5-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-3-oxo-2-(triphenyl-λ⁵-phosphanylidene)-octanenitrile

Base Information

• Chemical Name: 5-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-3-oxo-2-(triphenyl-λ⁵-phosphanylidene)-octanenitrile
• CAS No.: 488863-83-8
• Molecular Formula: C₃₄H₂₉N₂O₃P
• Molecular Weight: 544.59
• Mol file: 488863-83-8.mol

Synonyms:5-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-3-oxo-2-(triphenyl-λ⁵-phosphanylidene)-octanenitrile

Chemical Property of 5-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-3-oxo-2-(triphenyl-λ⁵-phosphanylidene)-octanenitrile

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 5-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-3-oxo-2-(triphenyl-λ⁵-phosphanylidene)-octanenitrile

There total 5 articles about 5-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-3-oxo-2-(triphenyl-λ⁵-phosphanylidene)-octanenitrile 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: 79.0%

3-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-hexanoic acid (488863-82-7) + cyanomethylene triphenylphosphorane (16640-68-9) → 5-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-3-oxo-2-(triphenyl-λ5-phosphanylidene)-octanenitrile (488863-83-8)

Guidance literature:

With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In dichloromethane; at 20 ℃;

DOI:10.1021/ja028357l

Reference yield:

phthalic anhydride (85-44-9) → 5-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-3-oxo-2-(triphenyl-λ5-phosphanylidene)-octanenitrile (488863-83-8)

Guidance literature:

Multi-step reaction with 4 steps

1.1: 98 percent / Et₃N / toluene / Heating

2.1: Et₃N; ClCOOEt / tetrahydrofuran / 0.25 h / 20 °C

2.2: 82 percent / tetrahydrofuran; diethyl ether / 0 °C

3.1: 81 percent / Et₃N; PhCOOAg / tetrahydrofuran; H₂O / -25 - 0 °C

4.1: 79 percent / 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride; 4-dimethylaminopyridine / CH₂Cl₂ / 20 °C

With dmap; silver benzoate; chloroformic acid ethyl ester; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; In tetrahydrofuran; dichloromethane; water; toluene;

DOI:10.1021/ja028357l

Reference yield:

2-aminopentanoic acid (760-78-1,498-18-0) → 5-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-3-oxo-2-(triphenyl-λ5-phosphanylidene)-octanenitrile (488863-83-8)

Guidance literature:

Multi-step reaction with 4 steps

1.1: 98 percent / Et₃N / toluene / Heating

2.1: Et₃N; ClCOOEt / tetrahydrofuran / 0.25 h / 20 °C

2.2: 82 percent / tetrahydrofuran; diethyl ether / 0 °C

3.1: 81 percent / Et₃N; PhCOOAg / tetrahydrofuran; H₂O / -25 - 0 °C

4.1: 79 percent / 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride; 4-dimethylaminopyridine / CH₂Cl₂ / 20 °C

With dmap; silver benzoate; chloroformic acid ethyl ester; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; In tetrahydrofuran; dichloromethane; water; toluene;

DOI:10.1021/ja028357l

upstream raw materials:

3-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-hexanoic acid

cyanomethylene triphenylphosphorane

phthalic anhydride

2-aminopentanoic acid

Refernces