(1R,4R)-2,5-Diphenylbicyclo[2.2.2]octa-2,5-diene

Base Information

Chemical Name:(1R,4R)-2,5-Diphenylbicyclo[2.2.2]octa-2,5-diene
CAS No.:796966-15-9
Molecular Formula:C₂₀H₁₈
Molecular Weight:258.363
Hs Code.:
European Community (EC) Number:632-828-9
DSSTox Substance ID:DTXSID40459513
Nikkaji Number:J2.105.947A
Wikidata:Q76416829

Synonyms:(1R,4R)-2,5-Diphenylbicyclo[2.2.2]octa-2,5-diene;796966-15-9;(1S,4S)-2,5-Diphenylbicylco-[2.2.2]octadiene (Hayashi ligand);DTXSID40459513;BDYBOFJAEBJDMI-QZTJIDSGSA-N;MFCD15143646;AKOS032962821;E84877;2,5-Diphenyl-1beta,4beta-ethano-2,5-cyclohexadiene;(1R,4R)-2,5-diphenylbicyclo-[2,2,2]octa-2,5-diene;(1R,4R)-2,5-diphenylbicyclo[2,2,2]octa-2,5-diene;(1R,4R)-2,5-Diphenylbicyclo[2.2.2]octa-2,5-diene, 95%

Suppliers and Price of (1R,4R)-2,5-Diphenylbicyclo[2.2.2]octa-2,5-diene

Supply Marketing:

Business phase:: The product has achieved commercial mass production^*data from LookChem market partment

Manufacturers and distributors:

Manufacture/Brand
Chemicals and raw materials
Packaging
price

Total 4 raw suppliers

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

Chemical Property:

XLogP3:5
Hydrogen Bond Donor Count:0
Hydrogen Bond Acceptor Count:0
Rotatable Bond Count:2
Exact Mass:258.140850574
Heavy Atom Count:20
Complexity:362

Purity/Quality:: 99% ^*data from raw suppliers

Safty Information:

Pictogram(s):
Hazard Codes:

MSDS Files:: Total 1 MSDS from other Authors

Useful:

Canonical SMILES:C1CC2C=C(C1C=C2C3=CC=CC=C3)C4=CC=CC=C4
Isomeric SMILES:C1C[C@@H]2C=C([C@H]1C=C2C3=CC=CC=C3)C4=CC=CC=C4

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

There total 22 articles about (1R,4R)-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: 78.0%

: phenylmagnesium bromide

: 796966-13-7
(1R,4R)-2,5-bis(trifluoromethanesulfonyloxy)bicyclo[2.2.2]octa-2,5-diene

: 796966-15-9,850409-83-5
(1R,4R)-2,5-diphenylbicyclo[2.2.2]octa-2,5-diene

Guidance literature:: With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; In diethyl ether; for 8h; Heating;
DOI:10.1021/ja044790e

Reference yield: 78.0%

: 1,1-diphenyl-3-(triisopropylsilyl)prop-2-yn-1-ol

: [RhCl((R,R)-Ph-bicyclo[2.2.2]octa-2,5-diene)]₂

: C₆₂H₇₈Rh₂Si₂

: 796966-15-9,850409-83-5
(1R,4R)-2,5-diphenylbicyclo[2.2.2]octa-2,5-diene

Guidance literature:: With caesium carbonate; In 1,4-dioxane; at 80 ℃; for 24h; Schlenk technique; Inert atmosphere;
DOI:10.1002/anie.201509778

Reference yield:

: 57346-05-1
Bicyclo<2.2.2>octane-2,4-dione

: 796966-15-9,850409-83-5
(1R,4R)-2,5-diphenylbicyclo[2.2.2]octa-2,5-diene

Guidance literature:: Multi-step reaction with 3 steps

1.1: NaOAc; AcOH / ethanol / 3 h / Heating

1.2: 4.5 percent / H₂SO₄ / H₂O / 4 h / Heating

2.1: lithium diisopropylamide / tetrahydrofuran; hexane / 1 h / -78 °C

2.2: 70 percent / tetrahydrofuran; hexane / -78 - 20 °C

3.1: 78 percent / PdCl₂(dppf) / diethyl ether / 8 h / Heating

With sodium acetate; acetic acid; lithium diisopropyl amide; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; In tetrahydrofuran; diethyl ether; ethanol; hexane;
DOI:10.1021/jo047831y