Aristololactam

Base Information

• Chemical Name: Aristololactam
• CAS No.: 13395-02-3
• Molecular Formula: C₁₇H₁₁NO₄
• Molecular Weight: 293.279
• Hs Code.: 2933990090
• European Community (EC) Number: 683-187-7
• NSC Number: 87406
• UNII: 3G8CFM4T9A
• DSSTox Substance ID: DTXSID60158430
• Nikkaji Number: J13.455D
• Wikidata: Q72443760
• Metabolomics Workbench ID: 137837
• ChEMBL ID: CHEMBL479127
• Mol file: 13395-02-3.mol

Synonyms:8-methoxy -6-nitrophenanthro(3,4-d)-1,3-dioxolo-5-carboxylic acid;aristolactam I

Chemical Property of Aristololactam

Chemical Property:

• Vapor Pressure: 8.75E-09mmHg at 25°C
• Melting Point: 319 °C
• Refractive Index: 1.763
• Boiling Point: 463.9 °C at 760 mmHg
• PKA: 12.36±0.20(Predicted)
• Flash Point: 234.4 °C
• PSA: 60.55000
• Density: 1.49 g/cm³
• LogP: 3.00960
• Storage Temp.: Refrigerator
• Solubility.: Acetone (Slightly), DMSO (Slightly, Heated), Methanol (Slightly)
• XLogP3: 3.1
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 1
• Exact Mass: 293.06880783
• Heavy Atom Count: 22
• Complexity: 483

Purity/Quality:

98%,99%, ^*data from raw suppliers

Aristololactam ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: COC1=CC=CC2=C3C4=C(C=C21)NC(=O)C4=CC5=C3OCO5
• General Description: Aristolactam I is a naturally occurring alkaloid belonging to the aristolactam family, which is structurally characterized by a lactam-fused aromatic system. It is of interest in medicinal chemistry and natural product synthesis due to its bioactive properties. The referenced study highlights its synthesis via a Pd(II)/Cu(II)-catalyzed oxidative coupling method, demonstrating its relevance as a target in efficient and sustainable synthetic approaches for alkaloid derivatives.

Technology Process of Aristololactam

There total 5 articles about Aristololactam which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield:

→ aristololactam I (13395-02-3)

Guidance literature:

With acetic acid; platinum; Hydrogenation;

DOI:10.1007/BF00902543

Reference yield:

aristolochic acid I (313-67-7,61117-05-3) → aristololactam I (13395-02-3)

Guidance literature:

With ammonium hydroxide; iron(II) sulfite; at 22 ℃; for 1h; Yield given;

DOI:10.1002/ardp.19873200314

Reference yield:

→ aristololactam I (13395-02-3)

Guidance literature:

With acetic acid; platinum; Hydrogenation;

DOI:10.1007/BF00902543

upstream raw materials:

aristolochic acid I

acetic acid

Downstream raw materials:

aristololactam Ia

Refernces

Pd(II)/Cu(II)-Catalyzed Regio- and Stereoselective Synthesis of (E)-3-Arylmethyleneisoindolin-1-ones Using Air as the Terminal Oxidant

10.1021/acs.orglett.8b03409

The study reports a Pd(II)/Cu(II)-catalyzed regio- and stereoselective synthesis of (E)-3-arylmethyleneisoindolin-1-ones using air as the terminal oxidant. The reaction involves a one-pot C?C/C?N bond forming sequence between amides and styrenes. The Pd(II) catalyst is crucial for the initial bond formation and cyclization, while Cu(II) acts as a co-oxidant, with air serving as a sustainable oxidant to regenerate the active Pd(II) catalyst. This method provides a mild, efficient, and environmentally friendly route to synthesize a wide range of (E)-3-arylmethyleneisoindolin-1-ones with good functional group tolerance. The study also demonstrates the synthetic utility of this method in the efficient total syntheses of aristolactam and indoloisoquinolinone alkaloids, highlighting its potential in natural product and pharmaceutical synthesis.