Structure of 1846-68-0
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| CAS No. : | 1846-68-0 |
| Formula : | C8H12O |
| M.W : | 124.18 |
| SMILES Code : | CCCCCC#CC=O |
| English Name : | Oct-2-ynal |
| MDL No. : | MFCD00134098 |
* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

| Yield | Reaction Conditions | Operation in experiment |
|---|---|---|
| 100% | With zirconium(IV) tetraisopropoxide 2-propanol; 4 Angstroem MS; 1,1'-bi-2-naphthol In isopropyl alcohol; toluene at 20℃; for 3h; | |
| 100% | With zirconium(IV) tetraisopropoxide 2-propanol; 1,1'-bi-2-naphthol In toluene at 20℃; for 0.5h; | |
| 96% | With MnBr(CO)2[NH(CH2CH2P(iPr)2)2]; hydrogen; sodium t-butanolate In toluene at 100℃; for 24h; Autoclave; chemoselective reaction; |
| 91% | With diisobutylaluminium hydride In tetrahydrofuran; toluene at -20℃; for 3h; | |
| With copper(II) sulfate; acetic acid; zinc | ||
| With hydrogen In tetrahydrofuran at 60℃; for 18h; Autoclave; chemoselective reaction; | ||
| With C20H29IrO2P2; hydrogen In tetrahydrofuran at 20℃; for 18h; Inert atmosphere; Glovebox; | ||
| With sodium borodeuteride; ethanol at 0℃; for 0.5h; | 6 Synthesis of II-D-Linoleic Acid To a solution of oct-2-ynal [See Corey, E. J.; Schmidt, G. Tetrahedron Lett. 1979, 20, 399; Meyer, M. P.; Klinman, J. P. Tetrahedron Lett. 2008, 49, 3600] ((612); 1.00 g, 8.1 mmol)) in ethanol (15 ml) cooled to 0° C., 0.11 g (2.6 mmol) of NaBD4 was added in portions over 5 min. Upon addition, the solution was stirred for another 30 min, diluted with water (100 ml), and then extracted with Et2O (4×20 ml). The combined organic fractions were washed with saturated NaCl, dried (Na2SO4), and the solvent was removed at reduced pressure. Alcohol 613 (0.85 g, 83%) was purified by column chromatography (silica gel, petroleum ether:EtOAc (15:1)). 1H NMR (400 MHz, CDCl3) δ 0.88 (t, J=7.0 Hz, 3H, CH3), 1.32 (m, 4H, CH2), 1.49 (quint, J=7.0 Hz, 2H, CH2), 1.81 (br s, 1H, OH), 2.19 (td, J=7.0 Hz, 2.0 Hz, 2H, CH2), 4.22 (m, 1H, CHD). |

| Yield | Reaction Conditions | Operation in experiment |
|---|---|---|
| 86% | With Iron(III) nitrate nonahydrate; TEMPOL; oxygen; sodium chloride In dichloromethane at 20℃; for 24h; | 1 Under an oxygen atmosphere, Fe(NO3)3·9H2O(4 g, 10 mmol), 4-OH-TEMPO (1.7 g, 10 mmol), NaCl (0.58 g, 10 mmol), 2-octyne-1-ol (12.6 g, 100 mmol), and dichloromethane (300 mL) were added sequentially to the reaction flask. The mixture was stirred at room temperature for 24 hours until the reaction was complete. The organic solvent was removed by vacuum distillation, and the crude product was separated by column chromatography to obtain 10.7 g of 2-octynealdehyde, with a yield of 86%. |
| 84% | With Oxone; potassium 2-iodo-5-methylbenzenesulfonate In acetonitrile at 70℃; for 3h; chemoselective reaction; | |
| 80% | With oxalyl dichloride; dimethyl sulfoxide; triethylamine In dichloromethane at -78 - 25℃; for 0.583333h; |
| 72% | With manganese(IV) oxide | |
| 65% | With potassium osmate(VI) dihydrate; potassium carbonate; potassium hexacyanoferrate(III) In water; acetonitrile at 60℃; for 18h; chemoselective reaction; | |
| 64% | With pyridinium chlorochromate | |
| With Py*HClCrO3 In dichloromethane | ||
| With dipyridinium dichromate In dichloromethane | ||
| With pyridinium chlorochromate | ||
| With manganese(IV) oxide In dichloromethane | ||
| With Celite; pyridinium chlorochromate In dichloromethane for 1h; | ||
| With manganese(IV) oxide In dichloromethane at 20℃; | ||
| 14 %Chromat. | With acetaldehyde at 30℃; for 24h; aq. phosphate buffer; Microbiological reaction; Combinatorial reaction / High throughput screening (HTS); chemoselective reaction; | |
| With Dess-Martin periodane In N,N-dimethyl-formamide at 0 - 20℃; Inert atmosphere; | ||
| With manganese(IV) oxide In dichloromethane | ||
| With [2,2]bipyridinyl; 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; oxygen; copper(ll) bromide In acetonitrile for 0.0833333h; | ||
| 94 % | With 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical In acetonitrile at 20℃; | 2.3 General Procedure for HeterogeneousCopper-Catalyzed Aerobic Oxidation of Primary Alcohols General procedure: Under an air atmosphere, a reaction tube was charged withDpu-SBA-15-CuI (58mg, 0.03mmol), primary alcohol(1mmol), TEMPO (6.3mg, 0.04mmol), and MeCN (3mL).The reaction mixture was stirred at room temperature for 6 or 24h depending on the substrate. After completion of the reaction (monitored by TLC), the copper catalyst was separatedby centrifugation and washed with acetone (2 × 3mL)and dried under vacuum at 90 C for 1h and reused in thenext cycle. The reaction solution was evaporated in vacuo and the residue was then purified by flash column chromatographyon silica gel (petroleum ether/ethyl acetate) toafford the desired aldehyde 2. |
