114368-05-7

Basic information

• Product Name: 1-Benzyl-5-oxopyrrolidine-3-carbonyl chloride
• Synonyms: 1-Benzyl-5-oxopyrrolidine-3-carbonyl chloride;1-(benzyl)-5-keto-pyrrolidine-3-carbonyl chloride;5-oxo-1-(phenylmethyl)-3-pyrrolidinecarbonyl chloride;5-oxo-1-(phenylmethyl)pyrrolidine-3-carbonyl chloride
• CAS NO: 114368-05-7
• Molecular Formula: C₁₂H₁₂ClNO₂
• Molecular Weight: 237.68218
• Mol File: 114368-05-7.mol

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 1-Benzyl-5-oxopyrrolidine-3-carbonyl chloride(CAS DataBase Reference)
• NIST Chemistry Reference: 1-Benzyl-5-oxopyrrolidine-3-carbonyl chloride(114368-05-7)
• EPA Substance Registry System: 1-Benzyl-5-oxopyrrolidine-3-carbonyl chloride(114368-05-7)

Safety Data

• HazardClass: IRRITANT
• Hazardous Substances Data: 114368-05-7(Hazardous Substances Data)

Usage

Chemical classification

1-Benzyl-5-oxopyrrolidine-3-carbonyl chloride is a carbonyl chloride derivative derived from pyrrolidine.

Molecular structure

It consists of a benzyl group attached to the nitrogen atom of the pyrrolidine ring and a carbonyl chloride group attached to one of the carbon atoms in the ring.

Organic synthesis

It has potential applications in organic synthesis and pharmaceutical research.

Reagent usage

It can be used as a reagent for the synthesis of other organic compounds.

Reactivity

Carbonyl chlorides are highly reactive.

Safety precautions

It is important to handle this chemical with care to avoid irritation to the skin, eyes, and respiratory system.

Upstream product

• 100-46-9 benzylamine 
• 97-65-4 2-methylenesuccinic acid 
• 5733-86-8 1-benzyl-5-oxopyrrolidine-3-carboxylic acid 

Downstream Products

• 107259-25-6 1-benzyl-3-(1-tert-butoxycarbonylaminopropyl)pyrrolidine 
• 107259-20-1 4-(1-aminopropyl)-1-benzyl-2-pyrrolidone 
• 107259-24-5 3-(1-Aminopropyl)-1-benzylpyrrolidine 
• 107259-21-2 1-benzyl-4-(1-hydroxyiminopropyl)-2-pyrrolidone 
• 163554-77-6 1-benzyl-4-propionylpyrrolidin-2-one 
• 1026820-45-0 2-(1-Benzyl-5-oxo-pyrrolidine-3-carbonyl)-malonic acid diethyl ester 
• 1027599-40-1 2-(1-Benzyl-5-oxo-pyrrolidine-3-carbonyl)-2-methyl-malonic acid diethyl ester 

Relevant articles and documents

1-benzyl-2- [...] -4-amide compound and its preparation method and application

The invention discloses 1-benzyl-2-pyrroline ketone-4-amide compounds represented by the general formula. According to independent R1, R2, R3, R4, R5, R6, R7, R8, R9 or R10, 1-3 C1-4 alkyl groups substituted by substituent groups are selected from a non-substituent C1-4 alkyl group, a non-substituent C1-3 alkoxy group, halogen, an amine sulfonyl group, a nitryl group and hydrogen or from halogen, a nitryl group, a C1-3 alkyl group and a C1-2 alkoxy group, or 1-3 C1-3 alkoxy groups substituted by substituent groups are selected from halogen, a nitryl group, a C1-3 alkyl group and a C1-2 alkyl group. The halogen is fluorine, chlorine or bromine. The invention further discloses a preparing method and application of the compounds. The compounds can restrain tyrosine kinase signal transduction and unhealthy cell hyperplasia and angiogenesis, and obvious curative effect is achieved on diseases such as tumors especially.

CCR5 antagonists as anti-HIV-1 agents. 1. Synthesis and biological evaluation of 5-oxopyrrolidine-3-carboxamide derivatives

A novel lead compound, N-{3-[4-(4-fluorobenzoyl)piperidin-1-yl]propyl}-1- methyl-5-oxo-N-phenylpyrrolidine-3-carboxamide (1), was identified as a CCR5 antagonist by high-throughput screening using [125I]RANTES and CCR5-expressing CHO cells. The IC50 value of 1 was 1.9 μM. In an effort to improve the binding affinity of 1, a series of 5-oxopyrrolidine-3- carboxamides was synthesized. Introduction of 3,4-dichloro substituents to the central phenyl ring (10i, IC50=0.057 μM; 11b, IC 50=0.050 μM) or replacing the 1-methyl group of the 5-oxopyrrolidine moiety with a 1-benzyl group (12e, IC50=0.038 μM) was found to be effective for improving CCR5 affinity. Compound 10i, 11b, and 12e also inhibited CCR5-using HIV-1 envelope-mediated membrane fusion with IC50 values of 0.44, 0.19, and 0.49 μM, respectively.

Synthesis and structure-activity relationships of 7-[3-(1- aminoalkyl)pyrrolidinyl]- and 7-[3-1-aminocycloalkyl)pyrrolidinyl]-quinolone antibacterials

A series of 7-[3-(1-aminoalkyl and 1-aminocycloalkyl)-1- pyrrolidinyl]quinolones have been prepared and their biological properties evaluated. Among them, 1-(S)-aminoalkyl derivatives exhibited potent antibacterial activities against gram-positive and gram-negative organisms. They had moderate lipophilicity and high aqueous solubility compared to their aminomethyl counterparts; e.g., the 3-(1-aminoethyl)-1-pyrrolidinyl compound (83) showed superior pharmacokinetic properties to its aminomethyl counterpart (6).