1579-14-2

Usage

Physical state

White or light yellow crystalline solid

Uses

Building block in the synthesis of various organic compounds, production of pharmaceuticals, agrochemicals, and other specialty chemicals

Importance

Useful intermediate in the manufacturing of various aromatic and heterocyclic compounds, potential as a reactive intermediate in organic synthesis, and has several applications in the chemical industry.

Upstream product

• 83-33-0 inden-1-one 
• 73951-59-4 trans-2-chloro-indan-1-ol 
• 185436-23-1 (-)-(1S,2R)-2-chloro-2,3-dihydro-1H-inden-1-ol 
• 107-21-1 ethylene glycol 
• 31928-64-0 1-trimethylsilyloxy-3H-indene 
• 17215-77-9 2,2-dichloro-2,3-dihydro-1H-inden-1-one 
• 67864-28-2 2-chloroindan-1-ol 

Downstream Products

• 53446-63-2 2-isopropyl-2,3-dihydro-1H-inden-1-one 
• 697-64-3 (R)-indan-1-ol 
• 404-24-0 2,2,2-trifluoro-N-phenylacetamide 
• 65738-56-9 methyl 5-chloro-1-oxo-2,3-dihydro-1H-indene-2-carboxylate 
• 54763-67-6 trans-(+)-3'-(4-methylphenyl)spiro(inden-2,2'-oxiran)-1(3H)-one 
• 54763-67-6 trans-(-)-3'-(4-methylphenyl)spiro(inden-2,2'-oxiran)-1(3H)-one 

Relevant academic research and scientific papers

Catalytic Enantioselective Protonation of Monofluorinated Silyl Enol Ethers towards Chiral α-Fluoroketones

Described herein is an organocatalytic enantioselective protonation of monofluorinated silyl enol ethers, affording an array of optically active α-secondary α-fluoroketones in good to high yields and enantioselectivities, under the catalysis of bifunction

Efficient Synthesis of α-Chloroketones Catalyzed by Fluorous Hydrazine-1,2-Bis(Carbothioate) Organocatalyst

A novel and recoverable fluorous hydrazine-carbothioate organocatalyst was prepared. It could catalyze α-chlorination of alkyl ketones with N-chlorosuccinimide as chlorine source under mild reaction conditions. The reaction afforded the corresponding α-ch

Synthesis and biological evaluation of α-hydroxyalkylphosphonates as new antimicrobial agents

A set of α-quaternary 3-chloro-1-hydroxyalkylphosphonates, analogues of fosfomycin and fosfonochlorin, some of which are new compounds, was synthesized. The compounds were screened for bioactivity against several clinical and standard microbial isolates. Some were found to have moderate activity. The activity was higher with phenyl protection of the phosphoryl ester groups and α-phenyl substitution. Compound 11 was as effective or more potent than fosfomycin or chloramphenicol against several Gram-negative bacteria as well as against some Gram-positive ones.

Trifluorinated Tetralins via I(I)/I(III)-Catalysed Ring Expansion: Programming Conformation by [CH2CH2] → [CF2CHF] Isosterism

Saturated, fluorinated carbocycles are emerging as important modules for contemporary drug discovery. To expand the current portfolio, the synthesis of novel trifluorinated tetralins has been achieved. Fluorinated methyleneindanes serve as convenient precursors and undergo efficient difluorinative ring expansion with in situ generated p-TolIF2 (>20 examples, up to >95 %). A range of diverse substituents are tolerated under standard catalysis conditions and this is interrogated by Hammett analysis. X-ray analysis indicates a preference for the CH?F bond to occupy a pseudo-axial orientation, consistent with stabilising σC?H→σC?F* interactions. The replacement of the symmetric [CH2?CH2] motif by [CF2?CHF] removes the conformational degeneracy intrinsic to the parent tetralin scaffold leading to a predictable half-chair. The conformational behavior of this novel structural balance has been investigated by computational analysis and is consistent with stereoelectronic theory.

