52909-94-1

Usage

Uses

Used in Pharmaceutical Synthesis:
2-(3,4-DICHLORO-PHENYL)-OXIRANE is used as a key intermediate in the synthesis of various pharmaceuticals. Its unique structure allows for the creation of a wide range of medicinal compounds, contributing to the development of new drugs and therapies.
Used in Organic Chemical Synthesis:
In the field of organic chemistry, 2-(3,4-DICHLORO-PHENYL)-OXIRANE serves as a versatile building block for the synthesis of different organic compounds. Its reactivity enables the formation of various chemical bonds, facilitating the production of a diverse array of organic molecules.
Used in Agricultural Applications:
2-(3,4-DICHLORO-PHENYL)-OXIRANE is studied for its potential use as a fungicide in agriculture. Its ability to inhibit fungal growth could lead to the development of new and effective crop protection agents, enhancing crop yields and food security.
Used in Chemical Research:
Due to its reactivity and unique structure, 2-(3,4-DICHLORO-PHENYL)-OXIRANE is also utilized in chemical research to explore new reaction pathways, understand the mechanisms of epoxide reactions, and develop innovative synthetic methods. This research can contribute to the advancement of chemical science and the discovery of new applications for 2-(3,4-DICHLORO-PHENYL)-OXIRANE.

InChI:InChI=1/C8H6Cl2O/c9-6-2-1-5(3-7(6)10)8-4-11-8/h1-3,8H,4H2

Upstream product

• 2632-10-2 2-bromo-1-(3,4-dichlorophenyl)ethanone 
• 2039-83-0 3,4-dichlorostyrene 
• 2642-63-9 3',4'-dichloroacetophenone 
• 1475-11-2 1-(3,4-dichlorophenyl)ethan-1-ol 

Downstream Products

• 18970-70-2 2-[2-(2-Chloro-phenyl)-ethylamino]-1-(3,4-dichloro-phenyl)-ethanol 
• 30332-45-7 2-diethylamino-1-(3,4-dichloro-phenyl)-ethanol 
• 5402-86-8 2-dibutylamino-1-(3,4-dichloro-phenyl)-ethanol 
• 2971-04-2 2-Diallylamino-1-<3,4-dichlor-phenyl>-aethanol 
• 30332-47-9 2-dibenzylamino-1-(3,4-dichloro-phenyl)-ethanol 
• 19045-46-6 1-(3,4-Dichloro-phenyl)-2-[2-(3,4-dichloro-phenyl)-2-hydroxy-ethylamino]-ethanol 
• 1475-11-2 1-(3,4-dichlorophenyl)ethan-1-ol 
• 35364-79-5 2-(3,4-dichlorophenyl)ethanol 
• 1095616-43-5 2-(3,4-dichlorophenyl)-2-hydroperoxyethanol 
• 586418-02-2 (R)-1-(3,4-dichlorophenyl)-1,2-ethanediol 
• 1255924-12-9 4-(3,4-dichlorophenyl)-7-(6-(trifluoromethyl)pyridazin-3-yl)-1,1-dimethyl-1,2,3,4-tetrahydroisoquinoline 

Relevant academic research and scientific papers

Reprogramming Epoxide Hydrolase to Improve Enantioconvergence in Hydrolysis of Styrene Oxide Scaffolds

Enantioconvergent hydrolysis by epoxide hydrolase is a promising method for the synthesis of important vicinal diols. However, the poor regioselectivity of the naturally occurring enzymes results in low enantioconvergence in the enzymatic hydrolysis of styrene oxides. Herein, modulated residue No. 263 was redesigned based on structural information and a smart variant library was constructed by site-directed modification using an “optimized amino acid alphabet” to improve the regioselectivity of epoxide hydrolase from Vigna radiata (VrEH2). The regioselectivity coefficient (r) of variant M263Q for the R-isomer of meta-substituted styrene oxides was improved 40–63-fold, and variant M263V also exhibited higher regioselectivity towards the R-isomer of para-substituted styrene oxides compared with the wild type, which resulted in improved enantioconvergence in hydrolysis of styrene oxide scaffolds. Structural insight showed the crucial role of residue No. 263 in modulating the substrate binding conformation by altering the binding surroundings. Furthermore, increased differences in the attacking distance between nucleophilic residue Asp101 and the two carbon atoms of the epoxide ring provided evidence for improved regioselectivity. Several high-value vicinal diols were readily synthesized (>88% yield, 90%–98% ee) by enantioconvergent hydrolysis using the reprogrammed variants. These findings provide a successful strategy for enhancing the enantioconvergence of native epoxide hydrolases through key single-site mutation and more powerful enzyme tools for the enantioconvergent hydrolysis of styrene oxide scaffolds into single (R)-enantiomers of chiral vicinal diols. (Figure presented.).

ARYL, HETEROARYL, AND HETEROCYCLE SUBSTITUTED TETRAHYDROISOQUINOLINES AND USE THEREOF

Novel aryl, heteroaryl, and non-aromatic heterocyle substituted tetrahydroisoquinolines are described in the present invention. These compounds are used in the treatment of various neurological and physiological disorders. Methods of making these compounds are also described in the present invention.

Modified ibogaine fragments: Synthesis and preliminary pharmacological characterization of 3-ethyl-5-phenyl-1,2,3,4,5,6-hexahydroazepino[4,5- b]benzothiophenes

Five phenyl-substituted derivatives and analogues of 1,2,3,4,5,6- hexahydroazepino[4,5-b]indole, 5, a major fragment of ibogaine (1), were synthesized and tested for binding to monoamine transporters, the NMDA receptor-coupled cation channel, and dopamine and opioid receptors. All five derivatives, 9 and 17a-d, displayed 8-10-fold higher affinity at the DA transporter than ibogaine and noribogaine (4). At the serotonin transporter, two compounds (9 and 17a) exhibited higher potency than ibogaine, while the rest had weaker binding affinities than the lead compound. In keeping with their structural similarity to ibogaine, all five compounds displayed weak to poor affinity for dopamine D1 and D2 receptors. However, two compounds, 17a,c, demonstrated moderate binding affinities at dopamine D3 receptors. All five compounds displayed weak to poor affinities for μ and κ opioid receptors and for the NMDA receptor-coupled cation channel. Despite the qualitative differences, derivatives and analogues of 5 may serve as useful substitutes for ibogaine.

N-hydroxyalkyl derivatives of 3β-phenyltropane and 1-methylspiro[1H- indoline-3,4'-piperidine]: Vesamicol analogues with affinity for monoamine transporters

As part of our ongoing structure-activity studies of the vesicular acetylcholine transporter ligand 2-(4-phenylpiperidino)cyclohexanol [vesamicol, 1), 22 N-hydroxy(phenyl)alkyl derivatives of 3β-phenyltropane, 6, and 1-methylspiro[1H-indoline-3,4'-piperidine], 7, were synthesized and tested for binding in vitro. Although a few compounds displayed moderately high affinity for the vesicular acetylcholine transporter, no compound was more potent than the prototypical vesicular acetylcholine transporter ligand vesamicol. However, a few derivatives of 6 displayed higher affinity for the dopamine transporter than cocaine. We conclude that modification of the piperidyl fragment of 1 will not lead to more potent vesicular acetylcholine transporter ligands.