85662-98-2

Upstream product

• 140-10-3 (E)-3-phenylacrylic acid 
• 95-50-1 1,2-dichloro-benzene 
• 7312-27-8 3,4-Dichlorocinnamic acid 
• 71-43-2 benzene 
• 2142-69-0 2-bromophenyl methyl ketone 
• 108-86-1 bromobenzene 
• 873-32-5 2-Chlorobenzonitrile 
• 5653-29-2 2-(1,3-dithiolan-2-yl)-1-phenylethan-1-one 
• 2142-70-3 2-iodoacetophenone 
• 620964-90-1 3-(3,4-dichlorophenyl)-1H-inden-1-one 
• 80272-06-6 3-(3',4'-dichlorophenyl)-3-phenylpropanoic acid 
• 40774-41-2 3-Bromoindan-1-one 
• 551-93-9 2-aminoacetophenone 
• 87694-37-9 4-methyl-N'-(3-oxo-2,3-dihydro-1H-inden-1-ylidene)benzenesulfonohydrazide 

Downstream Products

• 80272-59-9 cis-3-(3,4-dichlorophenyl)-2,3-dihydro-1H-inden-1-ol 
• 85720-99-6 3-(3,4-dichloro-phenyl)-indan-1-ol 
• 1334338-09-8 butyric acid (1R,3R)-3-(3,4-dichloro-phenyl)-indan-1-yl ester 
• 86939-10-8 indatraline 
• 748724-48-3 LNK 131 
• 96850-13-4 LNK 131 hydrochloride 
• 1422045-78-0 (1R,3S)-1-(benzyloxy)-3-(3,4-dichlorophenyl)-2,3-dihydro-1H-indene 
• 1422045-79-1 benzyl ((1R,3S)-3-(3,4-dichlorophenyl)-2,3-dihydro-1H-inden-1-yl)carbamate 
• 1422045-80-4 benzyl ((1R,3S)-3-(3,4-dichlorophenyl)-2,3-dihydro-1H-inden-1-yl)methylcarbamate 
• 86939-40-4 Indatraline hydrochloride 
• 85721-00-2 C₁₆H₁₅Cl₂N*ClH 

Relevant academic research and scientific papers

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

Sertraline derivative and preparation method and application thereof

The invention discloses a sertraline derivative or a medicinal salt thereof. The structural general formula of the sertraline derivative is shown in the specification. The sertraline derivative has a good inhibition effect on cryptococcus neoformans, particularly, the compound D16 disclosed by the invention has a relatively good inhibition effect on candida glabrata 9073, candida tropicalis 10186, cryptococcus neoformans, candida albicans 5314, candida albicans 904, candida tropicalis 10186, drug-resistant candida albicans 103 and cryptococcus gottii.

Metal free decarboxylative aminoxylation of carboxylic acids using a biphasic solvent system

The smooth oxidative radical decarboxylation of carboxylic acids with TEMPO and other derivatives as radical scavengers is reported. The key to success was the use of a two-phase solvent system to avoid otherwise predominant side reactions such as the oxidation of TEMPO by persulfate and enabled the selective formation of synthetically useful alkoxyamines. The method does not require transition metals and was successfully used in a new synthetic approach for the antidepressant indatraline.

Synthesis of 2-sulfonyl indenes and indanes

In this paper, we developed facile and high-yield synthetic routes for the preparation of 2-sulfonyl indenes and indanes, including: (i) Amberlyst-15-promoted Knoevenagel reaction of β-ketosulfones and arylaldehydes in refluxing toluene; (ii) Grignard reagent (R′MgBr) or reducing reagent (NaBH4) promoted regio-and/or stereocontrolled 1,4-Addition or 1,4-/1,2-reduction of the resulting sulfonyl chalcones in THF or MeOH/THF at 25 °C; and then (iii) Amberlyst-15 mediated intramolecular Friedel-Crafts annulation of the corresponding β-ketosulfones or β-hydroxysulfones in toluene at reflux. This present method describes a highly efficient (3 + 2) annulation via the formation of two carbon-carbon (C-C) bonds. The DFT calculations were utilized to rationalize the regioselectivity of the addition reaction.

