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CAS

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134003-02-4

(-)-2-Azabicyclo<2.2.1>heptan-3-one, also known as quinoxaline, is a bicyclic chemical compound with the molecular formula C7H7NO. It features a nitrogen atom and is widely recognized as an intermediate in the synthesis of pharmaceuticals and agrochemicals. Its distinctive structure and reactivity contribute to its value as a building block for a variety of organic compounds. Studies have revealed potential biological activities of quinoxaline derivatives, such as antimicrobial, antifungal, and anticancer properties. Furthermore, quinoxaline-based compounds have been considered for applications as fluorescent probes and in the realm of organic electronics. This makes (-)-2-Azabicyclo<2.2.1>heptan-3-one a versatile chemical with broad applications across pharmaceuticals, agriculture, and materials science.

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  • 134003-02-4 Structure

  • Basic information

    1. Product Name: (-)-2-Azabicyclo<2.2.1>heptan-3-one
    2. Synonyms: (-)-2-Azabicyclo<2.2.1>heptan-3-one
    3. CAS NO:134003-02-4
    4. Molecular Formula:
    5. Molecular Weight: 111.144
    6. EINECS: N/A
    7. Product Categories: N/A
    8. Mol File: 134003-02-4.mol

  • Chemical Properties

    1. Melting Point: N/A
    2. Boiling Point: N/A
    3. Flash Point: N/A
    4. Appearance: N/A
    5. Density: N/A
    6. Refractive Index: N/A
    7. Storage Temp.: N/A
    8. Solubility: N/A
    9. CAS DataBase Reference: (-)-2-Azabicyclo<2.2.1>heptan-3-one(CAS DataBase Reference)
    10. NIST Chemistry Reference: (-)-2-Azabicyclo<2.2.1>heptan-3-one(134003-02-4)
    11. EPA Substance Registry System: (-)-2-Azabicyclo<2.2.1>heptan-3-one(134003-02-4)

  • Safety Data

    1. Hazard Codes: N/A
    2. Statements: N/A
    3. Safety Statements: N/A
    4. WGK Germany:
    5. RTECS:
    6. HazardClass: N/A
    7. PackingGroup: N/A
    8. Hazardous Substances Data: 134003-02-4(Hazardous Substances Data)

134003-02-4 Usage

Uses

Used in Pharmaceutical Industry:
(-)-2-Azabicyclo<2.2.1>heptan-3-one is used as a key intermediate in the synthesis of various pharmaceuticals due to its unique reactivity and structural properties, which facilitate the development of new drugs with potential therapeutic benefits.
Used in Agrochemical Industry:
In the agrochemical sector, (-)-2-Azabicyclo<2.2.1>heptan-3-one serves as an essential component in the creation of agrochemicals, contributing to the development of effective products for agricultural use.
Used in Antimicrobial Applications:
(-)-2-Azabicyclo<2.2.1>heptan-3-one is utilized as an antimicrobial agent, leveraging its biological activity to combat microbial infections, making it a valuable asset in the development of antibiotics and antifungal agents.
Used in Anticancer Research:
(-)-2-Azabicyclo<2.2.1>heptan-3-one is employed in anticancer research for its potential to develop into effective cancer treatments, with ongoing studies exploring its impact on various types of cancer.
Used in Fluorescent Probes and Organic Electronics:
(-)-2-Azabicyclo<2.2.1>heptan-3-one is used as a component in the development of fluorescent probes and materials for organic electronics, capitalizing on its unique properties to advance these fields.

Check Digit Verification of cas no

The CAS Registry Mumber 134003-02-4 includes 9 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 6 digits, 1,3,4,0,0 and 3 respectively; the second part has 2 digits, 0 and 2 respectively.
Calculate Digit Verification of CAS Registry Number 134003-02:
(8*1)+(7*3)+(6*4)+(5*0)+(4*0)+(3*3)+(2*0)+(1*2)=64
64 % 10 = 4
So 134003-02-4 is a valid CAS Registry Number.

134003-02-4Relevant articles and documents

Enzymatic method for the synthesis of blockbuster drug intermediates - Synthesis of five-membered cyclic γ-amino acid and γ-lactam enantiomers

Forro, Eniko,Fueloep, Ferenc

, p. 5263 - 5268 (2008)

A very efficient enzymatic method was developed for the synthesis of cyclic γ-lactam and γ-amino acid enantiomers, intermediates for drugs with a prominent turnover (e.g., abacavir and carbovir), through the CAL-B-catalysed enantioselective (E > 200) hydrolysis of the corresponding N-Boc protected and unprotected racemic γ-lactams with H2O in iPr2O. Wiley-VCH Verlag GmbH & Co. KGaA, 2008.

Enhanced enzymatic synthesis of the enantiopure intermediate for the blockbuster drug intermediate abacavir through a two-step enzymatic cascade reaction

Galla, Zsolt,Forró, Enik?,Fül?p, Ferenc

, p. 729 - 731 (2016/08/01)

A very efficient enzymatic two-step cascade reaction was devised (E?>?200) for the resolution of activated γ-lactams (±)-1 and (±)-2. The N-hydroxymethyl group worked as a traceless activating group, when the reactions were performed with H2O (0.5?equiv) in the presence of benzylamine (1?equiv) in i-Pr2O at 60?°C. The ring-opened enantiomerically pure γ-amino acids (1S,4R)-6 (ee?=?99%, intermediate of abacavir) and (1S,3R)-8 (ee?=?99%) and unreacted lactams (1S,4R)-1 and (1R,4S)-2 (ee???96%) were obtained in good yields (?43%). Treatment of (1S,4R)-1 and (1R,4S)-2 with 18% HCl or NH4OH resulted in (1R,4S)-6·HCl and (1S,3R)-8·HCl or (1S,4R)-3 and (1R,4S)-4 quantitatively, with ee???96%.

Identification and application of enantiocomplementary lactamases for Vince lactam derivatives

Assaf, Zeinab,Eger, Elisabeth,Vitnik, Zeljko,Fabian, Walter M. F.,Ribitsch, Doris,Guebitz, Georg M.,Faber, Kurt,Hall, Mélanie

, p. 2517 - 2521 (2015/04/14)

Four enzymes showing hydrolytic activity on derivatives of 2-azabicyclo[2.2.1]hept-5-en-3-one (Vince lactam) were successfully identified through analysis of protein crystal structure and amino acid sequence alignments. Enantiocomplementary activities were observed on Vince lactam and its saturated analog 2-azabicyclo[2.2.1]heptan-3-one with non-heme chloroperoxidase (CPO-T) from Streptomyces aureofaciens, cyclic imide hydrolase (CIH) from Pseudomonas putida, polyamidase (NfpolyA) from Nocardia farcinica, and amidase (AMI) from Rhodococcus globerulus, and perfect kinetic resolution was achieved (E>200). Computational analysis of amide bond resonance stabilization in lactams correlated well with the overall reactivity pattern of the lactams as a function of ring size and strain. The biocatalysts cloned and investigated in this study could be of interest for the synthesis of enantiopure carbocyclic nucleoside analogues.

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