62770-67-6

Basic information

• Product Name: clausarin
• Synonyms: clausarin;3,10-Bis(1,1-dimethyl-2-propenyl)-5-hydroxy-8,8-dimethyl-2H,8H-benzo[1,2-b:5,4-b']dipyran-2-one
• CAS NO: 62770-67-6
• Molecular Formula: C24H28O4
• Molecular Weight: 380.47672
• Mol File: 62770-67-6.mol
• Article Data: 3

Chemical Properties

• Boiling Point: 513.5°Cat760mmHg
• Flash Point: 171.4°C
• Appearance: /
• Density: 1.121g/cm³
• Vapor Pressure: 3.65E-11mmHg at 25°C
• Refractive Index: 1.559
• PKA: 7.08±0.40(Predicted)
• CAS DataBase Reference: clausarin(CAS DataBase Reference)
• NIST Chemistry Reference: clausarin(62770-67-6)
• EPA Substance Registry System: clausarin(62770-67-6)

Safety Data

• Hazardous Substances Data: 62770-67-6(Hazardous Substances Data)

Usage

InChI:InChI=1/C24H28O4/c1-9-22(3,4)16-13-15-18(25)14-11-12-24(7,8)28-20(14)17(23(5,6)10-2)19(15)27-21(16)26/h9-13,25H,1-2H2,3-8H3

Upstream product

• 62770-68-7 clausarin acetate 
• 108-24-7 acetic anhydride 
• 90363-10-3 3,10-bis-(1,1-dimethylallyl)-5-methoxy-8,8-dimethyl-8H-pyrano[3,2-g]chromen-2-one 
• 88223-87-4 5-hydroxy-6-(1,1-dimethylallyl)seselin 
• 88223-86-3 5-acetoxy-6-(1,1-dimethylallyl)seselin 
• 88223-89-6 nordentatin 1,1-dimethylallyl ether 
• 88223-88-5 nordentatin 1,1-dimethylpropargyl ether 
• 23351-43-1 7-hydroxy-5-methoxy-8-(1,1-dimethylallyl)coumarin 
• 31525-67-4 dimethylacetal of 3-methyl-3-hydroxybutyraldehyde 
• 90363-08-9 5-Methoxy-7-O-(3,3-dimethylallyl)-8-(1,1-dimethylallyl)coumarin 
• 90363-09-0 7-hydroxy-5-methoxy-3,8-bis(1,1-dimethylallyl)coumarin 
• 30779-97-6 7-butyryloxy-5-methoxy-8-(1,1-dimethylallyl)coumarin 
• 92171-50-1 7-butyryloxy-5-methoxy-3,8-bis(1,1-dimethylallyl)coumarin 

Relevant articles and documents

CLAISEN REARRANGEMENTS-XIII SYNHESIS OF THE NATURAL COUMARINS, NORDENTATIN, DENTATIN AND CLAUSARIN

The structure of the natural coumarin, clausarin 10 has been confirmed by an eight step synthesis from 5-hydroxyseselin 1 in 56percent overall yield.The efficient synthesis of its precursor, nordentatin 5 provides a convenient alternative synthetic route to dentatin 6.The revised structure 13 is suggested for clausenidinaric acid.

Synthesis of Clausarin

The synthesis of clausarin (14), a novel coumarin isolated from the roots of Clausena pentaphylla has been achieved.The synthetic strategy involves triple Claisen rearrangement of 5-methoxy-7-O-(3,3-dimethylallyl)coumarin (5) in butyric anhydride to afford the products (6) and (7).The latter 7 on alkaline hydrolysis followed by reaction with 1-bromo-3-methylbut-2-ene furnishes 5-methox-7-O-(3,3-dimethylallyl)coumarin (10).A similar Claisen rearrangement of 10 followed by alkaline hydrolysis gives the phenol (12) which on condensation with 3-hydroxyisovaleraldehyde dimethyl acetal affords O-methylclausarin (15).Demethylation of 15 with boron tribromide finally yields the title compound.