198649-20-6Relevant articles and documents
Molecular assembly of C2-symmetric Bis-(2S)-2-methyldodecanoylamides of α,ω-alkylidenediamines into coiled coil and twisted ribbon aggregates
Sumiyoshi, Takaaki,Nishimura, Katsumi,Nakano, Minoru,Handa, Tetsuro,Miwa, Yoshihisa,Tomioka, Kiyoshi
, p. 12137 - 12142 (2003)
A series of 10 didodecanoylamides of α,Ω-alkylidenediamines bridged by a straight carbon chain varying in length from 0 to 9 carbons was examined as possible gelator molecules of organic liquids to gain information on the relationships between the spacial arrangement of two amide groups in a molecule and their effects on the microscopic structures of the gel. The structural characteristics of these amides are parallel and antiparallel arrangements of two amide carbonyl groups, which depend on the even and odd numbers of a bridging zigzag carbon chain. The linear alkyl chain moieties and a center carbon chain of diamides intermolecularly interact with each other within the van der Waals contact. Two amide moieties of an even number carbon chain diamide intermolecularly interact with each other by using two pairs of hydrogen bonds with two other molecules in a plane, which formed ribbonlike self-complementarily assembled aggregates. On the other hand, a diamide of an odd number carbon chain forms four independent hydrogen bonds with four other molecules not in a plane, which assembled into woven aggregates. Asymmetric introduction of a methyl group at the α-position of the amide groups successfully twists the two side chain van der Waals cores of the chiral diamides in the fixed direction, giving helically twisted ribbon and coiled coil aggregates. The helically twisted ribbon and coiled coil aggregates of these chiral diamides were directly observed by CD, SEM, and TEM, providing a basis for the design of a sophisticated small molecular gelator of a tailor-made shape.
Convergent synthesis of panclicin-D via intramolecular SN2 displacement approach
Yadav, Jhillu Singh,Dachavaram, Soma Shekar,Peddapuram, Adithya,Das, Saibal
supporting information, p. 1952 - 1955 (2014/03/21)
A convergent enantioselective synthesis of panclicin-D has been reported from simple octanal using syn aldol reaction via intramolecular SN2 displacement reaction for the first time towards the construction of anti-β-lactones in panclicin-D. The key steps involved are C-allylation, asymmetric aldolization under Crimmins condition, intramolecular SN2 displacement, and Mitsunobu esterification reaction.
Autopoietic self-reproduction of chiral fatty acid vesicles
Morigaki, Kenichi,Dallavalle, Sabrina,Walde, Peter,Colonna, Stefano,Luisi, Pier Luigi
, p. 292 - 301 (2007/10/03)
The self-reproduction of vesicles formed by (S)- and (R)-2-methyldodecanoic acid (4) was investigated in order to relate the autocatalytic increase of the vesicle concentration with enantioselectivity. 4(R) and 4(S) were synthesized with an enantiomeric excess greater than 98%. 4 forms vesicles in aqueous solution in the pH region between 8.8 and 7.5. Chiral properties of the vesicles were studied by differential scanning calorimetry (DSC) and circular dichroism (CD). For self-reproduction studies, the hydrolysis of the water-insoluble 2-methyldodecanoic anhydride (8) was investigated in a biphasic system consisting of an aqueous solution and 8. The reaction rates of 8(RR) and 8(SS) catalyzed by 4(R) or 4(S) vesicles were the same within experimental errors, indicating that the chiral vesicles cannot induce significant enantioselectivity. However, a clear effect was observed at 10°C: racemic vesicles destabilized during hydrolysis, causing phase separation, whereas homochiral vesicles remained stable and continued to self-reproduce.
