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関連する概念動画

Preparation of 1° Amines: Hofmann and Curtius Rearrangement Overview01:07

Preparation of 1° Amines: Hofmann and Curtius Rearrangement Overview

3.2K
In the presence of an aqueous base and a halogen, primary amides can lose the carbonyl (as carbon dioxide) and undergo rearrangement to form primary amines. This reaction, called the Hofmann rearrangement, can produce primary amines (aryl and alkyl) in high yields without contamination by secondary and tertiary amines.
3.2K
[3,3] Sigmatropic Rearrangement of 1,5-Dienes: Cope Rearrangement01:21

[3,3] Sigmatropic Rearrangement of 1,5-Dienes: Cope Rearrangement

2.7K
The Cope rearrangement is classified as a [3,3] sigmatropic shift in 1,5-dienes, leading to a more stable, isomeric 1,5-diene. The reaction involves a concerted movement of six electrons, four from two π bonds and two from a σ bond, via an energetically favorable chair-like transition state.
2.7K
Stereoisomerism of Cyclic Compounds02:33

Stereoisomerism of Cyclic Compounds

9.0K
In this lesson, we delve into the role of ring conformation and its stability, which determines the spatial arrangement and, consequently, the molecular symmetry and stereoisomerism of cyclic compounds. 1,2-Dimethylcyclohexane is used as a case study to evaluate the possible number of stereoisomers. Here, given the multiple (n = 2) chiral centers, there are 2n = 4 possible configurations that lack a plane of symmetry, as the ring skeleton exists in a non-planar chair conformation. In addition,...
9.0K
Disubstituted Cyclohexanes: cis-trans Isomerism02:37

Disubstituted Cyclohexanes: cis-trans Isomerism

12.0K
Depending upon the different spatial orientation of the substituents, the disubstituted cycloalkanes exhibit two types of stereoisomers. The cis isomers have the substituents on the same side of the ring, whereas the trans isomers have the substituents on the opposite sides. These stereoisomers exhibit different physical properties and cannot be interconverted without breaking the carbon-carbon bonds.
In cyclohexane, the substituents can occupy different positions generating distinct isomers....
12.0K
Naming Enantiomers02:21

Naming Enantiomers

20.5K
The naming of enantiomers employs the Cahn–Ingold–Prelog rules that involve assigning priorities to different substituent groups at a chiral center. Each enantiomer, being a distinct molecule, is assigned a unique name by the Cahn–Ingold–Prelog (CIP) rules, also called the R–S system. The prefix R- or S- attached to the chiral centers in an enantiomer is dependent on the spatial arrangement of the four substituents on the chiral center. The R–S system...
20.5K
[3,3] Sigmatropic Rearrangement of Allyl Vinyl Ethers: Claisen Rearrangement01:24

[3,3] Sigmatropic Rearrangement of Allyl Vinyl Ethers: Claisen Rearrangement

2.1K
The Claisen rearrangement is a [3,3] sigmatropic rearrangement of allyl vinyl ethers to unsaturated carbonyl compounds. The rearrangement is a concerted pericyclic reaction proceeding via a chair-like transition state.
2.1K

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関連する実験動画

Updated: Jul 15, 2025

Preparation of Enantiopure Non-Activated Aziridines and Synthesis of Biemamide B, D, and epiallo-Isomuscarine
11:04

Preparation of Enantiopure Non-Activated Aziridines and Synthesis of Biemamide B, D, and epiallo-Isomuscarine

Published on: June 13, 2022

3.0K

(-) - カウラミジンDと (-) - アイソカウラミジンDのエナンチオセレクティブ・トータル・シンセシスと,それらの絶対的構成の再配置

Haiyong Yu1, Junhao Zhang1, Dongxu Ma1

  • 1Molecular Synthesis Center and Key Laboratory of Marine Drugs, MOE, and School of Medicine and Pharmacy, Ocean University of China, Qingdao 266003, China.

Journal of the American Chemical Society
|October 4, 2023
PubMed
まとめ

最初のエナチオセレクティブの (-) - カウラミジンDと (-) - アイソカウラミジンDの総合成は,統一された16段階の戦略を用いて達成された. 主な反応には,非対称的な再配置とカスケードサイクルが含まれ,それらのTFA塩の形態が確認されました.

さらに関連する動画

A Direct, Early Stage Guanidinylation Protocol for the Synthesis of Complex Aminoguanidine-containing Natural Products
09:04

A Direct, Early Stage Guanidinylation Protocol for the Synthesis of Complex Aminoguanidine-containing Natural Products

Published on: September 9, 2016

10.7K
Preparation of Stable Bicyclic Aziridinium Ions and Their Ring-Opening for the Synthesis of Azaheterocycles
11:45

Preparation of Stable Bicyclic Aziridinium Ions and Their Ring-Opening for the Synthesis of Azaheterocycles

Published on: August 22, 2018

8.5K

関連する実験動画

Last Updated: Jul 15, 2025

Preparation of Enantiopure Non-Activated Aziridines and Synthesis of Biemamide B, D, and epiallo-Isomuscarine
11:04

Preparation of Enantiopure Non-Activated Aziridines and Synthesis of Biemamide B, D, and epiallo-Isomuscarine

Published on: June 13, 2022

3.0K
A Direct, Early Stage Guanidinylation Protocol for the Synthesis of Complex Aminoguanidine-containing Natural Products
09:04

A Direct, Early Stage Guanidinylation Protocol for the Synthesis of Complex Aminoguanidine-containing Natural Products

Published on: September 9, 2016

10.7K
Preparation of Stable Bicyclic Aziridinium Ions and Their Ring-Opening for the Synthesis of Azaheterocycles
11:45

Preparation of Stable Bicyclic Aziridinium Ions and Their Ring-Opening for the Synthesis of Azaheterocycles

Published on: August 22, 2018

8.5K

科学分野:

  • 有機化学
  • 総合成
  • 自然製品化学

背景:

  • (-) カオラミジンDと (-) アイソカオラミジンDは複合的な天然製品です.
  • ステレオ化学と天然形態 (TFA塩) は以前は不明でした.

研究 の 目的:

  • (-) - カウラミジンDと (-) - アイソカウラミジンDの最初のエナンチオセレクティブ・トータル合成を達成する.
  • 絶対的な構成と自然形式を明確に決定する.

主な方法:

  • 統合された16段階の合成戦略が採用された.
  • 主なステップは,ステレオセンターの建設のための非対称的なメアウェイン-エシェンモサー-クライセン再配置でした.
  • 6 - エクソディグ/ 6 - エクソテトアミン/ ニトリルサイクリングを用いた.

主要な成果:

  • (-) - イソカウラミジンD (5) と (-) - イソカウラミジンD (6) の完全合成が成功しました.
  • 2つの化合物の絶対的な構成が確認されました.
  • 孤立した天然のサンプルは中性型ではなくトリフオロアセテート (TFA) 塩として特定された.

結論:

  • この研究は,これらの挑戦的な天然製品の最初の完全な合成を提供します.
  • 合成経路は,ステレオセンターの構築とサイクリングのための新しい方法論を強調しています.
  • TFA塩として自然形態の決定的な特徴は,それらの化学的アイデンティティを明確にします.