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CAS No. : | 112-31-2 | MDL No. : | MFCD00007031 |
Formula : | C10H20O | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | KSMVZQYAVGTKIV-UHFFFAOYSA-N |
M.W : | 156.27 | Pubchem ID : | 8175 |
Synonyms : |
Decyl aldehyde;Capraldehyde;Decylic aldehyde.;Caprinic aldehyde;Caprinaldehyde;Capric aldehyde;1-Decyl aldehyde;1-Decanal;Decaldehyde;Decanaldehyde
|
Num. heavy atoms : | 11 |
Num. arom. heavy atoms : | 0 |
Fraction Csp3 : | 0.9 |
Num. rotatable bonds : | 8 |
Num. H-bond acceptors : | 1.0 |
Num. H-bond donors : | 0.0 |
Molar Refractivity : | 50.38 |
TPSA : | 17.07 Ų |
GI absorption : | High |
BBB permeant : | Yes |
P-gp substrate : | No |
CYP1A2 inhibitor : | No |
CYP2C19 inhibitor : | No |
CYP2C9 inhibitor : | No |
CYP2D6 inhibitor : | No |
CYP3A4 inhibitor : | No |
Log Kp (skin permeation) : | -4.56 cm/s |
Log Po/w (iLOGP) : | 2.72 |
Log Po/w (XLOGP3) : | 3.8 |
Log Po/w (WLOGP) : | 3.33 |
Log Po/w (MLOGP) : | 2.7 |
Log Po/w (SILICOS-IT) : | 3.32 |
Consensus Log Po/w : | 3.17 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 2.0 |
Bioavailability Score : | 0.55 |
Log S (ESOL) : | -2.67 |
Solubility : | 0.33 mg/ml ; 0.00211 mol/l |
Class : | Soluble |
Log S (Ali) : | -3.85 |
Solubility : | 0.0219 mg/ml ; 0.00014 mol/l |
Class : | Soluble |
Log S (SILICOS-IT) : | -3.44 |
Solubility : | 0.0567 mg/ml ; 0.000363 mol/l |
Class : | Soluble |
PAINS : | 0.0 alert |
Brenk : | 1.0 alert |
Leadlikeness : | 3.0 |
Synthetic accessibility : | 1.62 |
Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P261-P305+P351+P338 | UN#: | N/A |
Hazard Statements: | H302-H315-H319-H335 | Packing Group: | N/A |
GHS Pictogram: |
* 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 |
---|---|---|
98% | Stage #1: caprinaldehyde; propargyl bromide With iron(III) chloride In tetrahydrofuran at 10 - 15℃; for 0.166667h; Stage #2: With zinc In tetrahydrofuran at 20℃; for 16h; regioselective reaction; | General procedure of propargylation of aldehydes General procedure: A mixture of aldehyde 3 (0.01 mol), propargyl bromide (3.57 g, 0.03 mol), and FeCl3 (4.86 g, 0.03 mol for iron mediated reaction) or SnCl2-2H2O (6.75 g, 0.03 mol for tin mediated reaction) or CuCl2-2H2O (5.1 g, 0.03 mol for copper mediated reaction) in THF (100 mL) was stirred thoroughly in a water bath at around 10-15 °C (maintained by addition of pieces of ice). After stirring the mixture for 10 min. zinc dust (Aldrich make, 1.95 g, 0.03 mol) was added in a few portions over a period of 15 min. The mixture was stirred at the ambient temperature for the period as shown in Table. It was then treated successively with diethyl ether (100 mL) and water (50 mL), stirred for 10 min more and then filtered. The filtrate was treated with 2% aqueous HCl to dissolve a little amount of suspended particles. The organic layer was separated. The aqueous layer was extracted with EtOAc. The combined organic layer was washed with water, brine, and then dried. Solvent removal under reduced pressure afforded the crude residue which was passed through a short silica gel pad eluting with 20% EtOAc in petroleum ether to obtain a fraction containing the mixture of homopropargyl (4) and allenyl (5) alcohols only. The eluent was concentrated under reduced pressure for its NMR analysis. |
96% | With 2,4,6-trimethyl-pyridine; bis(cyclopentadienyl)titanium dichloride; manganese; chloro-trimethyl-silane In tetrahydrofuran for 7h; Inert atmosphere; | |
94% | With (3S,3aS,4S,4aS,6S,8aR,8bR,11S)-6,11-dihydroxy-3-methyl-12-methylene-2-oxo-4a,6-ethano-3,8b-prop-1-enoperhydroindeno[1,2-b]furan-4-carboxylic acid; potassium iodide; lithium chloride In tetrahydrofuran Heating; |
61% | With ethylene dibromide; zinc In tetrahydrofuran at 20℃; for 43h; Inert atmosphere; | |
With tetrahydrofuran; amalgamated zinc | ||
With n-butyl magnesium bromide; tributylstibine Yield given. Multistep reaction; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
74% | With ammonium cerium (IV) nitrate; lithium bromide; In neat liquid; at 35 - 40℃; for 3.5h; | General procedure: Into glassy pear-shaped two-necked reactor (volume 25 mL) equipped with thermometer and reflux condenser CAN (1.1 g, 2.0 mmol) and LiBr (26 mg, 0.3 mmol) were added and stirred. After that methanol (64 mg, 2.0 mmol) was added, the reaction mixture was stirred. Then aldehyde 1a-f (86-156 mg, 1.0 mmol) was added, the reaction mixture was stirred and left for 3.5 hours at 35-40 C. After that the reaction mixture was cooled, diluted with water (10-15 mL) and extracted with diethyl ether (2*10-15 mL). The combined organic phases were washed with aqueous solution of NaHCO3 (10 mL) and water (10 mL) and dried over MgSO4. The solvent was removed with the use of rotary evaporator (water bath temperature 25-28 C). The conversion of 1a-f and the yield of 3a-f were determined by GLC using methyl pentanoate and methyl decanoate as internal standards. The preparative isolation of alpha-bromoesters 3a-f was performed using gradient silica gel column chromatography with petroleum ether (b.p. 40-70C): chloroform, 10-1:1, as the eluent. Preparative yield of 3a-f was 70-76%. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
34% | In ethanol | 2 1,10-Bis-n-decyl-1,5,10-triazadecane, trihydrochloride (1b) EXAMPLE 2 1,10-Bis-n-decyl-1,5,10-triazadecane, trihydrochloride (1b) To an EtOH (95%, 50 mL) solution of spermidine (7.3 g, 50 mmol) immersed in a water bath (20°-5°) was added dropwise, with stirring, n-decyl aldehyde (17.2 g, 110 mmol). The reaction solution was stored under argon overnight before 5% Pd/C (1 g, cat.) was added as an aqueous slurry. Hydrogenation (72 hrs) and recrystallization from hot, acidic, aq. EtOH gave (1b) (9.2 g, 34%): mp 292°-5°d; H-NMR (TFA) 0.8-2.3 (complex m, 44H,+ --CH2 (CH2)8 CH3 and --NH2 --CH2 CH2 --), 3.0-4.0 (broad m, 12H, --NH2 CH2 --), 7.0-8.7 (broad m, 6H, --NH2 --). Anal. Calcd for C27 H59 N3.3HCl; C, 60.60; H, 11.68; N, 7.85; Cl, 19.87. Found: C, 60.97; H, 11.62; N, 7.63; Cl, 19.62. |
With hydrogenchloride; hydrogen 1) 95percent EtOH, 15 h, 2) 95percent EtOH, 20 to 25 deg C, 1 to 3 atm, 72 h; Yield given. Multistep reaction; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
