37629-52-0

Usage

Chemical structure

A derivative of propene with a chlorophenyl group and a nitro group

Usage

Intermediate in the synthesis of various organic compounds

Applications

Production of pharmaceuticals, agrochemicals, and specialty chemicals

Reactivity

Known to possess certain reactivity

Toxicity

Known to possess certain toxicity

Handling precautions

Should be handled with proper care and precautions

InChI:InChI=1/C9H8ClNO2/c1-7(11(12)13)6-8-2-4-9(10)5-3-8/h2-6H,1H3/b7-6+

Upstream product

• 79-24-3 Nitroethane 
• 104-88-1 4-chlorobenzaldehyde 
• 27852-91-1 1-(4-chlorophenyl)-2-nitro-propan-1-ol 
• 873-76-7 para-Chlorobenzyl alcohol 

Downstream Products

• 10341-75-0 (E)-1-phenylethanone oxime 
• 69361-54-2 ((4-chlorophenyl)methylene)dibenzene 
• 5586-88-9 1-(4-chlorophenyl)propan-2-one 
• 929878-89-7 4-(4-chlorophenyl)-3,6,6-trimethyl-5,6-dihydro-4H-1,2-oxazine 2-oxide 
• 1163136-87-5 C₉H₁₀ClNO₂ 
• 1163136-86-4 1-chloro-4-(2-nitro-1(Z)-propenyl)benzene 
• 1574110-55-6 1-benzyl-3-(4-chlorophenyl)-N,N,4-trimethyl-5-(trifluoromethyl)-1H-pyrrole-2-carboxylic acid amide 
• 1574110-57-8 [1-benzyl-3-(4-chlorophenyl)-4-methyl-5-(trifluoromethyl)-1H-pyrrol-2-yl]-(1-oxo-[1,4]-thiazinan-4-yl)methanone 
• 1574110-65-8 1-benzyl-3-(4-chlorophenyl )-N,4-dimethyl-5-(trifluoromethyl)-1H-pyrrole-2-carboxylic acid amide 
• 1574110-75-0 [1-benzyl-3-(4-chlorophenyl)-4-methyl-5-(trifluoromethyl)-1H-pyrrol-2-yl]-(1,1-dioxo-[1,4]-thiazinan-4-yl)methanone 
• 1574110-80-7 [3-(4-chlorophenyl)-1-(3-methoxyphenyl)-4-methyl-5-(trifluoromethyl)-1H-pyrrol-2-yl]-(3,3-difluoro-azetidin-1-yl)-methanone 
• 1574111-14-0 1-benzyl-3-(4-chlorophenyl)-N-[1-(hydroxymethyl)-cyclopropyl]-N,4-dimethyl-5-(trifluoromethyl)-1H-pyrrole-2-carboxylic acid amide 
• 1574111-17-3 1-benzyl-N-(1-carbamoyl-cyclopropyl)-3-(4-chlorophenyl)-N,4-dimethyl-5-(trifluoromethyl)-1H-pyrrole-2-carboxylic acid amide 

Relevant academic research and scientific papers

Regioselective Opening of Nitroepoxides with Unsymmetrical Diamines

Nitroepoxides are easily transformed into benzodiazepines, tetrahydrobenzodiazepines, imidazopyridines, and N-alkyl tetrahydroquinoxalines by treatment with 2-aminobenzylamines, 2-aminopyridines, and N-alkyl 1,2-diaminobenzenes, respectively. Regioselectivity is controlled through attack of the most nucleophilic nitrogen of the unsymmetrical diamine to the β position of the epoxide. These reactions represent an efficient way to prepare privileged bioactive structures.

Catalyst- and Substituent-Controlled Switching of Chemoselectivity for the Enantioselective Synthesis of Fully Substituted Cyclobutane Derivatives via 2 + 2 Annulation of Vinylogous Ketone Enolates and Nitroalkene

The first regioselective, diastereoselective, and enantioselective organocatalyzed Michael-Michael cascade of vinylogous ketone enolates and nitroalkenes for the construction of fully substituted cyclobutanes is achieved by the deployment of the appropriate chiral squaramide catalyst and the pertinent substituent on the substrate. The domino reaction provided cyclobutanes with four contiguous stereocenters, including a quaternary center in good yields with diastereomeric ratio of >20:1 and with enantioselectivities of mostly up to 98% enantiomeric excess (ee). The structures and the absolute configurations of the adducts were confirmed by single-crystal X-ray crystallographic analyses of the appropriate products.

