142010-85-3

Basic information

• Product Name: 2,2'-Bis-methoxymethoxy-3,3'-bis-phenylsulfanyl-[1,1']binaphthalenyl
• CAS NO: 142010-85-3
• Molecular Weight: 590.764
• Mol File: 142010-85-3.mol
• Article Data: 2

Chemical Properties

• CAS DataBase Reference: 2,2'-Bis-methoxymethoxy-3,3'-bis-phenylsulfanyl-[1,1']binaphthalenyl(CAS DataBase Reference)
• NIST Chemistry Reference: 2,2'-Bis-methoxymethoxy-3,3'-bis-phenylsulfanyl-[1,1']binaphthalenyl(142010-85-3)
• EPA Substance Registry System: 2,2'-Bis-methoxymethoxy-3,3'-bis-phenylsulfanyl-[1,1']binaphthalenyl(142010-85-3)

Safety Data

• Hazardous Substances Data: 142010-85-3(Hazardous Substances Data)

Upstream product

• 74292-20-9 (S)-2,2'-bis(methoxymethoxy)-1,1'-binaphthyl 
• 882-33-7 diphenyldisulfane 
• 173831-50-0 rac-2,2'-bis-(methoxymethoxy)-1,1'-binaphthalene 

Relevant articles and documents

Copper-catalysed asymmetric 1,4-addition of organozinc compounds to linear aliphatic enones using 2,2′-dihydroxy 3,3′-dithioether derivatives of 1,1′-binaphthalene

Directed ortho dilithiation of bis(diethylcarbamate) or bis(MOM)-protected (Sa)-1,1,′-bi(2-naphthol) followed by treatment with R2S2 [R = Me, Ph (X-ray structure)] or Me2Se2 cleanly affords the 3,3′ derivatives; the free naphthols are produced on deprotection. In the case of the bis(MOM) series, but not that of the bis(carbamates), some racemisation occurs. The ligand 2,2′-dihydroxy-3,3′-dimethylthio-1,1′-binaphthalene shows optimal performance in the addition of ZnEt2 to linear aliphatic enones (E)-R1C(O)CH=CHR2. Variation of the steric demands of R1 and R2 generates catalytic results consistent with binding of a zinc-based Lewis acid anti to the ene function and with the reactive conformation being s-cis. With enones containing the functions R2 = (CH2)nCH(OAlkyl)2 (n = 0-2), the ZnEt2 addition products undergo base-promoted cyclisation.