96599-47-2

Upstream product

• 941-69-5 N-phenyl-maleimide 
• 78-79-5 isoprene 
• 108-31-6 maleic anhydride 
• 62-53-3 aniline 
• 115-11-7 isobutene 

Downstream Products

• 133638-34-3 N-phenyl-5-(3,5-dioxo-4-benzyl-1,2,4-triazolidin-1-yl)-4-methylcyclohex-3-ene-1,2-dicarboximide 

Relevant academic research and scientific papers

Enantioselective Diels-Alder reaction in the confined space of homochiral metal-organic frameworks

A novel homochiral porous metal-organic framework (MOF) has been synthesized using (R)-2,2′-dihydroxy-1,1′-binaphthyl-4,4′-dibenzoic acid as the chiral ligand. This MOF acts as an effective heterogeneous catalyst for the enantioselective Diels-Alder react

Oxathiaborolium-Catalyzed Enantioselective [4 + 2] Cycloaddition and Its Application in Lewis Acid Coordinated and Chiral Lewis Acid Catalyzed [4 + 2] Cycloaddition

The nascency of second-generation sulfur-stabilized borenium cations by halophilic Lewis acid SnCl4 leads to highly active chiral Lewis acids that are very effective catalysts for [4 + 2] cycloaddition. Oxathiaborolium pentachlorostannate (5-10 mol %) successfully catalyzed cycloaddition of various dienes and dienophiles to afford cycloadducts with excellent enantioselectivity (20 examples, up to 99% ee). This super Lewis acid also exhibited good enantioselectivity for the first Lewis acid coordinated and chiral Lewis acid catalyzed [4 + 2] cycloaddition to α,β-unsaturated mixed ester amide.

A dehydrogenative diels-alder reaction of prenyl derivatives with 2,3-dichloro-5,6-dicyanobenzoquinone

An efficient dehydrogenative Diels-Alder (DHDA) reaction of prenyl derivatives with 2,3-dichloro-5,6-dicyanobenzoquinone (DDQ) has been developed under mild conditions, leading to a series of cyclohexene derivatives with good to excellent yields and excellent diastereoselectivity.

Controlled radical polymerization of 3-methylenecyclopentene with N-substituted maleimides to yield highly alternating and regiospecific copolymers

High-molecular-weight diene copolymers with a regiospecific repeating structure were produced in a high yield during the alternating radical copolymerization of N-substituted maleimides (RMIs) and 3-methylenecyclopentene (MCP) as the cyclic 1,3-diene monomer including a reactive exomethylene moiety. The eminent copolymerization reactivity of MCP was in contrast to the predominant occurrence of the Diels-Alder reaction of isoprene with the RMIs rather than copolymerization. The highly alternating structure of the copolymers was confirmed based on the monomer reactivity ratios for the copolymerization of MCP (M1) and N-phenylmaleimide (PhMI, M2), r 1 = 0.010 and r2 = 0.0080. A mechanism for the highly controlled 1,4-regiospecific propagation, which consists of the addition of an RMI radical to the exomethylene group of MCP and subsequent 1,4-regiospecific propagation, was supported by the DFT calculations using model reactions as well as the precise structure determination of oligomers produced during telomerization in the presence of 1-butanethiol as a chain transfer agent. The resulting copolymers exhibited no weight-loss under 340 C during heating in a nitrogen atmosphere and their glass transition temperature was over the wide temperature range of 66-159 C, depending on the structure of the N-alkyl substituents. The transparent and flexible films were fabricated by a casting method. The optical properties of the films were as follows: the visible light transmittance over 95% at 380 nm, the refractive indices of 1.54-1.58, and the Abbe number of 42-45.

Synthesis of Diels-Alder adducts of N-arylmaleimides by a multicomponent reaction between maleic anhydride, dienes, and anilines

We have carried out the synthesis and characterization of some hexahydroisoindolyl benzoic acids and their corresponding ethyl esters by a multicomponent reaction (MCR) between aminobenzoic acids or aminobenzoates, maleic anhydride, and isoprene in the ab

[AlCl3 + 2THF]: A new and efficient catalytic system for Diels-Alder cycloaddition of α,β-unsaturated carbonyl compounds under solvent-free conditions

[AlCl3 + 2THF] is a new catalytic system for the Diels-Alder cycloaddition under SFC and air atmosphere. By using equimolar amounts of reactants, this catalyst prevents the polymerization of the diene and allows the corresponding adducts to be isolated with high regio- and stereocontrol and in excellent yields.

Asymmetric Diels-Alder and ene reactions promoted by a Ti(IV) complex bearing a C2-symmetric tridentate ligand

A new Ti(IV) complex obtained from the C2-symmetric amino diol (1R,5R)-3-aza-3-benzyl-1,5-diphenyl pentan-1,5-diol,(1R,5R)-1, is used effectively as a Lewis acid promoter in asymmetric Diels-Alder reactions. Using various Evans' oxazolidinones

Volumes of Activation for Catalysed Diels-Alder Reactions

The Diels-Alder reactions between isoprene and N-phenylmaleimide catalysed by Lewis acids, in particular by aluminium chloride and by lithium perchlorate have volumes of activation more negative than does the uncatalyzed reaction.That between anthracene-9

Carboxylic acid amide compounds and their derivatives

Described herein are novel carboxylic acid amide compounds or carboximide compounds represented by the general formula: STR1 wherein Z represents a group of the formula (1) or (2): STR2 wherein R1 and R2 are hydrogen atom or methyl group, respectively; Xs, which may be the same or different, are hydrogen atom, a lower alkyl, lower alkoxy, halo, or alkyl halide group, respectively, and n represents an integer of 0 to 2, and their pharmaceutically acceptable salts; process for the production thereof; and medicines containing the same. The novel compounds are useful as treating, preventing and improving agents for diseases attended with cerebral dysfunction as well as various symptoms caused by the said diseases. Further, the compounds are useful for the improvement of neurosis of the stomach; and treatment and prevention for various constipation.

Investigation of the Cyclopentenone Formation via the α-Alkynone Cyclisation: Synthesis of the Acorone Intermediate 8-Methylspirodeca-3,7-dien-2-one

As a further application of the cyclopentenone formation A-->C via the thermal α-alkynone cyclisation B-->C and in order to test the fate of an isolated C,C-double bond within a molecule under these conditions, we investigated the synthesis of the acorone intermediate 3 starting from the known carboxylic acid 1.The α-alkynone 2 was obtained from 1 via the acyl chloride 6 and a Pd(II)-catalysed route (22percent).The thermolysis of 2 at 550 deg provided the target molecule 3 (48percent) together with the product 9 (20percent) of a competing intramolecular ene reaction and its dimer 10 (4percent).At a higher thermolysis temperature (650 deg), the spiro ketone 3 was found to be unstable, affording the retro-Diels-Alder fragments 4-methylidene-2-cyclopentenone (12) (33percent) and isoprene (32percent).A further example of the influence of an isolated double bond on the yield of the cyclopentenone-formation sequence A-->C was provided by the comparison of the annelation 14-->20 (5percent overall with Pd(II)-catalysed acylation) with that of its non-olefinic analogue 17-->21 (53percent overall with Friedel-Crafts acylation).