2,3-bis<(o-nitrophenyl)seleno>-5,7αH,4,8,11βH-eleman-8,12-olide

Base Information

• Chemical Name: 2,3-bis<(o-nitrophenyl)seleno>-5,7αH,4,8,11βH-eleman-8,12-olide
• CAS No.: 126733-40-2
• Molecular Formula: C₂₇H₃₂N₂O₆Se₂
• Molecular Weight: 638.481
• Mol file: 126733-40-2.mol

Synonyms:2,3-bis<(o-nitrophenyl)seleno>-5,7αH,4,8,11βH-eleman-8,12-olide

Chemical Property of 2,3-bis<(o-nitrophenyl)seleno>-5,7αH,4,8,11βH-eleman-8,12-olide

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 2,3-bis<(o-nitrophenyl)seleno>-5,7αH,4,8,11βH-eleman-8,12-olide

There total 8 articles about 2,3-bis<(o-nitrophenyl)seleno>-5,7αH,4,8,11βH-eleman-8,12-olide 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: 93.0%

ortho-nitrophenyl selenocyanate (51694-22-5) + 2,3-dihydroxy-5,7αH,4,8,11βH-eleman-8,12-olide (67690-62-4,126685-47-0) → 2,3-bis<(o-nitrophenyl)seleno>-5,7αH,4,8,11βH-eleman-8,12-olide (126733-40-2)

Guidance literature:

With tributylphosphine; In tetrahydrofuran; for 6h; Ambient temperature;

DOI:10.1016/S0040-4020(01)89119-5

Reference yield:

methyl 8α-hydroxy-3-oxo-7αH,11βH-eudesma-1,4-dien-12-oate (91914-35-1) → 2,3-bis<(o-nitrophenyl)seleno>-5,7αH,4,8,11βH-eleman-8,12-olide (126733-40-2)

Guidance literature:

Multi-step reaction with 7 steps

1: H₂ / 5 percent Pd/C / acetone / 12 h / Ambient temperature

2: p-toluenesulphonic acid / benzene / 1.5 h / Heating

3: 1.) lithium diisopropylamide / 1.) THF, -78 deg C, 15 min; 2.) THF, 0 deg C, 2 h

4: BF₃*OEt₂ / benzene / 3 h / Ambient temperature

5: 1.) lithium diisopropylamide / 1.) THF, -78 deg C, 15 min; 2.) THF, 0 deg C, 2 h

6: 1.) ozone; 2.) NaBH₄ / 1.) methanol, methylene dichloride, -78 deg C, 20 min; 2.) -78 deg C, 45 min

7: 93 percent / n-Bu₃P / tetrahydrofuran / 6 h / Ambient temperature

With sodium tetrahydroborate; tributylphosphine; boron trifluoride diethyl etherate; hydrogen; toluene-4-sulfonic acid; ozone; lithium diisopropyl amide; palladium on activated charcoal; In tetrahydrofuran; acetone; benzene;

DOI:10.1016/S0040-4020(01)89119-5

Reference yield:

artemisin (481-05-0,1750-99-8,17367-67-8,46961-87-9,96847-33-5,103617-15-8) → 2,3-bis<(o-nitrophenyl)seleno>-5,7αH,4,8,11βH-eleman-8,12-olide (126733-40-2)

Guidance literature:

Multi-step reaction with 9 steps

1: 57 percent / 5 percent HCl / dimethylformamide / 4 h / 85 - 90 °C

2: 1.) Zn, AcOH; 2.) conc. H₂SO₄ / 1.) reflux, 15 min; 2.) reflux, 2 h

3: H₂ / 5 percent Pd/C / acetone / 12 h / Ambient temperature

4: p-toluenesulphonic acid / benzene / 1.5 h / Heating

5: 1.) lithium diisopropylamide / 1.) THF, -78 deg C, 15 min; 2.) THF, 0 deg C, 2 h

6: BF₃*OEt₂ / benzene / 3 h / Ambient temperature

7: 1.) lithium diisopropylamide / 1.) THF, -78 deg C, 15 min; 2.) THF, 0 deg C, 2 h

8: 1.) ozone; 2.) NaBH₄ / 1.) methanol, methylene dichloride, -78 deg C, 20 min; 2.) -78 deg C, 45 min

9: 93 percent / n-Bu₃P / tetrahydrofuran / 6 h / Ambient temperature

With hydrogenchloride; sodium tetrahydroborate; tributylphosphine; sulfuric acid; boron trifluoride diethyl etherate; hydrogen; toluene-4-sulfonic acid; ozone; acetic acid; zinc; lithium diisopropyl amide; palladium on activated charcoal; In tetrahydrofuran; N,N-dimethyl-formamide; acetone; benzene;

DOI:10.1016/S0040-4020(01)89119-5

upstream raw materials:

ortho-nitrophenyl selenocyanate

2,3-dihydroxy-5,7αH,4,8,11βH-eleman-8,12-olide

3-oxo-5,7,11αH,4,8βH-eudesman-8,12-olide

(S)-2-((2R,3S,4aR)-3-Hydroxy-4a,8-dimethyl-7-oxo-decahydro-naphthalen-2-yl)-propionic acid methyl ester

Downstream raw materials:

11β-phenylseleno-5,7,8αH-elema-1,3-dien-8,12-olide

5,7αH,8βH-elema-1,3,11(13)trien-8,12-olide

11β-phenylseleno-5,7αH,8βH-elema-1,3-dien-8,12-olide

1β-hydroxy-11β-(phenylseleno)-5,7αH,8βH-eudesm-3-en-8,12-olide