1-Propanone, 3-hydroxy-2-methyl-1,3-diphenyl-, (2R,3R)-

Base Information

• Chemical Name: 1-Propanone, 3-hydroxy-2-methyl-1,3-diphenyl-, (2R,3R)-
• CAS No.: 283151-71-3
• Molecular Formula: C16H16O2
• Molecular Weight: 240.302
• DSSTox Substance ID: DTXSID20444422
• Nikkaji Number: J896.269C
• Wikidata: Q82262555
• Mol file: 283151-71-3.mol

Synonyms:1-Propanone, 3-hydroxy-2-methyl-1,3-diphenyl-, (2R,3R)-;283151-71-3;DTXSID20444422;(R)-1-Phenyl-2-[(R)-alpha-hydroxybenzyl]-1-propanone

Chemical Property of 1-Propanone, 3-hydroxy-2-methyl-1,3-diphenyl-, (2R,3R)-

Chemical Property:

• XLogP3: 3
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 4
• Exact Mass: 240.115029749
• Heavy Atom Count: 18
• Complexity: 262

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

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

Technology Process of 1-Propanone, 3-hydroxy-2-methyl-1,3-diphenyl-, (2R,3R)-

There total 29 articles about 1-Propanone, 3-hydroxy-2-methyl-1,3-diphenyl-, (2R,3R)- 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: 93.0%

1-phenyl-1-trimethylsiloxypropene (37471-46-8) + benzaldehyde (100-52-7) → (2R,3R)-3-hydroxy-2-methyl-1,3-diphenylpropan-1-one (283151-71-3)

Guidance literature:

With (2R,2'R)-dimethyl 2,2'-(1,7-dioxa-4,10-diazacyclododecane-4,10-diyl)dipropanoate; neodymium(III) trifluoromethanesufonate; In ethanol; water; at -25 ℃; for 168h; optical yield given as %ee; stereoselective reaction;

DOI:10.1021/jo300800b

Reference yield: 82.0%

(2R,3R)-1-(2,3-dihydro-1H-pyrrolo[2,3-b]pyridin-1-yl)-3-hydroxy-2-methyl-3-phenylpropan-1-one + phenylmagnesium bromide (100-58-3) → (2R,3R)-3-hydroxy-2-methyl-1,3-diphenylpropan-1-one (283151-71-3)

Guidance literature:

In tetrahydrofuran; at -20 ℃; for 2h;

DOI:10.1021/acs.orglett.6b03890

Reference yield: 81.0%

phenyllithium (591-51-5) + (2R,3R,1'S,2'S)-(+)-N-(2'-hydroxy-1'-methyl-2'-phenylethyl)-3-hydroxy-N,2-dimethyl-3-phenylpropanamide (219783-11-6) → (2R,3R)-3-hydroxy-2-methyl-1,3-diphenylpropan-1-one (283151-71-3)

Guidance literature:

phenyllithium; (2R,3R,1'S,2'S)-(+)-N-(2'-hydroxy-1'-methyl-2'-phenylethyl)-3-hydroxy-N,2-dimethyl-3-phenylpropanamide; In tetrahydrofuran; at -78 - 0 ℃; for 0.416667h;

With diisopropylamine; In tetrahydrofuran; for 0.25h; Further stages.;

DOI:10.1021/jo000035h

upstream raw materials:

1-phenyl-1-propenyloxytriethyltin

benzaldehyde

1-phenyl-1-propenyloxytributyltin

1-phenyl-propan-1-one

Downstream raw materials:

(1S*,2r*,3R*)-2-Methyl-1,3-diphenylpropan-1,3-diol