79836-44-5

Usage

Uses

Used in Pharmaceutical Synthesis:
4-(3,4-Dichlorophenyl)-3,4-dihydro-1(2H)-naphthalenone is used as a precursor in the pharmaceutical industry for the synthesis of various pharmaceuticals and organic compounds. Its unique structure and functional groups make it a valuable building block in the development of new drugs and therapeutic agents.
Used in Medicinal Chemistry Research:
In the field of medicinal chemistry, 4-(3,4-Dichlorophenyl)-3,4-dihydro-1(2H)-naphthalenone is employed as a research compound to explore its potential biological and pharmacological activities. Its complex structure and chemical properties provide opportunities for investigating its interactions with biological targets and evaluating its efficacy in treating various diseases and conditions.
Used in Organic Chemistry:
4-(3,4-Dichlorophenyl)-3,4-dihydro-1(2H)-naphthalenone is utilized in organic chemistry as a versatile intermediate for the synthesis of a wide range of organic compounds. Its reactivity and functional groups allow for various chemical reactions and transformations, enabling the preparation of diverse organic molecules with potential applications in various industries.
Used in Drug Development:
In the drug development process, 4-(3,4-Dichlorophenyl)-3,4-dihydro-1(2H)-naphthalenone serves as a key compound for the design and synthesis of new drug candidates. Its potential biological activities and pharmacological properties make it an attractive target for the development of innovative therapeutic agents to address unmet medical needs.
Used in Chemical Education and Training:
4-(3,4-Dichlorophenyl)-3,4-dihydro-1(2H)-naphthalenone is also used in chemical education and training programs to teach students and researchers about the synthesis, properties, and applications of complex organic compounds. Its unique structure and reactivity provide valuable learning opportunities for understanding the principles of organic chemistry and the development of new synthetic strategies.

Upstream product

• 95-50-1 1,2-dichloro-benzene 
• 95609-48-6 rac-5-(3,4-dichlorophenyl)dihydrofuran-2(3H)-one 
• 866018-46-4 4-(3,4-dichlorophenyl)-1,2,3,4-tetrahydro-naphthalen-1-ol 
• 127404-77-7 (E)-4-(3,4-dichlorophenyl)but-3-enoic acid 
• 123849-23-0 (R)-(+)-1-hydroxy-1,2-dihydronaphthalene 
• 90-15-3 α-naphthol 
• 79560-19-3 4-(3,4-dichlorophenyl)-3,4-dihydro-2H-naphthalen-1-one 
• 1063723-88-5 (S)-N,N-diisopropylcarbamic acid 1-phenyl-but-3-enyl ester 
• 1338922-77-2 (R)-2-(1-(3,4-dichlorophenyl)-1-phenylbut-3-enyl)-4,4,5,5-tetramethyl-[1,3,2]-dioxaborolane 
• 1338922-76-1 (R)-1,2-dichloro-4-(1-phenylbut-3-enyl)benzene 
• 80735-94-0 1-Phenyl-3-buten-1-ol 
• 77118-87-7 (S)-1-Phenyl-3-buten-1-ol 
• 100-52-7 benzaldehyde 
• 151169-75-4 3,4-dichlophenylboronic acid 

Downstream Products

• 1271002-87-9 C₂₂H₂₅Cl₂NO₂ 
• 1186422-36-5 4(S)-(3,4-dichlorophenyl)-3,4-dihydro-N-methyl-1(2H)-naphthalenimine 
• 1333478-73-1 C₂₅H₁₉Cl₂N₃O 
• 1333478-74-2 C₂₆H₂₁Cl₂N₃O₂ 
• 1333478-76-4 C₂₇H₂₃Cl₂N₃O₃ 
• 1333478-77-5 C₂₉H₂₁Cl₂N₃O 
• 1006692-60-9 N-((S)-1-(3,4-dichlorophenyl)-1,2-dihydronaphthalen-4-yl)acetamide 
• 1234376-87-4 7-(3,4-dichlorophenyl)-3-(4-methoxybenzyl)-6,7-dihydro-3H-benzo[f]pyrazolo[3,4-c]isoquinoline 
• 1234371-47-1 7-(3,4-dichlorophenyl)-6,7-dihydro-3H-benzo[f]pyrazolo[3,4-c]isoquinoline 

