145240-28-4Relevant articles and documents
Transformation of mutagenic aromatic amines into non-mutagenic species by alkyl substituents: Part II: Alkylation far away from the amino function
Glende, Carsten,Klein, Markus,Schmitt, Heimo,Erdinger, Lothar,Boche, Gernot
, p. 15 - 38 (2002)
Alkyl and trifluoromethyl derivatives of 4-aminobiphenyl (1) (4ABP) and 2-aminofluorene (7) (2AF) were synthesised and assayed for mutagenicity using Salmonella typhimurium tester strains TA98 and TA100 with and without the addition of S9 mix. Modification of 1 was achieved by attachment of alkyl groups (methyl, ethyl, iso-propyl, n-butyl, tert-butyl) and a trifluoromethyl group (CF3) in the 4′-position, the 3′-position (Me, CF3) and the 3′-, 5′-positions (DiMe, DiCF3). Compound 7 was modified by introduction of alkyl groups (methyl, tert-butyl, adamantyl) and a trifluoromethyl group (CF3) in the 7-position. The derivatives of 1 and 7 show for groups with growing steric demand decreased mutagenic activity. The bulkiest groups (CF3, tert-butyl and adamantyl) induce the strongest effects on the mutagenicity. It was even possible to eliminate the mutagenicity of 1 and 7 by introduction of such substituents. In the last part of the work, we compared the experimental mutagenicities with calculated values derived from QSAR correlations. Our findings show that the predictions for aromatic amines with bulky substituents were generally too high. The strongest deviations were observed in the case of the CF3-, tert-butyl- and the adamantyl-group. Only the parent compounds and derivatives with small alkyl groups were predicted well. These investigations show that "large" substituents have an influence on the mutagenicity caused by their steric demand. To predict the correct mutagenicities of such compounds, it is necessary to introduce steric parameters in the respective QSAR equations which will be done in a forthcoming paper.
Alkyl Carbagermatranes Enable Practical Palladium-Catalyzed sp2-sp3 Cross-Coupling
Xu, Meng-Yu,Jiang, Wei-Tao,Li, Ying,Xu, Qing-Hao,Zhou, Qiao-Lan,Yang, Shuo,Xiao, Bin
supporting information, p. 7582 - 7588 (2019/05/16)
Pd-catalyzed cross-coupling reactions have achieved tremendous accomplishments in the past decades. However, C(sp3)-hybridized nucleophiles generally remain as challenging coupling partners due to their sluggish transmetalation compared to the C(sp2)-hybridized counterparts. While a single-electron-transfer-based strategy using C(sp3)-hybridized nucleophiles had made significant progress recently, fewer breakthroughs have been made concerning the traditional two-electron mechanism involving C(sp3)-hybridized nucleophiles. In this report, we present a series of unique alkyl carbagermatranes that were proven to be highly reactive in cross-coupling reactions with our newly developed electron-deficient phosphine ligands. Generally, secondary alkyl carbagermatranes show slightly lower, yet comparable activity to its Sn analogue. Meanwhile, primary alkyl carbagermatranes exhibit high activity, and they were also proved stable enough to be compatible with various reactions. Chiral secondary benzyl carbagermatrane gave the coupling product under base/additive-free conditions with its configuration fully inversed, suggesting that transmetalation was carried out in an "SE2(open) Inv" pathway, which is consistent with Hiyama's previous observation. Notably, the cross-coupling of primary alkyl carbagermatranes could be performed under base/additive-free conditions with excellent functional group tolerance and therefore may have potentially important applications such as stapled peptide synthesis.
Magnesium promoted autocatalytic dehydrogenation of amine borane complexes: A reliable, non-cryogenic, scalable access to boronic acids
Marciasini, Ludovic D.,Richard, Jimmy,Cacciuttolo, Bastien,Sartori, Guillaume,Birepinte, Melodie,Chabaud, Laurent,Pinet, Sandra,Pucheault, Mathieu
, p. 164 - 171 (2018/12/05)
Owing to the unusual reactivity of dialkylamine-borane complexes, a methodology was developed to simply access boronic acids. The intrinsic instability of magnesium aminoborohydride was tweaked into a tandem dehydrogenation borylation sequence. Proceeding via an autocatalytic cycle, amineborane dehydrogenation was induced by a variety of Grignard reagents. Overall, addition of the organomagnesium species onto specially designed dialkylamine-borane complexes led to a variety of boronic acids in high yields. In addition, the reaction can be performed under Barbier conditions, on a large scale.
