calophyllolid

Base Information

• Chemical Name: calophyllolid
• CAS No.: 548-27-6
• Molecular Formula: C26H24 O5
• Molecular Weight: 416.474
• Mol file: 548-27-6.mol

Synonyms:2H,8H-Benzo[1,2-b:3,4-b']dipyran-8-one,5-methoxy-2,2-dimethyl-6-(2-methyl-1-oxo-2-butenyl)-10-phenyl-, (E)-;2H,8H-Benzo[1,2-b:3,4-b']dipyran-8-one,5-methoxy-2,2-dimethyl-6-(2-methylcrotonoyl)-10-phenyl-, (E)- (8CI);2H,8H-Benzo[1,2-b:3,4-b']dipyran-8-one,5-methoxy-2,2-dimethyl-6-[(2E)-2-methyl-1-oxo-2-butenyl]-10-phenyl- (9CI);2H-1-Benzopyran-8-acrylic acid, 7-hydroxy-5-methoxy-2,2-dimethyl-b-phenyl-6-tigloyl-, d-lactone (6CI,7CI);Calophyllolide

Chemical Property of calophyllolid

Chemical Property:

• Vapor Pressure: 2.2E-18mmHg at 25°C
• Boiling Point: 661.2°C at 760 mmHg
• Flash Point: 224.4°C
• PSA: 65.74000
• Density: 1.213g/cm³
• LogP: 5.80170

Purity/Quality:

≥98% （HPLC） ^*data from raw suppliers

CALOPHYLLOLID 95.00% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of calophyllolid

There total 8 articles about calophyllolid 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: 53.0%

6-(2-Bromo-2-methylbutanoyl)-5-methoxy-2,2-dimethyl-10-phenyl-2H,8H-benzo<1,2-b:3,4-b'>dipyran-8-one (172805-13-9) → calophyllolide (548-27-6)

Guidance literature:

With 1,8-diazabicyclo[5.4.0]undec-7-ene; Ambient temperature;

Reference yield:

mammea A/BB cyclo D (5302-74-9,34107-37-4) → calophyllolide (548-27-6)

Guidance literature:

Multi-step reaction with 5 steps

1: 91 percent / K₂CO₃ / acetone / Heating

2: HBr / CCl₄ / 0.25 h / 0 °C

3: Br₂ / CCl₄

4: Et₃N / CCl₄

5: 53 percent / DBU / Ambient temperature

With hydrogen bromide; bromine; potassium carbonate; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; In tetrachloromethane; acetone;

Reference yield:

dimethylacetal of 3-methyl-3-hydroxybutyraldehyde (31525-67-4) → calophyllolide (548-27-6)

Guidance literature:

Multi-step reaction with 6 steps

1: 98 percent / pyridine / 48 h / 160 °C

2: 91 percent / K₂CO₃ / acetone / Heating

3: HBr / CCl₄ / 0.25 h / 0 °C

4: Br₂ / CCl₄

5: Et₃N / CCl₄

6: 53 percent / DBU / Ambient temperature

With hydrogen bromide; bromine; potassium carbonate; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; In pyridine; tetrachloromethane; acetone;

upstream raw materials:

6-(2-Bromo-2-methylbutanoyl)-5-methoxy-2,2-dimethyl-10-phenyl-2H,8H-benzo<1,2-b:3,4-b'>dipyran-8-one

3ξ-(5-methoxy-2,3,8,8-tetramethyl-4-oxo-3,4-dihydro-2H,8H-pyrano[3,2-g]chromen-10-yl)-3ξ-phenyl-acrylic acid

mammea A/BB cyclo D

dimethylacetal of 3-methyl-3-hydroxybutyraldehyde

Downstream raw materials:

10-cyclohexyl-5-methoxy-2,2-dimethyl-3,4,9,10-tetrahydro-2H-pyrano[2,3-f]chromen-8-one

5-methoxy-2,2-dimethyl-10-phenyl-3,4-dihydro-2H-pyrano[2,3-f]chromen-8-one

(+/-)-Inophyllum B

(+/-)-Inophyllum D

Refernces

• 1、 Palmer, Christopher J.,Josephs, Jonathan L.. "Synthesis of the calophyllum coumarins". . p. 5363 - 5366. Retrieved 2007/10/02.