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相关概念视频

Cycloaddition Reactions: Overview01:16

Cycloaddition Reactions: Overview

2.4K
Cycloadditions are one of the most valuable and effective synthesis routes to form cyclic compounds. These are concerted pericyclic reactions between two unsaturated compounds resulting in a cyclic product with two new σ bonds formed at the expense of π bonds. The [4 + 2] cycloaddition, known as the Diels–Alder reaction, is the most common. The other example is a [2 + 2] cycloaddition.
2.4K
[4+2] Cycloaddition of Conjugated Dienes: Diels–Alder Reaction01:16

[4+2] Cycloaddition of Conjugated Dienes: Diels–Alder Reaction

8.0K
The Diels–Alder reaction is an example of a thermal pericyclic reaction between a conjugated diene and an alkene or alkyne, commonly referred to as a dienophile. The reaction involves a concerted movement of six π electrons, four from the diene and two from the dienophile, forming an unsaturated six-membered ring. As a result, these reactions are classified as [4+2] cycloadditions.
8.0K
Cycloaddition Reactions: MO Requirements for Thermal Activation01:16

Cycloaddition Reactions: MO Requirements for Thermal Activation

29.7K
Thermal cycloadditions are reactions where the source of activation energy needed to initiate the reaction is provided in the form of heat. A typical example of a thermally-allowed cycloaddition is the Diels–Alder reaction, which is a [4 + 2] cycloaddition. In contrast, a [2 + 2] cycloaddition is thermally forbidden.
29.7K
Diels–Alder Reaction Forming Cyclic Products: Stereochemistry01:28

Diels–Alder Reaction Forming Cyclic Products: Stereochemistry

3.1K
The Diels–Alder reaction is one of the robust methods for synthesizing unsaturated six-membered rings. The reaction involves a concerted cyclic movement of six π electrons: four π electrons from the diene and two π electrons from the dienophile.
3.1K
Cyclohexenones via Michael Addition and Aldol Condensation: The Robinson Annulation01:27

Cyclohexenones via Michael Addition and Aldol Condensation: The Robinson Annulation

2.3K
Robinson annulation is a base-catalyzed reaction for the synthesis of 2-cyclohexenone derivatives from 1,3-dicarbonyl donors (such as cyclic diketones, β-ketoesters, or β-diketones) and α,β-unsaturated carbonyl acceptors. Named after Sir Robert Robinson, who discovered it, this reaction yields a six-membered ring with three new C–C bonds (two σ bonds and one π bond).
2.3K
Diels–Alder Reaction Forming Bridged Bicyclic Products: Stereochemistry01:29

Diels–Alder Reaction Forming Bridged Bicyclic Products: Stereochemistry

4.3K
Diels–Alder reactions between cyclic dienes locked in an s-cis configuration and dienophiles yield bridged bicyclic products.
4.3K

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相关实验视频

Updated: May 1, 2026

A Direct, Regioselective and Atom-Economical Synthesis of 3-Aroyl-N-hydroxy-5-nitroindoles by Cycloaddition of 4-Nitronitrosobenzene with Alkynones
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A Direct, Regioselective and Atom-Economical Synthesis of 3-Aroyl-N-hydroxy-5-nitroindoles by Cycloaddition of 4-Nitronitrosobenzene with Alkynones

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Dearomative 内醇 (3 + 2) 循环添加反应的反应.

Hui Li1, Russell P Hughes, Jimmy Wu

  • 1Department of Chemistry, Dartmouth College , Hanover, New Hampshire 03755, United States.

Journal of the American Chemical Society
|April 18, 2014
PubMed
概括
此摘要是机器生成的。

一种新的二聚体选择性废除反应使功能化的印丁化合物的高效合成成为可能. 这种方法可以访问自然产品的核心结构,并澄清反应机制.

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Synthesis of Indoxyl-glycosides for Detection of Glycosidase Activities
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Microwave-assisted Intramolecular Dehydrogenative Diels-Alder Reactions for the Synthesis of Functionalized Naphthalenes/Solvatochromic Dyes

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Synthesis of Indoxyl-glycosides for Detection of Glycosidase Activities
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科学领域:

  • 有机化学 有机化学
  • 合成化学 合成化学
  • 药用化学 医学化学

背景情况:

  • 在许多具有显著生物活性的自然产品中,印林支架普遍存在.
  • 开发高效的合成路径,以复杂的化工业素仍然是有机合成的一个关键挑战.

研究的目的:

  • 开发一种新型的二分体选择性 (3 + 2) 芳香式无效反应,用于合成功能化的印林衍生物.
  • 为了证明这种方法在自然产品核心的简洁合成中的实用性.
  • 通过计算研究来阐明反应机制.

主要方法:

  • 开发了一种以α-基子替代3基醇的二聚选择性 (3 + 2) dearomative 取消.
  • 使用密度函数理论 (DFT) 计算 (B3LYP-D3/6-311++G**/MeOH) 来研究反应途径.
  • 应用了合成温科林,异科林和阿司匹多菲林A的核心结构的方法.

主要成果:

  • 在无效反应中实现了显著的区域化学控制.
  • 提供了易于获得高度功能化的环和环素融合的印度化合物.
  • DFT研究支持了2-基基和氧基基通路的可行性,解释了区域化学和立体化学结果.

结论:

  • 开发的无效反应是构建复杂的印林框架的强大工具.
  • 该方法提供了一条简短的途径,以获得有价值的自然产品结构.
  • 计算分析提供了对反应机制的详细了解,包括动力学和热力学偏好.