Convincing Catalytic Performance of Oxo-Tethered Ruthenium Complexes for Asymmetric Transfer Hydrogenation of Cyclic α-Halogenated Ketones through Dynamic Kinetic Resolution

A highly efficient dynamic kinetic resolution of cyclic halohydrins was achieved by the asymmetric transfer hydrogenation of racemic α-haloketones. Bifunctional oxo-tethered Ru(II) catalysts could promote the reduction without deterioration of halogens. By structural tuning of the catalyst, chiral alcohols having halogen, ester, carboxamide, and sulfone functions were obtained variably with excellent diastereo- and enantioselectivities (up to >99:1 d.r. and >99.9 ee), which provided a concise synthetic approach to a dopamine D3 receptor ligand, (+)-PHNO.

A Simple and Efficient Method for the Preparation of α-Halogenated Ketones Using Iron(III) Chloride and Iron(III) Bromide as Halogen Sources with Phenyliodonium Diacetate as Oxidant

α-Halogenated ketones are both unique structure moieties existing in biologically natural products and valuable synthetic intermediates for the preparation of functional molecules. An efficient and scalable method for the preparation of α-halogenated ketone using iron (III) chloride and iron (III) bromide as halogen sources with phenyliodonium diacetate as oxidant has been developed, featuring mild reaction conditions, environmentally friendly reagents, and wide substrate scope. Notably, the three-step synthesis of drug prasugrel was achieved using this developed method as a key step with 30% yield on gram-scale. Additionally, the reaction mechanism involving chloride cation was proposed based on some preliminary control experiments. (Figure presented.).

Synthesis of α-oxygenated ketones and substituted catechols via the rearrangement of N-enoxy- and N-aryloxyphthalimides

A common approach to the synthesis of α-oxygenated carbonyl compounds and catechols is the treatment of a carbonyl compound or a phenol with an electrophilic oxygen source. As an alternative approach to these important structures, formal [3,3]-rearrangements of N-enoxyphthalimides, N-enoxyisoindolinones, and N-aryloxyphthalimides have been explored. When used in combination with an initial Chan-Lam coupling, these transformations facilitate the dioxygenation of alkenylboronic acids for the synthesis of α-oxygenated ketones and the dioxygenation of arylboronic acids for the synthesis of catechols. The rearrangements of N-enoxyisoindolinones have also been shown to be diastereoselective.

Mechanochemical solid-state synthesis of 2-aminothiazoles, quinoxalines and benzoylbenzofurans from ketones by one-pot sequential acid- and base-mediated reactions

α-Chloroketones-obtained by the atom-economical chlorination of ketones with trichloroisocyanuric acid (TCCA) in the presence of p-TSA under ball-milling conditions-were set up for a sequential base-mediated condensation reaction with thiourea/thiosemicarbazides, o-phenylenediamine and salicylaldehyde to afford 2-aminothiazoles, 2-hydrazinylthiazoles, quinoxalines and benzoylbenzofurans, respectively, in respectable yields. The viability of one-pot sequential acid- and base-mediated reactions in the solid state under ball-milling conditions is thus demonstrated.

A simple and convenient method for direct α-chlorination of ketones with ammonium chloride and Oxone

When ketones were treated with ammonium chloride and Oxone in MeOH at room temperature, a direct α-chlorination of ketones was occurred and a series of the corresponding α-chloroketones were obtained in moderate to good yields after 24 h. In this reaction, ammonium chloride was used as the source of chlorine and Oxone was used as an oxidant. This method was simple, convenient and providing a novel procedure for preparation of α-chloroketones.

The use of sodium chlorate/hydrochloric acid mixtures as a novel and selective chlorination agent

Sodium chlorate/hydrochloric acid mixtures were used to chlorinate activated arenes and the α-position of ketones. This chlorination method was used to produce selectively mono-, di-, and trichlorinated compounds by controlling the molarity of sodium chlorate. This reagent proved to be much more efficient and easier to handle than chlorine gas.