versatile building block for the synthesis of various pharmaceuticals and agrochemicals, due to its unique chemical structure that allows for the creation of diverse and complex molecules.
Used in Antimicrobial Applications:
2,4-DIMETHYL-2-PENTENOIC ACID is studied for its potential as an antimicrobial agent, which could be utilized in the development of new treatments for bacterial infections.
Used in Metal-Catalyzed Reactions:
2,4-DIMETHYL-2-PENTENOIC ACID is also considered as a ligand in metal-catalyzed reactions, which are important in the field of organic chemistry for facilitating various types of chemical transformations.
Used in Material Development:
2,4-DIMETHYL-2-PENTENOIC ACID has been investigated for its potential role in the development of new materials, indicating its possible use in creating innovative substances with unique properties.
Used in Organic Synthesis:
As a component in organic synthesis, 2,4-DIMETHYL-2-PENTENOIC ACID contributes to the creation of a wide range of chemical compounds, showcasing its broad applicability in the field of chemistry.

InChI:InChI=1/C7H12O2/c1-5(2)4-6(3)7(8)9/h4-5H,1-3H3,(H,8,9)

Upstream product

• 3699-66-9 ethyl 2-diethoxyphosphorylpropionate 
• 78-84-2 isobutyraldehyde 
• 21382-82-1 (carbethoxyethylidene)triphenylphosphorane 
• 21016-47-7 ethyl (Z)-2,4-dimethylpent-2-enoate 
• 77772-22-6 Ethyl 2-(diphenylmethylsilyl)propionate 
• 105-37-3 Ethyl propionate 
• 535-11-5 Ethyl 2-bromopropionate 

Downstream Products

• 67513-47-7 4,6-Dimethyl-(E,E)-heptadiensaeure 

Relevant academic research and scientific papers

First concise total synthesis of 5-epi-prelactone B

First short total synthesis of 5-epi-prelactone B has been achieved involving Sharpless asymmetric epoxidation and intramolecular hydride transfer reaction for formation of the aldol product by nonaldol chemistry as the key steps. Copyright Taylor & Francis Group, LLC.

Directed γ-C(sp3)-H Alkylation of Carboxylic Acid Derivatives through Visible Light Photoredox Catalysis

Visible light photoredox catalysis enables direct γ- C(sp3)-H alkylation of saturated aliphatic carbonyl compounds. Electron-deficient alkenes are used as the coupling partners in this reaction. Distinguished site selectivity is controlled by the predominant 1,5-hydrogen atom transfer of an amidyl radical generated in situ.

Eight Diasteromers of Vittatalactone and Methods of Making, and Methods of Attracting Acalymma vittatum

Disclosed are methods for preparing a mixture of eight diasteromers of vittatalactone Also disclosed are mixtures of eight diasteromers of vittatalactone produced by the methods described herein. In addition there are described compositions comprising a mixture of eight diasteromers of vittatalactone and optionally (2E,6Z)-nona-2,6-dienal and optionally cucurbitacin B or cucurbitacin B, and optionally a carrier. Furthermore, there are describe methods of attracting Acalymma vittatum to an object or area, involving treating said object or area with a Acalymma vittatum attracting composition containing a Acalymma vittatum attracting effective amount of the compositions described herein.

Ene-diene transmissive cycloaddition reactions with singlet oxygen: The vinylogous gem effect and its use for polyoxyfunctionalization of dienes

