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Radical Oxidation of Allylic and Benzylic Alcohols

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A Strategy for Sensitive, Large Scale Quantitative Metabolomics

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Published on: May 27, 2014

17-Acet-oxy-mulinic acid.

Iván Brito, Jorge Bórquez, Joselyn Albanez

Acta Crystallographica. Section E, Structure Reports Online

|May 19, 2011

Summary

This summary is machine-generated.

This study details the crystal structure of a dodeca-hydro-cyclo-hepta-[e]indene derivative, highlighting molecular conformations and hydrogen bonding. Differences in acet-oxy-methyl fragment disorder were observed compared to a related compound.

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Area of Science:

Crystallography
Organic Chemistry
Structural Chemistry

Background:

The title compound, 5a-acet-oxy-methyl-3-isopropyl-8-methyl-1,2,3,3a,4,5,5a,6,7,10,10a,10b-dodeca-hydro-7,10-endo-epidi-oxy-cyclo-hepta-[e]indene-3a-carboxylic acid (I), is structurally similar to a previously reported methyl ester derivative (II).
Understanding the structural nuances and intermolecular interactions of such polycyclic compounds is crucial for predicting their chemical behavior and potential applications.

Purpose of the Study:

To elucidate the crystal structure and molecular conformation of compound (I).
To compare the structural features, particularly the presence of disorder and hydrogen bonding capabilities, with the related compound (II).

Main Methods:

Single-crystal X-ray diffraction analysis was employed to determine the crystal structure of compound (I).
Analysis of the crystal structure included identification of molecular conformation, hydrogen bonding patterns (intra- and intermolecular), and assessment of molecular disorder.

Main Results:

The asymmetric unit of compound (I) contains two molecules linked by intramolecular hydrogen bonds (R(2)(2)(8)).
Both compounds (I) and (II) exhibit similar three-ring conformations: envelope (five-membered), chair (six-membered), and boat (seven-membered).
Compound (I) displays disorder in the acet-oxy-methyl fragments, which is absent in compound (II), and intermolecular C-H⋯O hydrogen bonds stabilize the crystal structure.

Conclusions:

The crystal structure of compound (I) reveals specific conformational preferences and hydrogen bonding interactions.
The observed disorder in compound (I) represents a key structural difference compared to compound (II), potentially influencing their physical and chemical properties.
The study provides detailed structural insights into this class of complex organic molecules.