361342-51-0

Basic information

• Product Name: (11bR)-2,6-Di-9-anthracenyl-4-hydroxy-dinaphtho[2,1-d:1μ,2μ-f][1,3,2]dioxaphosphepin-4-oxide
• Synonyms: (11bR)-2,6-Di-9-anthracenyl-4-hydroxy-dinaphtho[2,1-d:1μ,2μ-f][1,3,2]dioxaphosphepin-4-oxide;(R)-3,3μ-Bis(9-anthracenyl)-1,1μ-binaphthyl-2,2μ-diyl hydrogenphosphate;(R)-3,3′-Bis(9-anthracenyl)-1,1′-binaphthyl-2,2′-diyl hydrogenphosphate,(11bR)-2,6-Di-9-anthracenyl-4-hydroxy-dinaphtho[2,1-d:1′,2′-f][1,3,2]dioxaphosphepin-4-oxide;(11Br)-2,6-Di(anthracen-9-yl)-4-hydroxydinaphtho-[2,1-d:1',2'-f][1,3,2]dioxaphosphepine 4-oxide;(R)-3,3'-Bis(9-anthracenyl)-1,1'-binaphthyl-2,2'-diyl hydrogenphosphate 95%;(R)-3,3'-Bis(anthracenyl-9-yl)-1,1'-binapthyl-2,2'-diyl hydrogenphosphate;(2r)-2,6-di(anthracen-9-yl)-4-hydroxydinaphtho[2,1-d:1',2'-f][1,3,2]dioxaphosphepine 4-oxide;(11br)
• CAS NO: 361342-51-0
• Molecular Formula: C48H29O4P
• Molecular Weight: 700.727
• Mol File: 361342-51-0.mol
• Article Data: 5

Chemical Properties

• Melting Point: 288-292 °C (D)
• Appearance: /
• Density: 1.46±0.1 g/cm3(Predicted)
• Storage Temp.: ?20°C
• PKA: 1.11±0.20(Predicted)
• CAS DataBase Reference: (11bR)-2,6-Di-9-anthracenyl-4-hydroxy-dinaphtho[2,1-d:1μ,2μ-f][1,3,2]dioxaphosphepin-4-oxide(CAS DataBase Reference)
• NIST Chemistry Reference: (11bR)-2,6-Di-9-anthracenyl-4-hydroxy-dinaphtho[2,1-d:1μ,2μ-f][1,3,2]dioxaphosphepin-4-oxide(361342-51-0)
• EPA Substance Registry System: (11bR)-2,6-Di-9-anthracenyl-4-hydroxy-dinaphtho[2,1-d:1μ,2μ-f][1,3,2]dioxaphosphepin-4-oxide(361342-51-0)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26
• WGK Germany: 3
• Hazardous Substances Data: 361342-51-0(Hazardous Substances Data)

Usage

Uses

Catalyst used in asymmetric direct alkylation of α-diazoester via C-H bond cleavage.

Upstream product

• 35294-28-1 (R)-2,2'-dimethoxy-1,1'-dinaphthyl 
• 189518-78-3 (Ra)-3,3’-diiodo-2,2’-bis(methoxymethoxy)-1,1’-binaphthalene 
• 18531-94-7 (R)-1,1'-Bi-2-naphthol 

Relevant articles and documents

Hypercrosslinking chiral Br?nsted acids into porous organic polymers for efficient heterogeneous asymmetric organosynthesis

Here, we developed a construction strategy for directly immobilizing the axially chiral phosphoric acid into hypercrosslinked polymers by a one-pot Friedel-Crafts alkylation reaction. The obtained chiral polymers have high porosity, excellent stability and tailorable catalytic centers, and display excellent activity, enantioselectivity and recyclability for asymmetric transfer hydrogenation.

Enantioselective halogenative semi-pinacol rearrangement: Extension of substrate scope and mechanistic investigations

The present Full Paper article discloses a survey of our recent results obtained in the context of the enantioselective halogenation-initiated semi-pinacol rearrangement. Commencing with the fluorination/semi-pinacol reaction first and moving to the heavier halogens (bromine and iodine) second, the scope and limitations of the halogenative phase-transfer methodology will be discussed and compared. An extension of the fluorination/semi-pinacol reaction to the ring-expansion of five-membered allylic cyclopentanols will be also described, as well as some preliminary results on substrates prone to desymmetrization will be given. Finally, the present manuscript will culminate with a detailed mechanistic investigation of the canonical fluorination/semi-pinacol reaction. Our mechanistic discussion will be based on in situ reaction progress monitoring, complemented with substituent effect, kinetic isotopic effect and non-linear behaviour studies.

Enantioselective organocatalytic iodination-initiated Wagner-Meerwein rearrangement

The present manuscript describes a high-yielding enantioselective semipinacol transposition, initiated by an electrophilic iodination event. The title transformation makes use of the anionic phase-transfer catalysis (PTC) paradigm for chirality induction. Thus, when combined appropriately, the insoluble cationic iodinating reagent S9 and the lipophilic phosphoric acid L9 act as an efficient source of chiral iodine that performs the semipinacol transposition of strained allylic alcohols A x to β-iodo spiroketones Bx in good yields and with high levels of diastereo- and enantio-induction. The product β-iodo spiroketones could be derivatized stereospecifically and without stereoerosion, giving rise to products inaccessible directly from a semipinacol rearrangement.