(-)-Bis[(S)-1-phenylethyl]amine - CAS 56210-72-1
Category:
Main Product
Product Name:
(-)-Bis[(S)-1-phenylethyl]amine
Catalog Number:
56210-72-1
Synonyms:
(S-(R* R*))-(-)-BIS(ALPHA-METHYLBENZYL)&; (-)-Bis[(S)-1-phenylethyl]amine, 99% (99+% EE/GLC); (S,S)-Bis-(1-phenylethyl)amin; (-)-bis[(s)-α-methylbenzyl]amine; (S)-(-)-Bis-(1-phenylethyl)-amine hydrochloride; (-)-Bis[(S)-1-phenylethyl]amine, ChiPros 99%, ee 98
CAS Number:
56210-72-1
Molecular Weight:
225.33
Molecular Formula:
C16H19N
COA:
Inquire
MSDS:
Inquire
Canonical SMILES:
CC(C1=CC=CC=C1)NC(C)C2=CC=CC=C2
InChI:
InChI=1S/C16H19N/c1-13(15-9-5-3-6-10-15)17-14(2)16-11-7-4-8-12-16/h3-14,17H,1-2H3/t13-,14-/m0/s1
InChIKey:
NXLACVVNHYIYJN-KBPBESRZSA-N
Chemical Structure
CAS 56210-72-1 (-)-Bis[(S)-1-phenylethyl]amine

Reference Reading


1.Synthesis, characterization and reactivity of single-site aluminium amides bearing benzotriazole phenoxide ligands: catalysis for ring-opening polymerization of lactide and carbon dioxide/propylene oxide coupling.
Li CY1, Liu DC, Ko BT. Dalton Trans. 2013 Aug 28;42(32):11488-96. doi: 10.1039/c3dt51003d. Epub 2013 Jul 2.
New aluminium complexes containing bis-BTP ligands (BTP = N,O-bidentate benzotriazole phenoxide) were synthesized and structurally characterized. Amine elimination of Al(NMe2)3 with (R)BTP-H ligands ((CMe2Ph)BTP-H = 2-(2H-benzotriazol-2-yl)-4,6-bis(1-methyl-1-phenylethyl)phenol, (t-Bu)BTP-H = 2-(2H-benzotriazol-2-yl)-4,6-di-tert-butylphenol and (TMCl)BTP-H = 2-tert-butyl-6-(5-chloro-2H-benzotriazol-2-yl)-4-methylphenol) (2.0 mol equiv.) in toluene or hexane afforded the penta-coordinated single-site amidoaluminium complexes [((R)BTP)2Al(NMe2)] (R = CMe2Ph for 1; R = t-Bu for 2; R = TMCl for 3) in satisfactory yields. With the addition of H2O (0.5 molar equiv.), the hydrolysis of Al amides 2 and 3 in a mixed solvent of THF/toluene at 25 °C produced oxo-bridged bimetallic aluminium complexes [{((R)BTP)2Al}2(μ-O)] (R = t-Bu for 4 and R = TMCl for 5) in ≥70% yield. According to single crystal X-ray diffraction studies, complex 2 shows a monomeric Al(iii) amide with bis((t-Bu)BTP) ligands and one -NMe2 group, whereas alumoxane 4 is a dinuclear species, in which the bonding mode of the Al-O-Al moiety from μ2-oxo assumes a linear type.
2.The excitatory effect of cholecystokinin on rat neostriatal neurons: ionic and molecular mechanisms.
Wu T1, Wang HL. Eur J Pharmacol. 1996 Jun 27;307(2):125-32.
