2-(4-Morpholinyl)-8-phenyl-4H-1-benzopyran-4-one

Base Information

• Chemical Name: 2-(4-Morpholinyl)-8-phenyl-4H-1-benzopyran-4-one
• CAS No.: 154447-36-6
• Molecular Formula: C19H17NO3
• Molecular Weight: 307.349
• Hs Code.: 29349990
• NSC Number: 697286
• UNII: 31M2U1DVID
• DSSTox Substance ID: DTXSID6042650
• Nikkaji Number: J615.849H
• Wikipedia: LY294002
• Wikidata: Q4042503
• NCI Thesaurus Code: C148229
• Pharos Ligand ID: 8V6MHDGWBBM5
• Metabolomics Workbench ID: 63788
• ChEMBL ID: CHEMBL98350
• Mol file: 154447-36-6.mol

Synonyms:2-(4-morpholinyl)-8-phenyl-4H-1-benzopyran-4-one;LY 29400;LY 294002;LY-294002;LY294002

Chemical Property of 2-(4-Morpholinyl)-8-phenyl-4H-1-benzopyran-4-one

Chemical Property:

• Appearance/Colour: Pale yellow solid
• Vapor Pressure: 6.33E-10mmHg at 25°C
• Melting Point: 183-185 °C
• Boiling Point: 494.6 °C at 760 mmHg
• PKA: 0.55±0.20(Predicted)
• Flash Point: 253 °C
• PSA: 42.68000
• Density: 1.266 g/cm³
• LogP: 3.36160
• Storage Temp.: 2-8°C
• Solubility.: DMSO: >5 mg/mL
• Water Solubility.: Soluble in DMSO at 5mg/ml. Insoluble in water
• XLogP3: 3.1
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 2
• Exact Mass: 307.12084340
• Heavy Atom Count: 23
• Complexity: 463

Purity/Quality:

99% ^*data from raw suppliers

LY 294002 ^*data from reagent suppliers

Safty Information:

• Safety Statements: 24-25

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: C1COCCN1C2=CC(=O)C3=C(O2)C(=CC=C3)C4=CC=CC=C4
• Description: LY294002 is a selective phosphatidylinositol 3-kinase (PI3K) inhibitor with a 2.7-fold greater potency than quercetin. LY294002 inhibits purified PI3K with an IC50 of 1.4 μM.
• Uses: LY 294002 Hydrochloride is a highly selective inhibitor of Phosphatidylinositol 3-kinase (PI3K). It is a salt analogue of LY 294002 (L486590). A potent blocker of PI 3-kinase/Akt signaling. LY294002 is a selective phosphatidylinositol 3-kinase (PI3K) inhibitor with a 2.7-fold greater potency than quercetin. LY294002 inhibits purified PI3K with an IC50 of 1.4 μM. LY 294002 is a Phosphatidylinositol 3-kinase (PI3K) inhibitor which has shown to block the formation of tumor tissues in bone marrow cavity an abolish multiple myeloma (MM) induced osteoclast formation and osteolysis in SCID mice.

Technology Process of 2-(4-Morpholinyl)-8-phenyl-4H-1-benzopyran-4-one

There total 20 articles about 2-(4-Morpholinyl)-8-phenyl-4H-1-benzopyran-4-one 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: 81.0%

1-(2-hydroxy-3-phenylphenyl)-3-(morpholin-4-yl)-propane-1,3-dione (688745-45-1) → LY 294002 (154447-36-6)

Guidance literature:

With trifluoromethylsulfonic anhydride; In dichloromethane; at 0 - 20 ℃; for 20h; Inert atmosphere;

DOI:10.1002/anie.201404495

Reference yield: 12.0%

phenylboronic acid (98-80-6) + trifluoromethanesulfonic acid 2-(morpholin-4-yl)-4-oxo-4H-chromen-8-yl ester (351002-11-4) → LY 294002 (154447-36-6)

Guidance literature:

With tetrabutylammomium bromide; potassium carbonate; palladium diacetate; at 70 ℃; for 4h;

DOI:10.1071/CH03113

Reference yield:

methyl 2-hydroxy-3-phenylbenzoate (4906-69-8) → LY 294002 (154447-36-6)

Guidance literature:

Multi-step reaction with 2 steps

1.1: LDA / tetrahydrofuran; hexane / 1.5 h / -10 °C

1.2: 73 percent / tetrahydrofuran; hexane / 16 h / 25 °C

2.1: 74 percent / triflic anhydride / CH₂Cl₂ / 20 h / 0 °C

With trifluoromethylsulfonic anhydride; lithium diisopropyl amide; In tetrahydrofuran; hexane; dichloromethane;

DOI:10.1021/jm049526a

upstream raw materials:

phenylboronic acid

trifluoromethanesulfonic acid 2-(morpholin-4-yl)-4-oxo-4H-chromen-8-yl ester

1-(2-hydroxy-3-phenylphenyl)-3-(morpholin-4-yl)-propane-1,3-dione

4-acetylmorpholine

Downstream raw materials:

C₂₈H₂₃N₂O₅S⁽¹⁺⁾*I^(1-)

C₂₈H₂₃N₂O₅⁽¹⁺⁾

C₂₇H₂₄NO₅⁽¹⁺⁾

Refernces

• 1、 Zhou, Guoqiang,Lim, Daniel,Coltart, Don M.. "Direct carbon - Carbon bond formation via chemoselective soft enolization of thioesters: A remarkably simple and versatile crossed-claisen reaction applied to the synthesis of LY294002". supporting information; experimental part. p. 3809 - 3812. Retrieved 2009/07/01.
• 2、 -. "PI-3 KINASE INHIBITOR PRODRUGS". Page 42. . Retrieved 2010/02/09.