rac-3-methyl-2-(2-methylnaphthalen-1-yl)-4-phenyl-5,6-dihydrobenzo[1,2-h]phosphinoline

Base Information

• Chemical Name: rac-3-methyl-2-(2-methylnaphthalen-1-yl)-4-phenyl-5,6-dihydrobenzo[1,2-h]phosphinoline
• CAS No.: 1448591-90-9
• Molecular Formula: C₃₁H₂₅P
• Molecular Weight: 428.513

Synonyms:

Chemical Property of rac-3-methyl-2-(2-methylnaphthalen-1-yl)-4-phenyl-5,6-dihydrobenzo[1,2-h]phosphinoline

Chemical Property:

Purity/Quality:

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Technology Process of rac-3-methyl-2-(2-methylnaphthalen-1-yl)-4-phenyl-5,6-dihydrobenzo[1,2-h]phosphinoline

There total 7 articles about rac-3-methyl-2-(2-methylnaphthalen-1-yl)-4-phenyl-5,6-dihydrobenzo[1,2-h]phosphinoline 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: 13.0%

rac-3-methyl-2-(2-methylnaphthalen-1-yl)-4-phenyl-5,6-dihydrobenzo[1,2-h]chromenium tetrafluoroborate → rac-3-methyl-2-(2-methylnaphthalen-1-yl)-4-phenyl-5,6-dihydrobenzo[1,2-h]phosphinoline (1448591-90-9,1448617-14-8,1448617-15-9)

Guidance literature:

With Tris(trimethylsilyl)phosphane; In 1,2-dimethoxyethane; at 90 ℃; for 17h; Inert atmosphere; Schlenk technique;

DOI:10.1002/chem.201300557

Reference yield:

benzaldehyde (100-52-7) → rac-3-methyl-2-(2-methylnaphthalen-1-yl)-4-phenyl-5,6-dihydrobenzo[1,2-h]phosphinoline (1448591-90-9,1448617-14-8,1448617-15-9)

Guidance literature:

Multi-step reaction with 4 steps

1.1: potassium hydroxide / ethanol / 24 h / Inert atmosphere; Schlenk technique

2.1: tetra-(n-butyl)ammonium iodide; potassium hydroxide / water; dimethyl sulfoxide / 0.75 h / Inert atmosphere; Schlenk technique

2.2: 4.5 h / Inert atmosphere; Schlenk technique

3.1: 1,3-diphenyl-propen-3-one / 1,2-dichloro-ethane / 70 °C / Inert atmosphere; Schlenk technique

4.1: Tris(trimethylsilyl)phosphane / 1,2-dimethoxyethane / 17 h / 90 °C / Inert atmosphere; Schlenk technique

With Tris(trimethylsilyl)phosphane; tetra-(n-butyl)ammonium iodide; 1,3-diphenyl-propen-3-one; potassium hydroxide; In 1,2-dimethoxyethane; ethanol; water; dimethyl sulfoxide; 1,2-dichloro-ethane;

DOI:10.1002/chem.201300557

Reference yield:

1-bromo-2-methylnaphtalene (2586-62-1) → rac-3-methyl-2-(2-methylnaphthalen-1-yl)-4-phenyl-5,6-dihydrobenzo[1,2-h]phosphinoline (1448591-90-9,1448617-14-8,1448617-15-9)

Guidance literature:

Multi-step reaction with 5 steps

1.1: magnesium / tetrahydrofuran / 3.5 h / 20 °C / Inert atmosphere; Reflux; Schlenk technique

1.2: 2 h / 20 °C / Inert atmosphere; Cooling with ice; Schlenk technique

2.1: chromium(VI) oxide; sulfuric acid / water; acetone / 1.5 h / Inert atmosphere; Schlenk technique; Cooling with ice

3.1: tetra-(n-butyl)ammonium iodide; potassium hydroxide / water; dimethyl sulfoxide / 0.75 h / Inert atmosphere; Schlenk technique

3.2: 4.5 h / Inert atmosphere; Schlenk technique

4.1: 1,3-diphenyl-propen-3-one / 1,2-dichloro-ethane / 70 °C / Inert atmosphere; Schlenk technique

5.1: Tris(trimethylsilyl)phosphane / 1,2-dimethoxyethane / 17 h / 90 °C / Inert atmosphere; Schlenk technique

With chromium(VI) oxide; Tris(trimethylsilyl)phosphane; sulfuric acid; tetra-(n-butyl)ammonium iodide; magnesium; 1,3-diphenyl-propen-3-one; potassium hydroxide; In tetrahydrofuran; 1,2-dimethoxyethane; water; dimethyl sulfoxide; 1,2-dichloro-ethane; acetone;

DOI:10.1002/chem.201300557

upstream raw materials:

benzaldehyde

2-[2-methyl-3-(2-methylnaphthalen-1-yl)-3-oxo-1-phenylpropyl]-3,4-dihydronaphthalen-1-one

1-(2-methylnaphthalen-1-yl)propan-1-ol

1-bromo-2-methylnaphtalene

Downstream raw materials:

C₄₁H₃₉ClIrP*CH₂Cl₂

C₃₁H₂₅AuClP

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