91% | Stage #1: caprinaldehyde; malonic acid With 4-methyl-morpholine at 80℃; for 7h; Inert atmosphere; Stage #2: With sulfuric acid In water at 20℃; for 0.166667h; | 4.1. General procedure 1: decarboxylative Knoevenagel reaction General procedure: According to the procedure reported by Zhang et al. [17], a solutionof malonic acid and the appropriate aldehyde in N-methylmorpholine (NMM, 2.3 mL) was heated to 80 °C for 7 h. Sulfuric acid11% aqueous solution (10 mL) was added to the reaction mixture at RT and stirring was continued for 10 min. The mixture was extracted with CH2Cl2 (3 x 30 mL) and the organic layers were washed with H2O, dried (MgSO4), filtered and concentrated in vacuo to give a colorless gel which was used without further purification. |
90% | With silica gel for 0.0833333h; Irradiation; | |
87% | With piperdinium acetate In dimethyl sulfoxide at 100℃; |
85% | With piperidine; acetic acid at 100℃; for 8h; Inert atmosphere; | |
76% | With piperdinium acetate In dimethyl sulfoxide at 100℃; | (E)-Alken-3-enoic Acids 1d-f; General Procedure General procedure: To a 250-mL round-bottomed flask equipped with a condenser and a bubbler connected to the exit of the condenser was added a solution of malonic acid (26 g, 0.25 mol), piperidinium acetate [from piperidine (0.22 g) and AcOH (0.15 g, 2.5 mmol)], and aliphatic aldehyde (0.125 mol) in DMSO (100 mL). The mixture was stirred at 40 °C for 2 h. Then, the solution was heated in an oil bath at 100 °C. A rapid evolution of CO2 was observed. Heating was maintained until the evolution of CO2 ceased. The solution was cooled to r.t., poured into cold water (200 mL) and extracted with Et2O. The combined extracts were washed with water and brine, dried (anhyd MgSO4), and evaporated under reduced pressure. The residue was distilled under vacuum to give the (E)-alk-3-enoic acid. |
75% | With piperidine; acetic acid In dimethyl sulfoxide at 40 - 100℃; for 7h; | 3 (3) Preparation of (E) -3-dodecenoic acid Malonic acid (52 g, 0.5 mol) was added to a flask equipped with a thermometer,Magnetic stirrer,Reflux condenser in a 500 mL four-necked flask,Then, the solvent dimethylsulfoxide (100 mL) was added,Piperidine (1 mL),Acetic acid (0.6 mL, 10 mmol) and decanal (47 mL,0.25 mol),Oil bath heating,Stirring at 40 ° C for 2 h,And then heated to 100 ° C for about 5 hours.After cooling,The reaction solution was poured into 200 mL of ice water,Extracted with ether (50 mL x 4),Combine organic phase,Washed with saturated brine,Dried over anhydrous magnesium sulfate.The ether was removed by steaming,The residue was distilled under reduced pressure,The fractions of 113-119 & lt; 0 & gt; C / 14 Pa were then collected,(E) -3-nonenoic acid (37.1 g) in a yield of 75%. |
70% | With piperidine In xylene for 4h; Heating; | |
63% | With piperidine In xylene Heating; | |
7.0 g | With piperidine In xylene for 4h; Heating; azeotropic removal of water; | |
1.) DMSO, r.t., 20 min, 2.) DMSO, 100 deg C, 4 h; Yield given. Multistep reaction; | ||
With piperdinium acetate In dimethyl sulfoxide at 40 - 100℃; for 3.5h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
68.09% | With nanosolid superacid sulfonated carbon; In cyclohexanone; N,N-dimethyl-formamide; for 3h;Reflux; | General procedure: A solution of <strong>[20605-01-0]diethyl 2,2-bis(hydroxymethyl) malonate</strong>(12 mmol), 1 (10 mmol) and sulfonated carbon(1.0 g) were heated to reflux in a mixture of N,N-dimethylformamide(10 mL) and cyclohexane (6 mL)under stirring for 3 h. After cooling to room temperature,the solution was filtered and the solvent was removed in vacuo, the residue was dissolved in EtOAc (15 mL),washed with saturated brine (10 mL × 2) and water(10 mL×2), dried over anhydrous Na2SO4. The solventwas filtered and concentrated to give 2a-2d as colorless oil. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
97% | With diethylzinc In tetrahydrofuran; hexane Heating; | |
77% | With samarium diiodide In tetrahydrofuran; N,N,N,N,N,N-hexamethylphosphoric triamide Ambient temperature; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
1: 9 % Chromat. 2: 74 % Chromat. 3: 6 % Chromat. | With bis(cyclopentadienyl)dihydrozirconium; cyclohexanone; nickel dichloride at 130℃; for 8h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
94% | With hydroxylamine hydrochloride; sodium iodide In acetonitrile for 1.41667h; Heating; | |
93% | With trifluorormethanesulfonic acid; O-benzenesulfonyl-acetohydroxamic acid ethyl ester In dichloromethane at 23℃; for 24h; Inert atmosphere; | |
89% | With hydroxylamine hydrochloride at 105℃; for 0.0333333h; microwave irradiation; |
87% | With XY-zeolite; hydroxylamine hydrochloride for 0.0333333h; microwave irradiation; | |
86% | With hydroxylamine hydrochloride In o-xylene at 133℃; for 4h; | |
78% | With aluminum oxide; potassium fluoride; hydroxylamine hydrochloride In N,N-dimethyl-formamide at 100℃; for 8.5h; | |
68% | With hydroxyammonium sulfate; iron(III) trifluoromethanesulfonate In toluene at 125℃; for 24h; Inert atmosphere; Green chemistry; | |
62% | With ammonium acetate; acetic acid; 4-acetylamino-2,2,6,6-tetramethylpiperidine-1-oxoammonium tetrafluoroborate at 70℃; for 12h; Inert atmosphere; | General procedures for 4-AcNH-TEMPO+BF4- mediated nitriles synthesis General procedure: A 15 mm flame-dried test tube, which was equipped with a magnetic stir bar and charged with aldehyde (0.3 mmol, in case of solid), 4-AcNH-TEMPO+BF4- (2.0 equiv, 0.6 mmol), and NH4OAc (4.0 equiv, 1.2 mmol), was evacuated and backfilled with nitrogen (this process was repeated 3 times). After 0.3 mL of AcOH was added, aldehyde (0.3 mmol, in case of liquid), and AcOH (0.3 mL) were added in sequence. The reaction mixture was stirred for 12 h at 70 oC under N2 balloon, and then cooled to room temperature. The reaction was diluted by adding EtOAc and washed 4 M HCl aqueous solution. Two layers were separated, and the aqueous layer was extracted with EtOAc. The combined organic layers were washed with Na2CO3 aqueous solution. The organic layer was dried over MgSO4, filtered, and concentrated to a volume of approximately 20 mL by evaporator. To eliminate remaining aldehyde, aqueous 2 M Na2S2O5 aqueous solution (20 mL) was added to the organic layer and stirred for 2 hours. Two layers were separated, and the organic layer was dried over MgSO4, filtered, and concentrated in vacuo. The residue was purified by column chromatography to give nitrile products. |
