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C1CC2=CC=CC=C2C(C3=CC=CC=C31)C#NChemical Intermediate
Structures, identifiers and computed properties have been matched to the database record by CAS.
| Intermediates | tricyclo[9.4.0.03,8]pentadeca-1(15),3,5,7,11,13-hexaene-2-carbonitrile |
|---|---|
| IUPAC Name | — |
| CAS Number | 1729-63-1 |
| Database ID | 14091111 |
| Molecular Formula | — |
| Molecular Weight | — |
Product Information
tricyclo[9.4.0.03,8]pentadeca-1(15),3,5,7,11,13-hexaene-2-carbonitrile (CAS 1729-63-1) 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 14091111
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-1d5eb5b2409d486bbc98b8ba279b5375Conditions: temp:50.01; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: In a 50 ml roundbottom flask equipped with magnetical stirring, thermometer and addition funnel, sodium hydride (0.8 g, 0.02 mol, 60% dispersion in oil) was suspended in dry toluene under an atmosphere of nitrogen. A solution of 10,11-dihydro-5H-dibenzo[a,d]cycloheptene-5-carbonitrile (3.0 g, 0.014 mol, prepared in a similar way as described in J. Med. Chem., 6, (1963), 251) in dry toluene (15 ml) was added. The reaction mixture was heated to reflux temperature in 30 minutes and then heated at reflux temperature for 150 minutes. After cooling to about 50° C., a solution of 3-bromopropyl tetrahydropyranyl ether (4.5 g, 0.02 mol) in dry toluene (6 ml) was added dropwise. The reaction mixture was heated at reflux temperature for 5 h and then left stirring at room temperature overnight. After filtration of precipitated salts, the solution was washed with 1N HCl (100 ml), diluted with more toluene (100 ml) and finally washed with water. After drying (MgSO4), the organic phase was evaporated in vacuo affording 7.2 g (99%) of 5-(3-(tetrahydropyran-2-yloxy)-1-propyl)-10,11-dihydro-5H-dibenzo[a,d]cycloheptene-5-carbonitrile. In a 50 ml roundbottom flask equipped with magnetical stirring thermometer and addition funnel The reaction mixture was heated to reflux temperature in 30 minutes heated at reflux temperature for 150 minutes The reaction mixture was heated at reflux temperature for 5 h left After filtration of precipitated salts the solution was washed with 1N HCl (100 ml) diluted with more toluene (100 ml) finally washed with water After drying (MgSO4) the organic phase was evaporated in vacuo
Source ID: ord-dfa4422c36df4c33bc32416ad3ac3d34Conditions: temp:50.01; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: In a 50 ml roundbottom flask equipped with magnetical stirring, thermometer and addition funnel, sodium hydride (0.8 g, 0.02 mol, 60% dispersion in oil) was suspended in dry toluene under an atmosphere of nitrogen. A solution of 10,11-dihydro-5H-dibenzo[a,d]cycloheptene-5-carbonitrile (3.0 g, 0.014 mol, prepared in a similar way as described in J. Med. Chem., 6, (1963), 251) in dry toluene (15 ml) was added. The reaction mixture was heated to reflux temperature in 30 minutes and then heated at reflux temperature for 150 minutes. After cooling to about 50° C., a solution of 3-bromopropyl tetrahydropyranyl ether (4.5 g, 0.02 mol) in dry toluene (6 ml) was added dropwise. The reaction mixture was heated at reflux temperature for 5 h and then left stirring at room temperature overnight. After filtration of precipitated salts, the solution was washed with 1N HCl (100 ml), diluted with more toluene (100 ml) and finally washed with water. After drying (MgSO4), the organic phase was evaporated in vacuo affording 7.2 g (99% of 5-(3-(tetrahydropyran-2-yloxy)-1-propyl)-10,11-dihydro-5H-dibenzo[a,d]cycloheptene-5-carbonitrile. In a 50 ml roundbottom flask equipped with magnetical stirring thermometer and addition funnel The reaction mixture was heated to reflux temperature in 30 minutes heated at reflux temperature for 150 minutes The reaction mixture was heated at reflux temperature for 5 h left After filtration of precipitated salts the solution was washed with 1N HCl (100 ml) diluted with more toluene (100 ml) finally washed with water After drying (MgSO4) the organic phase was evaporated in vacuo