| 94 % | With 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical In acetonitrile at 20℃; | 2.3 General Procedure for HeterogeneousCopper-Catalyzed Aerobic Oxidation of Primary Alcohols General procedure: Under an air atmosphere, a reaction tube was charged withDpu-SBA-15-CuI (58mg, 0.03mmol), primary alcohol(1mmol), TEMPO (6.3mg, 0.04mmol), and MeCN (3mL).The reaction mixture was stirred at room temperature for 6 or 24h depending on the substrate. After completion of the reaction (monitored by TLC), the copper catalyst was separatedby centrifugation and washed with acetone (2 × 3mL)and dried under vacuum at 90 C for 1h and reused in thenext cycle. The reaction solution was evaporated in vacuo and the residue was then purified by flash column chromatographyon silica gel (petroleum ether/ethyl acetate) toafford the desired aldehyde 2. |
| With oxygen; 2,3-dicyano-5,6-dichloro-p-benzoquinone; sodium nitrite In dichloromethane; acetic acid at 20℃; | ||
| With 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione In dimethyl sulfoxide Heating; | 1-8.1 <First Step> 2-octyn-1-ol (0.15 g, 1.19 mmol) and dimethyl sulfoxide (DMSO, 2 mL) were added to a 5 mL eggplant flask, and 2-iodoxybenzoic acid (IBX, 0.5 g, 1.79 mmol) was added. Heating reflux stirring was performed for 5.0 hours, and the loss of the raw material was confirmed by gas-liquid chromatography. After cooling, hexane (2 mL) was added to the system, and then suction filtration was performed, and the filtrate was concentrated under reduced pressure to obtain a crude purified 2-octynal (0.15 g). This was used in the next second step without further purification. | |
| With 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione In dimethyl sulfoxide Reflux; | 1-8.1 <First Step> 2-octyn-1-ol (0.15 g, 1.19 mmol) and dimethyl sulfoxide (DMSO, 2 mL) were added to a 5 mL eggplant flask, and 2-iodoxybenzoic acid (IBX, 0.5 g, 1.79 mmol) was added. Heating reflux stirring was performed for 5.0 hours, and the loss of the raw material was confirmed by gas-liquid chromatography. After cooling, hexane (2 mL) was added to the system, and then suction filtration was performed, and the filtrate was concentrated under reduced pressure to obtain a crude purified 2-octynal (0.15 g). This was used in the next second step without further purification. | |
| 41 %Spectr. | With oxygen; vanadium(V)-(μ-O)2-perfluoropinacolate In N,N-dimethyl acetamide at 60℃; Molecular sieve; chemoselective reaction; |

| Yield | Reaction Conditions | Operation in experiment |
|---|---|---|
| 96% | With periodic acid; pyridinium chlorochromate In acetonitrile for 1.5h; | |
| 82% | With Iron(III) nitrate nonahydrate; oxygen; sodium 2,2,2-trifluoroacetate In ethyl acetate at 25℃; for 16h; | Typical procedure for the oxidation reaction (Table 1, entry 14). General procedure: In a test tube, trans-2-decenal (167 mg, 1.0 mmol) was added to a suspension of Fe(NO3)3·9H2O(4.1 mg, 0.010 mmol) and CF3COONa (28 mg, 0.20 mmol) in EtOAc (0.50 mL). O2 balloon (1atm) was attached at top of the test tube, and inner atmosphere was replaced by O2. After stirring16 h at 25 °C, EtOAc (3 mL) and 1M HCl aq. (1 mL) were added and resulting biphasic mixture wasstirred for 1 min. Organic phase was separated, and water phase was extracted by EtOAc (3 mL X2). To the collected organic phase was then added measured amount of biphenyl (as an internalstandard for NMR analysis). The conversion of substrate and the yield of products weredetermined by NMR analysis (400 MHz, CDCl3, 25 °C). Products were identified by comparison tothe NMR signals of authentic samples. The same reaction was performed twice for each reaction. |
| 74% | With copper acetylacetonate; N-hydroxyphthalimide; oxygen In acetonitrile at 70℃; for 20h; |
| Yield | Reaction Conditions | Operation in experiment |
|---|---|---|
| 94% | Stage #1: chloromethyl phenyl sulfoxide With lithium diisopropyl amide In tetrahydrofuran at -78℃; Stage #2: oct-2-ynal |
