4,8-Methanoazulene-3a,8a-diol, octahydro-9,9-dimethyl-5-methylene- (9CI)

Base Information

• Chemical Name: 4,8-Methanoazulene-3a,8a-diol, octahydro-9,9-dimethyl-5-methylene- (9CI)
• CAS No.: 519183-90-5
• Molecular Formula: C14H22O2
• Molecular Weight: 222.32328
• Mol file: 519183-90-5.mol

Synonyms:4,8-Methanoazulene-3a,8a-diol, octahydro-9,9-dimethyl-5-methylene- (9CI)

Chemical Property of 4,8-Methanoazulene-3a,8a-diol, octahydro-9,9-dimethyl-5-methylene- (9CI)

Chemical Property:

• PSA: 40.46000
• LogP: 2.25470

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 4,8-Methanoazulene-3a,8a-diol, octahydro-9,9-dimethyl-5-methylene- (9CI)

There total 11 articles about 4,8-Methanoazulene-3a,8a-diol, octahydro-9,9-dimethyl-5-methylene- (9CI) 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:

9,9-dimethyl-5-methylene-1,2,3,4,5,6,7,8-octahydro-4,8-methano-azulene (519183-73-4) → 9,9-dimethyl-5-methylene-hexahydro-4,8-methano-azulene-3a,8a-diol (519183-90-5)

Guidance literature:

With Quinuclidine; methanesulfonamide; potassium hexacyanoferrate(III); osmium(VIII) oxide; potassium carbonate; In water; tert-butyl alcohol; at 20 ℃;

DOI:10.1016/S0040-4039(02)02868-X

Reference yield:

8,8-dimethyl-7-methylene-bicyclo[3.2.1]octan-2-one (519183-76-7) → 9,9-dimethyl-5-methylene-hexahydro-4,8-methano-azulene-3a,8a-diol (519183-90-5)

Guidance literature:

Multi-step reaction with 10 steps

1.1: 98 percent / DIBALH / diethyl ether / -78 °C

2.1: 100 percent / imidazole / dimethylformamide / 20 °C

3.1: BH₃*THF / 20 °C

3.2: 97 percent / H₂O; NaOH; H₂O₂ / 20 °C

4.1: (COCl)2; DMSO; Et₃N / CH₂Cl₂ / 0 °C

4.2: 92 percent / O₂; t-BuOK / tetrahydrofuran; dimethylsulfoxide / -20 °C

5.1: LDA; HMPA / tetrahydrofuran / -78 - 0 °C

5.2: 98 percent / AcOH / tetrahydrofuran; H₂O / 20 °C

6.1: KHMDS; PhNTf₂ / tetrahydrofuran / -78 °C

6.2: 9-BBN / tetrahydrofuran / 20 °C

6.3: H₂O; K₃PO₄; Pd(PPh₃)4 / dioxane / 80 °C

7.1: 100 percent / TBAF / tetrahydrofuran / 20 °C

8.1: 100 percent / TPAP; NMP / CH₂Cl₂ / 20 °C

9.1: NaNH₂ / toluene / Heating

10.1: quinuclidine; K₃Fe(CN)6; MsNH₂ / K₂CO₃; OsO₄ / 2-methyl-propan-2-ol; H₂O / 20 °C

With Quinuclidine; 1H-imidazole; 1-methyl-pyrrolidin-2-one; N,N,N,N,N,N-hexamethylphosphoric triamide; N,N-phenylbistrifluoromethane-sulfonimide; tetrapropylammonium perruthennate; borane-THF; oxalyl dichloride; methanesulfonamide; tetrabutyl ammonium fluoride; potassium hexamethylsilazane; diisobutylaluminium hydride; sodium amide; dimethyl sulfoxide; triethylamine; potassium hexacyanoferrate(III); lithium diisopropyl amide; osmium(VIII) oxide; potassium carbonate; In tetrahydrofuran; diethyl ether; dichloromethane; water; N,N-dimethyl-formamide; toluene; tert-butyl alcohol; 9.1: Wittig olefination;

DOI:10.1016/S0040-4039(02)02868-X

Reference yield:

8,8-dimethyl-7-methylene-bicyclo[3.2.1]octan-2-ol (519183-94-9) → 9,9-dimethyl-5-methylene-hexahydro-4,8-methano-azulene-3a,8a-diol (519183-90-5)

Guidance literature:

Multi-step reaction with 9 steps

1.1: 100 percent / imidazole / dimethylformamide / 20 °C

2.1: BH₃*THF / 20 °C

2.2: 97 percent / H₂O; NaOH; H₂O₂ / 20 °C

3.1: (COCl)2; DMSO; Et₃N / CH₂Cl₂ / 0 °C

3.2: 92 percent / O₂; t-BuOK / tetrahydrofuran; dimethylsulfoxide / -20 °C

4.1: LDA; HMPA / tetrahydrofuran / -78 - 0 °C

4.2: 98 percent / AcOH / tetrahydrofuran; H₂O / 20 °C

5.1: KHMDS; PhNTf₂ / tetrahydrofuran / -78 °C

5.2: 9-BBN / tetrahydrofuran / 20 °C

5.3: H₂O; K₃PO₄; Pd(PPh₃)4 / dioxane / 80 °C

6.1: 100 percent / TBAF / tetrahydrofuran / 20 °C

7.1: 100 percent / TPAP; NMP / CH₂Cl₂ / 20 °C

8.1: NaNH₂ / toluene / Heating

9.1: quinuclidine; K₃Fe(CN)6; MsNH₂ / K₂CO₃; OsO₄ / 2-methyl-propan-2-ol; H₂O / 20 °C

With Quinuclidine; 1H-imidazole; 1-methyl-pyrrolidin-2-one; N,N,N,N,N,N-hexamethylphosphoric triamide; N,N-phenylbistrifluoromethane-sulfonimide; tetrapropylammonium perruthennate; borane-THF; oxalyl dichloride; methanesulfonamide; tetrabutyl ammonium fluoride; potassium hexamethylsilazane; sodium amide; dimethyl sulfoxide; triethylamine; potassium hexacyanoferrate(III); lithium diisopropyl amide; osmium(VIII) oxide; potassium carbonate; In tetrahydrofuran; dichloromethane; water; N,N-dimethyl-formamide; toluene; tert-butyl alcohol; 8.1: Wittig olefination;

DOI:10.1016/S0040-4039(02)02868-X

upstream raw materials:

9,9-dimethyl-5-methylene-1,2,3,4,5,6,7,8-octahydro-4,8-methano-azulene

8,8-dimethyl-7-methylene-bicyclo[3.2.1]octan-2-one

8,8-dimethyl-7-methylene-bicyclo[3.2.1]octan-2-ol

5-isopropyl-7-methylene-bicyclo[3.2.0]heptan-2-one