Δ7-mesembrenone

Base Information

• Chemical Name: Δ7-mesembrenone
• CAS No.: 35714-44-4
• Molecular Formula: C₁₇H₂₁NO₃
• Molecular Weight: 287.359
• Mol file: 35714-44-4.mol

Synonyms:Δ7-mesembrenone

Chemical Property of Δ7-mesembrenone

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of Δ7-mesembrenone

There total 11 articles about Δ7-mesembrenone 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: 85.0%

(S)-4-(3,4-Dimethoxy-phenyl)-4-(2-hydroxy-ethyl)-3-methylamino-cyclohex-2-enone (81369-83-7) → Δ7-mesembrenone (35714-44-4)

Guidance literature:

With triphenylphosphine; diethylazodicarboxylate; In tetrahydrofuran; for 0.166667h;

DOI:10.1016/S0040-4039(01)93019-9

Reference yield: 41.0%

(S)-3a-(3,4-Dimethoxy-phenyl)-3,3a,4,5-tetrahydro-2H-benzofuran-6-one (81369-82-6) + methylamine (74-89-5) → Δ7-mesembrenone (35714-44-4) + (S)-4-(3,4-Dimethoxy-phenyl)-4-(2-hydroxy-ethyl)-3-methylamino-cyclohex-2-enone (81369-83-7)

Guidance literature:

In water; at 180 ℃; for 1h; sealed tube;

DOI:10.1016/S0040-4039(01)93019-9

Reference yield:

3,4-dimethoxyphenylacetonitrile (93-17-4) → Δ7-mesembrenone (35714-44-4)

Guidance literature:

Multi-step reaction with 9 steps

1: LDA / tetrahydrofuran / -78 - 20 °C

2: 1.) 10percent KOH-EtOH, 2.) 10percent HCl-EtOH / 1.) reflux over night, 2.) room temperature

3: 1.) lithium diisopropylamide / tetrahydrofuran / from -78 degC up to room temperature

4: c.HCl / ethanol / 3 h / Heating

6: 1.) NaBH₄, 2.) acid

7: 73 percent / O₂ / PdCl₂-CuCl / dimethylformamide / 168 h

8: 66 percent / tetrahydrofuran / Heating

9: 7 percent / H₂O / 1 h / 180 °C / sealed tube

With hydrogenchloride; potassium hydroxide; sodium tetrahydroborate; oxygen; lithium diisopropyl amide; copper(l) chloride; palladium dichloride; In tetrahydrofuran; ethanol; water; N,N-dimethyl-formamide;

DOI:10.1016/S0040-4039(01)93019-9

upstream raw materials:

(S)-4-(3,4-Dimethoxy-phenyl)-4-(2-hydroxy-ethyl)-3-methylamino-cyclohex-2-enone

(S)-3a-(3,4-Dimethoxy-phenyl)-3,3a,4,5-tetrahydro-2H-benzofuran-6-one

methylamine

3,4-dimethoxyphenylacetonitrile

Downstream raw materials:

(-)-mesembrine

Refernces