| Yield | Reaction Conditions | Operation in experiment |
|---|---|---|
| Multi-step reaction with 3 steps 2: LiNH2 / liquid ammonia 3: H2 / Raney-Ni |
| Yield | Reaction Conditions | Operation in experiment |
|---|---|---|
| 86% | With potassium carbonate; In dichloromethane; at 20℃; for 3h; | General procedure: A mixture of ynal 1 (0.5 mmol), amidine hydrochloride 2 (0.6 mmol), K2CO3(1.0 mmol), and MCM-41-PPh3-AuCl (41 mg, 0.015 mmol) in DCM (3mL) was stirred at room temperature for 3 h (TLC monitored). The resulting mixture was then diluted with ethyl acetate (15 mL) and filtered. The gold catalyst was washed with distilled water(5 mL), and dry ethanol (25mL) and reused in the next run. The filtrate was concentrated under reduced pressure and the residue was purified by chromatography on silicagel (eluent: petroleum ether/ethyl acetate) to afford the desired product 3. |
| Yield | Reaction Conditions | Operation in experiment |
|---|---|---|
| 82% | With potassium carbonate; In dichloromethane; at 20℃; for 3h; | General procedure: A mixture of ynal 1 (0.5 mmol), amidine hydrochloride 2 (0.6 mmol), K2CO3(1.0 mmol), and MCM-41-PPh3-AuCl (41 mg, 0.015 mmol) in DCM (3mL) was stirred at room temperature for 3 h (TLC monitored). The resulting mixture was then diluted with ethyl acetate (15 mL) and filtered. The gold catalyst was washed with distilled water(5 mL), and dry ethanol (25mL) and reused in the next run. The filtrate was concentrated under reduced pressure and the residue was purified by chromatography on silicagel (eluent: petroleum ether/ethyl acetate) to afford the desired product 3. |
| Yield | Reaction Conditions | Operation in experiment |
|---|---|---|
| 80% | With (triphenylphosphine)gold(I) chloride; potassium carbonate In dichloromethane at 20℃; for 3h; |
| Yield | Reaction Conditions | Operation in experiment |
|---|---|---|
| With acetic acid In dichloromethane at 25℃; for 0.5h; | Synthesis of 3-benzoylimidazo[1,2-a]pyridine (3a); typical procedure General procedure: A mixture of 3-phenylpropiolaldehyde (1a) (0.5 mmol), 2-aminopyridine(2a) (0.7 mmol) and HOAc (5 mol%) was stirred in dry CH2Cl2 (3 mL) for30 min at 25 C. Then MCM-41-PPh3-AuCl (39.5 mg, 0.015 mmol) and AgSbF6 (5.2 mg, 0.015 mmol) were added and this mixture was stirred at 25 C for 12 h under air. After completion of the reaction, the mixture was diluted with ethyl acetate (15 mL) and filtered. The gold catalyst was washed with 25-28 wt% NH3·H2O (2 × 5 mL), distilled water (2 ×5 mL) and acetone (2×5 mL) and air-dried if to be reused. The filtrate was quenched with water (10 mL) and the aqueous phase was extracted with ethyl acetate (2 × 10 mL). The combined extract was dried over anhydrous MgSO4. After removal of the solvent, the residue waspurified by column chromatography using petroleum ether (60-90°C)/ethyl acetate (6:1) as eluent to afford the desired product 3a. |
| Yield | Reaction Conditions | Operation in experiment |
|---|---|---|
| 90% | With potassium carbonate In tetrahydrofuran at 65℃; for 10h; Green chemistry; regioselective reaction; | General procedure for the synthesis of 2-pyridones General procedure: A mixture of β-keto amide (0.2 mmol), ynal (0.2 mmol) and K2CO3 (30 mol%) in THF (1.0 mL) was placed in a test tube (10 mL) equipped with a magnetic stirring bar. The mixture was stirred at 65 °C for 10 h. After the reaction was finished, water (5 mL) was added and the solution was extracted with ethyl acetate (3×5 mL), the combined extract was dried with anhydrous MgSO4. Solvent was removed, and the residue was separated by column chromatography to give the pure sample. |
| Yield | Reaction Conditions | Operation in experiment |
|---|---|---|
| 80% | With potassium carbonate In dichloromethane at 20℃; for 3h; | General procedure for heterogeneous Au(I)-catalyzed synthesis of pyrimidines General procedure: A mixture of ynal 1 (0.5 mmol), amidine hydrochloride 2 (0.6 mmol), K2CO3(1.0 mmol), and MCM-41-PPh3-AuCl (41 mg, 0.015 mmol) in DCM (3mL) was stirred at room temperature for 3 h (TLC monitored). The resulting mixture was then diluted with ethyl acetate (15 mL) and filtered. The gold catalyst was washed with distilled water(5 mL), and dry ethanol (25mL) and reused in the next run. The filtrate was concentrated under reduced pressure and the residue was purified by chromatography on silicagel (eluent: petroleum ether/ethyl acetate) to afford the desired product 3. |