Benzene, 1-[[(1R)-1-phenyl-2-propenyl]oxy]-4-(trifluoromethyl)-

Base Information

• Chemical Name: Benzene, 1-[[(1R)-1-phenyl-2-propenyl]oxy]-4-(trifluoromethyl)-
• CAS No.: 444575-92-2
• Molecular Formula: C16H13F3O
• Molecular Weight: 278.274
• DSSTox Substance ID: DTXSID20465899
• Nikkaji Number: J1.887.976J
• Wikidata: Q82292196
• Mol file: 444575-92-2.mol

Synonyms:Benzene, 1-[[(1R)-1-phenyl-2-propenyl]oxy]-4-(trifluoromethyl)-;444575-92-2;SCHEMBL3300767;DTXSID20465899;ZHBPETNSKLJBDE-OAHLLOKOSA-N

Chemical Property of Benzene, 1-[[(1R)-1-phenyl-2-propenyl]oxy]-4-(trifluoromethyl)-

Chemical Property:

• XLogP3: 4.9
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 4
• Exact Mass: 278.09184952
• Heavy Atom Count: 20
• Complexity: 299

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C=CC(C1=CC=CC=C1)OC2=CC=C(C=C2)C(F)(F)F
• Isomeric SMILES: C=C[C@H](C1=CC=CC=C1)OC2=CC=C(C=C2)C(F)(F)F

Technology Process of Benzene, 1-[[(1R)-1-phenyl-2-propenyl]oxy]-4-(trifluoromethyl)-

There total 12 articles about Benzene, 1-[[(1R)-1-phenyl-2-propenyl]oxy]-4-(trifluoromethyl)- 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: 81.0%

1-trifluoromethyl-4-trimethylsilyloxybenzene (41571-86-2) + (R)-1-phenylprop-2-en-1-ol (104713-12-4) → 1-phenyl-3-(4-trifluoromethyl)phenoxyprop-1-ene + (R)-(-)-1-phenyl-1-(4-trifluoromethylphenoxy)-2-propene (444575-92-2)

Guidance literature:

With tetrabutylammonium triphenyldifluorosilicate; tris(acetonitrile)pentamethylcyclopentadienylruthenium(II) hexafluorophosphate; at 35 ℃;

DOI:10.1002/1521-3773(20020315)41:6<1059::AID-ANIE1059>3.0.CO;2-5

Reference yield:

trans-3-phenylprop-2-enyl chloride (21087-29-6) + 4-hydroxybenzotrifluoride (402-45-9) → (R)-(-)-1-phenyl-1-(4-trifluoromethylphenoxy)-2-propene (444575-92-2) + (S)-(+)-1-phenyl-1-(4-trifluoromethylphenoxy)-2-propene

Guidance literature:

With potassium carbonate; planar-chiral cyclopentadienyl ruthenium complex; In tetrahydrofuran; at 30 ℃; for 24h; Title compound not separated from byproducts.;

DOI:10.1002/anie.200704457

Reference yield:

(1S,2R)-(+)-ephedrine (321-98-2,7009-81-6,90-83-5,6912-63-6) → (R)-(-)-1-phenyl-1-(4-trifluoromethylphenoxy)-2-propene (444575-92-2)

Guidance literature:

Multi-step reaction with 3 steps

1: K₂CO₃ / methanol / 20 °C

2: lithium diisopropylamide / tetrahydrofuran; hexamethylphosphoric acid triamide / -50 - 0 °C

3: 81 percent / tetrabutylammonium triphenyldifluorosilicate / [(C₅Me₅)Ru(NCCH₃)3]PF₆ / 35 °C

With potassium carbonate; tetrabutylammonium triphenyldifluorosilicate; lithium diisopropyl amide; tris(acetonitrile)pentamethylcyclopentadienylruthenium(II) hexafluorophosphate; In tetrahydrofuran; methanol; N,N,N,N,N,N-hexamethylphosphoric triamide; 2: Hoffman elimination;

DOI:10.1002/1521-3773(20020315)41:6<1059::AID-ANIE1059>3.0.CO;2-5

upstream raw materials:

1-trifluoromethyl-4-trimethylsilyloxybenzene

(R)-1-phenylprop-2-en-1-ol

ethyl (E)-3-phenyl-2-propenyl carbonate

(1S,2R)-(+)-ephedrine

Downstream raw materials:

(R)-3-(4-trifluoromethylphenoxy)-3-phenylprop-1-yl methanesulfonate

(R)-fluoxetine

(R)-3-phenyl-3-(4-(trifluoromethyl)phenoxy)propan-1-ol

Refernces

• 1、 Austeri, Martina,Linder, David,Lacour, Jerome. "(Cyclopentadienyl)ruthenium-catalyzed regio- and enantioselective decarboxylative allylic etherification of allyl aryl and alkyl carbonates". experimental part. p. 3339 - 3347. Retrieved 2011/02/23.
• 2、 Lopez, Fernando,Ohmura, Toshimichi,Hartwig, John F.. "Regio- and enantioselective iridium-catalyzed intermolecular allylic etherification of achiral allylic carbonates with phenoxides". . p. 3426 - 3427. Retrieved 2007/10/03.