(2S)-2-[(2S,3S)-3-phenyloxiran-2-yl]-2,3-dihydropyran-6-one

Base Information

• Chemical Name: (2S)-2-[(2S,3S)-3-phenyloxiran-2-yl]-2,3-dihydropyran-6-one
• CAS No.: 916151-83-2
• Molecular Formula: C13H12O3
• Molecular Weight: 216.236
• ChEMBL ID: CHEMBL3358620
• DSSTox Substance ID: DTXSID30550700
• Nikkaji Number: J2.378.650H
• Wikidata: Q82430129
• Mol file: 916151-83-2.mol

Synonyms:916151-83-2;(2S)-2-[(2S,3S)-3-phenyloxiran-2-yl]-2,3-dihydropyran-6-one;CHEMBL3358620;DTXSID30550700

Chemical Property of (2S)-2-[(2S,3S)-3-phenyloxiran-2-yl]-2,3-dihydropyran-6-one

Chemical Property:

• XLogP3: 2
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 2
• Exact Mass: 216.078644241
• Heavy Atom Count: 16
• Complexity: 304

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1C=CC(=O)OC1C2C(O2)C3=CC=CC=C3
• Isomeric SMILES: C1C=CC(=O)O[C@@H]1[C@H]2[C@@H](O2)C3=CC=CC=C3

Technology Process of (2S)-2-[(2S,3S)-3-phenyloxiran-2-yl]-2,3-dihydropyran-6-one

There total 7 articles about (2S)-2-[(2S,3S)-3-phenyloxiran-2-yl]-2,3-dihydropyran-6-one 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: 92.0%

(S)-1-((2S,3S)-3-phenyloxiran-2-yl)but-3-en-1-yl acrylate → (S)-6-((2S,3S)-3-phenyloxiran-2-yl)-5,6-dihydro-2H-pyran-2-one (916151-83-2)

Guidance literature:

With Grubbs catalyst first generation; In dichloromethane; for 6h; Reflux;

DOI:10.1016/j.tetasy.2017.01.005

Reference yield: 90.0%

(S)-goniothalamin (122046-62-2) → (S)-6-((2S,3S)-3-phenyloxiran-2-yl)-5,6-dihydro-2H-pyran-2-one (916151-83-2)

Guidance literature:

With (S,S)-(+)-N,N’-bis(3,5-di-tert-butylsalicylidene)-1,2-cyclohexanediaminomanganese(III) chloride; oxone||potassium monopersulfate triple salt; tetra(n-butyl)ammonium hydrogensulfate; In acetonitrile; at 0 ℃; for 2h; diastereoselective reaction;

DOI:10.1021/acs.jnatprod.6b00386

Reference yield:

(S)-goniothalamin (122046-62-2) → (S)-6-((2R,3R)-3-phenyloxiran-2-yl)-5,6-dihydro-2H-pyran-2-one (110044-45-6) + (S)-6-((2S,3S)-3-phenyloxiran-2-yl)-5,6-dihydro-2H-pyran-2-one (916151-83-2)

Guidance literature:

With 3-chloro-benzenecarboperoxoic acid; In dichloromethane; Heating;

DOI:10.1016/S0040-4039(00)95462-5

upstream raw materials:

(S)-goniothalamin

(1S)-1-[(E)-2-phenylvinyl]but-3-enyl acrylate

(E)-3-phenylpropenal

trans-(S)-1-phenyl-1,5-hexadien-3-ol

Downstream raw materials:

(6S,7R,8S)-(-)-7-epi-goniodiol

(6S)-6-[(1R,2R)-1,2-dihydroxy-2-phenylethyl]-5,6-dihydro-2H-pyran-2-one