Cyclopenta[1,3]cyclopropa[1,2]cyclohepten-1(2H)-one, 3,3a,3b,4,5,8-hexahydro-3a,5,5-trimethyl-, (3aR,3bR,8aS)-rel- (9CI)

Base Information

Chemical Name:Cyclopenta[1,3]cyclopropa[1,2]cyclohepten-1(2H)-one, 3,3a,3b,4,5,8-hexahydro-3a,5,5-trimethyl-, (3aR,3bR,8aS)-rel- (9CI)
CAS No.:791810-04-3
Molecular Formula:C₁₄H₂₀O
Molecular Weight:204.312
Hs Code.:
Mol file:791810-04-3.mol

Synonyms:Cyclopenta[1,3]cyclopropa[1,2]cyclohepten-1(2H)-one, 3,3a,3b,4,5,8-hexahydro-3a,5,5-trimethyl-, (3aR,3bR,8aS)-rel- (9CI)

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Chemical Property of Cyclopenta[1,3]cyclopropa[1,2]cyclohepten-1(2H)-one, 3,3a,3b,4,5,8-hexahydro-3a,5,5-trimethyl-, (3aR,3bR,8aS)-rel- (9CI)

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Technology Process of Cyclopenta[1,3]cyclopropa[1,2]cyclohepten-1(2H)-one, 3,3a,3b,4,5,8-hexahydro-3a,5,5-trimethyl-, (3aR,3bR,8aS)-rel- (9CI)

There total 16 articles about Cyclopenta[1,3]cyclopropa[1,2]cyclohepten-1(2H)-one, 3,3a,3b,4,5,8-hexahydro-3a,5,5-trimethyl-, (3aR,3bR,8aS)-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: 89.0%

: 5,5,8-trimethyltricyclo[5.4.0.0^1,8]undeca-3,10-dien-11-yl p-nitrobenzoate

: 791810-04-3
5,5,8-trimethyltricyclo[5.4.0.0^1,8]undeca-3-en-11-one

Guidance literature:: With potassium carbonate; In methanol; at 20 ℃; for 1h;
DOI:10.1021/ol048463n

Reference yield:

: 35066-34-3
methyl (E)-3-methyl-5-<(2-tetrahydropyranyl)oxy>pent-2-enoate

: 791810-04-3
5,5,8-trimethyltricyclo[5.4.0.0^1,8]undeca-3-en-11-one

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: 79 percent / n-BuLi; HNPA / tetrahydrofuran / -78 - 0 °C

7.1: KF; H₂O / dimethylformamide / 15 h / 20 °C

8.1: 3.14 g / p-TsOH*H₂O / methanol / 8 h / 20 °C

9.1: 989 mg / NIS; AgNO₃ / acetone / 4 h / 20 °C

10.1: 963 mg / 2-iodoxybenzoic acid / dimethylsulfoxide / 2 h / 20 °C

11.1: 269 mg / CrCl₂ / tetrahydrofuran / 12 h / 20 °C

12.1: 80 percent / Et₃N; 4-DMAP / CH₂Cl₂ / 2 h / 20 °C

13.1: 89 percent / PtCl₂ / toluene / 6 h / 20 °C

14.1: 89 percent / K₂CO₃ / methanol / 1 h / 20 °C

With 2,6-dimethylpyridine; chromium dichloride; dmap; potassium fluoride; N-iodo-succinimide; lithium aluminium tetrahydride; n-butyllithium; oxalyl dichloride; water; potassium carbonate; toluene-4-sulfonic acid; silver nitrate; dimethyl sulfoxide; methanesulfonyl chloride; triethylamine; diisopropylamine; (3Z)(1S,2R,5R)-5-(6-aminopurin-9-yl)-3-(2-hydroxyethyl)cyclopent-3-ene-1,2-diol; 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; 5.1: Swern oxidation;
DOI:10.1021/ol048463n

Reference yield:

: 104939-54-0
methyl 5-(tetrahydro-2H-pyran-2-yloxy)pent-2-ynoate

: 791810-04-3
5,5,8-trimethyltricyclo[5.4.0.0^1,8]undeca-3-en-11-one

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: 79 percent / n-BuLi; HNPA / tetrahydrofuran / -78 - 0 °C

9.1: KF; H₂O / dimethylformamide / 15 h / 20 °C

10.1: 3.14 g / p-TsOH*H₂O / methanol / 8 h / 20 °C

11.1: 989 mg / NIS; AgNO₃ / acetone / 4 h / 20 °C

12.1: 963 mg / 2-iodoxybenzoic acid / dimethylsulfoxide / 2 h / 20 °C

13.1: 269 mg / CrCl₂ / tetrahydrofuran / 12 h / 20 °C

14.1: 80 percent / Et₃N; 4-DMAP / CH₂Cl₂ / 2 h / 20 °C

15.1: 89 percent / PtCl₂ / toluene / 6 h / 20 °C

16.1: 89 percent / K₂CO₃ / methanol / 1 h / 20 °C

With 2,6-dimethylpyridine; chromium dichloride; dmap; potassium fluoride; N-iodo-succinimide; lithium aluminium tetrahydride; n-butyllithium; oxalyl dichloride; copper(I) bromide dimethylsulfide complex; water; sodium; potassium carbonate; toluene-4-sulfonic acid; silver nitrate; dimethyl sulfoxide; methanesulfonyl chloride; triethylamine; diisopropylamine; (3Z)(1S,2R,5R)-5-(6-aminopurin-9-yl)-3-(2-hydroxyethyl)cyclopent-3-ene-1,2-diol; 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; 7.1: Swern oxidation;
DOI:10.1021/ol048463n