3156-34-1

Usage

Uses

Used in Pharmaceutical Industry:
1-(2-Chlorophenyl)-2-nitroethylene is used as an intermediate for the synthesis of various pharmaceutical compounds, contributing to the development of new drugs and medications.
Used in Agrochemical Industry:
In the agrochemical industry, 1-(2-Chlorophenyl)-2-nitroethylene serves as an intermediate in the production of agrochemicals, aiding in the development of pesticides and other agricultural chemicals to protect crops and enhance agricultural productivity.
Used in Organic Synthesis:
1-(2-Chlorophenyl)-2-nitroethylene is utilized as a precursor for the synthesis of other organic compounds, playing a crucial role in the creation of new chemical entities for various applications across different industries.

InChI:InChI=1/C8H6ClNO2/c9-8-4-2-1-3-7(8)5-6-10(11)12/h1-6H/b6-5+

Upstream product

• 75-52-5 nitromethane 
• 89-98-5 2-chloro-benzaldehyde 
• 89-97-4 2-CHLOROBENZYLAMINE 
• 1794-45-2 2-chlorocinnamaldehyde 
• 3752-25-8 o-chlorocinnamic acid 

Downstream Products

• 10125-43-6 2-Chlor-1-<1,3,3-trinitro-butyl-2>-benzol 
• 77484-21-0 dichloro-3,4 indolinone-2 
• 77484-31-2 acide N-acetyl chloro-2 (o.chlorophenyl)-2 acetohydroxamique 
• 77484-41-4 chlorure de l'acide N-acetoxy chloro-2 (o.chlorophenyl)-2 acetohydroximique 
• 90799-10-3 (1-<2-Chlor-phenyl>-2-nitro-ethylmercapto)-essigsaeure 
• 1092380-03-4 C₂₃H₂₂ClF₃N₂O₆ 
• 60610-77-7 methyl 2-carbomethoxy-4-nitro-3-(2-chloro-phenyl)-butyrate 
• 1094496-70-4 (S)-3-(2-chlorophenyl)-1-(furan-2-yl)-4-nitrobutan-1-one 
• 1094496-72-6 (R)-3-(2-chlorophenyl)-1-(furan-2-yl)-4-nitrobutan-1-one 
• 1092784-91-2 methyl 1-(1-(2-chlorophenyl)-2-nitroethyl)-2-oxocyclopentanecarboxylate 
• 1174179-95-3 (2R)-2-((1S)-1-(2-chlorophenyl)-2-nitroethyl)pentanal 
• 1173094-16-0 ethyl 3-(2-chlorophenyl)-4-nitro-1H-pyrrole-2-carboxylate 
• 1173374-63-4 (S)-dibenzyl 2-(1-(2-chlorophenyl)-2-nitroethyl)malonate 

Relevant academic research and scientific papers

Chiral 4 and 5 - disubstituted pyrrolidine -2 - ketone compound as well as preparation method and application thereof

The invention belongs to the technical field of organic synthesis, and particularly relates to chiral 4, 5 - disubstituted pyrrolidine -2 - ketone compounds as well as a preparation method and application thereof. The invention firstly uses nitro substituted alkyl (I) and trans α, β - unsaturated 3 - methyl -4 - nitroisoxazole (II) as raw materials, and the asymmetric Michael addition reaction of chiral superbase catalysis I and II is a key step and is hydrolyzed. Esterification and reduction closes the ring, synthesizing a chiral 3, 4 - disubstituted pyrrolidine -2 - ketone compound, including optically pure fenoxone. The asymmetric Michael addition reaction of chiral superbase catalyst for catalyzing 2 -substituted nitroethane (I) and trans α, β -unsaturated 3 - methyl -4 - nitroisoxazole (II) is used for preparing chiral 4 and 5 -disubstituted pyrroli -2 - ketone, and a strapdown is provided for synthesizing chiral 4 and 5 - disubstituted pyrrolidine -2 - ketone skeleton.

NHC-Catalyzed Dual Stetter Reaction: A Mild Cascade Annulation for the Syntheses of Naphthoquinones, Isoflavanones, and Sugar-Based Chiral Analogues

The N-heterocycle carbene (NHC)-catalyzed dual Stetter cascade reaction is discovered through coupling of β-nitrostyrene with phthalaldehyde under mild conditions to furnish valuable aryl-naphthoquinones. The generality of the new reaction is validated through the development of a C-C and O-C bond forming Stetter cascade reaction using salicylaldehydes to obtain functionalized dihydroisoflavanones. The mild NHC organocatalysis is successfully employed for the construction of optically pure sugar-based naphthoquinones and dihydroisoflavanones. Herein, NHC is found as a unique and powerful organocatalyst to construct homoatomic C-C cross-coupling, heteroatomic O-C bond formation, and cascade cyclization utilizing NO2 as a leaving group at ambient temperature. A mechanistic pathway of the new metal-free catalysis is predicted on the basis of our ESI-MS study of the ongoing reaction and literature.

Comprehensive evaluation of antioxidant effects of Japanese Kampo medicines led to identification of Tsudosan formulation as a potent antioxidant agent

Oxidative stress due to the overproduction of reactive oxygen species plays an important role in the pathogenesis of various diseases. In the present study, we comprehensively evaluated the antioxidant activities of 147 oral formulations of Japanese traditional herbal medicines (Kampo medicines), representing the entire panel of oral Kampo medicines listed in the Japanese National Health Insurance Drug List, using in vitro radical scavenging assays, including the 2,2-diphenyl-1-picrylhydrazyl free radical scavenging activity assay, the superoxide anion scavenging activity assay, and the oxygen radical absorption capacity assay. Three of the formulations tested, namely, Tsudosan, Daisaikoto, and Masiningan, showed the most potent in vitro antioxidant activities and were selected for further investigation of their intracellular and in vivo antioxidant effects. The results of the 2′,7′-dichlorodihydrofluorescin diacetate assay demonstrated that all three Kampo medicines significantly inhibited hydrogen peroxide-induced oxidative stress in human hepatocellular liver carcinoma HepG2 cells. In addition, Tsudosan significantly increased the serum biological antioxidant potential values when orally administrated to mice, indicating that it also had in vivo antioxidant activity. The potent antioxidant activity of Tsudosan may be one of the mechanisms closely correlated to its clinical usage against blood stasis.

