环氧化合物

具有环张力的三元环醚，可通过开环引入新的官能团。

官能团
three-membered C-O-C ring
Also known as
epoxide, oxiranes, oxirane rings, alkene oxides

概览

An epoxide is a three-membered ring containing oxygen. Ring strain makes it more susceptible to nucleophilic opening than ordinary ethers. Epoxide opening connects alkene oxidation to diols and other functionalised molecules; a monoepoxide is not automatically an epoxy resin.

Identifiers

官能团
three-membered C-O-C ring
Also known as
epoxide, oxiranes, oxirane rings, alkene oxides

性质

环结构的适用边界
四氢呋喃和 1,4-二氧六环是环醚，但其较大的环不属于环氧化合物。
开环
碱性条件下，亲核试剂通常进攻位阻较小的碳；酸促进反应的区域选择性取决于取代情况。

Related compounds

  • 环氧乙烷

    最小的环氧化合物，三元环由两个碳和一个氧组成。

  • 环氧丙烷

    带甲基取代基的环氧化合物，两个环碳不等价。

Connected reactions

  • Epoxidation: Alkenes → Epoxides

    过氧酸以协同步骤将氧转移到烯烃双键两端，形成两个 C-O 键并断开 C=C 的 π 键。两个键从同一面形成，使烯烃取代基的相对立体关系在环氧产物中保留。

  • Epoxide hydrolysis: Epoxides → Diols

    质子化使有张力的环更易受到水的进攻。背面进攻断开一个 C-O 键，质子转移后在相邻碳上形成羟基；当环几何结构允许区分时，两者呈反式加成关系。

参考文献

  1. Organic Chemistry: Cyclic Ethers: EpoxidesJohn McMurry · OpenStax Organic Chemistry · 2023

    Supports functional-group chemistry used to curate the linked examples. Checked 2026-09-16; named examples are applications of textbook scope, without claimed experimental yields.

  2. Organic Chemistry: Reactions of Epoxides: Ring-OpeningJohn McMurry · OpenStax Organic Chemistry · 2023

    Supports functional-group chemistry used to curate the linked examples. Checked 2026-09-16; named examples are applications of textbook scope, without claimed experimental yields.

  3. PubChem Compound Summary: Oxirane (CID 6354)National Center for Biotechnology Information · PubChem

    Identity, molecular formula, molecular weight and selected English aliases retrieved via PUG REST on 2026-09-16. Chinese search names are curated nomenclature translations. Unspecified stereochemistry remains unspecified.

  4. PubChem Compound Summary: Propylene oxide (CID 6378)National Center for Biotechnology Information · PubChem

    Identity, molecular formula, molecular weight and selected English aliases retrieved via PUG REST on 2026-09-16. Chinese search names are curated nomenclature translations. Unspecified stereochemistry remains unspecified.