3-[(1S,2R,5S)-2-isopropyl-5-methylcyclohexyloxy]cyclopent-2-enone

Base Information

Chemical Name:3-[(1S,2R,5S)-2-isopropyl-5-methylcyclohexyloxy]cyclopent-2-enone
CAS No.:914651-26-6
Molecular Formula:C₁₅H₂₄O₂
Molecular Weight:236.354
Hs Code.:

Synonyms:3-[(1S,2R,5S)-2-isopropyl-5-methylcyclohexyloxy]cyclopent-2-enone

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Chemical Property of 3-[(1S,2R,5S)-2-isopropyl-5-methylcyclohexyloxy]cyclopent-2-enone

Chemical Property:

Purity/Quality:

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Technology Process of 3-[(1S,2R,5S)-2-isopropyl-5-methylcyclohexyloxy]cyclopent-2-enone

There total 1 articles about 3-[(1S,2R,5S)-2-isopropyl-5-methylcyclohexyloxy]cyclopent-2-enone 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:

: 15356-60-2
(1S,2R,5S)-(+)-menthol

: 5870-62-2
3-hydroxy-2-cyclopenten-1-one

: 914651-26-6
3-[(1S,2R,5S)-2-isopropyl-5-methylcyclohexyloxy]cyclopent-2-enone

Guidance literature:: With toluene-4-sulfonic acid; In benzene; for 9h; Heating;
DOI:10.1021/ja0650504

Reference yield:

: 914651-26-6
3-[(1S,2R,5S)-2-isopropyl-5-methylcyclohexyloxy]cyclopent-2-enone

: C₂₇H₃₄O₄

Guidance literature:: Multi-step reaction with 15 steps

1.1: LDA / hexane; tetrahydrofuran / 0.33 h / -78 °C

1.2: Et₂Zn; DMPU / tetrahydrofuran; hexane / 20 h / 20 °C

2.1: diethyl ether; tetrahydrofuran / 3 h / -78 - 0 °C

3.1: t-BuLi / diethyl ether; pentane / 0.5 h / -78 °C

3.2: CuCN / diethyl ether; pentane / -78 - -30 °C

3.3: diethyl ether; pentane; tetrahydrofuran / 6 h / -78 °C

4.1: 2,6-lutidine / dimethylformamide / 1 h / 0 °C

4.2: MeI / diethyl ether / 12 h / 20 °C

4.3: 811 mg / K₂CO₃ / CH₂Cl₂; methanol; H₂O / 3 h / 20 °C

5.1: m-CPBA / CH₂Cl₂ / 3 h / 20 °C

6.1: NaBH₄; CeCl₃*7H₂O / methanol / 1 h / -78 °C

7.1: imidazole / CH₂Cl₂ / 0.5 h / 20 °C

8.1: LiEt₃BH / tetrahydrofuran / 2 h / 0 °C

8.2: 121 mg / N-methylmorpholine oxide hydrate / TPAP / CH₂Cl₂ / 1 h / 20 °C

9.1: LiHDMS / tetrahydrofuran / 0.17 h / -78 - -30 °C

9.2: 710 mg / DMPU / tetrahydrofuran / 0.17 h / -78 - -45 °C

10.1: KHMDS / tetrahydrofuran / 0.33 h / -78 °C

10.2: tetrahydrofuran / 0.17 h / -78 °C

11.1: aq. HF / acetonitrile; methanol / 3 h / 0 °C

12.1: 384 mg / NMO*H₂O / TPAP / CH₂Cl₂ / 4 h / 20 °C

13.1: 75 percent / bis(diphenylphosphino)butane; KOAc / Pd₂(dba)3*CHCl₃ / N,N-dimethyl-acetamide / 12 h / 80 °C

14.1: Et₃N / CH₂Cl₂ / 4 h / -78 °C

15.1: dimethyldioxirane / CH₂Cl₂; acetone / 10 h / -78 °C

With 1H-imidazole; 2,6-dimethylpyridine; sodium tetrahydroborate; cerium(III) chloride; bis(diphenylphosphino)butane; hydrogen fluoride; tert.-butyl lithium; potassium acetate; 3,3-dimethyldioxirane; potassium hexamethylsilazane; lithium triethylborohydride; 4-methylmorpholine N-oxide; triethylamine; 3-chloro-benzenecarboperoxoic acid; lithium hexamethyldisilazane; lithium diisopropyl amide; tris(dibenzylideneacetone)dipalladium⁽⁰⁾ chloroform complex; tetrapropylammonium perruthennate; In tetrahydrofuran; methanol; diethyl ether; hexane; dichloromethane; N,N-dimethyl acetamide; N,N-dimethyl-formamide; acetone; acetonitrile; pentane; 13.1: Heck cyclization reaction;
DOI:10.1021/ja0650504

Reference yield:

: 914651-26-6
3-[(1S,2R,5S)-2-isopropyl-5-methylcyclohexyloxy]cyclopent-2-enone

: 914651-32-4
benzyl (S)-3-[2-((1R,5R)-5-isopropyl-1-methyl-2-methylene-3-oxocyclopentyl)ethyl]-3-methyl-2-trifluoromethanesulfonyloxycyclohex-1-enecarboxylate

Guidance literature:: Multi-step reaction with 12 steps

1.1: LDA / hexane; tetrahydrofuran / 0.33 h / -78 °C

1.2: Et₂Zn; DMPU / tetrahydrofuran; hexane / 20 h / 20 °C

2.1: diethyl ether; tetrahydrofuran / 3 h / -78 - 0 °C

3.1: t-BuLi / diethyl ether; pentane / 0.5 h / -78 °C

3.2: CuCN / diethyl ether; pentane / -78 - -30 °C

3.3: diethyl ether; pentane; tetrahydrofuran / 6 h / -78 °C

4.1: 2,6-lutidine / dimethylformamide / 1 h / 0 °C

4.2: MeI / diethyl ether / 12 h / 20 °C

4.3: 811 mg / K₂CO₃ / CH₂Cl₂; methanol; H₂O / 3 h / 20 °C

5.1: m-CPBA / CH₂Cl₂ / 3 h / 20 °C

6.1: NaBH₄; CeCl₃*7H₂O / methanol / 1 h / -78 °C

7.1: imidazole / CH₂Cl₂ / 0.5 h / 20 °C

8.1: LiEt₃BH / tetrahydrofuran / 2 h / 0 °C

8.2: 121 mg / N-methylmorpholine oxide hydrate / TPAP / CH₂Cl₂ / 1 h / 20 °C

9.1: LiHDMS / tetrahydrofuran / 0.17 h / -78 - -30 °C

9.2: 710 mg / DMPU / tetrahydrofuran / 0.17 h / -78 - -45 °C

10.1: KHMDS / tetrahydrofuran / 0.33 h / -78 °C

10.2: tetrahydrofuran / 0.17 h / -78 °C

11.1: aq. HF / acetonitrile; methanol / 3 h / 0 °C

12.1: 384 mg / NMO*H₂O / TPAP / CH₂Cl₂ / 4 h / 20 °C

With 1H-imidazole; 2,6-dimethylpyridine; sodium tetrahydroborate; cerium(III) chloride; hydrogen fluoride; tert.-butyl lithium; potassium hexamethylsilazane; lithium triethylborohydride; 4-methylmorpholine N-oxide; 3-chloro-benzenecarboperoxoic acid; lithium hexamethyldisilazane; lithium diisopropyl amide; tetrapropylammonium perruthennate; In tetrahydrofuran; methanol; diethyl ether; hexane; dichloromethane; N,N-dimethyl-formamide; acetonitrile; pentane;
DOI:10.1021/ja0650504