No renderable structure data available
CCCC1CC(=O)CC(=O)C1Chemical Intermediate
Structures, identifiers and computed properties have been matched to the database record by CAS.
| Intermediates | 5-propylcyclohexane-1,3-dione |
|---|---|
| IUPAC Name | — |
| CAS Number | 57641-89-1 |
| Database ID | 2737224 |
| Molecular Formula | — |
| Molecular Weight | — |
Product Information
5-propylcyclohexane-1,3-dione (CAS 57641-89-1) product identity, structure identifiers and related reaction data for chemical intermediate research and sourcing review.
Potential Applications
For professional research and industrial use only
Database ID 2737224
Safety Notice
For professional research and industrial use only. Review the supplier safety data sheet before handling.
Synthesis data
12 reactions · 12 references
Conditions: temp:0.00; pressure:0.00; stir:
Source ID: ord-0a56e637b3f5471184eb3fac184011a4Conditions: temp:80.01; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: A mixture of (S)-3-amino-but-2-enoic acid [1-(4-methoxy-phenyl)-ethyl]-amide (10 g), 3-bromo-5-ethoxy-4-hydroxy-benzaldehyde (10.4 g) and 5-propylcyclohexane-1,3-dione (6.5 g) in ethanol (150 ml) was stirred at 80° C. for 18 hr. The mixture was concentrated in vacuo. The residue was dissolved in toluene (100 ml) and dichloromethane (50 ml) and evaporated until a precipitated formed. The solid obtained was then crystallized in EtOAc. The mixture was concentrated in vacuo The residue was dissolved in toluene (100 ml) dichloromethane (50 ml) and evaporated until a precipitated formed The solid obtained was then crystallized in EtOAc
Source ID: ord-a429293d35a64bc08d2dab2e8e49d804Conditions: temp:0.01; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: The title compound was prepared according to the method described in example 1b starting from 3-bromo-5-ethoxy-4-hydroxy-benzaldehyde (6 g), 3-aminocrotonitrile (2.01 g) and 5-propylcyclohexane-1,3-dione (3.8 g). The reaction mixture was cooled (0° C.) and the title compound was filtered off and washed with ethanol (cold). Yield: 6.3 g. MS-ESI: [M+H]+=445/447 the title compound was filtered off washed with ethanol (cold)
Source ID: ord-76f833dc7d034d7a9c5c326e1138a137Conditions: temp:80.01; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: A mixture of the product of step c (59 mg), 3-aminocrotonitrile (12.3 mg) and 5-propylcyclohexane-1,3-dione (23.1 mg) in ethanol (5 ml) was stirred at 80° C. for 17 h. The reaction mixture was concentrated in vacuo and the residue was purified by preparative HPLC (Method B). Yield: 57 mg. MS-ESI: [M+H]+=591.3/593.3; HPLC: Rt=18.43 min. Diast. ratio: 9:1 The reaction mixture was concentrated in vacuo the residue was purified by preparative HPLC (Method B)
Source ID: ord-1838a73898564ef3830e76f7c0e3774aConditions: temp:80.01; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: A mixture of the product of step c (59 mg), 3-aminocrotonitrile (12.3 mg) and 5-propylcyclohexane-1,3-dione (23.1 mg) in ethanol (5 ml) was stirred at 80° C. for 17 h. The reaction mixture was concentrated in vacuo and the residue was purified by preparative HPLC (Method B). Yield: 57 mg. MS-ESI: [M+H]+=591.3/593.3; HPLC: Rt=18.43 min. Diast. ratio: 9:1 The reaction mixture was concentrated in vacuo the residue was purified by preparative HPLC (Method B)
Source ID: ord-1838a73898564ef3830e76f7c0e3774aConditions: temp:80.01; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: A mixture of the product of step d (61 mg), 3-aminocrotonitrile (12.3 mg) and 5-propylcyclohexane-1,3-dione (23.1 mg) in ethanol (5 ml) was stirred at 80° C. for 17 h. The reaction mixture was concentrated in vacuo and the residue was purified by preparative HPLC (Method B). Yield: 57 mg. MS-ESI: [M+H]+=607.3/609.3; HPLC: Rt=16.51 min. (diast. 1) Rt=16.83 min. (diast. 2) (method 1). Diast. ratio: 9:1 The reaction mixture was concentrated in vacuo the residue was purified by preparative HPLC (Method B)
