(R,R)-(+)-1,4-dimethyl-2,5-diphenylbicyclo[2.2.2]octa-2,5-diene

Base Information

• Chemical Name: (R,R)-(+)-1,4-dimethyl-2,5-diphenylbicyclo[2.2.2]octa-2,5-diene
• CAS No.: 1288929-63-4
• Molecular Formula: C₂₂H₂₂
• Molecular Weight: 286.417
• Mol file: 1288929-63-4.mol

Synonyms:(R,R)-(+)-1,4-dimethyl-2,5-diphenylbicyclo[2.2.2]octa-2,5-diene

Chemical Property of (R,R)-(+)-1,4-dimethyl-2,5-diphenylbicyclo[2.2.2]octa-2,5-diene

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (R,R)-(+)-1,4-dimethyl-2,5-diphenylbicyclo[2.2.2]octa-2,5-diene

There total 6 articles about (R,R)-(+)-1,4-dimethyl-2,5-diphenylbicyclo[2.2.2]octa-2,5-diene which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 99.0%

C24H20F6O6S2 (1227928-21-3) → (R,R)-(+)-1,4-dimethyl-2,5-diphenylbicyclo[2.2.2]octa-2,5-diene (1288929-63-4)

Guidance literature:

C₂₄H₂₀F₆O₆S₂; With lithium triethylborohydride; In tetrahydrofuran; at -78 - 20 ℃; Inert atmosphere;

With silica gel; In tetrahydrofuran; Cooling with ice; Inert atmosphere;

DOI:10.1002/anie.200907033

Reference yield:

(S,S)-1,4-di(methoxycarbonyl) bicyclo[2.2.2]octane-2,5-dione (1227928-08-6) → (R,R)-(+)-1,4-dimethyl-2,5-diphenylbicyclo[2.2.2]octa-2,5-diene (1288929-63-4)

Guidance literature:

Multi-step reaction with 5 steps

1.1: lithium hexamethyldisilazane / tetrahydrofuran / 0.5 h / -78 °C

1.2: -78 °C

2.1: tetrakis(triphenylphosphine) palladium⁽⁰⁾; sodium carbonate / ethanol; water; toluene / 6 h / 20 °C / Inert atmosphere

3.1: lithium aluminium tetrahydride / tetrahydrofuran; diethyl ether / 0.08 h / Inert atmosphere

4.1: pyridine / dichloromethane / -78 - 20 °C

5.1: lithium triethylborohydride / tetrahydrofuran / 0.5 h / -78 - 20 °C

With pyridine; lithium aluminium tetrahydride; tetrakis(triphenylphosphine) palladium⁽⁰⁾; lithium triethylborohydride; sodium carbonate; lithium hexamethyldisilazane; In tetrahydrofuran; diethyl ether; ethanol; dichloromethane; water; toluene;

DOI:10.1039/c2cc17120a

Reference yield:

(S,S)-(+)-1,4-di(methoxycarbonyl)-2,5-diphenylbicyclo[2.2.2]octa-2,5-diene (1227928-13-3) → (R,R)-(+)-1,4-dimethyl-2,5-diphenylbicyclo[2.2.2]octa-2,5-diene (1288929-63-4)

Guidance literature:

Multi-step reaction with 3 steps

1: lithium aluminium tetrahydride / tetrahydrofuran; diethyl ether / 0.08 h / Inert atmosphere

2: pyridine / dichloromethane / -78 - 20 °C

3: lithium triethylborohydride / tetrahydrofuran / 0.5 h / -78 - 20 °C

With pyridine; lithium aluminium tetrahydride; lithium triethylborohydride; In tetrahydrofuran; diethyl ether; dichloromethane;

DOI:10.1039/c2cc17120a

upstream raw materials:

C₂₄H₂₀F₆O₆S₂

(S,S)-1,4-di(methoxycarbonyl) bicyclo[2.2.2]octane-2,5-dione

(S,S)-(+)-1,4-di(methoxycarbonyl)-2,5-diphenylbicyclo[2.2.2]octa-2,5-diene

(S,S)-1,4-di(methoxycarbonyl)-2,5-di(trifluromethylsulfonyloxy)bicyclo[2.2.2]octa-2,5-diene