Chemical Transformations of Tetracyclo[3.3.1.13,7.01,3]decane (1,3-Dehydroadamantane): VII. Reaction of 1,3-Dehydroadamantane with Alkanediols and Amino Alcohols
作者： G. M. Butov , V. M. Mokhov
DOI: 10.1134/S1070428018120035
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摘要: The reaction of 1,3-dehydroadamantane with C2–C6 α,ω-alkanediols selectively afforded ω-(adamantan- 1-yloxy)alkan-1-ols in 87–94% yield. ω-aminoalkan-1- ols (2-aminoethanol and 3-aminopropan-1-ol) gave mixtures addition products through the oxygen nitrogen atoms, which can be readily separated by fractional vacuum distillation or crystallization.
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A. N. Reznikov, M. Yu. Skomorokhov, Yu. N. Klimochkin, Synthesis of 1-adamantyloxyalkanols Russian Journal of Organic Chemistry. ,vol. 46, pp. 1741- 1742 ,(2010) , 10.1134/S1070428010110217
J.K. Chakrabarti, M.J. Foulis, S.S. Szinai, Chemistry of adamantane. Part II. Synthesis of 1-adamantyloxyalkylamines Tetrahedron Letters. ,vol. 9, pp. 6249- 6252 ,(1968) , 10.1016/S0040-4039(00)75445-1
Nagaraj Nayak, Karical R Gopidas, None, Unusual self-assembly of a hydrophilic β-cyclodextrin inclusion complex into vesicles capable of drug encapsulation and release. Journal of Materials Chemistry B. ,vol. 3, pp. 3425- 3428 ,(2015) , 10.1039/C4TB02114B
Sotaro Inomata, Yusuke Harada, Shin-ichi Matsuoka, Takashi Ishizone, Synthesis and ring-opening reaction of novel 1,3-dehydroadamantanes possessing phenyl and alkoxyl substituents Tetrahedron. ,vol. 69, pp. 3238- 3248 ,(2013) , 10.1016/J.TET.2013.02.042
R. E. Pincock, J. Schmidt, W. B. Scott, E. J. Torupka, Synthesis and Reactions of Strained Hydrocarbons Possessing Inverted Carbon Atoms. Tetracyclo[3.3.1.13.7.01.3]decanes Canadian Journal of Chemistry. ,vol. 50, pp. 3958- 3964 ,(1972) , 10.1139/V72-627
A. N. Reznikov, M. Yu. Skomorokhov, Yu. N. Klimochkin, Synthesis of di(adamantylalkyl) tosyloxymethylphosphonates and di(adamantyloxyalkyl) tosyloxymethylphosphonates Russian Journal of General Chemistry. ,vol. 82, pp. 835- 839 ,(2012) , 10.1134/S1070363212050052
A. N. Reznikov, M. V. Leonova, A. K. Shiryaev, Yu. N. Klimochkin, Synthesis of adamantylalkyl tosyloxymethylphosphonates Russian Journal of General Chemistry. ,vol. 79, pp. 1755- 1757 ,(2009) , 10.1134/S1070363209080313
G. M. Butov, V. M. Mokhov, Reaction of 1,3-dehydroadamantane with dicarboxylic acid imides Russian Journal of Organic Chemistry. ,vol. 49, pp. 1403- 1404 ,(2013) , 10.1134/S1070428013090303
Paul E. Aldrich, Edward C. Hermann, Walter E. Meier, Marvin Paulshock, William W. Prichard, Jack Austin Synder, John C. Watts, Antiviral agents. 2. Structure-activity relationships of compounds related to 1-adamantanamine. Journal of Medicinal Chemistry. ,vol. 14, pp. 535- 543 ,(1971) , 10.1021/JM00288A019
Paul J. Kropp, Graham S. Poindexter, Norbert J. Pienta, David C. Hamilton, Photochemistry of alkyl halides. 4. 1-Norbornyl, 1-norbornylmethyl, 1- and 2-adamantyl, and 1-octyl bromides and iodides Journal of the American Chemical Society. ,vol. 98, pp. 8135- 8144 ,(1976) , 10.1021/JA00441A043