CAS 851942-89-7 (11bS)-4,4-Dibutyl-2,6-bis(3,4,5-trifluorophenyl)-4,5-dihydro-3H-dinaphtho[2,1-c:1',2'-e]azepinium bromide

Synonyms

MFCD09264271; (S)-4,4-DIBUTYL-2,6-BIS(3,4,5-TRIFLUOROPHENYL)-4,5-DIHYDRO-3H-DINAPHTHO[7,6,1,2-CDE]AZEPINIUM BROMIDE; 887938-70-7; (S)-4,4-Dibutyl-2,6-bis(3,4,5-trifluorophenyl)-4,5-dihydro-3H-dinaphtho[2,1-c:1',2'-e]azepin-4-ium bromide; (11bR)-(-)-4,4-Dibutyl-4,5-dihydro-2,6-bis(3,4,5-trifluorophenyl)-3H-dinaphth[2,1-c:1 inverted exclamation marka,2 inverted exclamation marka-e]azepinium bromide; (11bS)-(+)-4,4-Dibutyl-4,5-dihydro-2,6-bis(3,4,5-trifluorophenyl)-3H-dinaphth[2,1-c;

IUPAC Name

13,13-dibutyl-10,16-bis(3,4,5-trifluorophenyl)-13-azoniapentacyclo[13.8.0.02,11.03,8.018,23]tricosa-1(15),2(11),3,5,7,9,16,18,20,22-decaene;bromide;

Molecular Weight

748.651g/mol

Molecular Formula

C42H36BrF6N;

Canonical SMILES

CCCC[N+]1(CC2=C(C3=CC=CC=C3C=C2C4=CC(=C(C(=C4)F)F)F)C5=C(C1)C(=CC6=CC=CC=C65)C7=CC(=C(C(=C7)F)F)F)CCCC.[Br-];

InChI

InChI=1S/C42H36F6N.BrH/c1-3-5-15-49(16-6-4-2)23-33-31(27-19-35(43)41(47)36(44)20-27)17-25-11-7-9-13-29(25)39(33)40-30-14-10-8-12-26(30)18-32(34(40)24-49)28-21-37(45)42(48)38(46)22-28;/h7-14,17-22H,3-6,15-16,23-24H2,1-2H3;1H/q+1;/p-1;

InChI Key

LOMUZNOWQYZTRP-UHFFFAOYSA-M;

Complexity

968

Covalently-Bonded Unit Count

Exact Mass

747.194g/mol

H-Bond Acceptor

Heavy Atom Count

Monoisotopic Mass

747.194g/mol

Rotatable Bond Count

Topological Polar Surface Area

0A^2

Application

(11bS)-4,4-Dibutyl-2,6-bis(3,4,5-trifluorophenyl)-4,5-dihydro-3H-dinaphtho[2,1-c:1',2'-e]azepinium bromide serves as a versatile chiral phase-transfer catalyst designed for the intricate process of asymmetrical alkylation of glycine and alanine Schiff bases, contributing to the advancement of enantioselective synthesis. As the 2nd generation Maruoka catalyst, it excels in enantioselective alkylation of α-amino acid derivatives and offers the advantage of easy recovery for reuse through extraction with fluorous solvents. Additionally, it facilitates asymmetric conjugate additions of α-substituted-α-cyanoacetates to α,β-unsaturated acetylenic esters, phase-transfer catalyzed enantioselective α-alkylation, asymmetric amination of β-keto esters, and both diastereo- and enantioselective conjugate addition of α-substituted nitroacetates to maleimides, with the capability of cyclizing β-alkynyl hydrazines, making it a pivotal tool in complex chemical transformations.

March 23, 2025

Exceptional Catalyst for Advanced Research

I employed this catalyst for asymmetric alkylation in synthesizing complex amino acid derivatives. Its efficiency and recyclability via fluorous solvents were impressive, significantly enhancing stereoselectivity in my experiments. Truly indispensable for cutting-edge research!