Cyclopenta[1,3]cyclopropa[1,2]cyclohepten-2(1H)-one, octahydro-7,7,8b-trimethyl-, (3aR,8aS,8bS)-rel- (9CI)

Base Information

• Chemical Name: Cyclopenta[1,3]cyclopropa[1,2]cyclohepten-2(1H)-one, octahydro-7,7,8b-trimethyl-, (3aR,8aS,8bS)-rel- (9CI)
• CAS No.: 791810-00-9
• Molecular Formula: C₁₄H₂₂O
• Molecular Weight: 206.328
• Mol file: 791810-00-9.mol

Synonyms:Cyclopenta[1,3]cyclopropa[1,2]cyclohepten-2(1H)-one,octahydro-7,7,8b-trimethyl-, (3aR,8aS,8bS)-rel- (9CI)

Chemical Property of Cyclopenta[1,3]cyclopropa[1,2]cyclohepten-2(1H)-one, octahydro-7,7,8b-trimethyl-, (3aR,8aS,8bS)-rel- (9CI)

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of Cyclopenta[1,3]cyclopropa[1,2]cyclohepten-2(1H)-one, octahydro-7,7,8b-trimethyl-, (3aR,8aS,8bS)-rel- (9CI)

There total 16 articles about Cyclopenta[1,3]cyclopropa[1,2]cyclohepten-2(1H)-one, octahydro-7,7,8b-trimethyl-, (3aR,8aS,8bS)-rel- (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: 55.0%

methyl [(3E)-3,6,6-trimethylcycloundec-3-en-10-yn-1-yl] ether (791809-97-7) → 5,5,8-trimethyltricyclo[5.4.0.O1,8]undecan-10-one (791810-00-9)

Guidance literature:

platinum(II) chloride; In toluene; at 20 ℃; for 3h;

DOI:10.1021/ol048463n

Reference yield:

methyl (E)-3-methyl-5-<(2-tetrahydropyranyl)oxy>pent-2-enoate (35066-34-3) → 5,5,8-trimethyltricyclo[5.4.0.O1,8]undecan-10-one (791810-00-9)

Guidance literature:

Multi-step reaction with 14 steps

1.1: 5.37 g / LiAlH₄ / diethyl ether / 3.25 h / -40 °C

2.1: 91 percent / LiCl; 2,6-lutidine; MsCl / dimethylformamide / 19 h / 0 °C

3.1: i-Pr₂NH; n-BuLi / tetrahydrofuran / 1 h / -78 °C

3.2: 100 percent / tetrahydrofuran / -78 - -20 °C

4.1: 97 percent / LiAlH₄ / diethyl ether / 1.75 h / 0 °C

5.1: 98 percent / oxalyl chloride; DMSO; Et₃N / CH₂Cl₂ / -78 - 20 °C

6.1: LiCl; Et₃N / acetonitrile / 0.17 h / 0 °C

6.2: 1.12 g / acetonitrile / 0 - 20 °C

7.1: LiAlH₄ / diethyl ether / 2 h / -78 - -40 °C

7.2: imidazole; PPh₃; I₂ / toluene / 1 h / 20 °C

7.3: 452 mg / n-BuLi; HMPA / tetrahydrofuran / -78 - 20 °C

8.1: K₂CO₃ / methanol / 20 °C

9.1: 250 mg / p-TsOH*H₂O / methanol / 20 °C

10.1: NIS; AgNO₃ / acetone / 1 h / 20 °C

11.1: 2-iodoxybenzoic acid / dimethylsulfoxide / 2 h / 20 °C

12.1: 44.6 mg / CrCl₂ / tetrahydrofuran / 12 h / 20 °C

13.1: 54 percent / NaH / tetrahydrofuran / 1.75 h / 0 - 20 °C

14.1: 55 percent / PtCl₂ / toluene / 3 h / 20 °C

With 2,6-dimethylpyridine; chromium dichloride; N-iodo-succinimide; lithium aluminium tetrahydride; n-butyllithium; oxalyl dichloride; sodium hydride; potassium carbonate; toluene-4-sulfonic acid; silver nitrate; dimethyl sulfoxide; methanesulfonyl chloride; triethylamine; diisopropylamine; lithium chloride; 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione; platinum(II) chloride; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; dimethyl sulfoxide; N,N-dimethyl-formamide; acetone; toluene; acetonitrile; 5.1: Swern oxidation;

