(4,5-dimethoxy-10-methylene-12-aza-tricyclo[7.2.1.0^2,7]dodeca-2⁽⁷⁾,3,5-trien-12-yl)-phenyl-methanone

Base Information

• Chemical Name: (4,5-dimethoxy-10-methylene-12-aza-tricyclo[7.2.1.0^2,7]dodeca-2⁽⁷⁾,3,5-trien-12-yl)-phenyl-methanone
• CAS No.: 263570-40-7
• Molecular Formula: C₂₁H₂₁NO₃
• Molecular Weight: 335.403

Synonyms:(4,5-dimethoxy-10-methylene-12-aza-tricyclo[7.2.1.0^2,7]dodeca-2⁽⁷⁾,3,5-trien-12-yl)-phenyl-methanone

Chemical Property of (4,5-dimethoxy-10-methylene-12-aza-tricyclo[7.2.1.0^2,7]dodeca-2⁽⁷⁾,3,5-trien-12-yl)-phenyl-methanone

Chemical Property:

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Technology Process of (4,5-dimethoxy-10-methylene-12-aza-tricyclo[7.2.1.0^2,7]dodeca-2⁽⁷⁾,3,5-trien-12-yl)-phenyl-methanone

There total 10 articles about (4,5-dimethoxy-10-methylene-12-aza-tricyclo[7.2.1.0^2,7]dodeca-2⁽⁷⁾,3,5-trien-12-yl)-phenyl-methanone 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: 78.0%

{4,5-Dimethoxy-10-[1-trimethylsilanyl-meth-(E)-ylidene]-12-aza-tricyclo[7.2.1.02,7]dodeca-2(7),3,5-trien-12-yl}-phenyl-methanone (263570-38-3) → (4,5-dimethoxy-10-methylene-12-aza-tricyclo[7.2.1.02,7]dodeca-2(7),3,5-trien-12-yl)-phenyl-methanone (263570-40-7)

Guidance literature:

With trifluoroacetic acid; In dichloromethane; at 20 ℃; for 2h;

DOI:10.3987/COM-99-S91

Reference yield:

2-Iodobenzoyl chloride (609-67-6) → (4,5-dimethoxy-10-methylene-12-aza-tricyclo[7.2.1.02,7]dodeca-2(7),3,5-trien-12-yl)-phenyl-methanone (263570-40-7)

Guidance literature:

Multi-step reaction with 3 steps

1: Et₃N; DMAP / benzene / 24 h / 20 °C

2: 95 percent / Bu₃SnH; AIBN / toluene / 2 h / Heating

3: 78 percent / TFA / CH₂Cl₂ / 2 h / 20 °C

With dmap; 2,2'-azobis(isobutyronitrile); tri-n-butyl-tin hydride; triethylamine; trifluoroacetic acid; In dichloromethane; toluene; benzene; 1: Acylation / 2: Reduction / 3: Substitution;

DOI:10.3987/COM-99-S91

Reference yield:

methyl 6,7-dimethoxy-1,2,3,4-tetrahydroisoquinoline-1-acetate (263570-28-1,417725-91-8) → (4,5-dimethoxy-10-methylene-12-aza-tricyclo[7.2.1.02,7]dodeca-2(7),3,5-trien-12-yl)-phenyl-methanone (263570-40-7)

Guidance literature:

Multi-step reaction with 9 steps

1.1: Et₃N; DMAP / ethyl acetate / 24 h / 20 °C

2.1: LiAlH₄ / tetrahydrofuran / 1 h / 20 °C

3.1: pyridine-SO₃/DMSO; Et₃N / CH₂Cl₂ / 2 h / 0 °C

4.1: 62 percent / PPh₃; t-BuOK / toluene / 1 h / -20 °C

5.1: n-BuLi; TMEDA / tetrahydrofuran / 1 h / -78 °C

5.2: 75 percent / tetrahydrofuran / 24 h / 20 °C

6.1: TMS-I / acetonitrile / 0.25 h / 20 °C

7.1: Et₃N; DMAP / benzene / 24 h / 20 °C

8.1: 95 percent / Bu₃SnH; AIBN / toluene / 2 h / Heating

9.1: 78 percent / TFA / CH₂Cl₂ / 2 h / 20 °C

With dmap; lithium aluminium tetrahydride; n-butyllithium; 2,2'-azobis(isobutyronitrile); trimethylsilyl iodide; N,N,N,N,-tetramethylethylenediamine; potassium tert-butylate; tri-n-butyl-tin hydride; sulfur trioxide pyridine complex; dimethyl sulfoxide; triethylamine; triphenylphosphine; trifluoroacetic acid; In tetrahydrofuran; dichloromethane; ethyl acetate; toluene; acetonitrile; benzene; 1.1: Acylation / 2.1: Reduction / 3.1: Oxidation / 4.1: Condensation / 5.1: Elimination / 5.2: Substitution / 6.1: Substitution / 7.1: Acylation / 8.1: Reduction / 9.1: Substitution;

DOI:10.3987/COM-99-S91

upstream raw materials:

{4,5-Dimethoxy-10-[1-trimethylsilanyl-meth-(E)-ylidene]-12-aza-tricyclo[7.2.1.0^2,7]dodeca-2⁽⁷⁾,3,5-trien-12-yl}-phenyl-methanone

2-Iodobenzoyl chloride

methyl 6,7-dimethoxy-1,2,3,4-tetrahydroisoquinoline-1-acetate

6,7-dimethoxy-1-(3-trimethylsilylprop-2-ynyl)-1,2,3,4-tetrahydroisoquinoline

Downstream raw materials:

7,8-Dimethoxy-10-benzoyl-4,5-dihydro-1H-1,4-epimino-benzocyclohepten-3(2H)-on

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