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Synthesis of chiral nonracemic 1-(2-pyridinyl)ethylamines: stereospecific introduction of amino function onto the 2-pyridinylmethyl carbon center.

The Journal of organic chemistry

Uenishi J, Hamada M, Aburatani S, Matsui K, Yonemitsu O, Tsukube H.
PMID: 15387603
J Org Chem. 2004 Oct 01;69(20):6781-9. doi: 10.1021/jo0491758.

Stereospecific substitutions of optically pure 1-(pyridinyl)ethyl methanesulfonates with various amines are described. The reaction of (R)- or (S)-1-(2-pyridinyl)ethyl methanesulfonate with primary amines, including amino acid esters, gives N-substituted (S)- or (R)-1-(2-pyridinyl)ethylamines (4) with inversion of the configuration. Secondary cyclic...

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Uenishi J, Hamada M, Aburatani S, et al. Synthesis of chiral nonracemic 1-(2-pyridinyl)ethylamines: stereospecific introduction of amino function onto the 2-pyridinylmethyl carbon center. J Org Chem. 2004;69(20):6781-9doi: 10.1021/jo0491758.
Uenishi, J., Hamada, M., Aburatani, S., Matsui, K., Yonemitsu, O., & Tsukube, H. (2004). Synthesis of chiral nonracemic 1-(2-pyridinyl)ethylamines: stereospecific introduction of amino function onto the 2-pyridinylmethyl carbon center. The Journal of organic chemistry, 69(20), 6781-9. https://doi.org/10.1021/jo0491758
Uenishi, Jun'ichi, et al. "Synthesis of chiral nonracemic 1-(2-pyridinyl)ethylamines: stereospecific introduction of amino function onto the 2-pyridinylmethyl carbon center." The Journal of organic chemistry vol. 69,20 (2004): 6781-9. doi: https://doi.org/10.1021/jo0491758
Uenishi J, Hamada M, Aburatani S, Matsui K, Yonemitsu O, Tsukube H. Synthesis of chiral nonracemic 1-(2-pyridinyl)ethylamines: stereospecific introduction of amino function onto the 2-pyridinylmethyl carbon center. J Org Chem. 2004 Oct 01;69(20):6781-9. doi: 10.1021/jo0491758. PMID: 15387603.
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Synthesis of Substituted 2-(2-Biphenylyl)ethylamines as Potential Analgeties.

Journal of medicinal chemistry

Tsatsas G, Parrea-Sandris A, Sandris C.
PMID: 22185162
J Med Chem. 1967 May 01;10(3):489-91. doi: 10.1021/jm00315a046.

No abstract available.

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Tsatsas G, Parrea-Sandris A, Sandris C. Synthesis of Substituted 2-(2-Biphenylyl)ethylamines as Potential Analgeties. J Med Chem. 1967;10(3):489-91doi: 10.1021/jm00315a046.
Tsatsas, G., Parrea-Sandris, A., & Sandris, C. (1967). Synthesis of Substituted 2-(2-Biphenylyl)ethylamines as Potential Analgeties. Journal of medicinal chemistry, 10(3), 489-91. https://doi.org/10.1021/jm00315a046
Tsatsas, G, et al. "Synthesis of Substituted 2-(2-Biphenylyl)ethylamines as Potential Analgeties." Journal of medicinal chemistry vol. 10,3 (1967): 489-91. doi: https://doi.org/10.1021/jm00315a046
Tsatsas G, Parrea-Sandris A, Sandris C. Synthesis of Substituted 2-(2-Biphenylyl)ethylamines as Potential Analgeties. J Med Chem. 1967 May 01;10(3):489-91. doi: 10.1021/jm00315a046. PMID: 22185162.
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Phase equilibrium and physical properties of biobased ionic liquid mixtures.

Physical chemistry chemical physics : PCCP

Toledo Hijo AAC, Maximo GJ, Cunha RL, Fonseca FHS, Cardoso LP, Pereira JFB, Costa MC, Batista EAC, Meirelles AJA.
PMID: 29445821
Phys Chem Chem Phys. 2018 Feb 28;20(9):6469-6479. doi: 10.1039/c7cp06841g.

Protic ionic liquid crystals (PILCs) obtained from natural sources are promising compounds due to their peculiar properties and sustainable appeal. However, obtaining PILCs with higher thermal and mechanical stabilities for product and process design is in demand and studies...

