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单词 Dipolarophile
释义

Dipolarophile

中文百科

1,3-偶极环加成反应 1,3-Dipolar cycloaddition

(重定向自Dipolarophile)
Estructura y nomenclatura de 1,3-dipolos que constan de carbono, nitrógeno y oxígeno. Los dipolos se clasifican de tipo alilo (allyl-type) o de tipo alenilo/propargilo (propargyl/allenyl-type) en base a la geometría del átomo central.

1,3-偶极环加成反应(1,3-dipolar cycloaddition),或被称为Huisgen反应Huisgen环加成反应,是发生在1,3-偶极体和烯烃、炔烃或其衍生物之间的一个协同周环的环加成反应。烯烃类化合物在反应中称亲偶极体(dipolarophile)。德国化学家Rolf Huisgen首个应用此类反应以制取五元杂环化合物。

1,3-偶极环加成反应与狄尔斯-阿尔德反应有些相似。根据前线轨道理论,基态时1,3-偶极体的LUMO和亲偶极体的HOMO,以及基态时1,3-偶极体的HOMO和亲偶极体的LUMO,都是为分子轨道对称守恒原理所允许的,因此反应可以发生。1,3-偶极环加成反应因此也分为三类:一类是由1,3-偶极体出HOMO,称为HOMO控制的反应;一类是由1,3-偶极体出LUMO,称为LUMO控制的反应;还有一类就是两种情况都存在,称为(HOMO-LUMO)控制的反应。

英语百科

1,3-Dipolar cycloaddition 1,3-偶极环加成反应

(重定向自Dipolarophile)
Structure and nomenclature of all second-row 1,3-dipoles consisting of carbon, nitrogen and oxygen centers. The dipoles are categorized as allyl-type or propargyl/allenyl-type based on the geometry of the central atom.

The 1,3-dipolar cycloaddition is a chemical reaction between a 1,3-dipole and a dipolarophile to form a five-membered ring. The earliest 1,3-dipolar cycloadditions were described in the late 19th century to the early 20th century, following the discovery of 1,3-dipoles. Mechanistic investigation and synthetic application were established in the 1960s, primarily through the work of Rolf Huisgen. Hence, the reaction is sometimes referred to as the Huisgen cycloaddition (this term is often used to specifically describe the 1,3-dipolar cycloaddition between an organic azide and an alkyne to generate 1,2,3-triazole). Currently, 1,3-dipolar cycloaddition is an important route to the regio- and stereoselective synthesis of five-membered heterocycles and their ring-opened acyclic derivatives.

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更新时间:2025/6/20 17:08:14