10039-57-3

Upstream product

• 6118-51-0 exo-3,6-epoxy-1,2,3,6-tetrahydrophthalic anhydride 
• 62-53-3 aniline 
• 110-00-9 furan 
• 941-69-5 N-phenyl-maleimide 
• 108-31-6 maleic anhydride 

Downstream Products

• 5145-71-1 1-(p-methoxyphenyl)pyrrole 

Relevant academic research and scientific papers

Gas transport in polymers prepared via metathesis copolymerization of exo-N-phenyl-7-oxanorbornene-5,6-dicarboximide and norbornene

This work reports the synthesis of exo-N-phenyl-7-oxanorbornene-5,6-dicarboximide and its ring-opening metathesis copolymerization with norbornene to yield poly(exo-N-phenyl-7-oxanorbornene-5,6-dicarboximide-co-norbornene), with molar ratio 50/50. The glass transition temperature of the copolymer is 125°C. Permeation and sorption processes of different gases (hydrogen, nitrogen, oxygen, carbon monoxide, carbon dioxide, methane, ethylene, and ethane) were measured in membranes prepared by casting from solutions of the copolymer in chloroform. The Langmuir capacity of the gases is relatively small due to the nearness of the glass transition temperature of the polymer to the working temperature. The solution of the most condensable gases in the continuous phase of the membrane is apparently described by the Flory-Huggins theory of polymer-diluent mixtures. In general, the membranes exhibit a reasonably high separation coefficient of hydrogen with respect to ethane, ethylene, nitrogen and methane. The value of α(O2/N2) at room temperature lies in the vicinity of 5.

Polyethylene as a Cosolvent and Catalyst Support in Ring-Opening Metathesis Polymerization

Polyethylene oligomers (PEOlig) can be used as cosolvents and sometimes soluble catalyst supports in ring-opening metathesis polymerization (ROMP) reactions. As a catalyst support, this polyolefin serves as an N-heterocyclic carbene ligand for a ROMP catalyst, making it soluble at 70 °C and insoluble at room temperature. As a cosolvent, unfunctionalized PE oligomers facilitate quantitative separation of PEOlig-bound Ru-catalyst residues from polymer products. In these cases, the insolubility of the unfunctionalized polyethylene (Polywax) and its entrapment of the PEOlig-supported Ru residue in the product phase at room temperature afford ROMP products with Ru contamination lower than other procedures that use soluble catalysts. These separations require only physical processes to separate the product and catalyst residues - no additional solvents are necessary. Control experiments suggest that most (ca. 90%) of the Ru leaching that is seen results from Ru byproducts formed in the vinyl ether quenching step and not from the polymerization processes involving the PEOlig-supported Ru complex. (Chemical Equation Presented).

A simple route for the synthesis of novel norcantharimide derivatives via acidolysis with hydrochloric acid(gas)

In this work, seven new norcantharimide derivatives were synthesized by an acidolysis method. The compounds were prepared by acidolyzing trans-1,4-diacetate and trans-1,2-chloroacetate structures, which were obtained by stereospecific cleavage of the internal etheric bond of the tricyclic imides. The HCl(gas) was produced from the reaction of H2SO4 with NaCl. The resulting gas was bubbled into the reaction mixture. Trans-1,4-diacetate and trans-1,2-chloroacetate were thus acidolyzed, and the corresponding diol and halohydrin products were obtained respectively in moderate overall yields from low-cost starting materials, using simple and easily scalable chemistry. The products were characterized by means of spectroscopic techniques. The synthesized compounds have high potential as anticancer agents and can be valuable for studies in this area.

Structural and theoretical study of four novel norcantharidine derivatives: Two new cases of conditional isomorphism

Structural and theoretical studies of four novel 5,6-dehydronorcantharidine (DNCA)/norcantharidine (NCA) derivatives, namely (3aR,4S,7R,7aS)-2-phenyl-3a,4,7,7a-tetrahydro-4,7-epoxy-1H-isoindole-1,3(2H)-dione, C14H11NO3 (DNCA-A), (3aR,4S,7R,7aS)-2-(4-nitrophenyl)-3a,4,7,7a-tetrahydro-4,7-epoxy-1H-isoindole-1,3(2H)-dione, C14H10N2O5 (DNCA-NA), (3aR,4S,7R,7aS)-2-(4-nitrophenyl)-3a,4,5,6,7,7a-hexahydro-1H-4,7-epoxyisoindole-1,3(2H)-dione, C14H12N2O5 (NCA-NA), and (3aR,4S,7R,7aS)-2-(2-hydroxyethyl)-3a,4,5,6,7,7a-hexahydro-1H-4,7-epoxyisoindole-1,3(2H)-dione, C10H13NO4 (NCA-AE), are reported. The supramolecular interactions and single-crystal structural characteristics of these molecules, together with the crystal structures of four other similar molecules, i.e. NCA-A (the 4-phenyl derivative of NCA-NA), DNCA-AE (the 5,6-unsaturated derivative of NCA-AE), DNCA and NCA, were analysed. Surprisingly, DNCA-A and NCA-A, as well as DNCA-NA and NCA-NA, proved to be isomorphic, while DNCA-AE and NCA-AE, as well as DNCA and NCA, have very different crystal structures. These are very rare isostructural examples between unsaturated and saturated oxanorbornene/oxanorbornane derivatives. To further explore how noncovalent interactions (NCIs) affect the degree of isomorphism in this particular series of rigid molecules where there is a fairly limited conformational degree of freedom, all four pairs of crystal structures were analyzed in parallel. The differentiation in NCIs which entails the packing mode of similar molecules is supported by energy calculations based on real or exchanged crystal structures. Our results show that minor structural differences may result in very different supramolecular interactions, and so lead to altered packing modes in the crystalline solids. Even if isostructurality sometimes occurs, the possibility of various molecular packing types cannot be ruled out. On the other hand, isomorphism may just be the result of kinetic possibilities instead of relative thermodynamic stabilities. Though crystal structure prediction is formidable, the comparison method based on existing crystal structures and quantum calculations can be used to predict the probability of isomorphism. This understanding will help us to design new norbornene derivatives with specified structures.

