4H-Pyran-4-one, 2,3-dihydro-2-(4-nitrophenyl)-, (2S)-

Base Information

• Chemical Name: 4H-Pyran-4-one, 2,3-dihydro-2-(4-nitrophenyl)-, (2S)-
• CAS No.: 162299-82-3
• Molecular Formula: C11H9NO4
• Molecular Weight: 219.197
• DSSTox Substance ID: DTXSID30459087
• Nikkaji Number: J1.221.764A
• Wikidata: Q82282696
• Mol file: 162299-82-3.mol

Synonyms:162299-82-3;DTXSID30459087;4H-Pyran-4-one, 2,3-dihydro-2-(4-nitrophenyl)-, (2S)-;2alpha-(4-Nitrophenyl)-2H-pyran-4(3H)-one

Chemical Property of 4H-Pyran-4-one, 2,3-dihydro-2-(4-nitrophenyl)-, (2S)-

Chemical Property:

• XLogP3: 1.3
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 1
• Exact Mass: 219.05315777
• Heavy Atom Count: 16
• Complexity: 312

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1C(OC=CC1=O)C2=CC=C(C=C2)[N+](=O)[O-]
• Isomeric SMILES: C1[C@H](OC=CC1=O)C2=CC=C(C=C2)[N+](=O)[O-]

Technology Process of 4H-Pyran-4-one, 2,3-dihydro-2-(4-nitrophenyl)-, (2S)-

There total 13 articles about 4H-Pyran-4-one, 2,3-dihydro-2-(4-nitrophenyl)-, (2S)- 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: 99.0%

C15H21NO5Si → (2S)-2-(4-nitrophenyl)-2,3-dihydro-4H-pyran-4-one (162299-82-3)

Guidance literature:

With trifluorormethanesulfonic acid; for 0.5h; optical yield given as %ee;

DOI:10.1021/ol2007378

Reference yield: 91.0%

C14H17NO6 (1197206-96-4) → (2S)-2-(4-nitrophenyl)-2,3-dihydro-4H-pyran-4-one (162299-82-3)

Guidance literature:

With trifluoroacetic acid; In dichloromethane; at 20 ℃; for 6h; enantioselective reaction;

DOI:10.1021/jo9021259

Reference yield: 87.0%

Acetic acid (2R,3R,4S,5R,6S)-3,5-diacetoxy-2-acetoxymethyl-6-[(2R,6S)-4-(tert-butyl-dimethyl-silanyloxy)-6-(4-nitro-phenyl)-5,6-dihydro-2H-pyran-2-yloxy]-tetrahydro-pyran-4-yl ester (162299-79-8) → (2S)-2-(4-nitrophenyl)-2,3-dihydro-4H-pyran-4-one (162299-82-3)

Guidance literature:

With trifluoroacetic acid;

DOI:10.1016/S0040-4039(00)73430-7

upstream raw materials:

Acetic acid (2R,3R,4S,5R,6S)-3,5-diacetoxy-2-acetoxymethyl-6-[(2S,6S)-4-(tert-butyl-dimethyl-silanyloxy)-6-(4-nitro-phenyl)-5,6-dihydro-2H-pyran-2-yloxy]-tetrahydro-pyran-4-yl ester

Acetic acid (2R,3R,4S,5R,6S)-3,5-diacetoxy-2-acetoxymethyl-6-[(2R,6S)-4-(tert-butyl-dimethyl-silanyloxy)-6-(4-nitro-phenyl)-5,6-dihydro-2H-pyran-2-yloxy]-tetrahydro-pyran-4-yl ester

danishefsky's diene

4-nitrobenzaldehdye

Downstream raw materials:

(2S,4S)-2-(4-Nitro-phenyl)-3,4-dihydro-2H-pyran-4-ol

(S)-3-hydroxy-3-phenylpropanoic acid

tert-butyl-dimethyl-[2-(4-nitro-phenyl)-3,4-dihydro-2H-pyran-4-yloxy]-silane

(S)-3-hydroxy-3-(4'-nitrophenyl)propanoic acid