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Toledo Hijo AAC, Maximo GJ, Cunha RL, et al. Phase equilibrium and physical properties of biobased ionic liquid mixtures. Phys Chem Chem Phys. 2018;20(9):6469-6479doi: 10.1039/c7cp06841g.
Toledo Hijo, A. A. C., Maximo, G. J., Cunha, R. L., Fonseca, F. H. S., Cardoso, L. P., Pereira, J. F. B., Costa, M. C., Batista, E. A. C., & Meirelles, A. J. A. (2018). Phase equilibrium and physical properties of biobased ionic liquid mixtures. Physical chemistry chemical physics : PCCP, 20(9), 6469-6479. https://doi.org/10.1039/c7cp06841g
Toledo Hijo, Ariel A C, et al. "Phase equilibrium and physical properties of biobased ionic liquid mixtures." Physical chemistry chemical physics : PCCP vol. 20,9 (2018): 6469-6479. doi: https://doi.org/10.1039/c7cp06841g
Toledo Hijo AAC, Maximo GJ, Cunha RL, Fonseca FHS, Cardoso LP, Pereira JFB, Costa MC, Batista EAC, Meirelles AJA. Phase equilibrium and physical properties of biobased ionic liquid mixtures. Phys Chem Chem Phys. 2018 Feb 28;20(9):6469-6479. doi: 10.1039/c7cp06841g. PMID: 29445821.
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Transition metal complexes bearing NHC ligands substituted with secondary polyfluoroalkyl groups.

Dalton transactions (Cambridge, England : 2003)

Kolaříková V, Šimůnek O, Rybáčková M, Cvačka J, Březinová A, Kvíčala J.
PMID: 26374142
Dalton Trans. 2015 Dec 07;44(45):19663-73. doi: 10.1039/c5dt02258d. Epub 2015 Sep 16.

Using three different approaches, racemic 1-(perfluoroalkyl)ethylamines were synthesized from perfluoroalkyl iodides or perfluoroalkanoic acids, and further transformed to the corresponding N,N'-disubstituted ethane-1,2-diimines and ethane-1,2-diamines as mixtures of diastereoisomers. Their cyclization afforded imidazolium or dihydroimidazolium salts, which led to silver...

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Kolaříková V, Šimůnek O, Rybáčková M, et al. Transition metal complexes bearing NHC ligands substituted with secondary polyfluoroalkyl groups. Dalton Trans. 2015;44(45):19663-73doi: 10.1039/c5dt02258d.
Kolaříková, V., Šimůnek, O., Rybáčková, M., Cvačka, J., Březinová, A., & Kvíčala, J. (2015). Transition metal complexes bearing NHC ligands substituted with secondary polyfluoroalkyl groups. Dalton transactions (Cambridge, England : 2003), 44(45), 19663-73. https://doi.org/10.1039/c5dt02258d
Kolaříková, V, et al. "Transition metal complexes bearing NHC ligands substituted with secondary polyfluoroalkyl groups." Dalton transactions (Cambridge, England : 2003) vol. 44,45 (2015): 19663-73. doi: https://doi.org/10.1039/c5dt02258d
Kolaříková V, Šimůnek O, Rybáčková M, Cvačka J, Březinová A, Kvíčala J. Transition metal complexes bearing NHC ligands substituted with secondary polyfluoroalkyl groups. Dalton Trans. 2015 Dec 07;44(45):19663-73. doi: 10.1039/c5dt02258d. Epub 2015 Sep 16. PMID: 26374142.
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Regioselective borylation of the C-H bonds in alkylamines and alkyl ethers. Observation and origin of high reactivity of primary C-H bonds beta to nitrogen and oxygen.

Journal of the American Chemical Society

Li Q, Liskey CW, Hartwig JF.
PMID: 24836159
J Am Chem Soc. 2014 Jun 18;136(24):8755-65. doi: 10.1021/ja503676d. Epub 2014 Jun 05.

Borylation of aliphatic C-H bonds in alkylamines and alkyl ethers to form primary aminoalkyl and alkoxyalkyl boronate esters and studies on the origin of the regioselectivity of these reactions are reported. The products of these reactions can be used...