Boosting the Charge Transport Property of Indeno[1,2-b]fluorene-6,12-dione though Incorporation of Sulfur- or Nitrogen-Linked Side Chains
Fan, Zhi-Ping,Li, Xiang-Yang,Luo, Xiao-E.,Fei, Xian,Sun, Bing,Chen, Li-Chuan,Shi, Zi-Fa,Sun, Chun-Lin,Shao, Xiangfeng,Zhang, Hao-Li
, (2017/10/12)
Alkyl chains are basic units in the design of organic semiconductors for purposes of enhancing solubility, tuning electronic energy levels, and tailoring molecular packing. This work demonstrates that the carrier mobilities of indeno[1,2-b]fluorene-6,12-d
Synthesis of tetraphenyl-substituted [12]cycloparaphenylene: Toward a rationally designed ultrashort carbon nanotube
Sisto, Thomas J.,Tian, Xia,Jasti, Ramesh
experimental part, p. 5857 - 5860 (2012/09/21)
The first phenyl-substituted [n]cycloparaphenylene (1) has been synthesized. The preparation of this structure addresses several challenges toward a more elaborate phenyl-substituted [n]cycloparaphenylene (2), a molecule that may lead to the homogeneous s
PROCESS FOR PURIFICATION OF BORONIC ACID AND ITS DERIVATIVES
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Page/Page column 6, (2008/06/13)
A process for purification of boronic acid or its derivatives of the formula (I): R-B(OH)2 wherein R is any unsubstituted or substituted alkyl, cycloalkyl, aryl, heterocycloalkyl or derivatives thereof. The process comprises (a) treating crude compound of the formula (I) with a base to afford a salt of boronic acid, (b) isolating the substantially pure salt of compound of formula (I) from other compounds (such as impurities etc) by solvent extraction etc, (c) treating the substantially pure salt with an acid to afford substantially pure boronic acid and (d) isolating the substantially pure compound of formula (I).
Novel synthesis of arylboronic acids by electroreduction of aromatic halides in the presence of trialkyl borates
Laza, Carine,Dunach, Elisabet,Serein-Spirau, Francoise,Moreau, Joel J. E.,Vellutini, Luc
, p. 373 - 375 (2007/10/03)
A novel preparation of aryl and heteroarylboronic acids by an electrochemical coupling reaction is described. It is based on the reductive coupling between aromatic or heteroaromatic halides and a trialkyl borate. The reactions are carried out in DMF or THF with the use of sacrificial aluminium or magnesium anodes in a single-compartment cell. Arylboronic acids are obtained with moderate to good selectivities and isolated yields.
PHENYL SULFONAMIDE ENDOTHELIN ANTAGONISTS
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, (2008/06/13)
Compounds of the formula STR1 inhibit the activity of endothelin. The symbols are defined as follows: R 1, R 2 and R. sup.3 are each independently(a) hydrogen, except that R. sup.1 is other than hydrogen;(b) alkyl, alkenyl, alkynyl, alkoxy, cycloalkyl, cycloalkylalkyl, cycloalkenyl, cycloalkenylalkyl, aryl, aryloxy, aralkyl or aralkoxy, any of which may be substituted with Z 1, Z 2 and Z. sup.3 ;(c) halo;(d) hydroxyl;(e) cyano; (f) nitro; (g)--C(O)H or--C(O)R 6 ;(h)--CO 2 H or--CO 2 R 6 ; (i)--SH,--S(O) n R 6,--S(O) m--OH,--S(O) m--OR 6,--O--S(O) m--R 6,--O--S(O) m OH or--O--S(O) m--OR. sup.6 ;(j)--Z. sup.4--NR 7 R 8 ; or (k)--Z 4--N(R 11--Z 5--NR 9 R 10 ; and the remaining symbols are as defined in the specification.
