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Methyl 12-bromo-dehydro-abietate.

Hong Gao¹, Zhan-Qian Song, Shi-Bin Shang

¹Institute of Chemical Industry of Forest Products, Chinese Academy of Forestry, Nanjing 210042, People's Republic of China.

Acta Crystallographica. Section E, Structure Reports Online

|May 18, 2011

Summary

This summary is machine-generated.

This study synthesized a novel brominated phenanthrene derivative. The research details its chemical structure, conformations, and crystal packing, offering insights into organic synthesis and molecular structure.

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Area of Science:

Organic Chemistry
Crystallography
Chemical Synthesis

Background:

Dehydro-abietic acid derivatives are valuable in organic synthesis.
Understanding the structural and conformational properties of complex organic molecules is crucial.

Purpose of the Study:

To synthesize and characterize a novel brominated phenanthrene derivative.
To elucidate the conformational preferences and crystal structure of the synthesized compound.

Main Methods:

Esterification of dehydro-abietic acid with methanol.
Bromination of methyl dehydro-abietate using N-bromo-succinimide.
X-ray crystallography to determine the crystal structure and molecular conformation.

Main Results:

Successful synthesis of (1R)-methyl 6-bromo-7-isopropyl-1,4a-dimethyl-1,2,3,4,4a,9,10,10a-octa-hydro-phen-anthrene-1-carboxylate.
The three six-membered rings adopt half-chair and chair conformations with a trans ring junction.
Crystal structure analysis revealed weak intermolecular C-H⋯O contacts stabilizing the packing.

Conclusions:

The synthesis provides a new route to functionalized phenanthrene derivatives.
The conformational analysis offers insights into the stereochemistry of related polycyclic compounds.
The crystal structure data contributes to the understanding of intermolecular interactions in organic solids.