40571-15-1Relevant articles and documents
Design and synthesis of bioactive adamantanaminoalcohols and adamantanamines
Zoidis, Grigoris,Kolocouris, Nicolas,Kelly, John M.,Prathalingam, S. Radhika,Naesens, Lieve,De Clercq, Erik
scheme or table, p. 5022 - 5030 (2010/12/24)
Adamantanamines 16, 18, 21, 24, 27, 28, 30, 32, 35, 36, 37, 40, 46 and 48 were synthesized and tested for anti-influenza A virus and trypanocidal activity. The stereoelectronic requirements for optimal antiviral and trypanocidal potency were investigated.
trans-2,2′-Bi(1-phenyladamantylidene): The most twisted biadamantylidene
Okazaki, Takao,Ogawa, Kohei,Kitagawa, Toshikazu,Takeuchi, Ken'ichi
, p. 5981 - 5986 (2007/10/03)
The Grignard coupling of 2,2-dibromo-1-phenyladamantane gave trans-2,2′-bi(1-phenyladamantylidene) (1-Ph). Single-crystal X-ray analysis indicated that 1-Ph has a 23.2° twisted double bond, which is much more distorted than that of parent 2,2′-biadamantylidene (1-H) and that of the ethyl-substituted derivative (1-Et). A cyclic voltammogram showed a reversible electron oxidation wave at 0.87 V vs Fc/Fc+, which is 0.19 V lower than 1-H, indicating a significant increase in the HOMO energy level due to the distortion. The reaction of 1-Ph with 0.9 equiv of bromine gave an intramolecular Friedel-Crafts alkylation product, while bromination of 1-H and 1-Me has been reported to give a bridged bromonium ion and a rearranged product, 2-(1-methyl-2-adamantylidene)-4-bromotricyclo [5,3,1,03.9]undec-4-ene, respectively.