112-16-3Relevant academic research and scientific papers
Studies of the tandem mukaiyama aldol-lactonization (TMAL) reaction: A concise and highly diastereoselective route to β-lactones applied to the total synthesis of the potent pancreatic lipase inhibitor, (-)-Panclicin D
Yang, Hong Woon,Zhao, Cunxiang,Romo, Daniel
, p. 16471 - 16488 (1997)
A concise and highly diastereoselective route to β-lactones has been developed based on a tandem Mukaiyama aldol-lactonization employing thiopyridylsilylketene acetals and various aldehydes. (-) - Panclicin D, a potent pancreatic lipase inhibitor, was synthesized using this methodology. Recent optimization and extensions of this method are described which include variation of the silyl group and leaving group of the ketene acetal.
Preparation and characterization of a series of thiourea derivatives as phase change materials for thermal energy storage
Alkan, Cemil,Tek, Yusuf,Kahraman, Derya
, p. 769 - 777 (2011)
A series of solid-liquid phase change materials, thiourea derivatives, were prepared via condensation of thiourea with the respective carboxyl chlorides (lauroyl chloride, myristoyl chloride, and palmitoyl chloride) and were then characterized by using FT-IR, 1H-NMR, differential scanning calorimetry (DSC), and thermogravimetric (TG) analysis. The thiourea derivatives (1,3-didodecanoyl thiourea, 1,3-ditetradecanoyl thiourea, and 1,3-dihexadecanoyl thiourea) were structurally symmetric and had long alkyl groups to crystallize. Thermal analysis by DSC and spectroscopic investigation by FT-IR spectroscopy were performed on the samples before and after thermal cycling tests to determine thermal reliability. The maximum latent heats of melting and freezing of the thiourea derivatives were found to be 114.6 and -110.0 J/g for 1,3-didodecanoyl thiourea, 119.5 and -122.4 J/g for 1,3-ditetradecanoyl thiourea, and 148.8 and -142.7 J/g for 1,3-dihexadecanoyl thiourea after accelerated thermal cycling. A TG instrument was used to determine the starting point of degradation in the thiourea derivatives; it was found that the thiourea derivatives degraded at sufficiently higher temperatures than the expected utility temperatures.
DECOMPOSITION DE L'ACIDE PEROXYDODECANOIQUE DANS CCl4: ROLE DU SOLVANT
Sorba, J.,Fossey, J.,Lefort, D.,Nedelec, J. Y.
, p. 69 - 74 (1981)
The decomposition of peroxydodecanoic acid in refluxing CCl4 proceeds by a complex process involving ionic and radical reactions.In the latter, this study has confirmed the important role, shown previously, of the character (nucleophilic or electrophilic) of the radical on the regioselectivity of the attack on the peracid. The (*)CCl3 radicals (electrophilic) proceed by abstraction of the H of the peracid; the analysis of the products confirms the presence of intermediary R-(*)CO radicals resulting from the equilibrium: This explains why the decomposition of a peracid in CCl4 leads mainly to the formation of the corresponding acid whereas in a hydrocarbon solvent one observes essentially the decarboxylation leading to the alcohol according to the mechanism previously proved.
Lipophilic pyrylium salts in the synthesis of efficient pyridinium-based cationic lipids, gemini surfactants, and lipophilic oligomers for gene delivery
Ilies, Marc Antoniu,Seitz, William A.,Johnson, Betty H.,Ezell, Edward L.,Miller, Aaron L.,Thompson, E. Brad,Balaban, Alexandru T.
, p. 3872 - 3887 (2006)
Several new classes of pyridinium cationic lipids were synthesized and tested as gene delivery agents. They were obtained through a procedure that generates simultaneously the heterocyclic ring and the positively charged nitrogen atom, using lipophilic pyrylium salts as key intermediates that react with primary amines, yielding pyridinium salts. The choice of the appropriately substituted primary amine, diamine or polyamine, allows the design of the shape of the final lipids, gemini surfactants, or lipophilic polycations. We report also a comprehensive structure-activity relationship study that identified the most efficient structural variables at the levels of the hydrophobic anchor, linker, and counterion for these classes of pyridinium cationic lipids. This study was also aimed at finding the best liposomal formulation for the new transfection agents.
Synthesis of neoglycolipids based on D-lactose
Gur'eva,Budanova,Sebyakin
, p. 173 - 177 (2009)
A synthesis was performed of amphiphilic D-lactose derivatives differing by the length and number of aliphatic chains. The compounds may be applied to the carbohydrate modification of phosphatidylcholine liposomes.
Trifluoromethyl ketone inhibitors of fatty acid amide hydrolase: A probe of structural and conformational features contributing to inhibition
Boger, Dale L.,Sato, Haruhiko,Lerner, Aaron E.,Austin, Bryce J.,Patterson, Jean E.,Patricelli, Matthew P.,Cravatt, Benjamin F.
, p. 265 - 270 (1999)
The examination of a series of trifluoromethyl ketone inhibitors of Fatty Acid Amide Hydrolase (FAAH, oleamide hydrolase, anandamide amidohydrolase) is detailed in efforts that define structural and conformational properties that contribute to enzyme inhibition and substrate binding. The results imply an extended bound conformation, highlight a role for the presence, position, and stereochemistry of a Δ cis double bond, and suggest little apparent role for C11-C18/C22 of the fatty acid amide substrates.