Source ID: ord-2046fe8fa1da43dc81c89b02d983cb7eConditions: temp:50.01; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: In a 50 ml roundbottom flask equipped with magnetical stirring, thermometer and addition funnel, sodium hydride (0.8 g, 0.02 mol, 60% dispersion in oil) was suspended in dry toluene under an atmosphere of nitrogen. A solution of 10,11 -dihydro-5H-dibenzo[a,d]cycloheptene-5-carbonitrile (3.0 g, 0.014 mol, prepared in a similar way as described in J. Med. Chem., 6, (1963), 251) in dry toluene (15 ml) was added. The reaction mixture was heated to reflux temperature in 30 minutes and then heated at reflux temperature for 150 minutes. After cooling to about 50° C., a solution of 3-bromopropyl tetrahydropyranyl ether (4.5 g, 0.02 mol) in dry toluene (6 ml) was added dropwise. The reaction mixture was heated at reflux temperature for 5 h and then left stirring at room temperature overnight. After filtration of precipitated salts, the solution was washed with 1N HCl (100 ml), diluted with more toluene (100 ml) and finally washed with water. After drying (MgSO4), the organic phase was evaporated in vacuo affording 7.2 g (99%) of 5-(3-(tetrahydropyran-2-yloxy)-1-propyl)-10,11-dihydro-5H-dibenzo-[a,d]cycloheptene-5-carbonitrile. In a 50 ml roundbottom flask equipped with magnetical stirring thermometer and addition funnel The reaction mixture was heated to reflux temperature in 30 minutes heated at reflux temperature for 150 minutes The reaction mixture was heated at reflux temperature for 5 h left After filtration of precipitated salts the solution was washed with 1N HCl (100 ml) diluted with more toluene (100 ml) finally washed with water After drying (MgSO4) the organic phase was evaporated in vacuo
Source ID: ord-b3ef0146bc1c45e9bd7756150881a8adConditions: temp:50.01; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: In a 50 ml roundbottom flask equipped with magnetical stirring, thermometer and addition funnel, sodium hydride (0.8 g, 0.02 mol, 60% dispersion in oil) was suspended in dry toluene under an atmosphere of nitrogen. A solution of 10,11-dihydro-5H-dibenzo[a,d]cycloheptene-5-carbonitrile (3.0 g 0.014 mol, prepared in a similar way as described in J. Med. Chem., 6, (1963), 251) in dry toluene (15 ml) was added. The reaction mixture was heated to reflux temperature in 30 minutes and then heated at reflux temperature for 150 minutes. After-cooling to about 50° C., a solution of 3-bromopropyl tetrahydropyranyl ether (4.5 g, 0.02 mol) in dry toluene (6 ml) was added dropwise. The reaction mixture was heated at reflux temperature for 5 h and then left stirring at room temperature overnight. After filtration of precipitated salts, the solution was washed with 1N HCl (100 ml), diluted with more toluene (100 ml) and finally washed with water. After drying (MgSO4), the organic phase was evaporated in vacuo affording 7.2 g (99%) of 5-(3-(tetrahydropyran-2-yloxy)-1propyl)-10,11dihydro-5H-dibenzo[a,d]cycloheptene-5-carbonitrile. In a 50 ml roundbottom flask equipped with magnetical stirring thermometer and addition funnel The reaction mixture was heated to reflux temperature in 30 minutes heated at reflux temperature for 150 minutes The reaction mixture was heated at reflux temperature for 5 h left After filtration of precipitated salts the solution was washed with 1N HCl (100 ml) diluted with more toluene (100 ml) finally washed with water After drying (MgSO4) the organic phase was evaporated in vacuo