Relevant academic research and scientific papers

Discovery of sertraline and its derivatives able to combat drug-resistant gastric cancer cell via inducing apoptosis

Resistance phenomena during chemotherapy of tumor has been severely hampering the applications of chemotherapeutics. Due to advantage of drug repurposing, discovery of new chemosensitizers based on approved drugs is an effect strategy to find new candidates. Herein, we found antidepressant drug – sertraline, could sensitize drug-resistant gastric cancer cell (SGC-7901/DDP) with the IC50 value of 18.73 μM. To understand the structure–activity relationship and improve the activity, 30 derivatives were synthesized and evaluated. The IC50 value of the best compound was improved to 5.2 μM. Moreover, we found apoptosis induction and cell cycle arrest was the reason for the cell death of the drug-resistant cells after treatment of sertraline and derivatives, and PI3K/Akt/mTOR pathway was involved.

Sertraline side chain amino structure derivative as well as preparation method and application thereof

The structural formula of the sertraline side chain amino structure derivative is shown as a formula I or a formula II, wherein R1 is H or cyclopropanyl, and R2 is selected from alkyl, naphthyl, alkylamine, cyclopropanyl, phenyl, or phenyl of which the No.3 position and/or the No.4 position is substituted by alkyl, methoxyalkyl, haloalkyl and halogen; and R3 is a hydrogen group or a 1-halogenated alkyl group. The invention also provides a preparation method of the sertraline derivative and application of the sertraline derivative in preparation of a medicine for treating gastric cancer. The sertraline derivative provided by the invention has an obvious sensitization effect on drug-resistant gastric cancer cells.

Copper-Catalyzed Enantioselective Arylation via Radical-Mediated C-C Bond Cleavage: Synthesis of Chiral ω,ω-Diaryl Alkyl Nitriles

The first example of copper-catalyzed ring-opening, enantioselective arylation of cyclic ketoxime esters to access ω,ω-diaryl alkyl nitriles has been developed in high yield (up to 92% yield) with excellent enantioselectivity (up to 91% ee). Side-arm bis(oxazoline) ligand plays a significant role in this asymmetric catalytic transformation, which provides an efficient route to construct diverse chiral ω,ω-diaryl alkyl nitriles. Synthetic utility has also been demonstrated in the further derivatization of the ω,ω-diaryl alkyl nitrile to the corresponding amide.

Exploring the synthetic potential of a marine transaminase including discrimination at a remote stereocentre

The marine transaminase, P-ω-TA, can be employed for the transamination from 1-aminotetralins and 1-aminoindanes with differentiation of stereochemistry at both the site of reaction and at a remote stereocentre resulting in formation of ketone products with up to 93% ee. While 4-substituents are tolerated on the tetralin core, the presence of 3- or 8-substituents is not tolerated by the transaminase. In general P-ω-TA shows capacity for remote diastereoselectivity, although both the stereoselectivity and efficiency are dependent on the specific substrate structure. Optimum efficiency and selectivity are seen with 4-haloaryl-1-aminotetralins and 3-haloaryl-1-aminoindanes, which may be associated with the marine origin of this enzyme. This journal is

Titanium(IV)-Mediated Ring-Opening/Dehydroxylative Cross-Coupling of Diaryl-Substituted Methanols with Cyclopropanol Derivatives

A titanium(IV)-mediated ring-opening/dehydroxylative cross-coupling of diaryl-substituted methanols with a cyclopropanol derivative was developed. The reactions proceeded efficiently to provide synthetically useful γ,γ-diaryl esters in moderate to good yields, which could be applied to the functionalization of complex molecules derived from bioactive fenofibrate and isoxepac and the synthesis of a precursor of Zoloft.