60% | With iron(III) trifluoromethanesulfonate; nitromethane; trifluoromethylsulfonic anhydride; acetic acid; triethylamine In formic acid at 30 - 120℃; | 47 Example 47 Decanonitrile Take a reaction tube, add 500-600mg (0.5mL) of nitromethane, 0.5mL of acetic acid, 150-200mg (0.6mmol) of trifluoromethanesulfonic anhydride, 30-60mg (0.75mmol) of formic acid, and stir at 80-120. hour. Then add decanal 30-60mg (0.3mmol), Fe(OTf)3 10-20mg (0.03mmol), triethylamine 50-70mg (0.6mmol), stir at 30-70 for 1-72 hour. After the reaction, 10 mL of sodium hydroxide solution was added to quench the reaction, extracted with ethyl acetate 3 times, the organic phase was washed with 5 mL of brine, and the organic phases were combined and separated by column chromatography to obtain 27.6 mg of 2-phenyl, decanonitrile, with a yield of 60 %. |
60% | With formic acid; iron(III) trifluoromethanesulfonate; nitromethane; trifluoromethylsulfonic anhydride; triethylamine In acetic acid at 60℃; for 12h; | |
55% | With Nitroethane; sodium acetate In acetic acid for 4h; Heating; | |
52% | With pyridine; hydroxylamine hydrochloride 1.) 10 min, 2.) toluene, 4 h, reflux; | |
With ammonia; oxygen In tetrahydrofuran at 130℃; for 16h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
95% | With trimethylamine-N-oxide In dimethyl sulfoxide for 24h; Ambient temperature; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
78% | With triiron dodecarbonyl at 25 - 30℃; for 2h; Irradiation; | |
75% | With diiron nonacarbonyl In benzene at 40 - 50℃; for 2h; | |
84 % Spectr. | In acetone at 70℃; for 4h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
97% | With thexylchloroborane-Me2SO4 In dichloromethane for 0.25h; Ambient temperature; | |
94% | With thexylbromoborane dimethyl sulfide complex In carbon disulfide; dichloromethane at -20 - 20℃; for 1h; | |
92% | With 9-borabicyclo[3.3.1]nonane dimer; lithium dihydrido borata-bicyclo[3.3.0]nonane In tetrahydrofuran for 1h; Ambient temperature; |
75% | With [2,2]bipyridinyl; (1,2-dimethoxyethane)dichloronickel(II); H2SiEt2; 2,2-dimethylpropanoic anhydride In toluene at 45℃; for 5h; Schlenk technique; Inert atmosphere; | 1 Example 1Preparation of Compound A Add n-decanoic acid (86mg, 0.50mmol) to a dry 10mL Schlenk reaction tube,Then add L1 (3.9mg, 0.025mmol) and NiCl2 · DME (1.1mg, 0.005mmol) in this order. Under the protection of argon,Toluene (1.0 mL) was added, pivalic anhydride (120 μL, 0.60 mmol), H2SiEt2 (19 μL, 0.15 mmol), and reacted at 45 ° C. for 5 h.After the reaction is completed, extract,The solvent was removed under reduced pressure and separated by column chromatography (petroleum ether / ethyl acetate = 13/1, volume ratio)The target product A was obtained. Experimental data of this compound:Colorlessliquid, isolated yield 75%, |
70% | With Ph3P*HClO4; triphenylphosphine In dichloromethane at -30℃; constant-current electrolysis; | |
With 9-borabicyclo[3.3.1]nonane dimer; tert.-butyl lithium 1.) THF, room temp.; 2.) THF, pentane, -20 deg C, 10 min and room temp., 1 h; Yield given. Multistep reaction; | ||
With thexylchloroborane*methyl sulfide In dichloromethane for 0.25h; Ambient temperature; | ||
With ThxBHO-s-Bu In tetrahydrofuran at 25℃; for 96h; Yield given; | ||
Multi-step reaction with 2 steps 1: 85.3 percent / toluene / 110 °C 2: 1.) Na, 2.) aq. oxalic acid / 1.) C2H5OH, 0 deg C to 5 deg C, 40 min, 2.) reflux | ||
Multi-step reaction with 3 steps 2: methanesulfonic acid, Et4NOTs, lead cathode, platinium anode / dimethylformamide / electroreduction 3: 82 percent / H3O(1+) | ||
Multi-step reaction with 2 steps 1: 69 percent / dicyclohexylcarbodi-imide / ethyl acetate / 24 h / Ambient temperature 2: 72 percent / di-isobutylaluminium hydride / hexane; CH2Cl2 / -50 °C | ||
Multi-step reaction with 2 steps 1: tris(pentafluorophenyl)borate / benzene-d6 / 1 h / 23 °C / Glovebox; Schlenk technique 2: hydrogenchloride; water / tetrahydrofuran / 3 h / 20 °C / Glovebox; Schlenk technique | ||
Multi-step reaction with 3 steps 1: thionyl chloride; N,N-dimethyl-formamide / toluene / 20 °C 2: triethylamine / dichloromethane / 0 - 20 °C 3: zirconocene dichloride; lithium tri-t-butoxyaluminum hydride / tetrahydrofuran / 0.03 h / 20 °C / Inert atmosphere |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
95% | With gallium; 1-n-butyl-3-methylimidazolim bromide at 20℃; for 5h; | |
91% | With 2,4,6-trimethyl-pyridine; chloro-trimethyl-silane; bis(cyclopentadienyl)titanium (III) chloride In tetrahydrofuran at 20℃; for 6h; Inert atmosphere; | |
88% | With tin(ll) chloride In water at 20℃; for 8h; |
87% | Stage #1: caprinaldehyde; allyl bromide With tin(II) chloride dihdyrate; aluminium In tetrahydrofuran at 20℃; for 0.0833333h; Stage #2: With water In tetrahydrofuran at 15℃; for 0.25h; | General procedure of allylation reaction: General procedure: To a stirred mixture of aldehyde 3(5 mmol), metal salt (SnCl22H2O, 7-8 mmol) and allyl or crotyl bromide(10 mmol) in THF (20 mL) was added aluminium foil (270 mg, 10 mmol, cut into thin pieces). The mixture was stirred for 5 min. at room temperature. A few drops of water were added to the reaction mixture which became considerably warm. It was then cooled (15 C) in a water bath containing ice water and then stirred for the period mentioned in Tables 1 and 2. The substrate aldehyde (3) disappeared (vide TLC) in the majority of the cases. The reaction mixture was treated with diethyl ether (20 mL) and stirred for 10 min more. It was then filtered through a short pad of silica gel and washed with EtOAc. The organic layer was successively washed with 5% dilute aqueous HCl, water and brine. Solvent removal and column chromatography of the residue afforded the corresponding homoallyl alcohols (4-7) in pureform. |
87% | With zinc In tetrahydrofuran at 0℃; | |
