4701-10-4

Usage

InChI:InChI=1/C10H9NO2/c12-11(13)9-5-4-8-10-6-2-1-3-7-10/h1-9H/b8-4+,9-5+

Upstream product

• 75-52-5 nitromethane 
• 1849-29-2 1,1,1-trideuteromethanol 
• 104-55-2 3-phenyl-propenal 
• 108030-46-2 (E,E)-1-(N,N-dimethylamino)-4-nitro-1,3-butadiene 
• 100-58-3 phenylmagnesium bromide 
• 14371-10-9 (E)-3-phenylpropenal 
• 16939-57-4 (E)-buta-1,3-dienylbenzene 
• 1515-78-2 buta-1,3-dien-1-ylbenzene 
• 28010-12-0 5-phenylpenta-2,4-dienoic acid 

Downstream Products

• 1134100-05-2 2-((R,E)-1-nitro-4-phenylbut-3-en-2-yl)-1,3-diphenylpropane-1,3-dione 
• 1211909-71-5 1-((2E,4E)-2-nitro-5-phenylpenta-2,4-dienyl)piperidine 
• 1224739-38-1 C₁₄H₁₄N₂O₂ 
• 1313052-80-0 C₁₅H₁₇NO₄ 
• 1253594-41-0 (2S)-2-[(2S)-1-nitro-4-phenylbut-3-en-2-yl]cyclohexanone 
• 76024-91-4 4-nitro-1-phenyl-1-butene 
• 1435819-78-5 (S)-2-(ethylthio)-4-isopropyl-4-[(S,E)-1-nitro-4-phenylbut-3-en-2-yl]-thiazol-5(4H)-one 
• 7349-06-6 1,5-diphenylpenta-1,3-diene 
• 1609469-10-4 C₁₃H₁₇NO₄*HNO₂ 

Relevant academic research and scientific papers

Palladium-Catalyzed Aminomethylation of Nitrodienes and Dienones via Double C—N Bond Activation

A new strategy for the generation of the active Pd-alkyl species from aminal via C—N bond activation has been established, in which the formation of zwitterionic intermediate through aza-Michael addition of aminal to nitrodienes or dienones is identified as a key step for the activation of the C—N bond. The efficient strategy has enabled a new palladium-catalyzed α-aminomethylation of nitrodienes and dienones via double C—N bond activation. The scope and versatility of the reaction were demonstrated and a broad range of substrates bearing electron-donating and -withdrawing groups on the aromatic rings were all compatible with this reaction to furnish the desired α-aminomethylated products in moderate to good yields with excellent regioselectivities and E/Z selectivities.

Tandem Michael Addition-Cyclization of Nitroalkenes with 1,3-Dicarbonyl Compounds Accompanied by Removal of Nitro Group

A tandem Michael addition-cyclization of nitroalkenes with 1,3-dicarbonyl compounds was developed using phase transfer catalyst (PTC), allowing for the synthesis of polysubstituted-[4,5]-dihydrofuran in high yields. A wide range of substrates were demonst

Geometrically Selective Denitrative Trifluoromethylthiolation of β-Nitrostyrenes with AgSCF3for (E)-Vinyl Trifluoromethyl Thioethers

An efficient copper(II)-promoted denitrative trifluoromethylthiolation under mild reaction conditions has been developed for vinyl trifluoromethyl thioethers to construct Cvinyl-SCF3 bonds with stable AgSCF3 as a source of the trifluoromethylthio. This reaction system tolerates a broad range of functional groups to commendably achieve a high product yield and excellent stereoselectivity of E/Z.

