3976-26-9

Basic information

• Product Name: (S)(-)-ALPHA-PHENETHYLPHTHALIMIDE
• Synonyms: (S)(-)-ALPHA-PHENETHYLPHTHALIMIDE;(S)-(-)-N-(1-PHENYLETHYL) PHTHALIMIDE
• CAS NO: 3976-26-9
• Molecular Formula: C₁₆H₁₃NO₂
• Molecular Weight: 251.28
• Mol File: 3976-26-9.mol
• Article Data: 18

Chemical Properties

• Appearance: /
• CAS DataBase Reference: (S)(-)-ALPHA-PHENETHYLPHTHALIMIDE(CAS DataBase Reference)
• NIST Chemistry Reference: (S)(-)-ALPHA-PHENETHYLPHTHALIMIDE(3976-26-9)
• EPA Substance Registry System: (S)(-)-ALPHA-PHENETHYLPHTHALIMIDE(3976-26-9)

Safety Data

• Hazardous Substances Data: 3976-26-9(Hazardous Substances Data)

Usage

Description

(S)(-)-ALPHA-PHENETHYLPHTHALIMIDE, also known as (-)-Phenylethylphthalimide or (-)-PEP, is a chiral chemical compound that serves as an intermediate in the production of pharmaceuticals and fine chemicals. Its unique spatial configuration, due to its chiral nature, allows it to be studied for potential applications in the treatment of neurological disorders and as a precursor in the synthesis of various bioactive compounds. Careful handling is required to avoid health hazards.

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 
• 203788-46-9 2-(1-Phenyl-ethyl)-2,3-dihydro-isoindol-1-one 
• 2306-33-4 monoethyl phthalate 
• 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 
• 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 
• 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 

Relevant articles and documents

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.]

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.

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.