85% | With pyridinium perchlorate; zinc In acetonitrile for 4h; | |
85% | Stage #1: allyl bromide With indium; 1-n-butyl-3-methylimidazolim bromide at 25℃; for 0.5h; Stage #2: caprinaldehyde at 25℃; for 24h; chemoselective reaction; | |
81% | With samarium; iodine In tetrahydrofuran at 20℃; for 0.333333h; | |
77% | With tetraethylammonium perchlorate In N,N-dimethyl-formamide platinum cathode, cadmium-modified platinum anode; | |
75% | In dichloromethane; water Ambient temperature; HBF4 supporting electrolyte, Pt cathode, 1.0 A dm-2; | |
68% | With bismuth(lll) trifluoromethanesulfonate; diethyl 2,6-dimethyl-1,4-dihydropyridine-3,5-dicarboxylate; 2,4,6-tri(9H-carbazol-9-yl)-5-chloroisophthalonitrile In ethanol; water at 20℃; for 72h; Schlenk technique; Inert atmosphere; Irradiation; | |
47% | With manganese In tetrahydrofuran; hexane at -42 - 20℃; | |
With ammonium chloride; zinc |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
70% | Stage #1: caprinaldehyde With toluene-4-sulfonic acid; trimethyl orthoformate at 0℃; for 1h; Stage #2: dimethyl L-tartrate In benzene Heating; Further stages.; | |
47% | With toluene-4-sulfonic acid In benzene Heating; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
87% | With formic acid at 190℃; for 6h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
> 99%Chromat. | With C11H25AlNO4(1-)*Na(1+); In tetrahydrofuran; toluene; at 0 - 20℃; for 0.5h; | General procedure: The following experimental procedure describes a representative example of the partial reduction of N,N-dimethylbenzamide to benzaldehyde. A dry and argon-flushed flask, equipped with a magnetic stirring bar and a septum,was charged with N,N-dimethylbenzamide (0.07 mL,0.5 mmol) and THF (5 mL). After cooling to 0 C, piperidine-modified Red-Al (2.5 mL, 0.4 M 1.0 mmol) was added dropwise and the mixture was stirred for 30 min at room temperature. The reaction was quenched with 1 N aqueous HCl (5 mL) and the product was extracted with diethyl ether (10 mL). The organic layer was dried over anhydrous magnesium sulfate. GC analysis showed quantitative conversion to benzaldehyde. All products listed in Table 2 were confirmed through comparison with the GC data of authentic samples. |
> 99%Chromat. | With benzoic acid ethyl ester; copper diisobutyl-t-butoxyaluminum hydride; In tetrahydrofuran; at 20℃; for 12h;Inert atmosphere; | General procedure: The following experimental procedure for the chemoselective partial reduction of ethyl benzoate and N,N-dimethyl 3-toluamide is representative. A dry and argon-flushed flask, equipped with a magnetic stirring bar and a septum, was charged with ethyl benzoate (0.07mL, 0.5mmol), N,N-dimethyl 3-toluamide (0.08mL, 0.5mmol) and 5mL THF. After CDBBA (9.01mL, 0.44M soln. 4.0mmol) was slowly added and stirred for 12h at room temperature. The reaction was quenched by aqueous 1N HCl (10mL) and extracted with diethyl ether (2×10mL). The combined organic layers were dried over MgSO4. GC analysis showed a 97% recovery yield of ethyl benzoate and 95% yield of 3-methylbenzaldehyde. All products in Table 2 were confirmed through comparison with GC data of authentic sample. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
94% | With Yb(OTf)3*9H2O In ethanol for 48h; Heating; | |
93% | With hydrogenchloride In 2-ethoxy-ethanol at 80℃; for 0.05h; microwave irradiation; | |
91% | With bismuth(lll) trifluoromethanesulfonate In ethanol at 80℃; for 24h; |
85% | With iodine In ethanol at 78℃; for 2.16667h; | 3 Typical procedure for the synthesis of resorcinarenes General procedure: Iodine (20 mol%) was added to a solution of resorcinol (1mmol) and of an aldehyde (1mmol) in 2mL of absolute ethanol. The solution was stirred at 78°C. After a given period of time, the solution was cooled and poured into 10mL of an ice-cold saturated sodium thiosulfate aqueous solution. The resulting precipitate was collected by filtration and washed with water. The precipate was dried at 90°C and identified. Spectroscopic data of 2,4,8,20-tetranonylpentacyclo[19.3.1.1.1.1]octacosa 1(25),3,5,7(28),9,11,13(27),15,17,19(26),21,23-dodecaene-4,6,10,12,16,18,22,24-octol (3a) 1H NMR (DMSO-d6) δ (ppm): 0.812 (t, 12H, J = 7.33 Hz, CH3), 1.20 (br, 56H, (CH2)7CH3), 1.96 (br, 8H, J = 6.84 Hz, CHCH2), 4.21 (t, 8H, J = 7.69 Hz, methine) 6.15 (s, 4H, ArH, ortho to OH), 7.06 (s, 4H, ArH, meta to OH), 8.87 (s, 8H, 8OH). 13C NMR (DMSO-d6): δ (ppm) =13.9, 14.1, 20.7, 22.1, 27.8, 28.7, 29.1, 29.2, 31.4, 59.8, 102.3, 122.8, 123.7, 151.7. EI-MS, m/z = 993 (M+). |
With hydrogenchloride In ethanol at 75℃; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
94% | With zinc In tetrahydrofuran at 66℃; for 0.0166667h; | Reformatsky Reaction; General Procedure General procedure: THF (200 mL) was added to an oven-dried 500 mL round-bottomedflask equipped with a condenser 30 cm in length and left open to theatmosphere. The THF was used directly as purchased without any furtherdrying or purification. The solvent was then rapidly stirred usinga magnetic stir bar and brought to reflux (66 °C) on a sand bath. Thecondenser was then temporarily raised and 6.5 g (0.1 mol, 2 equiv) ofZn granules were added to the hot solvent. This was followed by therapid addition of the aldehyde (0.1 mol) and the bromoacetate (as eitherthe methyl or ethyl ester) (0.2 mol, 2 equiv) into the reactionmixture. The condenser was immediately reattached to the roundbottomed flask at which point rapid boiling occurred. The reactionwas allowed to rapidly reflux for 1 min at which point the reactionvessel was removed from heat and allowed to cool to r.t. with stirring. The reaction was observed to be complete by TLC (eluent: hexanes-EtOAc, 80:20) within 20 min for all substrates. Excess THF was removed under vacuum and the resultant brown oil was dissolved inhexanes and quenched with H2O to form a yellow precipitate. Themixture was filtered and the hexane layer was washed with H2O (100mL), aq 1 M HCl (2 × 50 mL), H2O (100 mL) and brine (50 mL), anddried (Na2SO4). Removal of hexanes under vacuum furnished the products 1-8 in yields ranging from 86 to 95% (Table 1). |