Chemoenzymatic Synthesis of Sertraline

A chemoenzymatic approach has been developed for the preparation of sertraline, an established anti-depressant drug. Ketoreductases (KREDs) were employed to yield a key chiral precursor. The bioreduction of the racemic tetralone exhibited excellent enantioselectivity (>99 % ee) and diastereomeric ratio (99:1) at 29 % conversion (the maximum theoretical yield is 50 %) after 7 hours. The resulting (S,S)-alcohol was efficiently oxidized to an enantiopure (S)-ketone, an immediate precursor of sertraline, by using sodium hypochlorite as oxidant and 2-azaadamantane N-oxyl (AZADO) as organocatalyst. Alternative routes aiming at the direct biocatalytic amination using imine reductases and transaminases were unsuccessful.

Method for preparing serrine hydrochloride intermediate and impurities

The invention relates to a method for preparing a sertraline hydrochloride intermediate and an impurity. The invention provides a method for refining 4-(3,4-dichlorophenyl)-3,4-dihydro-1(2H)-naphthalenone. The content of the impurity 4-(2,3-dichlorophenyl)-3,4-dihydro-1(2H)-naphthalenone in the obtained product is less than 0.1%. The invention also relates to a method for preparing the isomer impurity 4-(2,3-dichlorophenyl)-3,4-dihydro-1(2H)-naphthalenone from the mother solution.

Nickel-Catalyzed α-Carbonylalkylarylation of Vinylarenes: Expedient Access to γ,γ-Diarylcarbonyl and Aryltetralone Derivatives

We report a Ni-catalyzed regioselective α-carbonylalkylarylation of vinylarenes with α-halocarbonyl compounds and arylzinc reagents. The reaction works with primary, secondary, and tertiary α-halocarbonyl molecules, and electronically varied arylzinc reagents. The reaction generates γ,γ-diarylcarbonyl derivatives with α-secondary, tertiary, and quaternary carbon centers. The products can be readily converted to aryltetralones, including a precursor to Zoloft, an antidepressant drug.

Identification of an Esterase Isolated Using Metagenomic Technology which Displays an Unusual Substrate Scope and its Characterisation as an Enantioselective Biocatalyst

Evaluation of an esterase annotated as 26D isolated from a marine metagenomic library is described. Esterase 26D was found to have a unique substrate scope, including synthetic transformations which could not be readily effected in a synthetically useful manner using commercially available enzymes. Esterase 26D was more selective towards substrates which had larger, more sterically demanding substituents (i. e. iso-propyl or tert-butyl groups) on the β-carbon, which is in contrast to previously tested commercially available enzymes which displayed a preference for substrates with sterically less demanding substituents (e.g. methyl group) at the β-carbon. (Figure presented.).

Correction to: Nickel-catalyzed asymmetric reductive cross-coupling to access 1,1-diarylalkanes (Journal of the American Chemical Society (2017) 139 (5684-5687) DOI: 10.1021/jacs.7b01705)

Pages 5684 and 5685, Table of Contents, and Supporting Information. The stereochemistry of L1, depicted as the (S,S)- enantiomer in Figure 1, Table 1, the TOC graphic (identical to Figure 1), and the Supporting Information of the original publication, was incorrect. (R,R)-L1 was used in this study. The stereochemistry of (R,R)-L1 has been confirmed by singlecrystal X-ray diffraction; the X-ray diffraction data and CIF file for (R,R)-L1 have been added to the Supporting Information. The corrected TOC graphic/Figure 1 is shown here. (R,R)-L4 and (R,R)-L5 were also used in Table 1 and incorrectly depicted as (S,S)-L4 and (S,S)-L5 in the original publication. To reflect that different enantiomeric series of catalysts were used, Table 1 has been updated to indicate that entries 2, 3, and 6 produce (S)-3a. This correction does not change the stereochemical assignment of the diarylalkane products, or the conclusions of the Communication. The stereochemistry of the products was assigned by obtaining an X-ray structure of diarylalkane 3k, and the rest of the compounds were assigned by analogy. (Table Presented).