Cyclohexanone, 2-[(R)-hydroxy(2-nitrophenyl)methyl]-, (2S)-

Base Information

• Chemical Name: Cyclohexanone, 2-[(R)-hydroxy(2-nitrophenyl)methyl]-, (2S)-
• CAS No.: 877032-08-1
• Molecular Formula: C13H15NO4
• Molecular Weight: 249.266
• DSSTox Substance ID: DTXSID50468095
• Nikkaji Number: J1.894.924E
• Wikidata: Q82295196
• Mol file: 877032-08-1.mol

Synonyms:877032-08-1;Cyclohexanone, 2-[(R)-hydroxy(2-nitrophenyl)methyl]-, (2S)-;SCHEMBL13254535;DTXSID50468095

Chemical Property of Cyclohexanone, 2-[(R)-hydroxy(2-nitrophenyl)methyl]-, (2S)-

Chemical Property:

• XLogP3: 2.2
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 2
• Exact Mass: 249.10010796
• Heavy Atom Count: 18
• Complexity: 325

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1CCC(=O)C(C1)C(C2=CC=CC=C2[N+](=O)[O-])O
• Isomeric SMILES: C1CCC(=O)[C@@H](C1)[C@H](C2=CC=CC=C2[N+](=O)[O-])O

Technology Process of Cyclohexanone, 2-[(R)-hydroxy(2-nitrophenyl)methyl]-, (2S)-

There total 29 articles about Cyclohexanone, 2-[(R)-hydroxy(2-nitrophenyl)methyl]-, (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%

cyclohexanone (108-94-1,11119-77-0,9003-41-2,9075-99-4) + 2-nitro-benzaldehyde (552-89-6) → (S)-2-[(R)-hydroxy(2-nitrophenyl)methyl]cyclohexan-1-one (877032-08-1)

Guidance literature:

With C₁₇H₂₇N₃O₆SSi; In water; at 20 ℃; for 48h; optical yield given as %ee; enantioselective reaction;

DOI:10.1016/j.tetasy.2009.09.019

Reference yield: 95.0%

cyclohexanone (108-94-1,11119-77-0,9003-41-2,9075-99-4) + 2-nitro-benzaldehyde (552-89-6) → (2R)-2-((S)-hydroxy-(2-nitrophenyl)methyl)cyclohexan-1-one + 2-(hydroxy-(2-nitrophenyl)methyl)cyclohexan-1-one (29202-79-7) + (S)-2-[(R)-hydroxy(2-nitrophenyl)methyl]cyclohexan-1-one (877032-08-1)

Guidance literature:

cyclohexanone; With formic acid; C₁₉H₁₉N₅O; benzoic acid; In water; at 20 ℃; for 0.5h; Inert atmosphere; Green chemistry;

2-nitro-benzaldehyde; In water; at 20 ℃; for 48h; Overall yield = 94 %; stereoselective reaction; Inert atmosphere; Green chemistry;

DOI:10.1002/adsc.201200856

Reference yield: 90.0%

2-Nitrobenzyl alcohol (612-25-9) + cyclohexanol (108-93-0) → (S)-2-[(R)-hydroxy(2-nitrophenyl)methyl]cyclohexan-1-one (877032-08-1)

Guidance literature:

2-Nitrobenzyl alcohol; cyclohexanol; With TEMPOL; laccase from Trametes versicolor; lithium triethylene glycol dimethyl ether bis(trifluoromethanesulfonyl)imide; In aq. buffer; at 30 ℃; pH=5; Inert atmosphere; Green chemistry; Enzymatic reaction;

With C₅H₈NO₂^(1-)*C₈H₁₈LiO₄⁽¹⁺⁾; In aq. buffer; at 30 ℃; pH=5; Reagent/catalyst; stereoselective reaction; Enzymatic reaction; Green chemistry;

DOI:10.1039/d1gc02831f

upstream raw materials:

cyclohexanone

2-nitro-benzaldehyde

cyclohexanecarbaldehyde

acetone