80% | With zinc In benzene for 3h; | Methyl 3-hydroxydodecanoate (Hon et al. 2005) [1]: A suspension of the activated zinc dust (2.28 g, 35 mmol) in benzene (10 mL) was heated up to reflux for 10 min. To the refluxing suspension, a mixture of n-decanal (5.15g, 6.20 mL, 33 mmol) and methyl bromoacetate (5.54 mL, 35 mmol) benzene (60 mL) was slowly added over a period of 1 h. After 2 h, the reaction mixture was cooled to 0 °C. 1 M HCl was added to acidify the reaction mixture which was extracted with ether (40 mL × 3). The combined organic phases were dried (Na2SO4) and the solvent was removed under reduced pressure. The crude product was purified was purified by flash chromatography (SiO2, petroleum ether : ethyl acetate, v : v = 9 : 1) to give the desired β-hydroxyester (6.10 g, 80%) as a pale yellow oil. |
60% | With zinc In diethyl ether; toluene for 1.5h; Heating; |
With Trimethyl borate; zinc In tetrahydrofuran at 20℃; for 3h; Inert atmosphere; | A.1.1-1 (1-1) Synthesis example of 3-hydroxydodecanoicacid methyl ester by Reformatsky reaction 10038] 6.5 g of zinc, 15.5 g ofdecanal, 25 ml oftrimethoxyborane, and 25 ml of dried THF were put into a 300 ml four-neck round-bottom flask, and 17.5 g of methyl bromoacetate was dripped at 20° C. for two hours in a nitrogen gas stream. Afier dripping, a resultant thereof was agitated at 20° C. for one hour, and thereafier, 25 ml of saturated ammonia aqueous solution and 25 ml of glycerin were added and agitated for ten minutes. An organic layer was separated and an aqueous solution layer was extracted two times by using diethyl ether. Thereafier, the organic solution was collected and subjected to desolvation. A residue thereof was purified by distillation to obtain a 3-hydroxydodecanoic acid methylester. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
90% | With Cu(II)-Mont K 10 clay In benzene at 80℃; for 2h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
100% | With water In tetrahydrofuran; diethyl ether at 80℃; Inert atmosphere; Autoclave; | |
96% | With C11H10N2O2Pd(1+)*ClO4(1-); water In acetonitrile at 50℃; | Large-scale hydrolysis of decanal dimethyl acetal catalyzed by complex 1 To a solution of decanal dimethyl acetal (10 mL, 41.02 mmols) and water (2 mL) inacetonitrile (50 mL), compound 1 was added (168.1 mg, 0.41 mmols). Theresulting orange solution was heated at 50 C. After 20 min, the solution wasconcentrated (6 mL) and diethyl ether was added (15 mL) to precipitate anorange solid that was filtered off, washed with diethyl ether, and dried invacuo. Yield: 161.3 mg, 0.39 mmols (95%). The filtrate was washed withsaturated aqueous solution of MgSO4 and the solvent was removed in vacuo toobtain decanal of 98% of purity. Yield: 6.20 g, 39.42 mmols, 96%. |
17% | With polymer-supported dicyanoketene acetal; water In acetonitrile at 20℃; for 0.5h; |
Multi-step reaction with 2 steps 1: 92 percent / CH2Cl2 / 0.5 h / 0 °C 2: 100 percent / PPTS; water / acetone / 2 h |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
98% | In dichloromethane at 20℃; for 18h; | |
88% | In dichloromethane for 18h; | |
83% | In dichloromethane for 18h; | 46 Example 46: Ethyl 2-methyldodec-2-enoate (Intermediate) Decanal (5 mmol) and (carbethoxyethylidene) triphenylphosphorane (10 mmol) were dissolved in CH2Cl2 (20 ml) and the reaction was stirred for 18 hours. The solvent was then removed in vacuo and the residue was filter through a plug of silica gel with the aid of 5% diethyl ether in hexanes. The collected eluent was reduced in vacuo to give (4-ethyl 2-methyldodec-2-enoate as an oil (1.02 g, 88%); vmaX/cm~l 1709 (CO), 1651 (C=C); on (500 MHz, CDCl3) 6.73 (1H, tq, J7. 5,1. 5, CH=C), 4.16 (2H, q, J7, OCH2), 2.13 (2H, br q, J7.5, CH2CH=C), 1.80 (3H, d, J 1.5, CH3C=CH), 1.45-1. 37 (2H, m, chain CH2), 1. 32-1.19 (15H, m, (CH2) 6 + OCH2CH3) and 0.85 (3H, t, J7, (CH2) 8CH3) ; 8c (125 MHz, CDC13) 168. 3 (CO), 142.4 (CH=C), 127.6 (CH=C), 60.3 (OCH2), 31. 8, 29.5, 29.4 (x2), 29.3, 28.6, 28.5, 22.6 (CH2), 14.3, 14.1 and 12.3 (CH3) ; m/z (MH+ C15H29O2 requires 241.2168) 241.2165. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
32% | With toluene-4-sulfonic acid; trimethyl orthoformate In benzene for 6h; Heating; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
41% | Stage #1: caprinaldehyde With toluene-4-sulfonic acid; trimethyl orthoformate at 0℃; for 1h; Stage #2: N,N,N',N'-tetramethyl L-tartramide In benzene Heating; Further stages.; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione In dimethyl sulfoxide at 20℃; for 16h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
95% | With 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione In ethyl acetate for 2h; Heating; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
32% | With potassium <i>tert</i>-butylate In ethanol at -18 - 10℃; for 6h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
79% | With tin; hydrogen bromide In diethyl ether at 20℃; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
3% | 7 EXAMPLE 7 EXAMPLE 7 The procedure of Example 1 was repeated, except that a mixture of 1-decanol (0.5 millimole) and 4-decanol (0.5 millimole) was used instead of 1-decanol, to give 1-decanal (yield 83%), and 4-decanone (yield 3%). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
17% | In hexane; chloroform; | REFERENTIAL EXAMPLE 1 3-(2-Dodecenoyl)-6-methyl-2H-pyran-2,4(3H)-dione To a solution of 30.2 g (0.18 mole) of dehydroacetic acid and 30.0 g (0.19 mole) of decyl aldehyde in 300 ml of chloroform was added dropwise 4.8 g of piperidine at room temperature. The mixture was refluxed for 7 hours, while removing the water formed on the reaction with the aid of a Soxhlet extractor charged with anhydrous sodium sulfate. After the reaction, the reaction mixture was extracted with 600 ml of chloroform. The organic layer was separated, washed with 2N HCl and then with water, and dried over anhydrous sodium sulfate. The extract was concentrated under a reduced pressure and 60 ml of ether/hexane (1/2) was added to the residue. The mixture was allowed to stand overnight. The precipitated crystal was recovered by filtration and recrystallized from tetrahydrofuran to obtain 9.5 g (yield: 17%) of 3-(2-dodecenoyl)-6-methyl-2H-pyran-2,4(3H)-dione in the form of a white crystal, m.p. 112-113 C. 1 H-NMR(CDCl3) delta(ppm) 6.03(s,1H), 2.7-2.8(m, 2H), 2.39(s, 3H), 0.9-2.0(m, 19H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With sodium tris(acetoxy)borohydride; In methanol; | Example 4 Preparation of N-Decyl-4-bromo-3-trifluoromethylaniline (4). Sodium triacetoxyborohydride (4 g) was added to a solution of 3-trifluoromethyl-4-bromoaniline (1.5 g) and decanal (4 mL) in methanol (90 mL). After stirring for 1 h the solution was partitioned between water and petroleum ether. The organic extract was concentrated under reduced pressure and the residue was purified via flash column chromatography using petroleum ether as eluent to give N-Decyl-4-broma-3-trifluoromethylaniline (4) (1.2 g, 53%). 