Source ID: ord-972105fa7d9546f58782b62d10f27b9fConditions: temp:50.01; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: In a 50 ml roundbottom flask equipped with magnetical stirring, thermometer and addition funnel, sodium hydride (0.8 g, 0.02 mol, 60% dispersion in oil) was suspended in dry toluene under an atmosphere of nitrogen. A solution of 10,11-dihydro-5H-dibenzo[a,d]cycloheptene-5-carbonitrile (3.0 g, 0.014 mol, prepared in a similar way as described in J. Med. Chem., 6, (1963), 251) in dry toluene (15 ml) was added. The reaction mixture was heated to reflux temperature in 30 minutes and then heated at reflux temperature for 150 minutes. After cooling to about 50° C., a solution of 3-bromopropyl tetrahydropyranyl ether (4.5 g, 0.02 mol) in dry toluene (6 ml) was added dropwise. The reaction mixture was heated at reflux temperature for 5 h and then left stirring at room temperature overnight. After filtration of precipitated salts, the solution was washed with 1N HCl (100 ml), diluted with more toluene (100 ml) and finally washed with water. After drying (MgSO4), the organic phase was evaporated in vacuo affording 7.2 g (99%) of 5-(3-(tetrahydropyran-2-yloxy)-1-propyl)-10,11-dihydro-5H-dibenzo[a,d]cycloheptene-5-carbonitrile. In a 50 ml roundbottom flask equipped with magnetical stirring thermometer and addition funnel The reaction mixture was heated to reflux temperature in 30 minutes heated at reflux temperature for 150 minutes The reaction mixture was heated at reflux temperature for 5 h left After filtration of precipitated salts the solution was washed with 1N HCl (100 ml) diluted with more toluene (100 ml) finally washed with water After drying (MgSO4) the organic phase was evaporated in vacuo
Source ID: ord-dfa4422c36df4c33bc32416ad3ac3d34Conditions: temp:50.01; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: In a 50 ml roundbottom flask equipped with magnetical stirring, thermometer and addition funnel, sodium hydride (0.8 g, 0.02 mol, 60% dispersion in oil) was suspended in dry toluene under an atmosphere of nitrogen. A solution of 10,11-dihydro-5H-dibenzo[a,d]cycloheptene-5-carbonitrile (3.0 g, 0.014 mol, prepared in a similar way as described in J. Med. Chem., 6, (1963), 251) in dry toluene (15 ml) was added. The reaction mixture was heated to reflux temperature in 30 minutes and then heated at reflux temperature for 150 minutes. After cooling to about 50° C., a solution of 3-bromopropyl tetrahydropyranyl ether (4.5 g, 0.02 mol) in dry toluene (6 ml) was added dropwise. The reaction mixture was heated at reflux temperature for 5 h and then left stirring at room temperature overnight. After filtration of precipitated salts, the solution was washed with 1N HCl (100 ml), diluted with more toluene (100 ml) and finally washed with water. After drying (MgSO4), the organic phase was evaporated in vacuo affording 7.2 g (99%) of 5-(3-(tetrahydropyran-2-yloxy) -1-propyl)-10,11-dihydro-5H-dibenzo[a,d]cycloheptene-5-carbonitrile. In a 50 ml roundbottom flask equipped with magnetical stirring thermometer and addition funnel The reaction mixture was heated to reflux temperature in 30 minutes heated at reflux temperature for 150 minutes The reaction mixture was heated at reflux temperature for 5 h left After filtration of precipitated salts the solution was washed with 1N HCl (100 ml) diluted with more toluene (100 ml) finally washed with water After drying (MgSO4) the organic phase was evaporated in vacuo
