7169-34-8 | 3-Coumaranone

Packsize	Purity	Availability	Price	Discounted Price
1g	98%	in stock	$13.00	$9.00
5g	98%	in stock	$23.00	$16.00
10g	98%	in stock	$29.00	$20.00
100g	97%	in stock	$271.00	$190.00
500g	97%	in stock	$1,350.00	$945.00

Description

• Catalog Number: AB44545
• Chemical Name: 3-Coumaranone
• CAS Number: 7169-34-8
• Molecular Formula: C8H6O2
• Molecular Weight: 134.1320
• MDL Number: MFCD00051810
• SMILES: O=C1COc2c1cccc2
• NSC Number: 512726

Computed Properties

• Complexity: 153
• Covalently-Bonded Unit Count: 1
• Heavy Atom Count: 10
• Hydrogen Bond Acceptor Count: 2
• Undefined Atom Stereocenter Count: 1
• XLogP3: 1.5

Upstream Synthesis Route

The upstream synthesis of 3-Coumaranone can be achieved through a few different synthetic routes. One common method involves the cyclization of 2-acetylphenol.

The process starts with the protection of the phenolic hydroxyl group of 2-acetylphenol by reacting it with an appropriate protecting group such as a silyl chloride in the presence of a base to yield a protected phenol intermediate.

Following protection, the ketone moiety is typically subjected to an alpha-halogenation to introduce a halogen atom alpha to the carbonyl group by using a halogenating agent such as N-bromosuccinimide (NBS) or phosphorus tribromide (PBr3) under acidic conditions.

The next step involves the formation of the coumaranone ring system via an intramolecular nucleophilic displacement, where the halogenated intermediate undergoes a base catalyzed cyclization, which can often be facilitated by a strong base like potassium t-butoxide, thus closing the ring and forming the 3-Coumaranone core.

Finally, the protecting group is removed from the phenolic hydroxyl using suitable conditions, such as exposure to a mild acid like hydrochloric acid or a fluoride ion source for silyl ether cleavage.

This results in the formation of 3-Coumaranone, which can then undergo further functionalization if required for specific applications. It is worth noting that the described approach is a generalized method; variations and modifications exist depending on the desired yield, purity, and scalability of the synthetic route.

Literature

• Synthesis and insect antifeedant activity of aurones against Spodoptera litura larvae.

  Journal of agricultural and food chemistry 20070207