The singlet oxygen reactivities and regioselectivities of the model compounds 1b-d were compared with those of the geminal (gem) selectivity model ethyl tiglate (1a). The kinetic cis effect is kE/kZ = 5.2 for the tiglate/angelate system 1a/1a′ without a change in the high gem regioselectivity. Further conjugation to vinyl groups enabled mode-selective processes, namely, [4 + 2] cycloadditions versus ene reactions. The site-specific effects of methylation on the mode selectivity and the regioselectivity of the ene reaction were studied for dienes 1e-g. A vinylogous gem effect was observed for the γ,δ-dimethylated and α,γ,δ-trimethylated substrates 1h and 1i, respectively. The corresponding phenylated substrates 1j-l showed similar mode selectivity, as monomethylated 1j exhibited exclusively [4 + 2] reactivity while the tandem products 12 and 14 were isolated from the di- and trimethylated substrates 1k and 1l, respectively. The vinylogous gem effect favors the formation of 1,3-dienes from the substrates, and thus, secondary singlet oxygen addition was observed to give hydroperoxy-1,2-dioxenes 19 and 20 in an ene-diene transmissive cycloaddition sequence. These products were reduced to give alcohols (16, 17, and 18) or furans (24 and 25), respectively, or treated with titanium(IV) alkoxides to give the epoxy alcohols 26 and 27. The vinylogous gem effect is rationalized by DFT calculations showing that biradicals are the low-energy intermediates and that no reaction path bifurcations compete.

An efficient synthesis of the fully elaborated isoindolinone unit of muironolide A

An efficient stereocontrolled construction of the fully substituted isoindolone subunit of muironolide A is described. The approach is centered on the intramolecular Diels-Alder reaction between the enol form of the β-keto amide and an α,β,γ,δ-unsaturated ester, followed by the installation of the cyclohexene double bond.

The total synthesis of the oxopolyene macrolide RK-397

It works both ways: The convergent total synthesis of the oxopolyene macrolide RK-397 utilizes remote asymmetric induction and a two-directional chain synthesis to prepare the polyol portion of the molecule, as well as a cross-metathesis reaction of a trienal with a terminal alkene to append the polyene to the polyol. (Chemical Equation Presented).

Asymmetric dihydroxylation of β,γ-unsaturated carboxylic esters with trisubstituted C=C bonds - Enantioselective syntheses of trisubstituted γ-butyrolactones

β,γ-Unsaturated esters with stereodefined trisubstitued C=C double bonds were prepared by the Arndt-Eistert homologation of α,β-unsaturated carboxyl halides, by two-step methoxycarbonylation of allylbarium reagents, by deconjugation of α,β-unsaturated esters, and by Horner-Wadsworth-Emmons variants of the Stobbe condensation. Sharpless asymmetric dihydroxylation of the β,γ-unsaturated esters, followed by spontaneous cyclization, afforded β-hydroxy-γ-lactones in moderate to good yields and with enantiomeric excesses of up to 97 %. Similarly, tetrahydroxy-γ-lactones were obtained from diunsaturated esters; these lactones were converted into a bislactone and an unsaturated β-hydroxy γ-lactone. Wiley-VCH Verlag GmbH & Co. KGaA, 2006.

A general and diastereoselective approach to the preparation of cis-2,6-disubstituted pyrans

The utility of preparing cis-2,6-disubstituted 5,6-dihydro-2H-pyrans by the methodology implied in Scheme 1 is demonstrated through the preparation of the two pyrans (1) and (2). The overall yields for the two nine-step sequences starting from the enals (3) and (4) were 57 and 54%, respectively, whilst the overall diastereochemical yield approached 100%. The key features of the method are (i) a highly regioselective Lewis acid-catalysed cyclocondensation reaction of a nucleophilic diene with an aldehyde to afford a 2,3-dihydro-4H-pyran-4-one, (ii) reduction of a pyranone with better than 98% regio- and stereo-chemical control to give the corresponding glycal, and (iii) an ester enolate Claisen rearrangement of a glycal acetate.

1,3-Dimethyl 2-oxo 1,3,2-diazaphospholidine precursor of (Z) α,β-unsaturated esters

α,β-Unsaturated esters of (Z) geometry are selectively obtained from cyclic phosphonocarboxylates derived from N,N'-dimethylethylenediamine.

A facile conversion of (Z)-2-alkenoic esters into the (E)-isomers with diphenyl disulfide

Diphenyl disulfide is shown to be an efficient catalyst for the isomerization of (Z)-2-alkenoic esters to (E)-2-alkenoic esters in boiling tetrahydrofuran.