Synthesis and biological evaluation of new chloro/acetoxy substituted isoindole analogues as new tyrosine kinase inhibitors

We have developed a versatile synthetic approach for the synthesis of new isoindole derivatives via the cleavage of ethers from tricyclic imide skeleton compounds. An exo-cycloadduct prepared from the Diels–Alder reaction of furan and maleic anhydride furnished imide derivatives. The epoxide ring was opened with Ac2O or Ac2O/AcCl in the presence of a catalytic amount of H2SO4 in order to yield new isoindole derivatives 8a-d and 9a-d. The anticancer activity of these compounds was evaluated against the HeLa cell lines. The synthesized compounds showed inhibitory effects on the viability of HeLa cells and the degree of cytotoxicity was increased with the level of bigger branched isoindole derivatives. To better understand the acting mechanism of these molecules, western blot analysis was performed with using mTOR and its downstream substrates. In addition, human mTOR and ribozomal S6 kinase β1 (RS6Kβ1) have been investigated with molecular modelling studies as possible targets for compound series 8 and 9.

Synthesis of Isoxazole-Linked Norcantharidin Analogues of Substituted Chromones

Eighteen novel norcantharidin derivatives, which were substituted by chromone ring, were synthesized in a single step by the [3 + 2] 1,3-dipolar cycloaddition reaction with three oximes in the presence of chloramine-T when compared with the conventional method.

Synthesis of Pyrazole-linked Norcantharidin Analogues of Substituted Chromones

Eighteen novel pyrazole-linked norcantharidin derivatives substituted by chromone ring were synthesized in a single step by the [3+2] 1,3-dipolar cycloaddition reaction of norcantharidin derivatives of substituted aromatic amines with hydrazone in the presence of chloramine-T as compared to the conventional method.

Palladium-Catalyzed [2+1] Cycloadditions Affording Vinylidenecyclopropanes as Precursors of 7-Membered Carbocycles

Palladium(II) acetate in association with secondary phosphine oxides provides an efficient catalytic system for [2+1] cycloadditions starting from oxanorbornene derivatives and tertiary propargyl esters giving rise to vinylidenecyclopropanes. This reaction is specific to bidentate phosphinito-phosphinous acid ligands generated from secondary phosphine oxides. The [2+1] cycloaddition was found broad in scope with a high tolerance to various functional groups. Moreover, vinylidenecyclopropanes were straightforwardly converted into oxabicyclo[3.2.1]oct-2-ene derivatives through a palladium-catalyzed ring-expansion. Finally, the oxa bridge cleavage of oxatricyclic compounds yields functionalized 7-membered carbocycles.

A pyrromonazole Norcantharidin derivative and its preparation method and application

The invention discloses a pyrazol norcantharidin derivative of a chromone structure, and a preparation method and an application of the derivative. The preparation method comprises the following steps: introducing a pyrazol ring into the positions of C5-C6 in a norcantharidin structure by using a 1,3-dipolar cycloaddition method, reacting with a chromone derivative, and introducing into a chromone structure, thereby synthesizing a series of pyrazol norcantharidin derivatives of the chromone structure, wherein the number of the derivatives is 6 in all, and the activity of norcantharidin is improved. The pyrazol norcantharidin derivative of the chromone structure, which is disclosed by the invention, is wide in application prospect when being applied to synthesis of anti-tumor medicines.

Glucoside-containing structured triazole norcantharidin derivative as well as preparation method and application thereof

The invention discloses a glucoside-containing structured triazole norcantharidin derivative as well as a preparation method and application thereof. The preparation method comprises the following steps: introducing 1,2,3-triazole into sites C5 and C6 in a norcantharidin structure by using a 1,3-dipolar cycloaddition method, enabling 1,2,3-triazole to react with 1-nitrine-acetyl-alpha-D-glucose, and introducing a glucoside structure, thereby synthesizing the glucoside-containing structured triazole norcantharidin derivative. The compound has multiple biological activities, and can be used for preparing anti-tumor medicines.