chalepin

Base Information

• Chemical Name: chalepin
• CAS No.: 13164-04-0
• Molecular Formula: C₁₉H₂₂O₄
• Molecular Weight: 314.381
• Mol file: 13164-04-0.mol

Synonyms:7H-Furo[3,2-g][1]benzopyran-7-one,6-(1,1-dimethyl-2-propenyl)-2,3-dihydro-2-(1-hydroxy-1-methylethyl)- (9CI);7H-Furo[3,2-g][1]benzopyran-7-one,6-(1,1-dimethylallyl)-2,3-dihydro-2-(1-hydroxy-1-methylethyl)- (8CI); Chalepin

Chemical Property of chalepin

Chemical Property:

• Vapor Pressure: 1.86E-09mmHg at 25°C
• Boiling Point: 465.3°C at 760 mmHg
• Flash Point: 164.8°C
• PSA: 59.67000
• Density: 1.207g/cm³
• LogP: 3.33100

Purity/Quality:

99% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of chalepin

There total 15 articles about chalepin 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: 91.0%

7-hydroxy-6-(3-methylbut-2-enyl)-3-(2-methylbut-3-en-2-yl)-2H-chromen-2-one (21316-80-3) → 2,3-dihydro-2-(2-hydroxypropan-2-yl)-6-(2-methylbut-3-en-2-yl)furo[3,2-g]chromen-7-one (13164-04-0,14755-47-6,33054-89-6)

Guidance literature:

7-hydroxy-6-(3-methylbut-2-enyl)-3-(2-methylbut-3-en-2-yl)-2H-chromen-2-one; With 3-chloro-benzenecarboperoxoic acid; In dichloromethane; at 0 - 20 ℃;

With dmap; In dichloromethane; at 20 ℃; for 16h; chemoselective reaction;

DOI:10.3987/COM-10-11962

Reference yield:

3-chloro-3-methylbut-1-yne (1111-97-3) → 2,3-dihydro-2-(2-hydroxypropan-2-yl)-6-(2-methylbut-3-en-2-yl)furo[3,2-g]chromen-7-one (13164-04-0,14755-47-6,33054-89-6)

Guidance literature:

Multi-step reaction with 6 steps

1: 78 percent / K₂CO₃, KI / acetone; H₂O / Heating

2: 100 percent / H₂ / Pd/BaSO₄ / toluene / 760 Torr

3: 53 percent / AcONa / 1 h / 150 °C

4: 61 percent / K₂CO₃ / acetone / 24 h / Heating

5: 10 percent / N,N-dimethyl-acetamide / 6 h / 200 °C

6: 73 percent / m-chloroperbenzoic acid (MCPBA) / diethyl ether / 6 h

With hydrogen; sodium acetate; potassium carbonate; 3-chloro-benzenecarboperoxoic acid; potassium iodide; Pd-BaSO₄; In diethyl ether; N,N-dimethyl acetamide; water; acetone; toluene;

Reference yield:

7-hydroxy-8-iodocoumarin (65763-00-0) → 2,3-dihydro-2-(2-hydroxypropan-2-yl)-6-(2-methylbut-3-en-2-yl)furo[3,2-g]chromen-7-one (13164-04-0,14755-47-6,33054-89-6)

Guidance literature:

Multi-step reaction with 6 steps

1: 78 percent / K₂CO₃, KI / acetone; H₂O / Heating

2: 100 percent / H₂ / Pd/BaSO₄ / toluene / 760 Torr

3: 53 percent / AcONa / 1 h / 150 °C

4: 61 percent / K₂CO₃ / acetone / 24 h / Heating

5: 10 percent / N,N-dimethyl-acetamide / 6 h / 200 °C

6: 73 percent / m-chloroperbenzoic acid (MCPBA) / diethyl ether / 6 h

With hydrogen; sodium acetate; potassium carbonate; 3-chloro-benzenecarboperoxoic acid; potassium iodide; Pd-BaSO₄; In diethyl ether; N,N-dimethyl acetamide; water; acetone; toluene;

upstream raw materials:

7-hydroxy-6-(3-methylbut-2-enyl)-3-(2-methylbut-3-en-2-yl)-2H-chromen-2-one

3-chloro-3-methylbut-1-yne

7-hydroxy-8-iodocoumarin

7-hydroxy-2H-chromen-2-one

Downstream raw materials:

(+/-)-rutamarin

Refernces

• 1、 Massanet, Guillermo M.,Pando, Enrique,Rodiriquez-Luis, Francisco,Salva, Javier. "SYNTHESIS OF 3-(1',1'-DIMETHYLALLYL)COUMARINS: GRAVELLIFERONE, CHALEPIN AND RUTAMARIN". . p. 1541 - 1548. Retrieved 2007/10/02.