(1R,4R)-2,5-dibenzylbicyclo[2.2.1]hepta-2,5-diene

Base Information

Chemical Name:(1R,4R)-2,5-dibenzylbicyclo[2.2.1]hepta-2,5-diene
CAS No.:608489-13-0
Molecular Formula:C21H20
Molecular Weight:272.39
Hs Code.:
DSSTox Substance ID:DTXSID80458828
Nikkaji Number:J1.957.667A
Wikidata:Q82282367

Synonyms:(1R,4R)-2,5-dibenzylbicyclo[2.2.1]hepta-2,5-diene;608489-13-0;DTXSID80458828;2,5-Dibenzyl-1beta,4beta-methano-2,5-cyclohexadiene

Suppliers and Price of (1R,4R)-2,5-dibenzylbicyclo[2.2.1]hepta-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 0 raw suppliers

Chemical Property of (1R,4R)-2,5-dibenzylbicyclo[2.2.1]hepta-2,5-diene

Chemical Property:

XLogP3:5
Hydrogen Bond Donor Count:0
Hydrogen Bond Acceptor Count:0
Rotatable Bond Count:4
Exact Mass:272.156500638
Heavy Atom Count:21
Complexity:375

Purity/Quality:

Safty Information:

Pictogram(s):
Hazard Codes:

MSDS Files:: SDS file from LookChem

Useful:

Canonical SMILES:C1C2C=C(C1C=C2CC3=CC=CC=C3)CC4=CC=CC=C4
Isomeric SMILES:C1[C@@H]2C=C([C@H]1C=C2CC3=CC=CC=C3)CC4=CC=CC=C4

Technology Process of (1R,4R)-2,5-dibenzylbicyclo[2.2.1]hepta-2,5-diene

There total 10 articles about (1R,4R)-2,5-dibenzylbicyclo[2.2.1]hepta-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: 45.0%

: 1589-82-8
phenylmagnesium bromide

: 608489-12-9
(1R,4R)-2-benzyl-5-trifluoromethanesulfonyloxybicyclo[2.2.1]hepta-2,5-diene

: 608489-13-0
(1R,4R)-2,5-dibenzylbicyclo[2.2.1]hepta-2,5-diene

Guidance literature:: With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; In diethyl ether; Heating;
DOI:10.1021/ja037367z

Reference yield:

: 916670-75-2
(1R,4R)-2,5-di(trifluoromethanesulfonyloxy)bicyclo[2.2.1]hepta-2,5-diene

: 6921-34-2
benzylmagnesium chloride

: 103-29-7
1,1'-(1,2-ethanediyl)bisbenzene

: 608489-13-0
(1R,4R)-2,5-dibenzylbicyclo[2.2.1]hepta-2,5-diene

Guidance literature:: With 1-methyl-pyrrolidin-2-one; iron(III)-acetylacetonate; In tetrahydrofuran; diethyl ether; at 0 ℃; for 0.25h;
DOI:10.1021/jo061385s

Reference yield:

: 121-46-0
bicyclo[2.2.1]hepta-2,5-diene

: 608489-13-0
(1R,4R)-2,5-dibenzylbicyclo[2.2.1]hepta-2,5-diene

Guidance literature:: Multi-step reaction with 8 steps

1.1: HSiCl3; [PdCl(π-C3H5)2]; (R)-MeO-MOP / 0 °C

1.2: Et₃N / methanol

1.3: aq. H₂O₂; KHF₂ / tetrahydrofuran; methanol

2.1: Me₂SO; (COCl)2; Et₃N / CH₂Cl₂

3.1: TsOH

4.1: n-BuLi; diisopropylamine / tetrahydrofuran; hexane / 1 h / -78 °C

4.2: 81 percent / tetrahydrofuran; hexane / -78 - 20 °C

5.1: 97 percent / PdCl₂(dppf) / diethyl ether / Heating

6.1: 94 percent / aq. HCl / tetrahydrofuran / 20 °C

7.1: n-BuLi; diisopropylamine / tetrahydrofuran; hexane / -78 °C

7.2: 70 percent / tetrahydrofuran; hexane / -78 - 20 °C

8.1: 45 percent / PdCl₂(dppf) / diethyl ether / Heating

With (Ra)-(2'-methoxy-[1,1']-binaphthalenyl-2-yl)-diphenylphosphine; hydrogenchloride; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; n-butyllithium; oxalyl dichloride; bis(η3-allyl-μ-chloropalladium(II)); trichlorosilane; toluene-4-sulfonic acid; dimethyl sulfoxide; triethylamine; diisopropylamine; In tetrahydrofuran; diethyl ether; hexane; dichloromethane; 2.1: Swern oxidation / 5.1: Grignard cross-coupling / 8.1: Grignard cross-coupling;
DOI:10.1021/ja037367z