1H NMR (CDCl3) delta 7.44 (d, 1H, ArH); 6.92 (d, 1H, ArH); 6.61 (dd, 1H, ArH); 3.11 (t, 2H, NCH2); 0.80 (t, 3H, CH2CH3). TLC (silica gel): Rf=0.35 (petroleum ether). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With sodium cyanoborohydride; at 4℃;pH 5;Aqueous acetate buffer; | 50 mg of <strong>[83150-76-9]octreotide</strong> was dissolved in 2 mL of 20 mM sodium cyanoborohydride (Mw 62.84, NaCNBH3) (2.51 mg) solution in 0.1 M acetate buffer at pH 5. 13.7 mg of Decanal (Mw 156.27) (OCTrDCL = 1:2) was added by direct injection to the peptide solution. The reaction was allowed to proceed for overnight at 4 C. The mixture was separated by centrifugation. The precipitated PAL- OCT was freeze-dried. The beneficial salt of the acylated peptide was formed by neutralizing the residual basic amine groups using a strong acid. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Stage #1: caprinaldehyde; hydrogen cyanide With citrate-phosphate buffer In di-isopropyl ether at 10℃; for 22h; Stage #2: heptafluorobutyric anhydride With pyridine In dichloromethane; di-isopropyl ether Further stages.; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
40% | With bis(cyclopentadienyl)titanium dichloride; manganese; triphenylphosphine; palladium dichloride In tetrahydrofuran at 20℃; for 6h; Inert atmosphere; | |
40% | With bis(cyclopentadienyl)titanium dichloride; manganese; triphenylphosphine; palladium dichloride In tetrahydrofuran at 20℃; Inert atmosphere; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
54% | Stage #1: (3-ethoxycarbonylpropyl)triphenylphosphonium bromide With sodium hexamethyldisilazane In tetrahydrofuran at -78℃; for 1h; Inert atmosphere; Stage #2: caprinaldehyde In tetrahydrofuran at -78 - 20℃; Inert atmosphere; optical yield given as %de; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
76% | General procedure: To a stirring suspension of phosphonium salts (5a-e) (1 equiv) in THF (250 mL) was added slowly 40% solution of sodium hexamethyldisilylamide (2 equiv) THF at room temperature in argon and stirring continued for 2 h. Aldehyde (1 equiv) was dissolved in THF (25 mL) and introduced drop wise. The mixture was stirred for further 3 h and then poured into 150 mL of water to get a clear solution. The resulting solution was concentrated in vacuum and the residue was extracted with diethyl ether (3 x 250 mL). The aqueous layer was acidified with 10% HCl and extracted with ether (3 x 200 mL). The organic layer obtained from the aqueous extract was dried and concentrated to afford the corresponding unsaturated carboxylic acids (6a-m). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
74% | General procedure: To a stirring suspension of phosphonium salts (5a-e) (1 equiv) in THF (250 mL) was added slowly 40% solution of sodium hexamethyldisilylamide (2 equiv) THF at room temperature in argon and stirring continued for 2 h. Aldehyde (1 equiv) was dissolved in THF (25 mL) and introduced drop wise. The mixture was stirred for further 3 h and then poured into 150 mL of water to get a clear solution. The resulting solution was concentrated in vacuum and the residue was extracted with diethyl ether (3 x 250 mL). The aqueous layer was acidified with 10% HCl and extracted with ether (3 x 200 mL). The organic layer obtained from the aqueous extract was dried and concentrated to afford the corresponding unsaturated carboxylic acids (6a-m). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
1: 9% 2: 16% 3: 45% | With (acetylacetonato)dicarbonylrhodium (l); hydrogen; triphenylphosphine In N,N-dimethyl-formamide at 130℃; for 3h; Autoclave; | |
1: 13% 2: 10% 3: 44% | With (acetylacetonato)dicarbonylrhodium (l); hydrogen; triphenylphosphine In N,N-dimethyl-formamide at 130℃; for 1h; Autoclave; | |
1: 29% 2: 38% 3: 7% | With (acetylacetonato)dicarbonylrhodium (l); dodecacarbonyl-triangulo-triruthenium; hydrogen; triphenylphosphine In N,N-dimethyl-formamide at 80℃; for 3h; Autoclave; |
1: 21% 2: 29% 3: 21% | With (acetylacetonato)dicarbonylrhodium (l); dodecacarbonyl-triangulo-triruthenium; hydrogen; triphenylphosphine In N,N-dimethyl-formamide at 80℃; for 6h; Autoclave; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
1: 65% 2: 7% | With (acetylacetonato)dicarbonylrhodium (l); hydrogen; triphenylphosphine at 80℃; for 3h; Autoclave; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
85% | Stage #1: N-cyclohexylformamide With N-ethyl-N,N-diisopropylamine; trichlorophosphate In toluene at 20℃; for 0.1h; Flow reactor; Sonication; Stage #2: caprinaldehyde; aniline With boron trifluoride diethyl etherate In toluene at 20℃; for 0.34h; Flow reactor; Sonication; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
98% | With 0.23Al(3+)*2HO(1-)*0.62H2O*0.77Mg(2+)*Eu0026O0.936W0.26(0.234-) In neat (no solvent) at 25℃; for 2.5h; | 2.5. Procedure for cyanosilylation General procedure: In a typical experiment, 1 mmol aldehyde or ketone, 1.5 mmolTMSCN and Mg3Al-LnW10(0.25 mol% LnW10 to substrate, Ln = Eu,Tb and Dy) as catalyst were placed in a 20 ml glass bottle at25C and the reaction mixture was kept stirring vigorously. The yield of cyanohydrin was periodically determined by GC analy-sis by reference standards. After the reaction was completed, the resulting oily product was extracted by diethyl ether. The cat-alyst of Mg3Al-LnW10 was recovered by centrifugation, washed with acetone, and dried in air. The corresponding cyanohy-drin was obtained by column chromatography on silica gel, and the isolated yield could be calculated based on the obtained cyanohydrin. |
