4570-11-0

Basic information

• Product Name: beta-dolabrin
• Synonyms: beta-dolabrin;2-Hydroxy-4-isopropenyl-2,4,6-cycloheptatrien-1-one;β-Dolabrin
• CAS NO: 4570-11-0
• Molecular Formula: C₁₀H₁₀O₂
• Molecular Weight: 162.187
• Mol File: 4570-11-0.mol
• Article Data: 3

Chemical Properties

• Boiling Point: 334.2°Cat760mmHg
• Flash Point: 142.1°C
• Appearance: /
• Density: 1.166g/cm³
• Vapor Pressure: 9.16E-06mmHg at 25°C
• Refractive Index: 1.578
• CAS DataBase Reference: beta-dolabrin(CAS DataBase Reference)
• NIST Chemistry Reference: beta-dolabrin(4570-11-0)
• EPA Substance Registry System: beta-dolabrin(4570-11-0)

Safety Data

• Hazardous Substances Data: 4570-11-0(Hazardous Substances Data)

Usage

Synthesis Reference(s)

Journal of the American Chemical Society, 100, p. 4593, 1978 DOI: 10.1021/ja00482a045

InChI:InChI=1/C10H10O2/c1-7(2)8-4-3-5-9(11)10(12)6-8/h3-6H,1H2,2H3,(H,11,12)

Upstream product

• 698-47-5 4-bromo-2-hydroxycycklohepta-2,4,6-trien-1-one 
• 3043-46-7 isopropenyltrimethylstannane 
• 1716-81-0 (3-(1-bromo-1-methylethyl)-7-oxo-1,3,5-cycloheptatrienyloxy)difluoroborane 
• 103205-12-5 2-Amino-4-isopropenyl-tropon 
• 109248-35-3 5-isopropenyl-2-tosyloxytropone 

Downstream Products

• 499-44-5 hinokitiol 

Relevant articles and documents

The Palladium-Mediated Cross Coupling of Bromotropolones with Organostannanes or Arylboronic Acids: Applications to the Synthesis of Natural Products and Natural Product Analogues

The bromotropolones (4), (5) and (10) undergo palladium-mediated cross coupling with a wide range of organostannanes to produce alkenyl-, alkyl- and aryl-substituted tropolones.The methodology has been applied to the synthesis of the monoterpenes β-dolabrin (11), β-thujaplicin (12), 4-isopropyl-7-methoxytropolone (13) and β-thujaplicinol (14).Cross coupling of bromotropolones (4), (5) and (10) with various aryltrimethylstannanes or arylboronic acids has permitted the preparation of the bicyclic colchicine analogues (30)-(43) which have been tested for tubulin-binding activity.The X-ray crystal structure of the most active of these systems, compound (38), is reported.