Luteoreticulin

Base Information

• Chemical Name: Luteoreticulin
• CAS No.: 22388-89-2
• Deprecated CAS: 150172-27-3
• Molecular Formula: C₁₉H₁₉NO₅
• Molecular Weight: 341.364
• Wikidata: Q77570203
• Metabolomics Workbench ID: 103019
• Mol file: 22388-89-2.mol

Synonyms:luteoreticulin

Chemical Property of Luteoreticulin

Chemical Property:

• PSA: 85.26000
• LogP: 4.89500
• XLogP3: 4.8
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 4
• Exact Mass: 341.12632271
• Heavy Atom Count: 25
• Complexity: 670

Purity/Quality:

98%Min ^*data from raw suppliers

Luteoreticulin ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1=C(C=C(OC1=O)C(=CC(=CC2=CC=C(C=C2)[N+](=O)[O-])C)C)OC
• Isomeric SMILES: CC1=C(C=C(OC1=O)/C(=C/C(=C/C2=CC=C(C=C2)[N+](=O)[O-])/C)/C)OC
• Uses: Luteoreticulin is a rare nitrophenyl pyranone closely related to aureothin, neoaureothin and its unusual photoisomers SNF4435C and SNF4435D. Metabolites within this class are potent antitumour agents with pronounced immunosuppressive activity, and more recently have been shown to reverse multi-drug resistance. The lack of availability of luteoreliculin has hitherto restricted a more intensive investigation of this interesting metabolite. Luteoreticulin is a nitrophenyl pyranone with immunosuppresive effects.

Technology Process of Luteoreticulin

There total 3 articles about Luteoreticulin 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: 14.0%

Methanesulfonic acid (E)-1-[1-(4-methoxy-5-methyl-6-oxo-6H-pyran-2-yl)-ethyl]-2-methyl-3-(4-nitro-phenyl)-allyl ester → 4-(4-methoxy-2-methyl-2H-pyran-2-on-6-yl)-2,4-dimethyl-1-(4-nitrophenyl)-1,3-butadiene (22388-89-2)

Guidance literature:

With lithium diisopropyl amide; In tetrahydrofuran; at -78 - 20 ℃;

DOI:10.1002/jhet.5570320223

Reference yield:

(E)-2-methyl-3-(4-nitrophenyl)acrylaldehyde (58550-34-8,37524-18-8) + 1-(4-methoxy-3-methyl-2H-pyran-2-on-6-yl)ethyltriphenylphosphonium iodide → 4-(4-methoxy-2-methyl-2H-pyran-2-on-6-yl)-2,4-dimethyl-1-(4-nitrophenyl)-1,3-butadiene (22388-89-2)

Guidance literature:

With potassium tert-butylate; Yield given. Multistep reaction; 1.) CH₂Cl₂, t-BuOH, RT, 30 min, 2.) CH₂Cl₂, t-BuOH, RT, 16 h;

DOI:10.1002/jhet.5570320223

Reference yield:

→ 4-(4-methoxy-2-methyl-2H-pyran-2-on-6-yl)-2,4-dimethyl-1-(4-nitrophenyl)-1,3-butadiene (22388-89-2)

Guidance literature:

Pyron 14, Dimethylsulfat, K2CO3/Aceton;

upstream raw materials:

(E)-2-methyl-3-(4-nitrophenyl)acrylaldehyde