1-Propanone, 1-[(2R,3S)-3-(4-methoxyphenyl)oxiranyl]-2,2-dimethyl-

Base Information

• Chemical Name: 1-Propanone, 1-[(2R,3S)-3-(4-methoxyphenyl)oxiranyl]-2,2-dimethyl-
• CAS No.: 201804-19-5
• Molecular Formula: C14H18O3
• Molecular Weight: 234.295
• DSSTox Substance ID: DTXSID80431479
• Nikkaji Number: J615.419K
• Wikidata: Q82245382
• Mol file: 201804-19-5.mol

Synonyms:1-Propanone, 1-[(2R,3S)-3-(4-methoxyphenyl)oxiranyl]-2,2-dimethyl-;201804-19-5;DTXSID80431479;1-[2beta-(4-Methoxyphenyl)oxiran-3alpha-yl]-2,2-dimethyl-1-propanone

Chemical Property of 1-Propanone, 1-[(2R,3S)-3-(4-methoxyphenyl)oxiranyl]-2,2-dimethyl-

Chemical Property:

• XLogP3: 2.5
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 4
• Exact Mass: 234.125594432
• Heavy Atom Count: 17
• Complexity: 284

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C)(C)C(=O)C1C(O1)C2=CC=C(C=C2)OC
• Isomeric SMILES: CC(C)(C)C(=O)[C@H]1[C@@H](O1)C2=CC=C(C=C2)OC

Technology Process of 1-Propanone, 1-[(2R,3S)-3-(4-methoxyphenyl)oxiranyl]-2,2-dimethyl-

There total 4 articles about 1-Propanone, 1-[(2R,3S)-3-(4-methoxyphenyl)oxiranyl]-2,2-dimethyl- 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: 70.0%

(E)-1-(4-methoxyphenyl)-4,4-dimethylpent-1-en-3-one (2419-67-2,24470-83-5,41564-61-8) → 1-((2R,3S)-4-methoxyphenyloxiranyl)-2,2-dimethylpropan-1-one (201804-19-5)

Guidance literature:

With immobilised poly-L-leucine; urea hydrogen peroxide; 1,8-diazabicyclo[5.4.0]undec-7-ene; In tetrahydrofuran; for 28h;

Reference yield:

(E)-1-(4-methoxyphenyl)-4,4-dimethylpent-1-en-3-one (2419-67-2,24470-83-5,41564-61-8) → 1-((2R,3S)-4-methoxyphenyloxiranyl)-2,2-dimethylpropan-1-one (201804-19-5) + 1-((2S,3R)-4-methoxyphenyloxiranyl)-2,2-dimethylpropan-1-one

Guidance literature:

With Cumene hydroperoxide; lithium cumyl peroxide; (-)-(1R,2R)-1-dimethylamino-2-(2-methoxyphenoxy)-1,2-diphenylethane; In toluene; at 20 ℃; for 12h; Title compound not separated from byproducts;

DOI:10.1016/S0040-4020(03)00658-6

Reference yield:

3,3-dimethyl-butan-2-one (75-97-8) → 1-((2R,3S)-4-methoxyphenyloxiranyl)-2,2-dimethylpropan-1-one (201804-19-5)

Guidance literature:

Multi-step reaction with 2 steps

1: 87 percent / NaOMe / methanol / 40 h / Heating

2: 70 percent / urea hydrogen peroxide, DBU, immobilised poly-L-leucine / tetrahydrofuran / 28 h

With immobilised poly-L-leucine; urea hydrogen peroxide; sodium methylate; 1,8-diazabicyclo[5.4.0]undec-7-ene; In tetrahydrofuran; methanol;

upstream raw materials:

(E)-1-(4-methoxyphenyl)-4,4-dimethylpent-1-en-3-one

3,3-dimethyl-butan-2-one

4-methoxy-benzaldehyde

Downstream raw materials:

(2S,3S)-3-(2-Amino-phenylsulfanyl)-2-hydroxy-3-(4-methoxy-phenyl)-propionic acid tert-butyl ester

(2S,3S)-3-hydroxy-2-(4-methoxyphenyl)-2,3-dihydro-1,5-benzothiazepin-4(5H)-one

diltiazem hydrochloride

(2S,3S)-5-(2-dimethylaminoethyl)-3-hydroxy-2-(4-methoxyphenyl)-2,3-dihydro-1,5-benzothiazepin-4(5H)-one hydrochloride