decahydro-1,3a,5a-trimethyl-4-<((2-nitrophenyl)seleno)methyl>-cyclopentapentalene

Base Information

• Chemical Name: decahydro-1,3a,5a-trimethyl-4-<((2-nitrophenyl)seleno)methyl>-cyclopentapentalene
• CAS No.: 71596-71-9
• Molecular Formula: C₂₁H₂₉NO₂Se
• Molecular Weight: 406.427
• Mol file: 71596-71-9.mol

Synonyms:decahydro-1,3a,5a-trimethyl-4-<((2-nitrophenyl)seleno)methyl>-cyclopentapentalene

Chemical Property of decahydro-1,3a,5a-trimethyl-4-<((2-nitrophenyl)seleno)methyl>-cyclopentapentalene

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of decahydro-1,3a,5a-trimethyl-4-<((2-nitrophenyl)seleno)methyl>-cyclopentapentalene

There total 9 articles about decahydro-1,3a,5a-trimethyl-4-<((2-nitrophenyl)seleno)methyl>-cyclopentapentalene 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: 74.0%

ortho-nitrophenyl selenocyanate (51694-22-5) + decahydro-1,3a,5a-trimethyl-cyclopentapentalene-4-methanol (82096-26-2) → decahydro-1,3a,5a-trimethyl-4-<((2-nitrophenyl)seleno)methyl>-cyclopentapentalene (71596-71-9)

Guidance literature:

With tributylphosphine; In pyridine; at 20 ℃; for 16h;

DOI:10.1016/0040-4020(81)80001-4

Reference yield: 74.0%

ortho-nitrophenyl selenocyanate (51694-22-5) + decahydro-1,3a,5a-trimethylcyclopenta[c]pentalene-4-methanol → C21H29NO2Se (71596-71-9)

Guidance literature:

With pyridine; tributylphosphine; at 20 ℃; for 16h; Inert atmosphere;

Reference yield:

1,2,3,3a,5,6,6a,7-octahydro-1,3a,6a-trimethyl-4H-cyclopentinden-4-one (71583-68-1) → decahydro-1,3a,5a-trimethyl-4-<((2-nitrophenyl)seleno)methyl>-cyclopentapentalene (71596-71-9)

Guidance literature:

Multi-step reaction with 6 steps

1: 97 percent / H₂ / 10percent Pd/C / methanol / 18 h / 760 Torr

2: 1) 0.15 M t-BuOK, 2) i-amylnitrite / 1) t-BuOH, 20 deg C, 30 min, 2) 20 deg C, 20 h

3: 97 percent / 13-15percent aq. NaOCl, aq. conc NH₄OH, aq. 5 M NaOH / diethyl ether; tetrahydrofuran / 1.5 h

4: 80 percent / 20 °C / Irradiation

5: 96 percent / LiAlH₄ / diethyl ether / 1 h / 20 °C

6: 74 percent / tri-n-butylphosphine / pyridine / 16 h / 20 °C

With ammonium hydroxide; sodium hydroxide; sodium hypochlorite; lithium aluminium tetrahydride; tributylphosphine; potassium tert-butylate; hydrogen; isopentyl nitrite; palladium on activated charcoal; In tetrahydrofuran; pyridine; methanol; diethyl ether;

DOI:10.1016/0040-4020(81)80001-4

upstream raw materials:

ortho-nitrophenyl selenocyanate

decahydro-1,3a,5a-trimethyl-cyclopentapentalene-4-methanol

1,2,3,3a,5,6,6a,7,8,9-decahydro-1,3a,6a-trimethyl-4H-cyclopentinden-4-one

1,2,3,3a,5,6,6a,7-octahydro-1,3a,6a-trimethyl-4H-cyclopentinden-4-one

Downstream raw materials:

isocomene

(+/-)-isocomene