Danishefsky's diene

Danishefsky's diene is a type of organic compound that is used in organic chemistry as a diene in Diels-Alder reactions. It was first synthesized by Samuel J. Danishefsky, a renowned American chemist, and hence, it bears his name.

Etymology

The term "Danishefsky's diene" is derived from the name of its discoverer, Samuel J. Danishefsky, and the term "diene", which is a type of organic compound that contains two alternating double bonds.

Structure and Properties

Danishefsky's diene is a cyclohexadiene derivative. It has a molecular formula of C9H10O2 and a molecular weight of 150.18 g/mol. The compound is characterized by its unique structure, which consists of a six-membered ring with two double bonds and an ester group attached to it.

Synthesis

The synthesis of Danishefsky's diene involves the reaction of dimethyl acetylenedicarboxylate with isopropylidene malonate in the presence of a base. The reaction proceeds via a Michael addition followed by an aldol condensation.

Applications

Danishefsky's diene is primarily used in Diels-Alder reactions. It acts as a diene, reacting with various dienophiles to form six-membered rings. The resulting products are often used in the synthesis of complex organic molecules, including natural products and pharmaceuticals.

Related Terms

• Diels-Alder reaction: A chemical reaction between a diene and a dienophile, resulting in a six-membered ring.
• Diene: An organic compound that contains two alternating double bonds.
• Dienophile: A compound that can react with a diene in a Diels-Alder reaction.
• Michael addition: A reaction where a nucleophile adds to an α,β-unsaturated carbonyl compound.
• Aldol condensation: A reaction where an enol or enolate ion reacts with a carbonyl compound to form a β-hydroxy aldehyde or ketone, followed by dehydration to give a conjugated enone.

Danishefsky's diene Resources
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