Source ID: ord-4edbcb78496f41e8ac427063e56f3ba4Conditions: temp:50.01; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: In a 50 ml roundbottom flask equipped with magnetical stirring, thermometer and addition funnel, sodium hydride (0.8 g, 0.02 mol, 60% dispersion in oil) was suspended in dry toluene under an atmosphere of nitrogen. A solution of 10,11-dihydro-5H-dibenzo[a,d]cycloheptene-5-carbonitrile (3.0 g, 0.014 mol, prepared in a similar way as described in J. Med. Chem., 6, (1963), 251) in dry toluene (15 ml) was added. The reaction mixture was heated to reflux temperature in 30 minutes and then heated at reflux temperature for 150 minutes. After cooling to about 50° C., a solution of 3-bromopropyl tetrahydropyranyl ether (4.5 g, 0.02 mol) in dry toluene (6 ml) was added dropwise. The reaction mixture was heated at reflux temperature for 5 h and then left stirring at room temperature overnight. After filtration of precipitated salts, the solution was washed with 1N HCl (100 ml), diluted with more toluene (100 ml) and finally washed with water. After drying (MgSO4), the organic phase was evaporated in vacuo affording 7.2 g (99%) of 5-(3-(tetrahydropyran-2-yloxy)-1-propyl)-10,11-dihydro-5H-dibenzo-[a,d]cycloheptene-5-carbonitrile. In a 50 ml roundbottom flask equipped with magnetical stirring thermometer and addition funnel The reaction mixture was heated to reflux temperature in 30 minutes heated at reflux temperature for 150 minutes The reaction mixture was heated at reflux temperature for 5 h left After filtration of precipitated salts the solution was washed with 1N HCl (100 ml) diluted with more toluene (100 ml) finally washed with water After drying (MgSO4) the organic phase was evaporated in vacuo
Source ID: ord-8c76fbbd1f81481582efd35f0894b523Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: To a solution of 10,11-dihydro-5H-dibenzo[a,d]cycloheptene-5-carbonitrile (100) (Med. Chem. Res. 1, 401 (1991)) (1.0 g, 4.56 mmol) and N-(2-chloroethyl)-N,N-dimethylamine hydrochloride (0.72 g, 5 mmol) in benzene (20 mL) was added 8.8 mL of a 1.3M solution of lithium hexamethyldisilazide (11.4 mmol). The mixture was heated at reflux under nitrogen for 18 hr and the solvent then removed under vacuum. The residue was treated with water (20 mL) and extracted twice with methylene chloride (20 mL). The organic layers were combined, dried over sodium sulfate, and chromatographed directly on silica gel eluted with methylene chloride followed by 95:5:0.5, then 90:10:1 methylene chloride:methanol:ammonium hydroxide. The product fractions were evaporated to dryness in vacuo to give the title compound as a yellow oil. The mixture was heated at reflux under nitrogen for 18 hr the solvent then removed under vacuum The residue was treated with water (20 mL) extracted twice with methylene chloride (20 mL) dried over sodium sulfate chromatographed directly on silica gel eluted with methylene chloride The product fractions were evaporated to dryness in vacuo
Source ID: ord-376fe045a93544238ec480c2bfad6350Conditions: temp:0.01; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: Dissolved diisopropylamine (11.07 g, 0.109 mol) in 150 mL of dry THF and cooled to 0° C. under a nitrogen atmosphere. Added 40.1 mL (0.100 mol) of 2.5M n-butyl lithium in hexane dropwise via addition funnel. Stirred at 0° C. for 10 mins then cooled to -78° C. Added 10,11-dihydro-5H-dibenzo[a,d]cyclohepten-5-nitrile (20.00 g, 0.0912 mol) dissolved in 100 mL of dry THF dropwise via addition funnel. Stirred at -78° C. for 45 mins. Added allyl bromide (14.34 g, 0.119 mol) via syringe, and allowed reaction mixture to warm slowly to room temperature. Stirred at room temperature for 90 mins. Added 250 mL of 0.5N HCl, and separated layers. Extracted aqueous solution with ethyl acetate. Washed combined organic extracts with saturated NaCl, dried with MgSO4, filtered, and evaporated. Purified crude product by flash chromatography on silica gel eluting with 5% ethyl acetate-hexane then 10% ethyl acetate-hexane. Combined appropriate fractions and evaporated to give 23.65 g (100% yield) of 10,11-dihydro-5-(2-propenyl)-5H-dibenzo[a,d]cyclohepten-5-nitrile. dropwise via addition funnel then cooled to -78° C Stirred at -78° C. for 45 mins reaction mixture to warm slowly to room temperature Stirred at room temperature for 90 mins separated layers Washed dried with MgSO4 filtered evaporated Purified crude product by flash chromatography on silica gel eluting with 5% ethyl acetate-hexane evaporated
