1469-54-1Relevant academic research and scientific papers
Synthesis and reactions of a monosubstituted dithiirane 1-oxide, 3-(9-triptycyl)dithiirane 1-oxide
Ishii, Akihiko,Kawai, Tetsuhiko,Noji, Mariko,Nakayama, Juzo
, p. 6693 - 6699 (2005)
A 3-monosubstituted dithiirane 1-oxide, 3-(9-triptycyl)dithiirane 1-oxide, was prepared for the first time, by the reaction of (9-triptycyl)diazomethane and S8O. The dithiirane 1-oxide was obtained as cis- and trans-isomers, and the structure of the trans-isomer was verified by X-ray crystallography. The cis-isomer isomerized gradually to the trans-isomer in solution. The divalent sulfur atom of the cis- and trans-dithiirane 1-oxides were removed on treatment with triphenylphosphine to give the corresponding Z- and E-sulfines, respectively. The reaction of the trans-dithiirane 1-oxide with (Ph3P)2Pt(C2H4) provided the (sulfenato-thiolato)PtII complex, and that with Lawesson's reagent yielded the 1,3,4,2-trithiaphospholane and 1,2,4,5,3-tetrathiaphosphorinane derivatives.
Integrating reaction and analysis: Investigation of higher-order reactions by cryogenic trapping
Stockinger, Skrollan,Trapp, Oliver
, p. 1837 - 1842 (2013)
A new approach for the investigation of a higher-order reaction by on-column reaction gas chromatography is presented. The reaction and the analytical separation are combined in a single experiment to investigate the Diels-Alder reaction of benzenediazonium-2-carboxylate as a benzyne precursor with various anthracene derivatives, i.e. anthracene, 9-bromoanthracene, 9-anthracenecarbox-aldehyde and 9-anthracenemethanol. To overcome limitations of short reaction contact times at elevated temperatures a novel experimental setup was developed involving a cooling trap to achieve focusing and mixing of the reactants at a defined spot in a fused-silica capillary. This trap functions as a reactor within the separation column in the oven of a gas chromatograph. The reac-tants are sequentially injected to avoid undefined mixing in the injection port. An experimental protocol was developed with optimized injection intervals and cooling times to achieve sufficient conversions at short reaction times. Reaction products were rapidly identified by mass spectrometric detection. This new approach represents a practical procedure to investigate higher-order reactions at an analytical level and it simultaneously provides valuable information for the optimization of the reaction conditions.
Synthesis and structures of 9-triptycylallene derivatives
Yamamoto, Gaku,Kobayashi, Yuriko,Ono, Kasumi,Yano, Emiko,Minoura, Mao,Mazaki, Yasuhiro
, p. 1293 - 1299 (2006)
9-Triptycylallene (1) was synthesized by LiAlH4 reduction of 1-(9-triptycyl)-2-propynyl methanesulfonate (7), and three 3-substituted derivatives of 1 were also obtained by reacting compound 7 with appropriate metal reagents. LiAlH4
Design, synthesis and biochemical evaluation of novel ethanoanthracenes and related compounds to target burkitt’s lymphoma
Byrne, Andrew J.,Bright, Sandra A.,McKeown, James P.,O’brien, John E.,Twamley, Brendan,Fayne, Darren,Williams, D. Clive,Meegan, Mary J.
, (2020/01/31)
Lymphomas (cancers of the lymphatic system) account for 12% of malignant diseases worldwide. Burkitt’s lymphoma (BL) is a rare form of non-Hodgkin’s lymphoma in which the cancer starts in the immune B-cells. We report the synthesis and preliminary studies on the antiproliferative activity of a library of 9,10-dihydro-9,10-ethanoanthracene based compounds structurally related to the antidepressant drug maprotiline against BL cell lines MUTU-1 and DG- 75. Structural modifications were achieved by Diels-Alder reaction of the core 9-(2- nitrovinyl)anthracene with number of dienophiles including maleic anhydride, maleimides, acrylonitrile and benzyne. The antiproliferative activity of these compounds was evaluated in BL cell lines EBV? MUTU-1 and EBV+ DG-75 (chemoresistant). The most potent compounds 13j, 15, 16a, 16b, 16c, 16d and 19a displayed IC50 values in the range 0.17–0.38 μM against the BL cell line EBV? MUTU-1 and IC50 values in the range 0.45–0.78 μM against the chemoresistant BL cell line EBV+ DG- 75. Compounds 15, 16b and 16c demonstrated potent ROS dependent apoptotic effects on the BL cell lines which were superior to the control drug taxol and showed minimal cytotoxicity to peripheral blood mononuclear cells (PBMCs). The results suggest that this class of compounds merits further investigation as antiproliferative agents for BL.
Copper-catalyzed site-selective direct arylation of triptycene
Miura, Masahiro,Nishii, Yuji,Ueno, Keisuke
supporting information, p. 689 - 692 (2020/07/03)
A site-selective direct CH arylation protocol for the triptycene skeleton is developed using copper catalyst and diaryliodonium reagents. With the aid of directing groups, C3-symmetric trisubstituted triptycenes are selectively synthesized, and the structure was determined by X-ray diffraction analysis. Further derivatization of the installed bromo functionalities is also described.
Molecular spur gears comprising triptycene rotators and bibenzimidazole-based stators
Frantz, Derik K.,Linden, Anthony,Baldridge, Kim K.,Siegel, Jay S.
supporting information; experimental part, p. 1528 - 1535 (2012/03/10)
Dynamic gearing of molecular spur gears, the most common type of mechanical gear, is elucidated. Molecular design and conformational analysis show that derivatives of 4,4-bis(triptycen-9-ylethynyl)bibenzimidazole represent suitable constructs to investigate gearing behavior of collateral triptycene (Tp) groups. To test this design, DFT calculations (B97-D/Def2-TZVP) were employed and the results suggest that these molecules undergo geared rotation preferentially to gear slippage. Synthesis of derivatives was carried out, providing a series of molecular spur gears, including the first desymmetrized spur gear molecules, which were subsequently subjected to stereochemical analysis.
New Molecular Devices: In Search of a Molecular Ratchet
Ross Kelly,Sestelo, José Pérez,Tellitu, Imanol
, p. 3655 - 3665 (2007/10/03)
The triptycene-substituted [3]- and [4]helicenes 1 and 2 were examined as possible molecular versions of mechanical ratchets, where the triptycene serves as the ratchet wheel and the hehcenes as pawl and spring. The syntheses of 1 and 2b are described. 1H NMR was employed to examine rotation around the triptycene/helicene single bond; at 20 °C rotation is frozen for both 1 and 2b but the NMR of 1 revealed a plane of symmetry, indicating that 1 cannot function as a unidirectional ratchet In contrast, NMR revealed that, like a ratchet, triptycvl[4]helicene 2b lacks the symmetry of 1 and has a barrier to rotation of 24.5 kcal/mol, but spin polarization transfer NMR expenments indicated the triptycene in 2b nonetheless rotates equally in both directions. That outcome is rationalized from the standpoint of thermodynamics.
