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Chemical Compound Review

adamantanol     adamantan-1-ol

Synonyms: Adamantan-1-ol, PubChem8734, SureCN148421, ACMC-1CKM3, AG-F-06401, ...
 
 
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Disease relevance of adamantan-1-ol

  • Among 470 strains tested, Streptomyces griseoplanus was highly regioselective to give 1-adamantanol (0.096 mmol) from adamantane (0.3 mmol) in a 32% molar conversion yield after 72-h cultivation in the presence of 3% (v/v) Tween 60 [1].
 

High impact information on adamantan-1-ol

  • The activation energies for the C-H cleavage step are 6.9 kcal/mol in the 1-adamantanol pathway and 8.4 kcal/mol in the 2-adamantanol pathway, respectively, at the B3LYP/6-311++G level of theory, whereas those of the second reaction step corresponding to the rebound step are relatively small [2].
  • The available database for OH-stretching bands of jet-cooled aliphatic alcohol dimers is extended to systems including 1-adamantanol and 2-adamantanol, using a heated pulsed nozzle coupled to an FTIR spectrometer [3].

References

  1. Regioselective hydroxylation of adamantane by Streptomyces griseoplanus cells. Mitsukura, K., Kondo, Y., Yoshida, T., Nagasawa, T. Appl. Microbiol. Biotechnol. (2006) [Pubmed]
  2. A theoretical study of reactivity and regioselectivity in the hydroxylation of adamantane by ferrate(VI). Shiota, Y., Kihara, N., Kamachi, T., Yoshizawa, K. J. Org. Chem. (2003) [Pubmed]
  3. OH-stretching red shifts in bulky hydrogen-bonded alcohols: jet spectroscopy and modeling. Cézard, C., Rice, C.A., Suhm, M.A. The journal of physical chemistry. A, Molecules, spectroscopy, kinetics, environment & general theory. (2006) [Pubmed]
 
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