Whole-cell patch-clamp recordings were performed to study ionic and molecular mechanisms by which cholecystokinin (CCK) peptides modulate the membrane excitability of acutely dissociated rat neostriatal neurons. Immunohistochemical staining studies indicated that about 95% of acutely isolated neostriatal neurons were GABA(gamma-aminobutyric acid)ergic medium-sized cells. During current-clamp recordings, sulfated cholecystokinin octapeptide (CCK-8) depolarized neostriatal neurons and evoked action potentials. During voltage-clamp recordings, CCK-8 induced inward currents at negative membrane potentials by increasing the voltage-insensitive and non-selective cationic conductance. Cholecystokinin tetrapeptide (CCK-4), a selective CCKB receptor agonist, also evoked cationic currents. The CCK-8-induced cation currents were antagonized by PD135,158 (4-{[2-[[3-(1H-indol-3yl)-2-mehtyl-1-oxo-2-[[[1.7.7.-trimeth yl-bicyclo [2.2.1]hept-2-yl)oxy]carbonyl]amino]propyl]amino]-1-phenylethyl]amino-4- oxo- [1S-1 alpha, 2 beta [S*(S*)]4 alpha]}-butanoate N-methyl-D-glucamine), a highly specific and potent CCKB receptor antagonist.
3.Chiral benzamidinate ligands in rare-earth-metal coordination chemistry.
Benndorf P1, Kratsch J, Hartenstein L, Preuss CM, Roesky PW. Chemistry. 2012 Nov 5;18(45):14454-63. doi: 10.1002/chem.201202457. Epub 2012 Sep 27.
The treatment of the recently reported potassium salt (S)-N,N'-bis-(1-phenylethyl)benzamidinate ((S)-KPEBA) and its racemic isomer (rac-KPEBA) with anhydrous lanthanide trichlorides (Ln = Sm, Er, Yb, Lu) afforded mostly chiral complexes. The tris(amidinate) complex [{(S)-PEBA}(3)Sm], bis(amidinate) complexes [{Ln(PEBA)(2)(μ-Cl)}(2)] (Ln = Sm, Er, Yb, Lu), and mono(amidinate) compounds [Ln(PEBA)(Cl)(2)(thf)(n)] (Ln = Sm, Yb, Lu) were isolated and structurally characterized. As a result of steric effects, the homoleptic 3:1 complexes of the smaller lanthanide atoms Yb and Lu were not accessible. Furthermore, chiral bis(amidinate)-amido complexes [{(S)-PEBA}(2)Ln{N(SiMe(3))(2)}] (Ln = Y, Lu) were synthesized by an amine-elimination reaction and salt metathesis. All of these chiral bis- and tris(amidinate) complexes had additional axial chirality and they all crystallized as diastereomerically pure compounds. By using rac-PEBA as a ligand, an achiral meso arrangement of the ligands was observed.
4.Optimisation of a lithium magnesiate for use in the non-cryogenic asymmetric deprotonation of prochiral ketones.
Francos J1, Zaragoza-Calero S, O'Hara CT. Dalton Trans. 2014 Jan 21;43(3):1408-12. doi: 10.1039/c3dt52577e. Epub 2013 Nov 8.
A study has been conducted to determine whether lithium magnesiates are feasible candidates for the enantioselective deprotonation of 4-alkylcyclohexanones. The commercially available chiral amine (+)-bis[(R)-1-phenylethyl]amine (2-H) was utilised to induce enantioselection. When transformed to its lithium salt and combined with (n)Bu2Mg, improved enantioselective deprotonation of 4-tert-butylcyclohexanone (with respect to the monometallic lithium amide) at 20 °C was observed. In an attempt to optimise the reaction further, different additives were added to the lithium amide. The best performing deprotonations at 0 °C were those in which (Me3SiCH2)2Mg (er pro-S 74 : 26) and (Me3SiCH2)2Mn (er pro-S 72 : 28) were added, hence the lithium magnesiate "LiMg(2)(CH2SiMe3)2" was used in the remainder of the study. The optimum solvent for the reaction was found to be THF. NMR spectroscopic studies of a D8-THF solution of "LiMg(2)(CH2SiMe3)2" appear to show that this mono-amide bis-alkyl species is in equilibrium with a bis-amide mono-alkyl compound (and a tris-alkyl lithium magnesiate).