Catalpalactone

Base Information

• Chemical Name: Catalpalactone
• CAS No.: 1585-68-8
• Deprecated CAS: 133591-03-4
• Molecular Formula: C₁₅H₁₄O₄
• Molecular Weight: 258.274
• UNII: P61GH0V29Z
• DSSTox Substance ID: DTXSID10928201
• Nikkaji Number: J13.166K
• Wikidata: Q27149847
• Metabolomics Workbench ID: 137458
• ChEMBL ID: CHEMBL471809
• Mol file: 1585-68-8.mol

Synonyms:Catalpalactone;1585-68-8;3-(2,2-dimethyl-6-oxo-3H-pyran-5-yl)-3H-2-benzofuran-1-one;UNII-P61GH0V29Z;P61GH0V29Z;CHEBI:80804;1(3H)-Isobenzofuranone, 3-(5,6-dihydro-6,6-dimethyl-2-oxo-2H-pyran-3-yl)-;3-(5,6-Dihydro-6,6-dimethyl-2-oxo-2H-pyran-3-yl)-1(3H)-isobenzofuranone;3-(6,6-Dimethyl-2-oxo-5,6-dihydro-2H-pyran-3-yl)isobenzofuran-1(3H)-one;1-Phthalanacetic acid, alpha-(3-hydroxy-3-methylbutylidene)-3-oxo-, delta-lactone;Phthalide, 3-(5,6-dihydro-6,6-dimethyl-2-oxo-2H-pyran-3-yl)-;starbld0005844;CHEMBL471809;DTXSID10928201;CATALPALACTONE, (+/-)-;AKOS032948471;C16929;Q27149847;3-(6,6-Dimethyl-2-oxo-5,6-dihydro-2H-pyran-3-yl)-2-benzofuran-1(3H)-one;1-Phthalanacetic acid, -(3-hydroxy-3-methylbutylidene)-3-oxo-, -lactone;1-PHTHALANACETIC ACID, .ALPHA.-(3-HYDROXY-3-METHYLBUTYLIDENE)-3-OXO-, .DELTA.-LACTONE;133591-03-4

Chemical Property of Catalpalactone

Chemical Property:

• Vapor Pressure: 6.69E-09mmHg at 25°C
• Boiling Point: 467.1°C at 760 mmHg
• Flash Point: 245.2°C
• PSA: 52.60000
• Density: 1.269g/cm³
• LogP: 2.55000
• XLogP3: 2.4
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 1
• Exact Mass: 258.08920892
• Heavy Atom Count: 19
• Complexity: 449

Purity/Quality:

98%min ^*data from raw suppliers

Catalpalactone ≥98% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1(CC=C(C(=O)O1)C2C3=CC=CC=C3C(=O)O2)C

Technology Process of Catalpalactone

There total 13 articles about Catalpalactone 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: 100.0%

2'-(phenylseleno)dihydrocatalpalactone (82027-10-9) → catalpalactone (1585-68-8)

Guidance literature:

With dihydrogen peroxide; acetic acid; In tetrahydrofuran; at 0 ℃; for 0.5h;

DOI:10.1021/jo00137a030

Reference yield:

5,6-dihydro-6,6-dimethyl-2H-pyran-2-one (19895-34-2) → catalpalactone (1585-68-8)

Guidance literature:

Multi-step reaction with 4 steps

1: 98 percent / H₂ / 10percent Pd/C / ethanol / 760 Torr / Ambient temperature

2: 1.) 2,2,6,6-tetramethylpiperidine, n-butyllithium / 1.) THF, from -78 deg C to RT, 30 min, 2.) THF, -78 deg C, 1 h

3: 1.) lithium 2,2,6,6-tetramethylpiperidide, hexamethylphosphoric triamide / 1.) THF, from -78 deg C to RT, 2.) THF, room temp., 30 min

4: 100 percent / acetic acid, 30percent H₂O₂ / tetrahydrofuran / 0.5 h / 0 °C

With 2,2,6,6-tetramethyl-piperidine; N,N,N,N,N,N-hexamethylphosphoric triamide; n-butyllithium; 2,2,6,6-tetramethylpiperidinyl-lithium; hydrogen; dihydrogen peroxide; acetic acid; palladium on activated charcoal; In tetrahydrofuran; ethanol;

DOI:10.1021/jo00137a030

Reference yield:

dihydrocatalpalactone (1585-50-8) → catalpalactone (1585-68-8)

Guidance literature:

Multi-step reaction with 2 steps

1: 1.) lithium 2,2,6,6-tetramethylpiperidide, hexamethylphosphoric triamide / 1.) THF, from -78 deg C to RT, 2.) THF, room temp., 30 min

2: 100 percent / acetic acid, 30percent H₂O₂ / tetrahydrofuran / 0.5 h / 0 °C

With N,N,N,N,N,N-hexamethylphosphoric triamide; 2,2,6,6-tetramethylpiperidinyl-lithium; dihydrogen peroxide; acetic acid; In tetrahydrofuran;

DOI:10.1021/jo00137a030

upstream raw materials:

2'-(phenylseleno)dihydrocatalpalactone

3-<(p-toluenesulfonyl)oxy>phthalide

6,6-dimethyltetrahydro-2H-pyran-2-one

3-Bromophthalide

Refernces

• 1、 Lane, Kimberley J.,Pinder, A. R.. "Synthesis of Catalpalactone". . p. 3171 - 3172. Retrieved 2007/10/02.