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Li Q, Liskey CW, Hartwig JF. Regioselective borylation of the C-H bonds in alkylamines and alkyl ethers. Observation and origin of high reactivity of primary C-H bonds beta to nitrogen and oxygen. J Am Chem Soc. 2014;136(24):8755-65doi: 10.1021/ja503676d.
Li, Q., Liskey, C. W., & Hartwig, J. F. (2014). Regioselective borylation of the C-H bonds in alkylamines and alkyl ethers. Observation and origin of high reactivity of primary C-H bonds beta to nitrogen and oxygen. Journal of the American Chemical Society, 136(24), 8755-65. https://doi.org/10.1021/ja503676d
Li, Qian, et al. "Regioselective borylation of the C-H bonds in alkylamines and alkyl ethers. Observation and origin of high reactivity of primary C-H bonds beta to nitrogen and oxygen." Journal of the American Chemical Society vol. 136,24 (2014): 8755-65. doi: https://doi.org/10.1021/ja503676d
Li Q, Liskey CW, Hartwig JF. Regioselective borylation of the C-H bonds in alkylamines and alkyl ethers. Observation and origin of high reactivity of primary C-H bonds beta to nitrogen and oxygen. J Am Chem Soc. 2014 Jun 18;136(24):8755-65. doi: 10.1021/ja503676d. Epub 2014 Jun 05. PMID: 24836159.
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Implication of tyramine in the biosynthesis of morphinan alkaloids in Papaver.

Planta

Roberts MF, Kutchan TM, Brown RT, Coscia CJ.
PMID: 24225875
Planta. 1987 Oct;172(2):230-7. doi: 10.1007/BF00394592.

Doubly-labeled [(3)H, (14)C]tyrosines, [1-(13)C-]tyramine or [2-(14)C]tyramine, administered to the stems of intact Papaver somniferum L. plants, were found to be incorporated into the morphinan alkaloids of the plant with comparable efficiency. (3)H/(14)C ratios of alkaloids from plants fed the...

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Roberts MF, Kutchan TM, Brown RT, et al. Implication of tyramine in the biosynthesis of morphinan alkaloids in Papaver. Planta. 1987;172(2):230-7doi: 10.1007/BF00394592.
Roberts, M. F., Kutchan, T. M., Brown, R. T., & Coscia, C. J. (1987). Implication of tyramine in the biosynthesis of morphinan alkaloids in Papaver. Planta, 172(2), 230-7. https://doi.org/10.1007/BF00394592
Roberts, M F, et al. "Implication of tyramine in the biosynthesis of morphinan alkaloids in Papaver." Planta vol. 172,2 (1987): 230-7. doi: https://doi.org/10.1007/BF00394592
Roberts MF, Kutchan TM, Brown RT, Coscia CJ. Implication of tyramine in the biosynthesis of morphinan alkaloids in Papaver. Planta. 1987 Oct;172(2):230-7. doi: 10.1007/BF00394592. PMID: 24225875.
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Catalytic Enantioselective Synthesis of α-Chiral Azaheteroaryl Ethylamines by Asymmetric Protonation.

Angewandte Chemie (International ed. in English)

Xu C, Muir CW, Leach AG, Kennedy AR, Watson AJB.
PMID: 29956430
Angew Chem Int Ed Engl. 2018 Aug 27;57(35):11374-11377. doi: 10.1002/anie.201806956. Epub 2018 Aug 01.

The direct enantioselective synthesis of chiral azaheteroaryl ethylamines from vinyl-substituted N-heterocycles and anilines is reported. A chiral phosphoric acid (CPA) catalyst promotes dearomatizing aza-Michael addition to give a prochiral exocyclic aryl enamine, which undergoes asymmetric protonation upon rearomatization. The...

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Xu C, Muir CW, Leach AG, et al. Catalytic Enantioselective Synthesis of α-Chiral Azaheteroaryl Ethylamines by Asymmetric Protonation. Angew Chem Int Ed Engl. 2018;57(35):11374-11377doi: 10.1002/anie.201806956.
Xu, C., Muir, C. W., Leach, A. G., Kennedy, A. R., & Watson, A. J. B. (2018). Catalytic Enantioselective Synthesis of α-Chiral Azaheteroaryl Ethylamines by Asymmetric Protonation. Angewandte Chemie (International ed. in English), 57(35), 11374-11377. https://doi.org/10.1002/anie.201806956
Xu, Chao, et al. "Catalytic Enantioselective Synthesis of α-Chiral Azaheteroaryl Ethylamines by Asymmetric Protonation." Angewandte Chemie (International ed. in English) vol. 57,35 (2018): 11374-11377. doi: https://doi.org/10.1002/anie.201806956
Xu C, Muir CW, Leach AG, Kennedy AR, Watson AJB. Catalytic Enantioselective Synthesis of α-Chiral Azaheteroaryl Ethylamines by Asymmetric Protonation. Angew Chem Int Ed Engl. 2018 Aug 27;57(35):11374-11377. doi: 10.1002/anie.201806956. Epub 2018 Aug 01. PMID: 29956430.
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Reductive Methylation of Homogeneous Primary β-Lauryl/myristyl 7/3 Polyethyleneoxy n = 3-18 Ethylamines under Phase-Transfer Catalysis Conditions.