Source ID: ord-b3007321c7f64c6fad9000e1d19d8875Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: A mixture of 1-methyl-2-nitro-vinylamine (1 g), 5-propylcyclohexane-1,3-dione (1.61 g) and 3-bromo-5-ethoxy-4-hydroxy-benzaldehyde (2.57 g) in ethanol (50 ml) was stirred at reflux for 17 h. The reaction mixture was concentrated in vacuo. The residue was dissolved in dichloromethane. A precipitate formed, which was collected by filtration. The solid was chromatographed on silicagel in heptane/EtOAc (from 1/0 to 0/1) as eluent. Yield: 2.8 g. MS-ESI: [M+H]+=465.0/467.0 at reflux for 17 h The reaction mixture was concentrated in vacuo The residue was dissolved in dichloromethane A precipitate formed which was collected by filtration The solid was chromatographed on silicagel in heptane/EtOAc (from 1/0 to 0/1) as eluent
Source ID: ord-6614b13ee94444c9a27fb18c52faee20Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: A mixture of 1-methyl-2-nitro-vinylamine (1 g), 5-propylcyclohexane-1,3-dione (1.61 g) and 3-bromo-5-ethoxy-4-hydroxy-benzaldehyde (2.57 g) in ethanol (50 ml) was stirred at reflux for 17 h. The reaction mixture was concentrated in vacuo. The residue was dissolved in dichloromethane. A precipitate formed, which was collected by filtration. The solid was chromatographed on silicagel in heptane/EtOAc (from 1/0 to 0/1) as eluent. Yield: 2.8 g. MS-ESI: [M+H]+=465.0/467.0 at reflux for 17 h The reaction mixture was concentrated in vacuo The residue was dissolved in dichloromethane A precipitate formed which was collected by filtration The solid was chromatographed on silicagel in heptane/EtOAc (from 1/0 to 0/1) as eluent
Source ID: ord-6614b13ee94444c9a27fb18c52faee20Conditions: temp:80.01; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: A mixture of the product of step b (1.06 g), 3-aminocrotonitrile (221 mg) and 5-propylcyclohexane-1,3-dione (415 mg) in ethanol (20 ml) was stirred at 80° C. for 17 h. The reaction mixture was concentrated in vacuo and the residue was chromatographed on silica gel in heptane/EtOAc=1/1 (v/v) as eluent. Yield: 750 mg. MS-ESI: [M+H]+=594.4/596.4 The reaction mixture was concentrated in vacuo the residue was chromatographed on silica gel in heptane/EtOAc=1/1 (v/v) as eluent
Source ID: ord-b0d54090278f41f0b2d4d3ee9cbc9484Conditions: temp:80.01; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: A mixture of the product of step b (1.06 g), 3-aminocrotonitrile (221 mg) and 5-propylcyclohexane-1,3-dione (415 mg) in ethanol (20 ml) was stirred at 80° C. for 17 h. The reaction mixture was concentrated in vacuo and the residue was chromatographed on silica gel in heptane/EtOAc=1/1 (v/v) as eluent. Yield: 750 mg. MS-ESI: [M+H]+=594.4/596.4 The reaction mixture was concentrated in vacuo the residue was chromatographed on silica gel in heptane/EtOAc=1/1 (v/v) as eluent
Source ID: ord-b0d54090278f41f0b2d4d3ee9cbc9484Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: The reaction of 3-bromo-4-hydroxy-benzaldehyde (13.07 g) with 3-aminocrotonitril (5.34 g) and 5-propylcyclohexane-1,3-dione (10.02 g) was performed according to the method described in example 1a. Yield: 20.25 g. MS-ESI: [M+H]+=401/403
Source ID: ord-85b90a07053d47d69bbd7eeb014e16deConditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: The reaction of 3-bromo-4-hydroxy-benzaldehyde (13.07 g) with 3-aminocrotonitril (5.34 g) and 5-propylcyclohexane-1,3-dione (10.02 g) was performed according to the method described in example 1a. Yield: 20.25 g. MS-ESI: [M+H]+=401/403
Source ID: ord-85b90a07053d47d69bbd7eeb014e16dePubChem References
These sources are listed in the compound's public database record.
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