96% | With 4Bi(3+)*4C15H26NO3Si2(3-) for 0.0833333h; Inert atmosphere; | |
91% | With Na8H[PW9O34]*7H2O In ethyl acetate at 25℃; for 6h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
88%Chromat. | With Na(1+)*C12H27AlNO5(1-); In tetrahydrofuran; toluene; at 0 - 20℃; for 0.5h; | General procedure: The following experimental procedure for the partial reduction of ethyl benzoate to benzaldehyde is representative. A dry and argon-flushed flask, equipped with a magnetic stirring bar and a septum, was charged with ethyl benzoate (0.07 mL, 0.5 mmol) and THF (5 mL). After cooling to 0 C, cis-2,6-dimethylmorpholine-modified Red-Al (2.5 mL, 0.4 M 1.0 mmol) was added dropwise and the mixture was stirred for 30 min at the room temperature. The reaction was stopped aqueous 1 N HCl (5 mL) and the product was extracted with diethyl ether (10 mL). The ether layer was dried over anhydrous magnesium sulfate. GC analysis showed a 98% yield of benzaldehyde. All products in Table 1 were confirmed through comparison with GC data of authentic sample. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
29%Chromat.; 53% | General procedure: To a pear-shaped two-necked reactor (25 mL) equipped with a thermometer and reflux condenser, CAN (2.2 g, 4.0 mmol) and LiBr (261 mg, 3.0 mmol) were added and stirred. Next, aldehyde 1a-f (1 mmol) was added and the reaction mixture stirred for 10-15 min. Then MeOH (64 mg, 2.0 mmol) was added and the reaction mixture stirred for 20 h at 20 C (3.5 h at 35-40 C). The reaction mixture was cooled, diluted with water (10-15 mL) and extracted with Et2O (3 * 10-15 mL). The combined organic phases were washed with aqueous NaHCO3 (10 mL) and water (10 mL), then dried (MgSO4). The solvent was removed under reduced pressure (water bath temperature 25-28 C). The conversion of 1a-f and the yields of 2a-f and 3a-f were determined by GLC using methyl pentanoate and methyl decanoate as internal standards. The isolation of 2-bromoesters 2a-f was performed using gradient silica gel column chromatography with petroleum ether (b.p. 40-70 C): chloroform (10-1:1), as eluent. Preparative yields of 2a-f were 53-82% |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With nickel-molybdenum sulfide; Dimethyldisulphide; C8H15N2(1+)*C8H18NO4S2(1-) In n-heptane; toluene at 339.84℃; Ionic liquid; | 2.4. Reaction conditions The particle size of the catalysts was in the range of 250-315 m.The catalysts were diluted with carborundum to keep the volumeof the catalyst bed constant and in order to prevent diffusion limi-tations.Catalytic activity measurements were carried out in a fixed-bedreactor at 613 K under a total pressure of 4 MPa [12]. The model feedwas composed of decanoic acid (7.8 wt%), DMDS (1.3 wt%) and n-heptane (2.6 wt%) diluted in toluene. Under these conditions (613 K,4 MPa), the initial partial pressures were 53 kPa of decanoic acid,32 kPa of both H2S and CH4(generated by the decomposition ofDMDS), 31 kPa of n-heptane (used as an internal standard for chro-matography analysis) and 1.13 MPa of toluene. The volume ratioH2/feed was equal to 487 NL/L. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With air at 120℃; for 10h; | Oxidation of triolein with Rancimat General procedure: The triolein oil samples were subjected to oxidation in aRancimat (679, Metrohm, Herisau, Switzerland). Elevengrammes of sample was used for the oxidation experiments.The temperature was set to 120 C and the air flowto 20 dm3/h. Triolein was treated for up to 10 h. Theoxidized samples were cooled immediately after the oxidationand stored under nitrogen below -18 C. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
25.3% | With sodium tris(acetoxy)borohydride; In 1,2-dichloro-ethane; at 20℃;Inert atmosphere; | General procedure: Alkylaldehyde (RCHO) (1.1 equiv) was added into a solution of deacetyl linezolid (1 equiv., 300mg) and NaBH(OAc)3 (1.3 equiv.) in 7.5mL 1,2-dichloroethane in a round-bottom flask. The mixture solution with N2 protected was stirred at room temperature for 12-24h. Then saturated NaHCO3 was used to quench the reaction and alkalified to pH=8. The reaction solution was then extracted with dichloromethane (DCM). The organic layer was subsequently washed with H2O (2-3 times) and brine (1-2 times). Then the organic layer was dried over anhydrous Na2SO4, filtrated, and concentrated under reduced pressure and the residue was purified using column chromatography (petroleum ether: ethyl acetate=5:1 to 1:1 v/v and with 0.5% triethylamine) to obtain the product. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
60% | In a 100 ml tetrahydrofuran (THF) aprotic solvent mixed with 1.3 g of magnesium turnings and 20 g of elemental iodine,Was added 1.09g 9- bromo-1-nonene,Nitrogen was bubbled through and stirred at 40-80 C until the solution became colorless and refluxed.Then slowly add 9-10 g of 9-bromo-1-decene.Reflow 0.5 to 1 h and cool at room temperature.At 0 added dropwise by syringe at THF10ml containing 5.0 ~ 5.5g decanal,Stir at room temperature overnight, chromatography column,Obtained pure (5.58 g, yield 60%) |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
