3976-26-9

Usage

Uses

Used in Pharmaceutical Industry:
(S)(-)-ALPHA-PHENETHYLPHTHALIMIDE is used as an intermediate for the production of pharmaceuticals and fine chemicals, taking advantage of its unique spatial configuration to create bioactive compounds.
Used in Neurological Disorder Treatment:
(S)(-)-ALPHA-PHENETHYLPHTHALIMIDE is used as a potential treatment for neurological disorders, leveraging its properties to develop new therapeutic approaches.
Used in Synthesis of Bioactive Compounds:
(S)(-)-ALPHA-PHENETHYLPHTHALIMIDE is used as a precursor in the synthesis of various bioactive compounds, contributing to the development of new drugs and treatments.

Upstream product

• 85-44-9 phthalic anhydride 
• 618-36-0 rac-methylbenzylamine 
• 1074-82-4 potassium phtalimide 
• 585-71-7 (1-bromoethyl)benzne 
• 98-85-1 1-Phenylethanol 
• 136918-14-4 phthalimide 
• 1971-49-9 N-acetylphthalimide 
• 4658-63-3 N-pivaloylphthalimide 
• 26268-95-1 N-propionylphthalimide 
• 98-86-2 acetophenone 
• 4545-21-5 acetophenone p-toluenesulfonylhydrazone 
• 1517-69-7 (R)-1-phenylethanol 
• 2627-86-3 (S)-1-phenyl-ethylamine 
• 100-41-4 ethylbenzene 

Downstream Products

• 178315-36-1 3-Hydroxy-3-(p-methoxyphenyl)-2-(1-phenylethyl)isoindolin-1-one 
• 178315-49-6 3-Hydroxy-2-(1-phenylethyl)-3-(3-phenylpropyl)isoindolin-1-one 
• 178315-47-4 3-Hydroxy-2-(1-phenylethyl)-3-(2-phenylethyl)isoindolin-1-one 
• 618-36-0 rac-methylbenzylamine 
• 257619-71-9 (1'S)-2,3-dihydro-3-hydroxy-3-(pentynyl)-2-(1'-phenylethyl)-1H-isoindol-1-one 
• 503859-63-0 (1'S,3R)-2,3-dihydro-3-hydroxy-1-(1'-phenylethyl)-1H-isoindol-1-one 
• 503859-65-2 (1'S,3S)-2,3-dihydro-3-hydroxy-1-(1'-phenylethyl)-1H-isoindol-1-one 
• 929206-57-5 (1'S)-2,3-dihydro-3-hydroxy-1-(1'-phenylethyl)-1H-isoindol-1-one 
• 929206-59-7 3-acetoxy-2-(1(S)-phenylethyl)isoindolin-1-one 
• 1357165-58-2 C₁₇H₁₇NO₂ 
• 257619-72-0 (E)-(1'S)-2,3-dihydro-3-(2-oxo-2-phenylethylidene)-2-(1'-phenylethyl)-1H-isoindol-1-one 

Relevant academic research and scientific papers

Inhibitory activity on cholinesterases produced by aryl-phthalimide derivatives: green synthesis, in silico and in vitro evaluation

Background: Alzheimer’s disease (AD) is characterized by cognitive impairment and loss of immediate memory resulting from neuronal death in different brain areas, mainly those producing acetylcholine. Acetylcholinesterase inhibitors improve cognitive function, delay mental deterioration, and reduce other symptoms. Despite being the cornerstone for treating mild–moderate AD, these compounds are only palliative agents and often have severe adverse effects. Recently, butyrylcholinesterase (BuChE) has been found to be involved in AD. The aim of this study was to synthesize a series of six phthalimides with structural relationship with monoamines and evaluate them in vitro and in silico as AChE and BuChE inhibitors. In addition, a modified version of the Bonting and Featherstone method for determining AChE activity was adapted for the assessment of BuChE activity. Results: Six molecules (dioxoisoindolines A–F) were synthesized in good yields using a green chemistry approach. Dioxoisoindolines E and F were more active for AChE, with a Ki of 232 and 193 μM, respectively. Contrarily, dioxoisoindolines C and D showed up to fivefold greater selectivity for BuChE than AchE, with a Ki of 200 and 100 μM, respectively. The competitive inhibitory activity of the latter two molecules was similar to that of the reference compounds. Molecular docking demonstrated the participation of carbonyl carbons and aromatic rings in the high affinity of dioxoisoindoles for cholinesterases. Conclusion: The modified version of the Bonting and Featherstone method was successfully adapted to quantify BuChE activity. Dioxoisoindolines C and D displayed greater inhibition of BuChE versus AChE, with good inhibition of both enzymes. Thus, they are promising lead compounds for developing new BuChE/AChE inhibitors. [Figure not available: see fulltext.]

