Acetic acid 4,5,8-triacetoxy-2-[4-(2-nitro-phenylselanyl)-butyl]-naphthalen-1-yl ester

Base Information

• Chemical Name: Acetic acid 4,5,8-triacetoxy-2-[4-(2-nitro-phenylselanyl)-butyl]-naphthalen-1-yl ester
• CAS No.: 155500-22-4
• Molecular Formula: C₂₈H₂₇NO₁₀Se
• Molecular Weight: 616.483
• Mol file: 155500-22-4.mol

Synonyms:

Chemical Property of Acetic acid 4,5,8-triacetoxy-2-[4-(2-nitro-phenylselanyl)-butyl]-naphthalen-1-yl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of Acetic acid 4,5,8-triacetoxy-2-[4-(2-nitro-phenylselanyl)-butyl]-naphthalen-1-yl ester

There total 8 articles about Acetic acid 4,5,8-triacetoxy-2-[4-(2-nitro-phenylselanyl)-butyl]-naphthalen-1-yl ester 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: 66.0%

ortho-nitrophenyl selenocyanate (51694-22-5) + 2-(4'-hydroxybutyl)-1,4,5,8-tetraacetoxynapthalene (155499-85-7) → Acetic acid 4,5,8-triacetoxy-2-[4-(2-nitro-phenylselanyl)-butyl]-naphthalen-1-yl ester (155500-22-4)

Guidance literature:

With tributylphosphine; In tetrahydrofuran; for 1h; Irradiation;

DOI:10.1248/cpb.41.1549

Reference yield:

2-(4-Hydroxy-5,8-dioxo-5,8-dihydro-naphthalen-1-yloxy)-but-3-enoic acid tert-butyl ester → Acetic acid 4,5,8-triacetoxy-2-[4-(2-nitro-phenylselanyl)-butyl]-naphthalen-1-yl ester (155500-22-4)

Guidance literature:

Multi-step reaction with 8 steps

1: aq. Na₂S₂O₄ / diethyl ether / 25 °C

2: 100 percent / H₂ / 10percent Pd/C / ethyl acetate; ethanol / 8 h / Ambient temperature

3: 83 percent / 1.) TMSCl, NaBr, 2.) DMSO / acetonitrile / 2 h / Ambient temperature

4: 88 percent / pyridine, DMAP / CH₂Cl₂ / 4 h / Ambient temperature

5: 1.) aq. Na₂S₂O₄, 2.) pyridine, DMAP / 1.) ether, 2.) CH₂Cl_2. RT

6: 100 percent / CF₃COOH / CH₂Cl₂ / 12 h / 0 °C

7: 69 percent / BH₃ / tetrahydrofuran / 6 h / 0 °C

8: 66 percent / n-Bu₃P / tetrahydrofuran / 1 h / Irradiation

With pyridine; dmap; chloro-trimethyl-silane; sodium dithionite; tributylphosphine; borane; hydrogen; dimethyl sulfoxide; trifluoroacetic acid; sodium bromide; palladium on activated charcoal; In tetrahydrofuran; diethyl ether; ethanol; dichloromethane; ethyl acetate; acetonitrile;

DOI:10.1248/cpb.41.1549

Reference yield:

(E)-4-(5,8-Dihydroxy-1,4-dioxo-1,2,3,4-tetrahydro-naphthalen-2-yl)-but-2-enoic acid tert-butyl ester (155499-74-4) → Acetic acid 4,5,8-triacetoxy-2-[4-(2-nitro-phenylselanyl)-butyl]-naphthalen-1-yl ester (155500-22-4)

Guidance literature:

Multi-step reaction with 7 steps

1: 100 percent / H₂ / 10percent Pd/C / ethyl acetate; ethanol / 8 h / Ambient temperature

2: 83 percent / 1.) TMSCl, NaBr, 2.) DMSO / acetonitrile / 2 h / Ambient temperature

3: 88 percent / pyridine, DMAP / CH₂Cl₂ / 4 h / Ambient temperature

4: 1.) aq. Na₂S₂O₄, 2.) pyridine, DMAP / 1.) ether, 2.) CH₂Cl_2. RT

5: 100 percent / CF₃COOH / CH₂Cl₂ / 12 h / 0 °C

6: 69 percent / BH₃ / tetrahydrofuran / 6 h / 0 °C

7: 66 percent / n-Bu₃P / tetrahydrofuran / 1 h / Irradiation

With pyridine; dmap; chloro-trimethyl-silane; sodium dithionite; tributylphosphine; borane; hydrogen; dimethyl sulfoxide; trifluoroacetic acid; sodium bromide; palladium on activated charcoal; In tetrahydrofuran; ethanol; dichloromethane; ethyl acetate; acetonitrile;

DOI:10.1248/cpb.41.1549

upstream raw materials:

ortho-nitrophenyl selenocyanate

2-(4'-hydroxybutyl)-1,4,5,8-tetraacetoxynapthalene

5,8-dihydroxy-2-(3'-carbo-tert-butoxypropyl)-1,4-naphthoquinone

(E)-4-(5,8-Dihydroxy-1,4-dioxo-1,2,3,4-tetrahydro-naphthalen-2-yl)-but-2-enoic acid tert-butyl ester