Palladium Nanoparticles-Catalyzed Synthesis of Indanone Derivatives via Intramolecular Reductive Heck Reaction

An efficient protocol for the straightforward, single-step synthesis of 3-aryl-1-indanones from 2′-iodochalcone via reductive Heck reaction using phosphine free, stable and reusable binaphthyl stabilized palladium nanoparticle (Pd-BNP) as a catalyst has been described. An immense array of substrate scope with electron-rich and deficient 2′-iodochalcones have been synthesized. Further derivatization of product indanones have been achieved successfully. The heterogeneous nature of the Pd-BNP has been validated by centrifugation test and mercury poisoning experiment. Pd-BNP has been successfully recycled up to 5 cycles without any significant loss in reaction yield and particle size of nanoparticles, confirmed by TEM analysis. (Figure presented.).

Synthesis of 3-aryl-1-indanones via CsF-promoted coupling of arylboronic acids with N-tosylhydrazones

A series of 17 3-aryl-1-indanones, four of which are novel, were prepared in good yield via a CsF-promoted reductive cross-coupling of the monotosylhydrazone of a 1,3-indanedione with an arylboronic acid. The method demonstrates wide substrate scope and good functional group tolerance. Moreover, the 3-aryl-1-indanones could also be prepared on a multi-gram scale.

A Weinreb Amide Based Building Block for Convenient Access to β,β-Diarylacroleins: Synthesis of 3-Arylindanones

Towards the synthesis of symmetrical and unsymmetrical β,β-diarylacroleins for assembling diarylmethine fragments present in biologically important molecules, we have developed a new Weinreb amide (WA) based building block, derived from propiolic acid. The WA functionality present in this compound allowed the sequential addition of various arylmagnesium bromide reagents in a controlled manner. The developed methodology for the access to β,β-diarylacroleins has been utilised for the synthesis of biologically important 3-arylindanone molecules. Synthesis of both symmetrical and unsymmetrical β,β-diarylacrolein and diarylmethine fragments, have been achieved via easily accessible and hitherto unknown Weinreb Amide (WA) based building block 11. The WA functionality allowed the sequential addition of nucleophiles such as arylmagnesium bromide in a controlled manner, which has enabled the synthesis of an important 3-arylindanone molecule.

Enantiopurity determination of the enantiomers of the triple reuptake inhibitor indatraline

The present study describes the development of two approaches for the determination of the enantiopurity of both enantiomers of indatraline. Initially, a method was developed using different chiral solvating agents (CSAs) for diastereomeric discrimination regarding signal separation in 1H nuclear magnetic resonance (NMR) spectroscopy, revealing MTPA as a promising choice for the differentiation of the indatraline enantiomers. This CSA was also tested for its ideal molar ratio, temperature, and solvent. Optimized conditions could be achieved that made determination of enantiopurity for (1R,3S)-indatraline up to 98.9% enantiomeric excess (ee) possible. To quantify even higher enantiopurities, a high-performance liquid chromatography (HPLC) method based on a modified β-cyclodextrine phase was established. The influence of buffer type, concentration, pH value, percentage and kind of organic modifier, temperature, injection volume as well as sample solvent on chromatographic parameters was investigated. Afterwards, the reliability of the established HPLC method was demonstrated by validation according to the ICH guideline Q2(R1) regarding specificity, accuracy, precision, linearity, and quantitation limit. The developed method proved to be strictly linear within a concentration range of 1.25-1000 μM for the (1R,3S)-enantiomer and 1.25-750 μM for its mirror image that enables a reliable determination of enantiopurities up to 99.75% ee for the (1R,3S)-enantiomer and up to 99.67% ee for the (1S,3R)-enantiomer.

Asymmetric total synthesis of (+)-indatraline via diastereoselective amination of chiral ethers using chlorosulfonyl isocyanate

A concise asymmetric total synthesis of (+)-indatraline from readily available cinnamic acid is described. The key steps include Corey's oxazaborolidine-catalyzed asymmetric carbonyl reduction and a highly stereoselective amination of chiral benzylic ether with retention of stereochemistry using chlorosulfonyl isocyanate.

AROMATIC KETONE SYNTHESIS WITH AMIDE REAGENTS AND RELATED REACTIONS

A method of preparing an aryl carbonyl or aryl thiocarbonyl compound, comprises reacting an N-(nitroaryl)-amide or N-(nitroaryl)-thioamide with an aromatic ring, with a superacid catalyst, to produce the aryl carbonyl or aryl thiocarbonyl compound. The superacid is present in an amount of at most 8 equivalents in proportion to the N-(nitroaryl)-amide or N-(nitroaryl)-thioamide. A method of preparing aryl amide or aryl thioamide, comprises reacting an N-(nitroaryl)-carbamide or N-(nitroaryl)-thiocarbamide with an aromatic ring, with a superacid catalyst, to produce the aryl amide or aryl thioamide.