Michael Addition
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CH2(COOC2H5)2 + CH2=CHCOCH3 → product
概要
A Michael donor (stabilized carbanion) adds to the beta-carbon of a Michael acceptor (alpha,beta-unsaturated carbonyl). This 1,4-conjugate addition forms a new carbon-carbon bond and is complementary to 1,2-addition. The Michael reaction is one of the most versatile C-C bond forming reactions.
日常の例
The Robinson annulation, combining Michael addition with aldol condensation, is used to build steroid ring systems in drug synthesis.
産業上の重要性
マイケル付加は医薬品合成、ポリマー化学(アクリレート重合、ゲル形成)、農薬合成に広く利用される。チオール-マイケル付加は生体直交型化学やバイオコンジュゲーション技術の基盤でもある。
特性
- タイプ
- Organic
- 可逆的
- はい
- エネルギー
- 発熱性
- ΔH
- -25.0 kJ/mol
- 触媒
- Base (e.g., NaOEt)