Molecules (Basel, Switzerland)

Jianu C, Cleveland-Innes M.
PMID: 34361763
Molecules. 2021 Jul 29;26(15). doi: 10.3390/molecules26154612.

Homogeneous tertiary

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Jianu C, Cleveland-Innes M. Reductive Methylation of Homogeneous Primary β-Lauryl/myristyl 7/3 Polyethyleneoxy n = 3-18 Ethylamines under Phase-Transfer Catalysis Conditions. Molecules. 2021;26(15)doi: 10.3390/molecules26154612.
Jianu, C., & Cleveland-Innes, M. (2021). Reductive Methylation of Homogeneous Primary β-Lauryl/myristyl 7/3 Polyethyleneoxy n = 3-18 Ethylamines under Phase-Transfer Catalysis Conditions. Molecules (Basel, Switzerland), 26(15), . https://doi.org/10.3390/molecules26154612
Jianu, Călin, and Cleveland-Innes. "Reductive Methylation of Homogeneous Primary β-Lauryl/myristyl 7/3 Polyethyleneoxy n = 3-18 Ethylamines under Phase-Transfer Catalysis Conditions." Molecules (Basel, Switzerland) vol. 26,15 (2021). doi: https://doi.org/10.3390/molecules26154612
Jianu C, Cleveland-Innes M. Reductive Methylation of Homogeneous Primary β-Lauryl/myristyl 7/3 Polyethyleneoxy n = 3-18 Ethylamines under Phase-Transfer Catalysis Conditions. Molecules. 2021 Jul 29;26(15). doi: 10.3390/molecules26154612. PMID: 34361763; PMCID: PMC8348736.
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Selective cleavage of the C-C bonds of aminoethyl groups, via a multistep pathway, by a pincer iridium complex.

Journal of the American Chemical Society

Zhang X, Emge TJ, Ghosh R, Goldman AS.
PMID: 15941235
J Am Chem Soc. 2005 Jun 15;127(23):8250-1. doi: 10.1021/ja051300p.

A pincer-ligated iridium complex is found to react with N-ethylamines, HN(Et)R (R = cyclohexyl, tert-butyl, ethyl), to give the corresponding iridium isocyanide complexes (PCP)Ir(CH3)(H)(CNR) (PCP = kappa3-2,6-(tBu2PCH2)2C6H3). This novel, regioselective C-C bond cleavage reaction occurs readily under mild conditions...

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Zhang X, Emge TJ, Ghosh R, et al. Selective cleavage of the C-C bonds of aminoethyl groups, via a multistep pathway, by a pincer iridium complex. J Am Chem Soc. 2005;127(23):8250-1doi: 10.1021/ja051300p.
Zhang, X., Emge, T. J., Ghosh, R., & Goldman, A. S. (2005). Selective cleavage of the C-C bonds of aminoethyl groups, via a multistep pathway, by a pincer iridium complex. Journal of the American Chemical Society, 127(23), 8250-1. https://doi.org/10.1021/ja051300p
Zhang, Xiawei, et al. "Selective cleavage of the C-C bonds of aminoethyl groups, via a multistep pathway, by a pincer iridium complex." Journal of the American Chemical Society vol. 127,23 (2005): 8250-1. doi: https://doi.org/10.1021/ja051300p
Zhang X, Emge TJ, Ghosh R, Goldman AS. Selective cleavage of the C-C bonds of aminoethyl groups, via a multistep pathway, by a pincer iridium complex. J Am Chem Soc. 2005 Jun 15;127(23):8250-1. doi: 10.1021/ja051300p. PMID: 15941235.
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Asymmetric addition of dimethylzinc to N-tosylarylimines catalyzed by a rhodium-diene complex toward the synthesis of chiral 1-arylethylamines.

Organic letters

Nishimura T, Yasuhara Y, Hayashi T.
PMID: 16494489
Org Lett. 2006 Mar 02;8(5):979-81. doi: 10.1021/ol060213e.

A rhodium complex coordinated with a chiral diene, (R,R)-2,5-diphenylbicyclo[2.2.2]octa-2,5-diene (Ph-bod), catalyzed the asymmetric addition of dimethylzinc to N-tosylarylimines to give high yields of chiral 1-aryl-1-ethylamines with high enantioselectivity (94-98% ee).

