(3aα,5aβ,9aα,9bα)-dodecahydro-9a,9b-dimethyl-2-(phenylamino)-1H-benzinden-1-one

Base Information

• Chemical Name: (3aα,5aβ,9aα,9bα)-dodecahydro-9a,9b-dimethyl-2-(phenylamino)-1H-benzinden-1-one
• CAS No.: 120174-16-5
• Molecular Formula: C₂₁H₂₉NO
• Molecular Weight: 311.467
• Mol file: 120174-16-5.mol

Synonyms:(3aα,5aβ,9aα,9bα)-dodecahydro-9a,9b-dimethyl-2-(phenylamino)-1H-benzinden-1-one

Chemical Property of (3aα,5aβ,9aα,9bα)-dodecahydro-9a,9b-dimethyl-2-(phenylamino)-1H-benzinden-1-one

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (3aα,5aβ,9aα,9bα)-dodecahydro-9a,9b-dimethyl-2-(phenylamino)-1H-benzinden-1-one

There total 13 articles about (3aα,5aβ,9aα,9bα)-dodecahydro-9a,9b-dimethyl-2-(phenylamino)-1H-benzinden-1-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: 86.0%

2-(2-aminophenyl)dodecahydro-9a,9b-dimethyl-2-(methylthio)-1H-benzinden-1-one (120174-12-1,120174-13-2,120174-20-1,120174-21-2) → (3aα,5aβ,9aα,9bα)-dodecahydro-9a,9b-dimethyl-2-(phenylamino)-1H-benzinden-1-one (120174-16-5)

Guidance literature:

With nickel; In ethanol; for 0.25h;

DOI:10.1021/jo00275a035

Reference yield:

(8aS)-1,1-(1,2-ethylenedioxy)-1,2,3,4,6,7,8,8a-octahydro-8a-methyl-6-oxonaphthalene (61950-54-7) → (3aα,5aβ,9aα,9bα)-dodecahydro-9a,9b-dimethyl-2-(phenylamino)-1H-benzinden-1-one (120174-16-5)

Guidance literature:

Multi-step reaction with 12 steps

1: 83 percent / lithium, ammonia / tetrahydrofuran; 2-methyl-propan-2-ol / 0.5 h

2: 1.) hydrazine, 2.) potassium hydroxide / 1.) triethylene glycol, 110 deg C, 1.5 h, 2.) 200 deg C, 3 h

3: 95 percent / 3 N hydrochloric acid / tetrahydrofuran / 10 h

4: 1.) n-butyllithium / 1.) THF, 0 deg C, 1 h, 2.) from -78 deg C to RT

5: 33 percent / conc. sulfuric acid / methanol / 0.25 h / 0 °C

6: 1.) lithium, water, 2.) HMPA / 1.) THF, ammonia, -78 deg C, 10 min, 2.) -20 deg C, 30 min

7: benzene / Heating

8: 1.) ozone, 2.) triphenylphosphine / 1.) methylene chloride, -78 deg C, 2.) from -78 deg C to RT

9: 23 percent / Rh(PPh₃)3Cl / benzene / 6 h / Heating

10: 1.) LDA, 2.) hexamethylphosphoramide (HMPA) / 1.) THF, 0 deg C, 5 min, 2.) 15 min

11: 1.) tert-butyl hypochlorite / 1.) methylene chloride, -78 deg C, 5 min, 2.) 4 h

12: 86 percent / Raney nickel / ethanol / 0.25 h

With hydrogenchloride; N,N,N,N,N,N-hexamethylphosphoric triamide; potassium hydroxide; Wilkinson's catalyst; n-butyllithium; tert-butylhypochlorite; sulfuric acid; ammonia; water; lithium; nickel; ozone; triphenylphosphine; hydrazine; lithium diisopropyl amide; In tetrahydrofuran; methanol; ethanol; tert-butyl alcohol; benzene;

DOI:10.1021/jo00275a035

Reference yield:

(4aR,8aS)-8a-methyloctahydronaphthalen-1(2H)-one (6102-38-1) → (3aα,5aβ,9aα,9bα)-dodecahydro-9a,9b-dimethyl-2-(phenylamino)-1H-benzinden-1-one (120174-16-5)

Guidance literature:

Multi-step reaction with 9 steps

1: 1.) n-butyllithium / 1.) THF, 0 deg C, 1 h, 2.) from -78 deg C to RT

2: 33 percent / conc. sulfuric acid / methanol / 0.25 h / 0 °C

3: 1.) lithium, water, 2.) HMPA / 1.) THF, ammonia, -78 deg C, 10 min, 2.) -20 deg C, 30 min

4: benzene / Heating

5: 1.) ozone, 2.) triphenylphosphine / 1.) methylene chloride, -78 deg C, 2.) from -78 deg C to RT

6: 23 percent / Rh(PPh₃)3Cl / benzene / 6 h / Heating

7: 1.) LDA, 2.) hexamethylphosphoramide (HMPA) / 1.) THF, 0 deg C, 5 min, 2.) 15 min

8: 1.) tert-butyl hypochlorite / 1.) methylene chloride, -78 deg C, 5 min, 2.) 4 h

9: 86 percent / Raney nickel / ethanol / 0.25 h

With N,N,N,N,N,N-hexamethylphosphoric triamide; Wilkinson's catalyst; n-butyllithium; tert-butylhypochlorite; sulfuric acid; water; lithium; nickel; ozone; triphenylphosphine; lithium diisopropyl amide; In methanol; ethanol; benzene;

DOI:10.1021/jo00275a035

upstream raw materials:

2-(2-aminophenyl)dodecahydro-9a,9b-dimethyl-2-(methylthio)-1H-benzinden-1-one

(8aS)-1,1-(1,2-ethylenedioxy)-1,2,3,4,6,7,8,8a-octahydro-8a-methyl-6-oxonaphthalene

(4aR,8aS)-8a-methyloctahydronaphthalen-1(2H)-one

(+)-(4aS,8aS)-1,1-(1,2-Ethylenedioxy)-1,2,3,4,4aα,5,6,7,8,8a-decahydro-8aβ-methyl-6-oxonaphthalene

Refernces