(6aβ,7aα,11aα,13aR^*)-7a-<2-<(o-nitrophenyl)seleno>ethyl>-6a,7,7a,11a,12,13-hexahydro-10H-indolizino<1',8':2,3,4>cyclopenta<1,2-c>quinolin-6(5H)-one

Base Information

• Chemical Name: (6aβ,7aα,11aα,13aR^*)-7a-<2-<(o-nitrophenyl)seleno>ethyl>-6a,7,7a,11a,12,13-hexahydro-10H-indolizino<1',8':2,3,4>cyclopenta<1,2-c>quinolin-6(5H)-one
• CAS No.: 119146-71-3
• Molecular Formula: C₂₅H₂₅N₃O₃Se
• Molecular Weight: 494.452
• Mol file: 119146-71-3.mol

Synonyms:

Chemical Property of (6aβ,7aα,11aα,13aR^*)-7a-<2-<(o-nitrophenyl)seleno>ethyl>-6a,7,7a,11a,12,13-hexahydro-10H-indolizino<1',8':2,3,4>cyclopenta<1,2-c>quinolin-6(5H)-one

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (6aβ,7aα,11aα,13aR^*)-7a-<2-<(o-nitrophenyl)seleno>ethyl>-6a,7,7a,11a,12,13-hexahydro-10H-indolizino<1',8':2,3,4>cyclopenta<1,2-c>quinolin-6(5H)-one

There total 55 articles about (6aβ,7aα,11aα,13aR^*)-7a-<2-<(o-nitrophenyl)seleno>ethyl>-6a,7,7a,11a,12,13-hexahydro-10H-indolizino<1',8':2,3,4>cyclopenta<1,2-c>quinolin-6(5H)-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: 58.0%

ortho-nitrophenyl selenocyanate (51694-22-5) + (6aβ,7aα,11aα,13aR*)-7a-(2-tosylethyl)-6a,7,7a,11a,12,13-hexahydro-10H-indolizino<1',8':2,3,4>cyclopenta<1,2-c>quinolin-6(5H)-one (119146-62-2,119146-70-2) → (6aβ,7aα,11aα,13aR*)-7a-<2-<(o-nitrophenyl)seleno>ethyl>-6a,7,7a,11a,12,13-hexahydro-10H-indolizino<1',8':2,3,4>cyclopenta<1,2-c>quinolin-6(5H)-one (119146-71-3,131685-35-3)

Guidance literature:

With sodium tetrahydroborate; In ethanol; at 23 ℃; for 20h;

DOI:10.1021/jo00267a003

Reference yield:

8-diazo-6aα-<2-(benzyloxy)ethyl>-9aα-<2-(trimethylacetamido)phenyl>-1,2,4,6a,7,8,9,9bα-octahydro-9H-pyrrolo<3,2,1-ij>quinolin-9-one → (6aα,7aα,11aα,13aR*)-7a-<2-<(o-nitrophenyl)seleno>ethyl>-6a,7,7a,11a,12,13-hexahydro-10H-indolizino<1',8':2,3,4>cyclopenta<1,2-c>quinolin-6(5H)-one (119146-71-3,131685-35-3)

Guidance literature:

Multi-step reaction with 5 steps

1: diethyl ether / 0.3 h / 23 °C / Irradiation

2: KOH / aq. ethanol / 1.) 0 deg C, 2.) from 0 deg C to 150 deg C, 24 h

3: Na/NH₃ / 0 h / -70 °C

4: pyridine / CHCl₃ / 16 h / 23 °C

5: NaBH₄ / ethanol / 20 h / 23 °C

With pyridine; potassium hydroxide; sodium tetrahydroborate; ammonia; sodium; In diethyl ether; ethanol; chloroform;

DOI:10.1021/jo00267a003

Reference yield:

methyl (6aα,8aα,8bα)-6a-<2-(benzyloxy)ethyl>-8a-<2-(trimethylacetamido)phenyl>-1,2,3,6a,7,8,8b-heptahydro-4H-cyclopentindolizine-8-carboxylate (119146-68-8,119239-80-4) → (6aα,7aα,11aα,13aR*)-7a-<2-<(o-nitrophenyl)seleno>ethyl>-6a,7,7a,11a,12,13-hexahydro-10H-indolizino<1',8':2,3,4>cyclopenta<1,2-c>quinolin-6(5H)-one (119146-71-3,131685-35-3)

Guidance literature:

Multi-step reaction with 4 steps

1: KOH / aq. ethanol / 1.) 0 deg C, 2.) from 0 deg C to 150 deg C, 24 h

2: Na/NH₃ / 0 h / -70 °C

3: pyridine / CHCl₃ / 16 h / 23 °C

4: NaBH₄ / ethanol / 20 h / 23 °C

With pyridine; potassium hydroxide; sodium tetrahydroborate; ammonia; sodium; In ethanol; chloroform;

DOI:10.1021/jo00267a003

upstream raw materials:

ortho-nitrophenyl selenocyanate

(6aα,7aα,11aα,13aR^*)-7a-(2-tosylethyl)-6a,7,7a,11a,12,13-hexahydro-10H-indolizino<1',8':2,3,4>cyclopenta<1,2-c>quinolin-6(5H)-one

methyl (6aα,8aα,8bα)-6a-<2-(benzyloxy)ethyl>-8a-<2-(trimethylacetamido)phenyl>-1,2,3,6a,7,8,8b-heptahydro-4H-cyclopentindolizine-8-carboxylate

(6aα,7aα,11aα,13aR^*)-7a-(2-hydroxyethyl)-6a,7,7a,11a,12,13-hexahydro-10H-indolizino<1',8':2,3,4>cyclopenta<1,2-c>quinolin-6(5H)-one

Downstream raw materials:

(+/-)-16-epimeloscine

(+/-)-meloscine