DOI:10.1021/ol048463n

Reference yield:

methyl 5-(tetrahydro-2H-pyran-2-yloxy)pent-2-ynoate (104939-54-0) → 5,5,8-trimethyltricyclo[5.4.0.O1,8]undecan-10-one (791810-00-9)

Guidance literature:

Multi-step reaction with 16 steps

1.1: Na / methanol / 1 h / 0 °C

1.2: 73 percent / methanol / 1.5 h / 0 °C

2.1: CuBr*Me₂S / tetrahydrofuran; diethyl ether / 1 h / -78 °C

2.2: tetrahydrofuran; diethyl ether / 4 h / -78 °C

3.1: 5.37 g / LiAlH₄ / diethyl ether / 3.25 h / -40 °C

4.1: 91 percent / LiCl; 2,6-lutidine; MsCl / dimethylformamide / 19 h / 0 °C

5.1: i-Pr₂NH; n-BuLi / tetrahydrofuran / 1 h / -78 °C

5.2: 100 percent / tetrahydrofuran / -78 - -20 °C

6.1: 97 percent / LiAlH₄ / diethyl ether / 1.75 h / 0 °C

7.1: 98 percent / oxalyl chloride; DMSO; Et₃N / CH₂Cl₂ / -78 - 20 °C

8.1: LiCl; Et₃N / acetonitrile / 0.17 h / 0 °C

8.2: 1.12 g / acetonitrile / 0 - 20 °C

9.1: LiAlH₄ / diethyl ether / 2 h / -78 - -40 °C

9.2: imidazole; PPh₃; I₂ / toluene / 1 h / 20 °C

9.3: 452 mg / n-BuLi; HMPA / tetrahydrofuran / -78 - 20 °C

10.1: K₂CO₃ / methanol / 20 °C

11.1: 250 mg / p-TsOH*H₂O / methanol / 20 °C

12.1: NIS; AgNO₃ / acetone / 1 h / 20 °C

13.1: 2-iodoxybenzoic acid / dimethylsulfoxide / 2 h / 20 °C

14.1: 44.6 mg / CrCl₂ / tetrahydrofuran / 12 h / 20 °C

15.1: 54 percent / NaH / tetrahydrofuran / 1.75 h / 0 - 20 °C

16.1: 55 percent / PtCl₂ / toluene / 3 h / 20 °C

With 2,6-dimethylpyridine; chromium dichloride; N-iodo-succinimide; lithium aluminium tetrahydride; n-butyllithium; oxalyl dichloride; copper(I) bromide dimethylsulfide complex; sodium; sodium hydride; potassium carbonate; toluene-4-sulfonic acid; silver nitrate; dimethyl sulfoxide; methanesulfonyl chloride; triethylamine; diisopropylamine; lithium chloride; 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione; platinum(II) chloride; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; dimethyl sulfoxide; N,N-dimethyl-formamide; acetone; toluene; acetonitrile; 7.1: Swern oxidation;

DOI:10.1021/ol048463n

upstream raw materials:

methyl [(3E)-3,6,6-trimethylcycloundec-3-en-10-yn-1-yl] ether

methyl (E)-3-methyl-5-<(2-tetrahydropyranyl)oxy>pent-2-enoate

methyl 5-(tetrahydro-2H-pyran-2-yloxy)pent-2-ynoate

(2E)-3-methyl-5-(tetrahydro-2H-pyran-2-yloxy)pent-2-en-1-ol

Refernces