6-[1-Amino-3-(3,4,5-trimethoxy-phenyl)-propyl]-2-methoxy-cyclohepta-2,4,6-trienone

Base Information

• Chemical Name: 6-[1-Amino-3-(3,4,5-trimethoxy-phenyl)-propyl]-2-methoxy-cyclohepta-2,4,6-trienone
• CAS No.: 125731-01-3
• Molecular Formula: C₂₀H₂₅NO₅
• Molecular Weight: 359.422
• Mol file: 125731-01-3.mol

Synonyms:6-[1-Amino-3-(3,4,5-trimethoxy-phenyl)-propyl]-2-methoxy-cyclohepta-2,4,6-trienone

Chemical Property of 6-[1-Amino-3-(3,4,5-trimethoxy-phenyl)-propyl]-2-methoxy-cyclohepta-2,4,6-trienone

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 6-[1-Amino-3-(3,4,5-trimethoxy-phenyl)-propyl]-2-methoxy-cyclohepta-2,4,6-trienone

There total 24 articles about 6-[1-Amino-3-(3,4,5-trimethoxy-phenyl)-propyl]-2-methoxy-cyclohepta-2,4,6-trienone 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:

(RS)-6-<1'-azido-3'-(3'',4'',5''-trimethoxyphenyl)propyl>-2-methoxycyclohepta-2,4,6-trienone (125731-00-2) → 6-[1-Amino-3-(3,4,5-trimethoxy-phenyl)-propyl]-2-methoxy-cyclohepta-2,4,6-trienone (125731-01-3)

Guidance literature:

With hydrogen; palladium on activated charcoal; In methanol; for 2.5h; under 760 Torr;

Reference yield:

3,4,5-trimethoxycinnamaldehyde (71277-13-9,34346-90-2,71277-12-8) → 6-[1-Amino-3-(3,4,5-trimethoxy-phenyl)-propyl]-2-methoxy-cyclohepta-2,4,6-trienone (125731-01-3)

Guidance literature:

Multi-step reaction with 10 steps

1: 77 percent / tetrahydrofuran / 2 h / -100 °C

2: hydrogen / 10 percent Pd on C / ethanol / 760 Torr

3: 4-N,N-dimethylaminopyridine, pyridine / 16 h / 18 °C

4: 90 percent / 0.5 M HCl / tetrahydrofuran; H₂O / 30 h / 18 °C

5: 1.) (CF₃CO)2O, Me₂SO; 2.)NEt₃ / 1.) CH₂Cl₂, -60 deg C, 1.5 h; 2.) -60 deg C, 1.5 h

6: 75 percent / K₂CO₃ / acetone / 5 h / 18 °C

7: 85 percent / 1,8-diazabicyclo<5.4.0>undec-7-ene / benzene / 1 h / 18 °C

8: 1.) K₂CO₃; 2.) NEt₃ / 1.) MeOH, 18 deg C, 2 h; 2.) CH₂Cl₂, 0 - 5 deg C, 0.5 h

9: 86 percent / sodium azide, 18-crown-6 / tetrahydrofuran / 16 h / 18 °C

10: hydrogen / 10 percent Pd on C / methanol / 760 Torr

With pyridine; hydrogenchloride; dmap; sodium azide; 18-crown-6 ether; hydrogen; potassium carbonate; dimethyl sulfoxide; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; trifluoroacetic anhydride; palladium on activated charcoal; In tetrahydrofuran; methanol; ethanol; water; acetone; benzene;

DOI:10.1039/c39890000865

Reference yield:

(E)-3-(3,4,5-trimethoxyphenyl)prop-2-en-1-ol (1504-56-9) → 6-[1-Amino-3-(3,4,5-trimethoxy-phenyl)-propyl]-2-methoxy-cyclohepta-2,4,6-trienone (125731-01-3)

Guidance literature:

Multi-step reaction with 12 steps

1: 75 percent / barium manganate / CH₂Cl₂ / 4 h / Ambient temperature

2: 77 percent / (3aα,5aβ,6aβ,6bα)-6,6-dibromo-2-dimethylhexahydro-3aH-cyclopropa<1,3>benzodioxole / tetrahydrofuran; hexane / 3 h / -100 °C

3: 96 percent / H₂ / 10percent palladium on charcoal / methanol / 1.5 h / 760 Torr

4: DMAP / pyridine / Ambient temperature

5: 90 percent / aq.HCl / tetrahydrofuran / 25 h / Ambient temperature

6: 1.) TFFA, DMSO, 2.) Et₃N / 1.) CH₂Cl₂, -60 deg C, 1.5 h, 2.) -60 deg C, 1.5 h

7: 75 percent / K₂CO₃ / acetone / 5 h / Ambient temperature

8: 85 percent / DBU / benzene / 1 h / Ambient temperature

9: 79 percent / K₂CO₃ / methanol / 2.5 h / Ambient temperature

10: Et₃N / CH₂Cl₂ / 0.33 h / 0 - 5 °C

11: 86 percent / NaN₃, 18-crown-6 / tetrahydrofuran / 16 h / Ambient temperature

12: H₂ / palladium on charcoal / methanol / 2.5 h / 760 Torr

With hydrogenchloride; dmap; sodium azide; barium manganate; 18-crown-6 ether; (3aα,5aβ,6aβ,6bα)-6,6-dibromo-2-dimethylhexahydro-3aH-cyclopropa<1,3>benzodioxole; hydrogen; potassium carbonate; dimethyl sulfoxide; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; palladium on activated charcoal; In tetrahydrofuran; pyridine; methanol; hexane; dichloromethane; acetone; benzene;

upstream raw materials:

(RS)-6-<1'-azido-3'-(3'',4'',5''-trimethoxyphenyl)propyl>-2-methoxycyclohepta-2,4,6-trienone

3,4,5-trimethoxycinnamaldehyde

(RS)-6-<1'-mesyloxy-3'-(3'',4'',5''-trimethoxyphenyl)propyl>-2-methoxycyclohepta-2,4,6-trienone

(RS)-6-<1'-benzoyloxy-3'-(3'',4'',5''-trimethoxyphenyl)propyl>-2-methoxycyclohepta-2,4,6-trienone

Refernces

• 1、 Banwell, Martin G.,Gravatt, G. Lance,Buckleton, John S.,Clark, George R.,Ricard, C. E. F.. "The Development of a Fully Regiocontrolled Synthesis of (+/-)-12a,12b-Monosecocolchicine using a Synthetic Equivalent for the 7-Methoxy-3-troponyl Anion". . p. 865 - 867. Retrieved 2007/10/02.