40 mg | Step 1: Commercially available <strong>[1404-90-6]vancomycin</strong> (100 mg) and DIPEA (30 muL) were dissolved in 3 mL of DMF to give an opaque solution, which was heated to 50 C to become clear. Decanal (30 muL) was added, and the mixture was heated under stirring for 4h. Then, NaCNBH3 (8 mg), 1 mL of methanol and 30 muL of TFA were added at room temperature, and the reaction was stirred overnight and monitored by HPLC. The reaction mixture was added with diethyl ether (50 mL) to generate precipitates, which was filtered to give a crude. The crude was purified by reverse-phase C18 HPLC and lyophilized to give Van-g (40 mg) as a white solid. HPLC: C18 column (5 mum, 4.6 x 250 mm), UV detection at 214 nm, elution conditions: a gradient of 2-90% acetonitrile containing 0.1% v/v TFA over 30 min. HRMS (ESI+) calculated for C76H95Cl2N9O24 [M+2H]2+ 1587.5867, found 794.8006. 1H NMR (600 MHz, DMSO-d6) delta 8.70 (s, 1H), 7.81 (d, J = 1.9 Hz, 1H), 7.52 (d, J = 8.6 Hz, 1H), 7.44 (dd, J = 8.3, 1.8 Hz, 1H), 7.29 (d, J = 8.4 Hz, 1H), 7.17 (d, J = 8.4 Hz, 1H), 7.15 - 7.11 (m, 1H), 6.76 (dd, J = 8.4, 2.0 Hz, 1H), 6.70 (d, J = 8.4 Hz, 2H), 6.38 (d, J = 2.3 Hz, 1H), 6.23 (d, J = 2.3 Hz, 1H), 5.73 (d, J = 7.8 Hz, 1H), 5.59 (s, 1H), 5.27 (dd, J = 22.9, 6.0 Hz, 2H), 5.14 (dd, J = 14.8, 2.8 Hz, 2H), 5.09 (s, 1H), 4.89 (s, 1H), 4.60 (d, J = 6.7 Hz, 1H), 4.42 (dd, J = 11.8, 5.6 Hz, 2H), 4.17 (s, 2H), 3.94 (s, 1H), 3.65 (d, J = 10.8 Hz, 1H), 3.54 (t, J = 8.5 Hz, 1H), 3.31 - 3.22 (m, 3H), 2.74 (s, 1H), 2.67 (d, J = 7.2 Hz, 1H), 2.60 (s, 4H), 2.12 (d, J = 12.6 Hz, 1H), 1.96 (d, J = 11.6 Hz, 1H), 1.77 (d, J = 13.1 Hz, 1H), 1.63 (ddd, J = 26.5, 12.5, 6.7 Hz, 2H), 1.51 (s, 3H), 1.32 (s, 3H), 1.23 (d, J = 18.1 Hz, 16H), 1.06 (d, J = 6.3 Hz, 3H), 0.89 (d, J = 6.2 Hz, 3H), 0.83 (td, J = 7.1, 6.7, 3.6 Hz, 6H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
97% | With uranyl(VI) triflate In dichloromethane-d2 at 20℃; for 0.1h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
80% | With 3-(7,7-dimethyl-2-oxobicyclo[2.2.1]hept-1-yl)methyl-1-(2,4,6-trimethylphenyl)-1H-imidazol-3-ium iodine salt; caesium carbonate; In toluene; at 60℃; for 3h; | Accurately weigh 0.1mol n-decaldehyde and add it to a 50mL round bottom flask.Then add 0.5mol ethanol,0.005mol 3- (7,7-dimethyl-2-oxobicyclo [2.2.1] hept-1-yl) methyl-1- (2,4,6-trimethyl) phenyl-1H- Imidazole-3-ium iodide,0.05mol of cesium carbonate, 150mL of toluene, put on an air balloon, and stir at 60 C for 3h.After the reaction, the reaction solution was cooled to room temperature.It was washed with saturated brine to neutrality, concentrated under reduced pressure, and subjected to column chromatography to obtain ethyl n-decanoate with a yield of 80%. |
80% | With C22H29N2O(1+)*I(1-); caesium carbonate; In toluene; at 60℃; for 3h; | General procedure: A three-neck flask was charged with aldehyde 7a-7p(1.0mmol), camphor-based imidazolium salts (5mol%),Cs2CO3(163mg, 0.5mmol), alcohol (5mmol) and 10ml oftoluene in an air atmosphere, then the mixture was stirred for3h at 60C. The reaction mixture was extracted with diethylether (3 × 30ml), concentrated under reduced pressure andthe residue was purified by flash column chromatography onsilica gel (PE (petroleum ether):EA (ethyl acetate) = 20:1)to give the desired product. All products were identified by1H and 13C NMR and in accord with literatures [42-52] (forspectra see Supplementary Data). |
Yield | Reaction Conditions | Operation in experiment |
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43% | Stage #1: caprinaldehyde With (S)-2-{bis[3,5-bis(trifluoromethyl)phenyl][(trimethylsilanyl)oxy]methyl}pyrrolidine; N-fluorobis(benzenesulfon)imide In tert-butyl methyl ether at 0 - 20℃; for 0.666667h; Inert atmosphere; Stage #2: acetonedicarboxylic acid With copper acetylacetonate In tert-butyl methyl ether at 20℃; for 4h; Inert atmosphere; | |
43% | Stage #1: caprinaldehyde With (S)-2-{bis[3,5-bis(trifluoromethyl)phenyl][(trimethylsilanyl)oxy]methyl}pyrrolidine; N-fluorobis(benzenesulfon)imide In tert-butyl methyl ether at 0 - 20℃; for 1.5h; Inert atmosphere; Stage #2: acetonedicarboxylic acid With copper acetylacetonate In tert-butyl methyl ether at 20℃; for 4h; | 1.a a) First step: Synthesis of a compound of formula (II) (“keto-diol”) General procedure: Procedure A: The corresponding aldehyde R-CH2-CHO (32 mmol, 3.2 eq.) was dissolved in 40 mL of MTBE and cooled to 0°C under argon. 896.2 mg of (S)-(III) (1.5 mmol, 15 mol%) were added followed by addition over 1 minute of 9.10 g of NFSI (29 mmol, 2.9 eq.). The reaction mixture was then stirred at 0°C for 5 minutes then at room temperature for 1.5 hours. 1.62 g of l,3-acetone-dicarboxylic acid (technical grade, 10 mmol, 1 eq.) and 392.4 mg of Cu(acae)2(1.5 mmol, 15 mol%) were simultaneously added and the reaction was stirred at room temperature for 4 hours more before addition of 40 mL of an aqueous solution saturated with NH4CI and 20 mL of aqueous HC1 1M. The aqueous layer was extracted by 3 times 50 mL diethyl ether, the combined organic layers were washed by 25 mL saturated aqueous NaCl, 3 times 40 mL of saturated aqueous NaHC03, 25 mL of saturated aqueous NaCl, dried over Na2S04, filtered and the solvent evaporated. Purification by recrystallization from a mixture of diethyl ether and -hexane or dichloromethane and -hexane directly provided the corresponding keto-diol of formula (II). The enantiomer of a compound of formula (II) obtained with (N)-(III) catalyst may be prepared by using the enantiomer (/?)-(III).Compound 2aCompound 2a was prepared according to procedure (A) using 3.8 mL g of decanal (20 mmol, 4 eq.), 435.1 mg of (S)-(III) (0.75 mmol, 15 mol%), 4.56 g ofNFSI (14.5 mmol, 2.9 eq.), 736.9 mg of 1 ,3-acetone-dicarboxylic acid (technical grade, 5 mmol, 1 eq.) and 196.2 mg of Cu(acae)2(0.75 mmol, 15 mol%). Purification over silica gel (petroleum ether/ethyl acetate (7/3)) yielded the keto-diol containing minor impurities. Recrystallization from a mixture of ethyl acetate and pentane gave the keto-diol 2a with 20: 1 dr.882 mg (2,17 mmol). 43% yield. Rf = 0.6 (petroleum ether / ethyl acetate (7/3)).[a]20D= +58.4° (THF, c = 1.1), 20: 1 dr.NMR (400 MHz, THF-d8): d (ppm) = 0.88 (t, 2 CH3), 1.28-1.40 (m, 12 CH2), 1.45-1.77 (m, 4 CH2), 2.55-2.68 (m, CH2), 4.00-4.07 (m, 2 CH), 4.14-4.18 (m, CH), 4.26-4.31 (m, CH).13C NMR (75 MHz, THF-d8): d (ppm) = 13.4 (s, CH3), 22.5 (s, CH2), 25.1 (d, J = 3 Hz, CH2), 29.2 (s, CH2), 29.4 (s, CH2), 30.8 (d, J = 20 Hz, CH2), 31.8 (s, CH2), 46.4 (d, J = 5 Hz, CH2), 68,5 (d, J = 23 Hz, CH(OH)), 95.7 (d, J = 170 Hz, CH(F)), 207.5 (CO).19F (NMR (400 MHz, THF-d8)): -190.7.HRMS ESI [M+Na]+calculated for C23H45F203+: 407.3331. Observed: 407.3326. |
Tags: 112-31-2 synthesis path| 112-31-2 SDS| 112-31-2 COA| 112-31-2 purity| 112-31-2 application| 112-31-2 NMR| 112-31-2 COA| 112-31-2 structure
[ 59-23-4 ]
(2R,3S,4S,5R)-2,3,4,5,6-Pentahydroxyhexanal
Similarity: 0.50
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