Source ID: ord-30208886545a4826985120116d021614Conditions: temp:50.01; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: In a 50 ml roundbottom flask equipped with magnetical stirring, thermometer and addition funnel, sodium hydride (0.8 g, 0.02 mol, 60% dispersion in oil) was suspended in dry toluene under an atmosphere of nitrogen. A solution of 10,11-dihydro-5H-dibenzo[a,d]cycloheptene-5-carbonitrile (3.0 g, 0.014 mol, prepared in a similar way as described in J. Med. Chem., 6 (1963), 251) in dry toluene (15 ml) was added. The reaction mixture was heated to reflux temperature in 30 minutes and then heated at reflux temperature for 150 minutes. After cooling to about 50° C., a solution of 3-bromopropyl tetrahydropyranyl ether (4.5 g, 0.02 mol) in dry toluene (6 ml) was added dropwise. The reaction mixture was heated at reflux temperature for 5 h and then left stirring at room temperature overnight. After filtration of precipitated salts, the solution was washed with 1N HCl (100 ml), diluted with more toluene (100 ml) and finally washed with water. After drying (MgSO4), the organic phase was evaporated in vacuo affording 7.2 g (99%) of 5-(3-(tetrahydropyran-2-yloxy)-1-propyl)-10,11-dihydro-5H-dibenzo[a,d]cycloheptene-5-carbonitrile. In a 50 ml roundbottom flask equipped with magnetical stirring thermometer and addition funnel The reaction mixture was heated to reflux temperature in 30 minutes heated at reflux temperature for 150 minutes The reaction mixture was heated at reflux temperature for 5 h left After filtration of precipitated salts the solution was washed with 1N HCl (100 ml) diluted with more toluene (100 ml) finally washed with water After drying (MgSO4) the organic phase was evaporated in vacuo
Source ID: ord-ebdacd97edd04487ab18ce967d34ff13Conditions: temp:50.01; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: In a 50 ml roundbottom flask equipped with magnetical stirring, thermometer and addition funnel, sodium hydride (0.8 g, 0.02 mol, 60% dispersion in oil) was suspended in dry toluene under an atmosphere of nitrogen. A solution of 10,11-dihydro-5H-dibenzo[a,d]cycloheptene-5-carbonitrile (3.0 g, 0.014 mol, prepared in a similar way as described in J. Med. Chem., 6, (1963), 251) in dry toluene (15 ml) was added. The reaction mixture was heated to reflux temperature in 30 minutes and then heated at reflux temperature for 150 minutes. After cooling to about 50° C., a solution of 3-bromopropyl tetrahydropyranyl ether (4.5 g, 0.02 mol) in dry toluene (6 ml) was added dropwise. The reaction mixture was heated at reflux temperature for 5 h and then left stirring at room temperature overnight. After filtration of precipitated salts, the solution was washed with 1N HCl (100 ml), diluted with more toluene (100 ml) and finally washed with water. After drying (MgSO4), the organic phase was evaporated in vacuo affording 7.2 g (99%) of 5-(3-(tetrahydropyran-2-yloxy)-1-propyl)-10,11-dihydro-5 H-dibenzo[a, d]cycloheptene-5-carbonitrile. In a 50 ml roundbottom flask equipped with magnetical stirring thermometer and addition funnel The reaction mixture was heated to reflux temperature in 30 minutes heated at reflux temperature for 150 minutes The reaction mixture was heated at reflux temperature for 5 h left After filtration of precipitated salts the solution was washed with 1N HCl (100 ml) diluted with more toluene (100 ml) finally washed with water After drying (MgSO4) the organic phase was evaporated in vacuo
Source ID: ord-e122e289c59d4ee6820938547a95b83cPubChem References
These sources are listed in the compound's public database record.
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