Synthesis and preliminary biochemical assessment of ethyl-terminated perfluoroalkylamine oxide surfactants
Chaudier, Yann,Zito, Francesca,Barthélémy, Philippe,Stroebel, David,Améduri, Bruno,Popot, Jean-Luc,Pucci, Bernard
, p. 1587 - 1590 (2002)
The synthesis and usefulness in membrane biochemistry of a new class of surfactants have been investigated. 1-Ethyl-2-dimethylamine oxide polar heads were grafted onto a hydrocarbon, a fluorocarbon or an ethyl-capped fluorocarbon hydrophobic tail. The ability of the resulting surfactants to extract and/or to stabilize in aqueous solution a test membrane protein, cytochrome b6 f, was evaluated. While it is not a detergent, the hemifluorinated derivative efficiently kept purified cytochrome b6 f soluble, native and functional. The data suggest that alkyl-capped fluorocarbon surfactants provide an interesting alternative to classical detergents for handling membrane proteins in aqueous solutions under non-dissociating conditions.
Liquid crystalline and light emitting polyacetylenes: Synthesis and properties of biphenyl-containing poly(1-alkynes) with different functional bridges and spacer lengths
Lam, Jacky W.Y.,Dong, Yuping,Cheuk, Kevin K.L.,Luo, Jingdong,Xie, Zhiliang,Kwok, Hoi Sing,Mo, Zhishen,Tang, Ben Zhong
, p. 1229 - 1240 (2002)
Biphenyl-(Biph-) containing 1-alkynes (3 and 4) and their polymers (1 and 2) with varying bridge groups and spacer lengths were synthesized and the effects of the structural variation on their properties, especially their mesomorphism and photoluminescence behaviors, were studied. The acetylene monomers 3(3) [HC≡C(CH2)3O-Biph-OCO(CH2)10CH 3] and 4(m) [HC≡C(CH2)m OCO-Biph-OCO(CH2)10-CH3, m = 3,4] were prepared by sequential etherization and esterification reactions of 1-alkynes. While 3(3) exhibits enantiotropic crystal E and SmB mesophases, its structural cousin 4(3) displays only monotropic SmB phase. Enantiotropic SmA and SmB mesophases are, however, developed when the spacer length is increased to 4. Polymerizations of the monomers are affected by Mo-, W-, Rh-, and Fe-based catalysts, with the WCl6-Ph4Sn catalyst giving the best results (isolation yield up to 85% and Mw up to 59000). The polymers were characterized by IR, UV, NMR, TGA, DSC, POM, XRD, and PL analyses. Compared to 1(3), 2(3) shows a red-shifted absorption, a higher Ti, and a better packed interdigitated bilayer SmAd structure, while the mesophase of 2(4) involves mionolayer-packing arrangements of the mesogens. Upon photoexcitation, 1(3) emits almost no light but 2(m) gives a strong ultraviolet emission (λmax ～ 350 nm), whose intensity increases with the spacer length.
Acene Ring Size Optimization in Fused Lactam Polymers Enabling High n-Type Organic Thermoelectric Performance
Chen, Hu,Moser, Maximilian,Wang, Suhao,Jellett, Cameron,Thorley, Karl,Harrison, George T.,Jiao, Xuechen,Xiao, Mingfei,Purushothaman, Balaji,Alsufyani, Maryam,Bristow, Helen,De Wolf, Stefaan,Gasparini, Nicola,Wadsworth, Andrew,McNeill, Christopher R.,Sirringhaus, Henning,Fabiano, Simone,McCulloch, Iain
, p. 260 - 268 (2021)
Three n-type fused lactam semiconducting polymers were synthesized for thermoelectric and transistor applications via a cheap, highly atom-efficient, and nontoxic transition-metal free aldol polycondensation. Energy level analysis of the three polymers demonstrated that reducing the central acene core size from two anthracenes (A-A), to mixed naphthalene-anthracene (A-N), and two naphthalene cores (N-N) resulted in progressively larger electron affinities, thereby suggesting an increasingly more favorable and efficient solution doping process when employing 4-(2,3-dihydro-1,3-dimethyl-1H-benzimidazol-2-yl)-N,N-dimethylbenzenamine (N-DMBI) as the dopant. Meanwhile, organic field effect transistor (OFET) mobility data showed the N-N and A-N polymers to feature the highest charge carrier mobilities, further highlighting the benefits of aryl core contraction to the electronic performance of the materials. Ultimately, the combination of these two factors resulted in N-N, A-N, and A-A to display power factors (PFs) of 3.2 μW m-1 K-2, 1.6 μW m-1 K-2, and 0.3 μW m-1 K-2, respectively, when doped with N-DMBI, whereby the PFs recorded for N-N and A-N are among the highest reported in the literature for n-type polymers. Importantly, the results reported in this study highlight that modulating the size of the central acene ring is a highly effective molecular design strategy to optimize the thermoelectric performance of conjugated polymers, thus also providing new insights into the molecular design guidelines for the next generation of high-performance n-type materials for thermoelectric applications.
A new method for the synthesis of 5-fluorouracil prodrugs
Jolima?tre, Pascale,André-Barres, Christiane,Malet-Martino, Myriam,Martino, Robert,Rico-Lattes, Isabelle
, p. 1829 - 1831 (1999)
Bromo-tris(dimethylamino)-phosphonium-hexafluorophosphate (BROP) is a particularly suitable reagent for synthesising some 5-fluorouracil prodrugs in a one step reaction. Several acids, especially retinoic acid, were bound to the N1 of 5-fluorou
