2-allyl-2-nitrocyclohexanone

Base Information

• Chemical Name: 2-allyl-2-nitrocyclohexanone
• CAS No.: 100820-08-4
• Molecular Formula: C₉H₁₃NO₃
• Molecular Weight: 183.207
• Mol file: 100820-08-4.mol

Synonyms:2-allyl-2-nitrocyclohexanone

Chemical Property of 2-allyl-2-nitrocyclohexanone

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
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MSDS Files:

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Technology Process of 2-allyl-2-nitrocyclohexanone

There total 1 articles about 2-allyl-2-nitrocyclohexanone 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: 90.0%

allyl ethyl carbonate (1469-70-1) + 2-nitrocyclohexanone (4883-67-4) → 2-allyl-2-nitrocyclohexanone (100820-08-4)

Guidance literature:

tetrakis(triphenylphosphine) palladium⁽⁰⁾; In tetrahydrofuran; for 0.166667h; Ambient temperature;

Reference yield: 62.0%

2-allyl-2-nitrocyclohexanone (100820-08-4) + allyl-trimethyl-silane (762-72-1) → 2-nitro-2-[4-(trimethylsilyl)but-2-enyl]cyclohexanone

Guidance literature:

With titanium(IV) isopropylate; tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride; In dichloromethane; at 60 ℃; for 0.666667h; microwave irradiation;

DOI:10.1055/s-2007-983825

Reference yield:

2-allyl-2-nitrocyclohexanone (100820-08-4) → (2R,5'R)-N-(1'-methyl-1'-azaspiro[4,5]dec-6-yl)-2-methoxy-2-phenylacetamide

Guidance literature:

Multi-step reaction with 11 steps

1: 36 percent / p-TsOH*H₂O / benzene / 168 h / Heating

2: 1.) 9-BBN, 2.) aq. NaOH, aq. H₂O₂ / 1.) THF, 0 deg C, 3.5 h; room temperature, 1 h, 2.) 0 deg C

3: 961 mg / PDC / 36 h / Ambient temperature

4: tetrahydrofuran; diethyl ether

5: 60 percent / H₂ / Raney Ni (W₇) / methanol / 96 h / 30 °C / 76000 Torr

6: 84 percent / LiAlH₄ / tetrahydrofuran / 40 h / Heating

7: 90 percent / Et₃N / CH₂Cl₂ / 1 h / Ambient temperature

8: 70 percent / aq. HCl / CH₂Cl₂ / 19 h / Ambient temperature

9: 87 percent / pyridine / 23 h / Ambient temperature

10: 93 percent / LiAlH₄ / tetrahydrofuran / 7 h / Ambient temperature

11: 5.5 mg / DCC / CH₂Cl₂ / 23 h / Ambient temperature

With pyridine; hydrogenchloride; sodium hydroxide; lithium aluminium tetrahydride; dipyridinium dichromate; 9-borabicyclo[3.3.1]nonane dimer; hydrogen; dihydrogen peroxide; toluene-4-sulfonic acid; triethylamine; dicyclohexyl-carbodiimide; Raney Ni (W₇); In tetrahydrofuran; methanol; diethyl ether; dichloromethane; benzene;

DOI:10.1021/jo961343b

upstream raw materials:

allyl ethyl carbonate

2-nitrocyclohexanone

Refernces