CAS 887938-70-7 (11bR)-4,4-Dibutyl-2,6-bis(3,4,5-trifluorophenyl)-4,5-dihydro-3H-dinaphtho[2,1-c:1',2'-e]azepinium bromide

Synonyms

(R)-4,4-Dibutyl-2,6-Bis(3,4,5-Trifluorophenyl)-4,5-Dihydro-3H-Dinaphtho[7,6,1,2-Cde]Azepinium Bromide

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

748.64

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

LOMUZNOWQYZTRP-UHFFFAOYSA-M

InChI Key

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

Melting Point

223-228 °C

Purity

98%

Appearance

Solid

Complexity

968

Covalently-Bonded Unit Count

Exact Mass

747.194g/mol

H-Bond Acceptor

Heavy Atom Count

Isomeric 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-]

Monoisotopic Mass

747.194g/mol

Rotatable Bond Count

Topological Polar Surface Area

0A^2

Application

The compound (11bR)-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 highly effective phase transfer organocatalyst, specifically designed for a range of enantioselective transformations. It excels in the asymmetric α-alkylation of glycine and α-amino acid derivatives at remarkably low catalyst loadings, enabling efficient and recyclable processes, particularly through extraction with fluorous solvents. This 2nd Generation Maruoka catalyst also facilitates the asymmetric conjugate addition of α-substituted-α-cyanoacetates to α,β-unsaturated acetylenic esters, and supports enantioselective α-alkylation through phase transfer. Moreover, it is instrumental in asymmetric amination of β-keto esters, diastereo- and enantioselective conjugate addition of α-substituted nitroacetates to maleimides, and the cyclization of β-alkynyl hydrazines, making it a versatile tool in asymmetric synthesis.

March 14, 2025

Highly Efficient Catalyst for Enantioselective Synthesis

Impressed by its efficiency in enantioselective α-alkylation of glycine derivatives. Used it in our lab for asymmetric amination of β-keto esters; recovery is seamless with fluorous solvent. Highly recommended for consistent and reliable results.