Facile Synthesis of 1,3,5-Triarylbenzenes and 4-Aryl-NH-1,2,3-Triazoles Using Mesoporous Pd-MCM-41 as Reusable Catalyst

We report mesoporous nano-Pd-MCM-41 catalyzed rapid and efficient synthesis of 1,3,5-triarylbenzenes via de-nitrative cyclotrimerization of β-nitrostyrenes. All the reactions were very fast and high yielding. The Pd-MCM-41 was also very effective in catalyzing de-nitrative [3+2] cycloaddition of β-nitrostyrenes with TMSN3 to synthesize 4-aryl-NH-1,2,3-triazoles. The catalyst was reused at least up to eight times with minimum loss of catalytic activity.

Cinnamic acid derivative and preparation method and application thereof

The invention provides a cinnamic acid derivative. The cinnamic acid derivative is of the structure as shown in the formula I. The invention also provides two methods for preparing the cinnamic acid derivative. The two methods depend on a single bond or double bonds in the structure shown in the formula I. The invention further provides a pesticide. The pesticide comprises the cinnamic acid derivative. In addition, the invention provides a sterilization method. The sterilization method includes the step of applying the cinnamic acid derivative or the pesticide to crops. The crops include rice,wheat, fruit trees and vegetables. The low-toxicity, low-residue-content and high-activity environment-friendly cinnamic acid derivative is developed, and the cinnamic acid derivative pesticide can replace traditional high-toxicity and high-residue-content pesticides.

Substrate promiscuity of ortho-naphthoquinone catalyst: Catalytic aerobic amine oxidation protocols to deaminative cross-coupling and n-nitrosation

ortho-Naphthoquinone-based organocatalysts have been identified as versatile aerobic oxidation catalysts. Primary amines were readily cross-coupled with primary nitroalkanes via deaminative pathway to give nitroalkene derivatives in good to excellent yields. Secondary and tertiary amines were inert to ortho-naphthoquinone catalysts; however, secondary nitroalkanes were readily converted by ortho-naphthoquinone catalysts to the corresponding nitrite species that in situ oxidized the amines to the corresponding N-nitroso compounds. Without using harsh oxidants in a stoichiometric amount, the present catalytic aerobic oxidation protocol utilizes the substrate promiscuity feature to provide a facile access to amine oxidation products under mild reaction conditions.

Base-catalyzed reactions enhanced by solid acids: Amine-catalyzed nitroaldol (Henry) reactions enhanced by silica gel or mesoporous silica SBA-15

The reactions of various aldehydes with CH3NO2 catalyzed by Et3N, n-C6H13NH2, and Me2N(CH2)2NH2 were accelerated by the addition of silica gel to give aromatic (aliphatic) β-nitroalcohols, aromatic nitroalkenes, and aromatic 1,3-dinitroalkanes, respectively. Mesoporous silica SBA-15 showed higher activity than silica gel for the synthesis of aromatic nitroalkenes by the reactions of the corresponding aldehydes with CH3NO2 catalyzed by n-C6H13NH2.

Squaramide-Linked Chloramphenicol Base Hybrid Catalysts for the Asymmetric Michael Addition of 2,3-Dihydrobenzofuran-2-carboxylates to Nitroolefins

An array of hybrid catalysts incorporating a chloramphenicol base moiety linked to another chiral scaffold through a squaramide linker were developed and successfully used in the Michael addition of 2,3-dihydrobenzofuran-2-carboxylates to nitroolefins. Control experiments suggested that the hybrid catalysts were more reactive than nonhybridized bifunctional catalysts, and matching of the chirality between the two scaffolds was crucial for high reactivity and stereoselectivity. These hybrid organocatalysts could be used with a variety of substrates. At a 0.5 mol-% catalyst loading, a range of 2,3-dihydrobenzofuran-2-carboxylates derivatives bearing quaternary and tertiary stereogenic centers were obtained in high yields (up to 98 %) with excellent enantioselectivities (up to 99 % ee) and moderate diastereoselectivities (up to 8:92 dr).

Method for synthesizing nitroolefin compound

The invention relates to a method for synthesizing an organic compound. The method is used for solving the problem of current synthesis of nitroolefin compounds that reaction byproducts are numerous,raw materials are expensive, and some methods are relatively troublesome in aftertreatment. The invention provides a method for preparing a nitroolefin compound. The nitroolefin compound is prepared through subjecting a cinnamyl aldehyde compound, which serves as a starting material, to a reaction with a nitrate and a solvent for 1 to 24 hours at the temperature of 25 DEG C to 150 DEG C. A methodfor direct nitration by using a cheap nitrate is achieved. The method is a new route for synthesizing the nitroolefin compound.

Catalyst-free sulfa-Michael addition of pyrimidine-2-thiol to nitroolefins

Catalyst-free sulfa-Michael addition of pyrimidine-2-thiol to nitroolefins is described. A series of 2-((2-nitro-1-arylethyl)thio)pyrimidines were efficiently synthesized. The protocol has advantages of wide range of substituents tolerance, no catalyst, additives and bases, mild condition, and high yield. The method can also extend to gram scale.