Amidation via ligand-free direct oxidative C(sp3)-H/N[sbnd]H coupling with Cu-CPO-27 metal-organic framework as a recyclable heterogeneous catalyst

A copper-based metal-organic framework Cu-CPO-27 was synthesized, and used as a recyclable catalyst for the amidation of unactivated alkanes by benzamides via direct oxidative C(sp3)-H/N[sbnd]H coupling under ligand-free conditions. Using a catalytic amount of the Cu-CPO-27 for the transformation, high yields of N-cyclohexyl benzamides were achieved. The Cu-CPO-27 was more catalytically active than other Cu-MOFs such as Cu3(BTC)2, Cu(BDC), Cu(EDB), Cu2(BPDC)2(BPY), Cu2(BDC)2(DABCO), and Cu2(EDB)2(BPY). The Cu-CPO-27 also exhibited advantages as compared to several copper-based salts, including Cu(OAc)2, CuCl2, CuBr, CuI, CuCl, Cu(NO3)2, and CuSO4. The Cu-CPO-27 catalyst could be reused several times for the amidation transformation while its catalytic activity was not decreased significantly. To the best of our knowledge, the amidation of unactivated alkanes by benzamides via direct oxidative C(sp3)-H/N[sbnd]H coupling was not previously performed under heterogeneous catalysis conditions.

H-β-zeolite catalyzed transamidation of carboxamides, phthalimide, formamides and thioamides with amines under neat conditions

Efficient transamidation of unactivated carboxamides, phthalimides, formamides and thioamides with amines under solvent-free conditions using H-β-zeolite as a green and recyclable heterogeneous catalyst is described. Easy work up, high purity of the products, recyclability and environmentally-friendly nature of the catalyst are the attractive features of the present methodology. This is the first report for the transamidation of thioamides under heterogeneous conditions.

An unprecedented approach to the Gabriel amine synthesis utilizing tosylhydrazones as alkylating agents

A new and one-pot version of the Gabriel phthalimide amine synthesis utilizing carbonyl compounds as alkylating agents via their tosylhydrazone surrogates is disclosed. The alkylation involves copper catalysed carbene insertion into the N-H bond of phthalimide. Basically, the protocol also offers a powerful tool for deoxygenative hydroamination of carbonyl compounds.

Benzoic acid-catalyzed transamidation reactions of carboxamides, phthalimide, ureas and thioamide with amines

An efficient and simple method for the transamidation of carboxamides, phthalimide, ureas and thioamide with amines catalyzed by commercially available benzoic acid under metal-free conditions is described. Furthermore, to the best of our knowledge, this is the first report about the transamidation of an aromatic thioamide with amines.

Microwave-assisted heteropolyanion-based ionic liquids catalyzed transamidation of non-activated carboxamides with amines under solvent-free conditions

An environmentally benign and highly efficient protocol for the transamidation of non-activated carboxamides with amines using heteropolyanion-based ionic liquids as catalysts under microwave-assisted and solvent-free conditions has been developed. As evaluated by the reactions of a structurally diverse set of amides and amines, the scope and utility of the transamidation proved to be quite general. Operational simplicity, solvent-free media, the potential reusability of catalysts and wide functional group tolerance are attractive features. This method provides a much improved protocol over the existing methods.

Synthesis and evaluation of some variants of the Nefkens' reagent

A series of N-substituted phthalimides have been prepared in an effort to explore synthetic variants of the Nefkens' reagent. Three N-acylphthalimides [R = -CH3, -CH2CH3, and -C(CH3) 3] were prepared and employed for the protection of a series of representative amines. In addition, an N-methanesulfonylphthalimide and N-(diethylphosphoryl)phthalimide were also prepared. It was determined that among the phthalimides that were prepared N-propanoylphthalimide was the most effective reagent for the protection reaction.

L-Proline: An efficient catalyst for transamidation of carboxamides with amines

In the presence of a catalytic amount of l-proline (10 mol %), transamidations of carboxamides with amines were achieved under solvent-free conditions. The transamidation process is compatible with a wide range of amines.

Preparation of ionic liquid-based vilsmier reagent from novel multi-purpose dimethyl formamide-like ionic liquid and its application

In continuation of research to explore the applied potential of DMF-like ionic liquid, the ionic liquid version of N,N-dimethyliminiumchloride (Vilsmier reagent) has been synthesized from DMF-like ionic liquid and tested effectively for its capacity to achieve more useful organic transformations. The results show that DMF-like ionic liquid is world's first task specific ionic liquid which has catalyzed numerous diverse type of reaction and is multipurpose in its application. Thus a new term for this DMF-like ionic liquid has been coined that is DMF-like "multipurpose" ionic liquid. Copyright

One-pot three-component highly diastereoselective synthesis of isoindolin-1-one-3-phosphonates under solvent and catalyst free-conditions

The one-pot three-component reaction of 2-formylbenzoic acid with (S)- and (R)-methylbenzylamine and dimethyl phosphite (Kabachnik-Fields reaction) proceeded in short reaction times under solvent and catalyst free-conditions to afford the corresponding (3R,1′S)- and (3S,1′R)-isoindolin-1-one-3- phosphonates 3, respectively, in good yield and with high diastereoselectivity (95:5 dr). The use of a solvent decreases the diastereoselectivity and slows the reaction rate. The reaction rate was also influenced by CO2H functionality through protonation of the imine intermediate. The absolute configuration at the new stereogenic center was determined by X-ray crystal analysis, and a mechanism was proposed to explain the high diastereoselectivity.