(1S,3aS,5R,7aR)-5-phenyl-3a-hydroxy-7a-methylperhydroinden-1-carboxaldehyde

Base Information

• Chemical Name: (1S,3aS,5R,7aR)-5-phenyl-3a-hydroxy-7a-methylperhydroinden-1-carboxaldehyde
• CAS No.: 392235-03-9
• Molecular Formula: C₁₇H₂₂O₂
• Molecular Weight: 258.36
• Mol file: 392235-03-9.mol

Synonyms:(1S,3aS,5R,7aR)-5-phenyl-3a-hydroxy-7a-methylperhydroinden-1-carboxaldehyde

Chemical Property of (1S,3aS,5R,7aR)-5-phenyl-3a-hydroxy-7a-methylperhydroinden-1-carboxaldehyde

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (1S,3aS,5R,7aR)-5-phenyl-3a-hydroxy-7a-methylperhydroinden-1-carboxaldehyde

There total 12 articles about (1S,3aS,5R,7aR)-5-phenyl-3a-hydroxy-7a-methylperhydroinden-1-carboxaldehyde 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: 100.0%

(1S,3aS,5R,7aR)-1-hydroxymethyl-5-phenyl-7a-methylperhydroinden-3a-ol (392235-02-8) → (1S,3aS,5R,7aR)-5-phenyl-3a-hydroxy-7a-methylperhydroinden-1-carboxaldehyde (392235-03-9)

Guidance literature:

With 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione; In dimethyl sulfoxide; for 1h;

DOI:10.1021/jm011001k

Reference yield:

(+)-(3aS,7aS)-2,3,3a,4,7,7a-hexahydro-3a-hydroxy-7a-methyl-1H-indene-1,5(6H)-dione (33879-04-8,51065-67-9) → (1S,3aS,5R,7aR)-5-phenyl-3a-hydroxy-7a-methylperhydroinden-1-carboxaldehyde (392235-03-9)

Guidance literature:

Multi-step reaction with 9 steps

1.1: 83 percent / oxalic acid / acetonitrile / 16 h

2.1: 77 percent / t-BuOK / 2-methyl-propan-2-ol; tetrahydrofuran / 2 h / Heating

3.1: BH₃ / tetrahydrofuran / 1 h / 20 °C

3.2: 20 percent / NaBO₃; aq. NaOH / 16 h / 20 °C

4.1: 68 percent / 1 N pTSA / acetonitrile; H₂O / 16 h

5.1: 82 percent / tetrahydrofuran; cyclohexane; diethyl ether / 1 h / -78 - 0 °C

6.1: 88 percent / H₂; HClO₄ / 5percent Pd/C / ethyl acetate / 2 h / atmospheric pressure

7.1: 48 percent / imidazole / dimethylformamide / 16 h / 20 °C

8.1: 100 percent / aq. HCl / dioxane / 2 h

9.1: 100 percent / IBX / dimethylsulfoxide / 1 h

With 1H-imidazole; hydrogenchloride; perchloric acid; borane; potassium tert-butylate; hydrogen; oxalic acid; toluene-4-sulfonic acid; 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione; 5percent Pd/C; In tetrahydrofuran; 1,4-dioxane; diethyl ether; cyclohexane; water; dimethyl sulfoxide; ethyl acetate; N,N-dimethyl-formamide; acetonitrile; tert-butyl alcohol; 2.1: Wittig reaction;

DOI:10.1021/jm011001k

Reference yield:

phenyllithium (591-51-5) → (1S,3aS,5R,7aR)-5-phenyl-3a-hydroxy-7a-methylperhydroinden-1-carboxaldehyde (392235-03-9)

Guidance literature:

Multi-step reaction with 5 steps

1: 82 percent / tetrahydrofuran; cyclohexane; diethyl ether / 1 h / -78 - 0 °C

2: 88 percent / H₂; HClO₄ / 5percent Pd/C / ethyl acetate / 2 h / atmospheric pressure

3: 48 percent / imidazole / dimethylformamide / 16 h / 20 °C

4: 100 percent / aq. HCl / dioxane / 2 h

5: 100 percent / IBX / dimethylsulfoxide / 1 h

With 1H-imidazole; hydrogenchloride; perchloric acid; hydrogen; 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione; 5percent Pd/C; In tetrahydrofuran; 1,4-dioxane; diethyl ether; cyclohexane; dimethyl sulfoxide; ethyl acetate; N,N-dimethyl-formamide;

DOI:10.1021/jm011001k

upstream raw materials:

(1S,3aS,5R,7aR)-1-hydroxymethyl-5-phenyl-7a-methylperhydroinden-3a-ol

(+)-(3aS,7aS)-2,3,3a,4,7,7a-hexahydro-3a-hydroxy-7a-methyl-1H-indene-1,5(6H)-dione

phenyllithium

(1S,3aS,7aR)-1-hydroxymethyl-3a-hydroxy-7a-methyl-5-perhydroindenone

Refernces