Related Experiment Video
Updated: Jun 5, 2026
07:56
Preparation of 6-aminocyclohepta-2,4-dien-1-one Derivatives via Tricarbonyl(tropone)iron
Published on: August 12, 2019
3,5,7-Tripropyl-1-aza-adamantane-4,6,10-triol
Acta Crystallographica. Section E, Structure Reports Online
|January 5, 2011
Summary
A new aza-adamantanetriol compound was synthesized using diastereoselective hydrogenation. Its crystal structure reveals intermolecular hydrogen bonding and no significant C-C bond elongation in the core structure.
Area of Science:
- Organic Chemistry
- Crystallography
- Stereochemistry
Background:
- Aza-adamantane derivatives are of interest in medicinal chemistry and materials science.
- Understanding the structural properties of novel aza-adamantane compounds is crucial for their applications.
Purpose of the Study:
- To synthesize a novel aza-adamantanetriol compound.
- To elucidate the crystal structure and bonding characteristics of the synthesized compound.
- To compare the structural features with related aza-adamantanone compounds.
Main Methods:
- Highly diastereoselective hydrogenation of 3,5,7-triallyl-1-aza-adamantane-4,6,10-trione.
- X-ray crystallography to determine the crystal structure.
- Analysis of bond lengths and intermolecular interactions.
Main Results:
- Successful synthesis of the title compound C(18)H(33)NO(3) with high diastereoselectivity.
- The crystal structure contains two independent molecules (Z' = 2) linked by intermolecular hydrogen bonds forming chains.
- The aza-adamantanetriol core does not exhibit significant C-C bond elongation, unlike aza-adamantanones.
Conclusions:
- The study presents a novel aza-adamantanetriol with defined stereochemistry.
- The crystal structure provides insights into the solid-state packing and hydrogen bonding of this class of compounds.
- The observed structural features contribute to the understanding of structure-property relationships in aza-adamantane derivatives.
More Related Videos
Related Concept Videos
01:10Nomenclature of Aryl and Heterocyclic Amines
The simplest aromatic amine is phenylamine, which contains an –NH2 functionality directly attached to an aromatic ring. The name aniline is designated for this skeleton. As shown in Figure 1, the common names of the functionalized anilines involve prefixes ortho-, meta-, and para- to indicate the substitution position. Different functionalized aniline derivatives also have notable trivial names.
![[3,3] Sigmatropic Rearrangement of 1,5-Dienes: Cope Rearrangement](/_next/image?url=https%3A%2F%2Fcloudfront.jove.com%2Ffiles%2Fmedia%2Fscience-education%2Fscience-education-thumbs%2F12422.jpg&w=3840&q=75)
01:21[3,3] Sigmatropic Rearrangement of 1,5-Dienes: Cope Rearrangement
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.
![[4+2] Cycloaddition of Conjugated Dienes: Diels–Alder Reaction](/_next/image?url=https%3A%2F%2Fcloudfront.jove.com%2Ffiles%2Fmedia%2Fscience-education%2Fscience-education-thumbs%2F12417.jpg&w=3840&q=75)
01:16[4+2] Cycloaddition of Conjugated Dienes: Diels–Alder Reaction
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.
01:18Aromatic Hydrocarbon Cations: Structural Overview
Cycloheptatriene is a neutral monocyclic unsaturated hydrocarbon that consists of an odd number of carbon atoms and an intervening sp3 carbon in the ring. The three double bonds in the ring correspond to 6 π electrons, which is a Huckel number, and therefore satisfies the criteria of 4n + 2 π electrons. However, the intervening sp3 carbon disrupts the continuous overlap of p orbitals. As a result, cycloheptatriene is not aromatic.
Removing one hydrogen from the intervening CH2 group with both...
Removing one hydrogen from the intervening CH2 group with both...
01:07Preparation of 1° Amines: Hofmann and Curtius Rearrangement Overview
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.
01:34Woodward–Hoffmann Selection Rules and Microscopic Reversibility
Electrocyclic reactions, cycloadditions, and sigmatropic rearrangements are concerted pericyclic reactions that proceed via a cyclic transition state. These reactions are stereospecific and regioselective. The stereochemistry of the products depends on the symmetry characteristics of the interacting orbitals and the reaction conditions. Accordingly, pericyclic reactions are classified as either symmetry-allowed or symmetry-forbidden. Woodward and Hoffmann presented the selection criteria for...