2-[1-(1,3-Benzodioxol-5-yl)-2-nitroethyl]cyclohexanone

Base Information

• Chemical Name: 2-[1-(1,3-Benzodioxol-5-yl)-2-nitroethyl]cyclohexanone
• CAS No.: 56579-87-4
• Molecular Formula: C15H17NO5
• Molecular Weight: 291.304
• DSSTox Substance ID: DTXSID001208473
• Mol file: 56579-87-4.mol

Synonyms:2-[1-(1,3-Benzodioxol-5-yl)-2-nitroethyl]cyclohexanone;DTXSID001208473;56579-87-4

Chemical Property of 2-[1-(1,3-Benzodioxol-5-yl)-2-nitroethyl]cyclohexanone

Chemical Property:

• XLogP3: 2.3
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 3
• Exact Mass: 291.11067264
• Heavy Atom Count: 21
• Complexity: 407

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: C1CCC(=O)C(C1)C(C[N+](=O)[O-])C2=CC3=C(C=C2)OCO3

Technology Process of 2-[1-(1,3-Benzodioxol-5-yl)-2-nitroethyl]cyclohexanone

There total 5 articles about 2-[1-(1,3-Benzodioxol-5-yl)-2-nitroethyl]cyclohexanone 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:

5-((E)-2-nitroethenyl)-1,3-benzodioxole (1485-00-3,22568-48-5) + cyclohexanone (108-94-1,11119-77-0,9003-41-2,9075-99-4) → (R*)-2-((R*)-1-(benzo[d][1,3]dioxol-5-yl)-2-nitroethyl)-cyclohexan-1-one (56579-87-4) + (S)-2-((R)-1-(benzo[d][1,3]dioxol-6-yl)-2-nitroethyl)cyclohexanone

Guidance literature:

With (S)-2-(((4-(perfluorooctyl)benzyl)amino)((pyrrolidin-2-ylmethyl)amino)methylene)malononitrile; acetic acid; In neat liquid; at 20 ℃; for 48h; Overall yield = 86 %; Overall yield = 50.2 mg; stereoselective reaction;

Reference yield:

5-(2-nitrovinyl)benzo[1,3]dioxole (1485-00-3) + cyclohexanone (108-94-1,11119-77-0,9003-41-2,9075-99-4) → 2-(1-(benzo[d][1,3]dioxol-5-yl)-2-nitroethyl)cyclohexan-1-one (56579-87-4) + (S)-2-((R)-1-(benzo[d][1,3]dioxol-6-yl)-2-nitroethyl)cyclohexanone

Guidance literature:

With C₁₈H₁₇F₆N₅; acetic acid; In neat (no solvent); at 20 ℃; for 48h; Overall yield = 84 %; enantioselective reaction; Green chemistry;

DOI:10.1016/j.tetlet.2014.03.042

Reference yield:

5-(2-nitrovinyl)benzo[1,3]dioxole (1485-00-3) + cyclohexanone (108-94-1,11119-77-0,9003-41-2,9075-99-4) → (2R)-2-((1S)-1-(benzo[d][1,3]dioxol-5-yl)-2-nitroethyl)cyclohexanone + (R*)-2-((R*)-1-(benzo[d][1,3]dioxol-5-yl)-2-nitroethyl)-cyclohexan-1-one (56579-87-4) + (S)-2-((R)-1-(benzo[d][1,3]dioxol-6-yl)-2-nitroethyl)cyclohexanone

Guidance literature:

With C₁₄H₂₆N₂O; N-ethyl-N,N-diisopropylamine; at 0 ℃; for 14h; optical yield given as %ee; enantioselective reaction;

DOI:10.1016/j.tet.2010.11.093

upstream raw materials:

5-(2-nitrovinyl)benzo[1,3]dioxole

cyclohexanone

5-((E)-2-nitroethenyl)-1,3-benzodioxole