(S)-5-benzyl-4b,5,12,13-tetrahydro-6H-isoquinolino[2,1-a]quinazolin-6-one

Base Information

Chemical Name:(S)-5-benzyl-4b,5,12,13-tetrahydro-6H-isoquinolino[2,1-a]quinazolin-6-one
CAS No.:1454933-36-8
Molecular Formula:C₂₃H₂₀N₂O
Molecular Weight:340.425
Hs Code.:

Synonyms:(S)-5-benzyl-4b,5,12,13-tetrahydro-6H-isoquinolino[2,1-a]quinazolin-6-one

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Chemical Property of (S)-5-benzyl-4b,5,12,13-tetrahydro-6H-isoquinolino[2,1-a]quinazolin-6-one

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Technology Process of (S)-5-benzyl-4b,5,12,13-tetrahydro-6H-isoquinolino[2,1-a]quinazolin-6-one

There total 4 articles about (S)-5-benzyl-4b,5,12,13-tetrahydro-6H-isoquinolino[2,1-a]quinazolin-6-one 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:

: 1454933-17-5
N-benzyl-2-(3,4-dihydroisoquinolin-2(1H)-yl)benzamide

: 1454933-36-8
(S)-5-benzyl-4b,5,12,13-tetrahydro-6H-isoquinolino[2,1-a]quinazolin-6-one

: 1454933-35-7
(R)-5-benzyl-4b,5,12,13-tetrahydro-6H-isoquinolino[2,1-a]quinazolin-6-one

Guidance literature:: With (4R,11bS)-4-hydroxy-2,6-bis(adamantan-1-yl-1H-1,2,3-triazol-4-yl)-9,14-dioctyldinaphtho[2,1-d:1',2'-f][1,3,2]dioxaphosphepine 4-oxide; sodium phosphate; 4-acetylamino-2,2,6,6-tetramethylpiperidine-1-oxoammonium tetrafluoroborate; In para-xylene; at 20 ℃; for 48h; Reagent/catalyst; Solvent; Overall yield = 83 %; Overall yield = 28 mg; Optical yield = 84 %ee; enantioselective reaction;
DOI:10.1021/ja407410b

Reference yield:

: 394-47-8
2-fluorobenzonitrile

: 1454933-36-8
(S)-5-benzyl-4b,5,12,13-tetrahydro-6H-isoquinolino[2,1-a]quinazolin-6-one

: 1454933-35-7
(R)-5-benzyl-4b,5,12,13-tetrahydro-6H-isoquinolino[2,1-a]quinazolin-6-one

Guidance literature:: Multi-step reaction with 4 steps

1: potassium carbonate / N,N-dimethyl-formamide / 150 °C

2: potassium hydroxide / water; 2-ethoxy-ethanol / 2 h / 150 °C

3: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; benzotriazol-1-ol; triethylamine / tetrahydrofuran / 20 °C

4: (4R,11bS)-4-hydroxy-2,6-bis(adamantan-1-yl-1H-1,2,3-triazol-4-yl)-9,14-dioctyldinaphtho[2,1-d:1',2'-f][1,3,2]dioxaphosphepine 4-oxide; sodium phosphate; 4-acetylamino-2,2,6,6-tetramethylpiperidine-1-oxoammonium tetrafluoroborate / para-xylene / 48 h / 20 °C

With (4R,11bS)-4-hydroxy-2,6-bis(adamantan-1-yl-1H-1,2,3-triazol-4-yl)-9,14-dioctyldinaphtho[2,1-d:1',2'-f][1,3,2]dioxaphosphepine 4-oxide; potassium carbonate; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; sodium phosphate; potassium hydroxide; 4-acetylamino-2,2,6,6-tetramethylpiperidine-1-oxoammonium tetrafluoroborate; In tetrahydrofuran; 2-ethoxy-ethanol; para-xylene; water; N,N-dimethyl-formamide;
DOI:10.1021/ja407410b

Reference yield:

: 1021244-03-0
2-(3,4-dihydro-(1H)-isoquinolin-2-yl)benzoic acid

: 1454933-36-8
(S)-5-benzyl-4b,5,12,13-tetrahydro-6H-isoquinolino[2,1-a]quinazolin-6-one

: 1454933-35-7
(R)-5-benzyl-4b,5,12,13-tetrahydro-6H-isoquinolino[2,1-a]quinazolin-6-one

Guidance literature:: Multi-step reaction with 2 steps

1: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; benzotriazol-1-ol; triethylamine / tetrahydrofuran / 20 °C

2: (4R,11bS)-4-hydroxy-2,6-bis(adamantan-1-yl-1H-1,2,3-triazol-4-yl)-9,14-dioctyldinaphtho[2,1-d:1',2'-f][1,3,2]dioxaphosphepine 4-oxide; sodium phosphate; 4-acetylamino-2,2,6,6-tetramethylpiperidine-1-oxoammonium tetrafluoroborate / para-xylene / 48 h / 20 °C

With (4R,11bS)-4-hydroxy-2,6-bis(adamantan-1-yl-1H-1,2,3-triazol-4-yl)-9,14-dioctyldinaphtho[2,1-d:1',2'-f][1,3,2]dioxaphosphepine 4-oxide; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; sodium phosphate; 4-acetylamino-2,2,6,6-tetramethylpiperidine-1-oxoammonium tetrafluoroborate; In tetrahydrofuran; para-xylene;
DOI:10.1021/ja407410b