2-(((Allyloxy)carbonyl)(methyl)amino)-1-(1-(1,3-benzodioxol-5-yl)-4-oxo-2,5-cyclohexadien-1-yl)ethyl pivalate

Base Information

• Chemical Name: 2-(((Allyloxy)carbonyl)(methyl)amino)-1-(1-(1,3-benzodioxol-5-yl)-4-oxo-2,5-cyclohexadien-1-yl)ethyl pivalate
• CAS No.: 107201-38-7
• Molecular Formula: C₂₅H₂₉NO₇
• Molecular Weight: 455.508
• NSC Number: 619795
• DSSTox Substance ID: DTXSID401102916
• Mol file: 107201-38-7.mol

Synonyms:NSC619795;DTXSID401102916;NSC-619795;[2-[allyloxycarbonyl(methyl)amino]-1-[1-(1,3-benzodioxol-5-yl)-4-oxo-cyclohexa-2,5-dien-1-yl]ethyl] 2,2-dimethylpropanoate;1-[1-(1,3-Benzodioxol-5-yl)-4-oxo-2,5-cyclohexadien-1-yl]-2-[methyl[(2-propen-1-yloxy)carbonyl]amino]ethyl 2,2-dimethylpropanoate;107201-38-7;2-(((Allyloxy)carbonyl)(methyl)amino)-1-(1-(1,3-benzodioxol-5-yl)-4-oxo-2,5-cyclohexadien-1-yl)ethyl pivalate

Chemical Property of 2-(((Allyloxy)carbonyl)(methyl)amino)-1-(1-(1,3-benzodioxol-5-yl)-4-oxo-2,5-cyclohexadien-1-yl)ethyl pivalate

Chemical Property:

• XLogP3: 4.3
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 7
• Rotatable Bond Count: 10
• Exact Mass: 455.19440226
• Heavy Atom Count: 33
• Complexity: 809

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: CC(C)(C)C(=O)OC(CN(C)C(=O)OCC=C)C1(C=CC(=O)C=C1)C2=CC3=C(C=C2)OCO3

Technology Process of 2-(((Allyloxy)carbonyl)(methyl)amino)-1-(1-(1,3-benzodioxol-5-yl)-4-oxo-2,5-cyclohexadien-1-yl)ethyl pivalate

There total 5 articles about 2-(((Allyloxy)carbonyl)(methyl)amino)-1-(1-(1,3-benzodioxol-5-yl)-4-oxo-2,5-cyclohexadien-1-yl)ethyl pivalate 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:

4-<1-(pivaloyloxy)-2-<<(allyloxy)carbonyl>methylamino>ethyl>-4-<3,4-(methylenedioxy)phenyl>-2-cyclohexenone (92143-70-9,92143-71-0) → 4-<1-(pivaloyloxy)-2-<<(allyloxy)carbonyl>methylamino>ethyl>-4-<3,4-(methylenedioxy)phenyl>cyclohexadienone (107201-38-7)

Guidance literature:

With phenyltrimethylammonium tribromide; 1,8-diazabicyclo[5.4.0]undec-7-ene; Yield given. Multistep reaction; 1.) EtOAc, 25 deg C, 24 h; 2.) C₆H₆, 85 deg C, 16 h;

DOI:10.1021/ja00333a061

Reference yield:

2,2-Dimethyl-propionic acid 2-(allyloxycarbonyl-methyl-amino)-1-(1-benzo[1,3]dioxol-5-yl-5-bromo-4-oxo-cyclohex-2-enyl)-ethyl ester → 4-<1-(pivaloyloxy)-2-<<(allyloxy)carbonyl>methylamino>ethyl>-4-<3,4-(methylenedioxy)phenyl>cyclohexadienone (107201-38-7)

Guidance literature:

With 1,8-diazabicyclo[5.4.0]undec-7-ene; In benzene; Yield given; Heating;

DOI:10.1021/jo00386a013

Reference yield:

N-<(allyloxy)carbonyl>-N-methylaminoacetaldehyde (92143-84-5) → 4-<1-(pivaloyloxy)-2-<<(allyloxy)carbonyl>methylamino>ethyl>-4-<3,4-(methylenedioxy)phenyl>cyclohexadienone (107201-38-7)

Guidance literature:

Multi-step reaction with 4 steps

2: 33percent aq. CH₃COOH, pyrrolidine / methanol / 42 h / Ambient temperature

3: conc. H₂SO₄, PTAB / ethyl acetate / 20 h / Ambient temperature

4: 1,8-diazabicyclo<5.4.0>undec-7-ene / benzene / Heating

With pyrrolidine; PTAB; sulfuric acid; acetic acid; 1,8-diazabicyclo[5.4.0]undec-7-ene; In methanol; ethyl acetate; benzene;

DOI:10.1021/jo00386a013

upstream raw materials:

4-<1-(pivaloyloxy)-2-<<(allyloxy)carbonyl>methylamino>ethyl>-4-<3,4-(methylenedioxy)phenyl>-2-cyclohexenone

N-<(allyloxy)carbonyl>-N-methylaminoacetaldehyde

N-<(allyloxy)carbonyl>-N-methylaminoacetaldehyde diethyl acetal

2,2-Dimethyl-propionic acid 1-[(allyloxycarbonyl-methyl-amino)-methyl]-2-benzo[1,3]dioxol-5-yl-2-formyl-5-oxo-hexyl ester