Synthesis, antiproliferative and pro-apoptotic effects of nitrostyrenes and related compounds in Burkitt’s lymphoma

Background: Cancers of the lymphatic cells (lymphomas) account for approximately 12% of malignant diseases worldwide. The nitrostyrene scaffold is identified as a lead target structure for the development of particularly effective compounds targeting Burkitt’s lymphoma (BL). Objectives: The aims of the curent study were to synthesise a panel of nitrostyrene compounds and to evaluate their activity in Burkitt’s lymphoma (BL). Methods: A panel of structurally varied compounds were designed and synthesised using Henry Knoevenagel condensation reactions. Single crystal X-Ray analysis confirmed the E configuration for six examples of these novel structures. A number of nitrostyrene-related compounds were also investigated including 1,3-bis(aryl)-2-nitropropenes together with heterocyclic scaffolds containing the nitrovinyl pharmacophore such as 3-nitro-2-phenyl-2H-chromenes. The antiproliferative activities of the compounds were evaluated using the BL cell lines EBV- MUTU-1 and EBV+ DG-75 (chemoresistant) to establish preliminary structure-activity relationships. Results: Lead compounds with optimized nitrostyrene scaffolds and 3-nitro-2-phenyl-2Hchromene structures were successfully established with typical IC50 values of 0.45 μM and 0.47 μM in MUTU-1 cells and 1.41 μM and 1.92 μM, respectively, in DG-75 cells. The mechanism of cell death was identified as apoptotic and the lead compound was found to elicit comparable apoptotic effects to Taxol in Burkitt’s lymphoma cell lines MUTU-1 and DG-75. Conclusion: This class of pharmaceutically active compounds with potential for the treatment of Burkitt’s lymphoma suggest a potential role for nitrostyrene based agents in chemotherapy.

Catalytic asymmetric Tamura cycloadditions involving nitroalkenes

The first examples of asymmetric Tamura cycloaddition reactions involving singly activated alkenes are reported. Homophthalic anhydride reacts with α-methyl nitrosytrenes in the presence of an alkaloid-based catalyst to generate fused bicyclic aromatic ketone products with three new stereocentres (which are susceptible to subsequent equilibration) in 12-99% ee. An unusual equilibration process which occurs in methanolic medium in the absence of a recognisable base via proton transfer at the α-carbon of an ester was investigated experimentally and computationally.

Catalytic enantioselective epoxidation of nitroalkenes

Nitroepoxides are potentially exploitable as synthons with vicinal electrophilic centers. Nevertheless, although advances have been made in the field, enantioselective epoxidation of nitroalkenes is still a challenging process. Herein we show a convenient procedure for the preparation of optically active nitroepoxides in high enantiomeric excess and high chemical yield. The kinetic data of the best catalyst have been examined using computational methods based on DFT calculations. Interestingly, the results demonstrate that the enantioselectivity of the epoxidation of nitroalkenes by this kind of catalyst is not only kinetically but also thermodynamically controlled.

FLUOROMETHYL-SUBSTITUTED PYRROLE CARBOXAMIDES III

The invention relates to pyrrole carboxamides bearing a fluoromethyl- moiety as voltage gated calcium channel blockers, to pharmaceutical compositions containing these compounds and also to these compounds for use in the treatment and/or prophylaxis of pa

FLUOROMETHYL-SUBSTITUTED PYRROLE CARBOXAMIDES IV

The invention relates to pyrrole carboxamides bearing a fluoromethyl- moiety as voltage gated calcium channel blockers, to pharmaceutical compositions containing these compounds and also to these compounds for use in the treatment and/or prophylaxis of pain and further diseases and/or disorders.

FLUOROMETHYL-SUBSTITUTED PYRROLE CARBOXAMIDES

The invention relates to pyrrole carboxamides bearing a fluoromethyl-moiety as voltage gated calcium channel blockers, to pharmaceutical compositions containing these compounds and also to these compounds for use in the treatment and/or prophylaxis of pain and further diseases and/or disorders.

FLUOROMETHYL-SUBSTITUTED PYRROLE CARBOXAMIDES

The invention relates to pyrrole carboxamides bearing a fluoromethyl- moiety as voltage gated calcium channel blockers, to pharmaceutical compositions containing these compounds and also to these compounds for use in the treatment and/or prophylaxis of pain and further diseases and/or disorders.

Enantioselective hydrogenation of α,β-disubstituted nitroalkenes

The first highly chemo- and enantioselective hydrogenation of α,β-disubstituted nitroalkenes was accomplished with rhodium/JosiPhos-J2 as a catalyst, with the yield and enantioselectivity of up to 95% and 94%, respectively. The α-chiral nitroalkanes will provide an entry to valuable chiral amphetamines which are otherwise not so easily accessed. This journal is the Partner Organisations 2014.