Asymmetric synthesis of tetrahydropyran[3,2-c]quinolinones via an organocatalyzed formal [3 + 3] annulation of quinolinones and MBH 2-naphthoates of nitroolefin

An efficient asymmetric and enantio-swithchable organocatalytic [3 + 3] annulation reaction using MBH-2-naphthoates of nitroalkenes and 4-hydroxyquinolin-2(1H)-ones has been developed. Densely substituted tetrahydropyrano[3,2-c]quinolinones scaffolds with two adjacent stereogenic centers are obtained with high yield (up to 95% yield) and good stereoselectivities (up to >20:1 dr and 96% ee) in an enantio-switchable manner. Furthermore, gram scale synthesis was achieved and the nitro group could easily transform into an amino group without any appreciable loss in the diastereo- and enantioselectivity.

Dealkenylative Alkenylation: Formal σ-Bond Metathesis of Olefins

The dealkenylative alkenylation of alkene C(sp3)?C(sp2) bonds has been an unexplored area for C?C bond formation. Herein 64 examples of β-alkylated styrene derivatives, synthesized through the reactions of readily accessible feedstock olefins with β-nitrostyrenes by ozone/FeII-mediated radical substitutions, are reported. These reactions proceed with good efficiencies and high stereoselectivities under mild reaction conditions and tolerate an array of functional groups. Also demonstrated is the applicability of the strategy through several synthetic transformations of the products, as well as the syntheses of the natural product iso-moracin and the drug (E)-metanicotine.

A Deprotonation Approach to the Unprecedented Amino-Trimethylenemethane Chemistry: Regio-, Diastereo-, and Enantioselective Synthesis of Complex Amino Cycles

The first realization of the amino-trimethylenemethane chemistry is reported using a deprotonation strategy to simplify the synthesis of the amino-trimethylenemethane donor in two steps from commercial and inexpensive materials. A broad scope of cycloaddition acceptors (seven different classes) participated in the chemistry, chemo-, regio-, diastereo-, and enantioselectively generating various types of highly valuable complex amino cycles. Multiple derivatization reactions that further elaborated the initial amino cycles were performed without isolation of the crude product. Ultimately, we applied the amino-trimethylenemethane chemistry to synthesize a potential pharmaceutical in 8 linear steps and 7.5 % overall yield, which previously was achieved in 18 linear steps and 0.6 % overall yield.

One-Step, Effective, and Cascade Syntheses of Highly Functionalized Cyclopentenes with High Diastereoselectivity

Tetrabutylammonium fluoride works as an effective organocatalyst for the cycloaddition between phenacylmalononitriles and electron-deficient olefins (having substituent groups of NO2, CHO, and COR), providing a facile synthetic route to versatile multifunctionalized cyclopentenes having an allylic quaternary carbon center bearing both cyano and carboxamide groups with high yields and high diastereoselectivity. Preliminary studies reveal that these functionalized cyclopentenes are convenient precursors for making α-cyano-functionalized cyclopentadienone oximes.

De novo endo-functionalized organic cages as cooperative multi-hydrogen-bond-donating catalysts

Two endo-functionalized organic cages as oxyanion hole mimics were achieved via dynamic covalent chemistry, which exhibit good size selectivity, catalytic activity and broad substrate scopes for Friedel-Crafts reactions. The modular character of the synth

Distribution of Catalytic Species as an Indicator to Overcome Reproducibility Problems

Irreproducibility is a common issue in catalysis. The ordinary way to minimize it is by ensuring enhanced control over the factors that affect the reaction. When control is insufficient, some parameters can be used as indicators of the reaction performanc

Substituted pyrrole synthesis from nitrodienes

Though the Cadogan-Sundberg approach has been employed to synthesize a variety of indole and carbazole derivatives from nitroarenes, surprisingly, very little is reported for making pyrroles using the same approach from non-arene nitrodienes. Herein, we report a general method to synthesize substituted pyrroles, in one step with modest yields, from nitrodienes using triphenylphosphine in the presence of an Mo catalyst, bis(acetylaceto)dioxomolybdenum (VI). To shed light on the mechanism of this reaction, we performed DFT calculations using uB3LYP/6-31+G(d) basis set and observed that the reaction favors a path through a nitrene intermediate.