Cyclopentanone, 2-[(1R)-2-nitro-1-phenylethyl]-, (2S)-

Base Information

• Chemical Name: Cyclopentanone, 2-[(1R)-2-nitro-1-phenylethyl]-, (2S)-
• CAS No.: 359876-14-5
• Molecular Formula: C13H15NO3
• Molecular Weight: 233.267
• DSSTox Substance ID: DTXSID00458002
• Nikkaji Number: J1.530.178C
• Wikidata: Q82281121
• Mol file: 359876-14-5.mol

Synonyms:359876-14-5;Cyclopentanone, 2-[(1R)-2-nitro-1-phenylethyl]-, (2S)-;DTXSID00458002;2alpha-[(R)-1-Phenyl-2-nitroethyl]cyclopentanone

Chemical Property of Cyclopentanone, 2-[(1R)-2-nitro-1-phenylethyl]-, (2S)-

Chemical Property:

• XLogP3: 2
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 3
• Exact Mass: 233.10519334
• Heavy Atom Count: 17
• Complexity: 292

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1CC(C(=O)C1)C(C[N+](=O)[O-])C2=CC=CC=C2
• Isomeric SMILES: C1C[C@H](C(=O)C1)[C@@H](C[N+](=O)[O-])C2=CC=CC=C2

Technology Process of Cyclopentanone, 2-[(1R)-2-nitro-1-phenylethyl]-, (2S)-

There total 27 articles about Cyclopentanone, 2-[(1R)-2-nitro-1-phenylethyl]-, (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: 97.0%

(2-nitroethenyl)benzene (102-96-5) + cyclopentanone (120-92-3) → (S)-2-((R)-2-nitro-1-phenylethyl)cyclopentanone (359876-14-5)

Guidance literature:

With (S)-1-(pyrrolidine-2-ylmethyl)-1H-pyrazole; trifluoroacetic acid; at 20 ℃; for 20h; optical yield given as %ee; enantioselective reaction; Neat (no solvent);

DOI:10.1016/j.tetasy.2011.04.010

Reference yield: 86.0%

(2-nitroethenyl)benzene (102-96-5) + cyclopentanone (120-92-3) → 2-(2'-nitro-1'-phenyl-ethyl)-cyclopentanone (4591-65-5) + (2R)-2-((S)-2-nitro-1-phenylethyl)cyclopentan-1-one (475294-96-3) + (S)-2-((R)-2-nitro-1-phenylethyl)cyclopentanone (359876-14-5)

Guidance literature:

With (3aR,5S,6R,6aR)-6-hydroxy-2,2-dimethyl-N-((S)-pyrrolidin-2-ylmethyl)tetrahydrofuro[2,3-d][1,3]dioxole-5-carboxamide; at 20 ℃; for 48h; stereoselective reaction;

DOI:10.1016/j.tetasy.2014.02.003

Reference yield: 10.0%

nitrostyrene (5153-67-3) + cyclopentanone (120-92-3) → (S)-2-((R)-2-nitro-1-phenylethyl)cyclopentanone (359876-14-5)

Guidance literature:

With BF₄^(1-)*C₁₀H₁₉N₄O₂S⁽¹⁺⁾; In isopropyl alcohol; at 20 ℃; for 36h; enantioselective reaction;

DOI:10.1021/ol900003e

upstream raw materials:

nitrostyrene

cyclopentanone

(2-nitroethenyl)benzene

benzaldehyde