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Nishimura T, Yasuhara Y, Hayashi T. Asymmetric addition of dimethylzinc to N-tosylarylimines catalyzed by a rhodium-diene complex toward the synthesis of chiral 1-arylethylamines. Org Lett. 2006;8(5):979-81doi: 10.1021/ol060213e.
Nishimura, T., Yasuhara, Y., & Hayashi, T. (2006). Asymmetric addition of dimethylzinc to N-tosylarylimines catalyzed by a rhodium-diene complex toward the synthesis of chiral 1-arylethylamines. Organic letters, 8(5), 979-81. https://doi.org/10.1021/ol060213e
Nishimura, Takahiro, et al. "Asymmetric addition of dimethylzinc to N-tosylarylimines catalyzed by a rhodium-diene complex toward the synthesis of chiral 1-arylethylamines." Organic letters vol. 8,5 (2006): 979-81. doi: https://doi.org/10.1021/ol060213e
Nishimura T, Yasuhara Y, Hayashi T. Asymmetric addition of dimethylzinc to N-tosylarylimines catalyzed by a rhodium-diene complex toward the synthesis of chiral 1-arylethylamines. Org Lett. 2006 Mar 02;8(5):979-81. doi: 10.1021/ol060213e. PMID: 16494489.
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Synthesis and Behavior at the Air-Water Interface of Fluorinated Nonionic Surfactants Containing Two Methylated Polyoxyethylene Moieties.

Journal of colloid and interface science

Guittard F, de Givenchy ET, Cambon A.
PMID: 10479421
J Colloid Interface Sci. 1996 Jan 15;177(1):101-105. doi: 10.1006/jcis.1996.0010.

The nonionic surfactants of the type polyoxyethylated monomethylated and containing a fluorinated tail were synthesized from 2-(F-alkyl)ethylamines. These compounds have two polyethoxylated tails with a perfectly defined number of oxyethylene motifs. Compared with their bipodal homologs within the F-alkylated...

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Guittard F, de Givenchy ET, Cambon A. Synthesis and Behavior at the Air-Water Interface of Fluorinated Nonionic Surfactants Containing Two Methylated Polyoxyethylene Moieties. J Colloid Interface Sci. 1996;177(1):101-105doi: 10.1006/jcis.1996.0010.
Guittard, F., de Givenchy ET, & Cambon, A. (1996). Synthesis and Behavior at the Air-Water Interface of Fluorinated Nonionic Surfactants Containing Two Methylated Polyoxyethylene Moieties. Journal of colloid and interface science, 177(1), 101-105. https://doi.org/10.1006/jcis.1996.0010
Guittard, et al. "Synthesis and Behavior at the Air-Water Interface of Fluorinated Nonionic Surfactants Containing Two Methylated Polyoxyethylene Moieties." Journal of colloid and interface science vol. 177,1 (1996): 101-105. doi: https://doi.org/10.1006/jcis.1996.0010
Guittard F, de Givenchy ET, Cambon A. Synthesis and Behavior at the Air-Water Interface of Fluorinated Nonionic Surfactants Containing Two Methylated Polyoxyethylene Moieties. J Colloid Interface Sci. 1996 Jan 15;177(1):101-105. doi: 10.1006/jcis.1996.0010. PMID: 10479421.
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Facile regio- and stereoselective carbon-carbon coupling of phenol derivatives with aryl aziridines.

Organic letters

Pineschi M, Bertolini F, Crotti P, Macchia F.
PMID: 16737330
Org Lett. 2006 Jun 08;8(12):2627-30. doi: 10.1021/ol060822m.

A chemo-, regio-, and stereoselective direct carbon-carbon coupling of readily available aryl borates with N-protected aryl aziridines provides a method for the synthesis of new 2-(o-hydroxyaryl)-2-aryl ethylamines which can be used, in a novel annulation sequence, to give stereodefined...

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Pineschi M, Bertolini F, Crotti P, et al. Facile regio- and stereoselective carbon-carbon coupling of phenol derivatives with aryl aziridines. Org Lett. 2006;8(12):2627-30doi: 10.1021/ol060822m.
Pineschi, M., Bertolini, F., Crotti, P., & Macchia, F. (2006). Facile regio- and stereoselective carbon-carbon coupling of phenol derivatives with aryl aziridines. Organic letters, 8(12), 2627-30. https://doi.org/10.1021/ol060822m
Pineschi, Mauro, et al. "Facile regio- and stereoselective carbon-carbon coupling of phenol derivatives with aryl aziridines." Organic letters vol. 8,12 (2006): 2627-30. doi: https://doi.org/10.1021/ol060822m
Pineschi M, Bertolini F, Crotti P, Macchia F. Facile regio- and stereoselective carbon-carbon coupling of phenol derivatives with aryl aziridines. Org Lett. 2006 Jun 08;8(12):2627-30. doi: 10.1021/ol060822m. PMID: 16737330.
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Showing 1 to 12 of 18 entries