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[ CAS No. 76509-17-6 ] {[proInfo.proName]}

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Product Details of [ 76509-17-6 ]

CAS No. :76509-17-6 MDL No. :MFCD13151998
Formula : C12H11NO Boiling Point : -
Linear Structure Formula :- InChI Key :LLWFWIZOFFLRKC-UHFFFAOYSA-N
M.W : 185.22 Pubchem ID :10012635
Synonyms :

Calculated chemistry of [ 76509-17-6 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 14
Num. arom. heavy atoms : 12
Fraction Csp3 : 0.08
Num. rotatable bonds : 3
Num. H-bond acceptors : 2.0
Num. H-bond donors : 0.0
Molar Refractivity : 55.22
TPSA : 22.12 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : Yes
P-gp substrate : No
CYP1A2 inhibitor : Yes
CYP2C19 inhibitor : Yes
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -5.78 cm/s

Lipophilicity

Log Po/w (iLOGP) : 2.39
Log Po/w (XLOGP3) : 2.32
Log Po/w (WLOGP) : 2.51
Log Po/w (MLOGP) : 1.75
Log Po/w (SILICOS-IT) : 2.88
Consensus Log Po/w : 2.37

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 1.0
Bioavailability Score : 0.55

Water Solubility

Log S (ESOL) : -2.89
Solubility : 0.241 mg/ml ; 0.0013 mol/l
Class : Soluble
Log S (Ali) : -2.42
Solubility : 0.699 mg/ml ; 0.00377 mol/l
Class : Soluble
Log S (SILICOS-IT) : -4.69
Solubility : 0.00381 mg/ml ; 0.0000206 mol/l
Class : Moderately soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.83

Safety of [ 76509-17-6 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P280-P305+P351+P338 UN#:N/A
Hazard Statements:H302 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 76509-17-6 ]

* 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.

  • Downstream synthetic route of [ 76509-17-6 ]

[ 76509-17-6 ] Synthesis Path-Downstream   1~101

  • 1
  • [ 109-00-2 ]
  • [ 3204-68-0 ]
  • [ 76509-17-6 ]
  • 3
  • [ 3389-21-7 ]
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  • [ 76509-18-7 ]
  • 4
  • [ 109-00-2 ]
  • [ 100-44-7 ]
  • [ 76509-17-6 ]
YieldReaction ConditionsOperation in experiment
With sodium hydroxide; In dichloromethane; EXAMPLE 1 Production of 3-benzyloxypyridine (2) To a suspension of 3-hydroxypyridine (24.7 g, 260 mmole) in distilled methylene chloride (260 ml) were added Adogen 464 (1.6 ml), 40% NaOH (130 ml), benzyl chloride (32 ml, 278 mmole), followed by stirring for 3 days at room temperature. The organic layer was separated from the reaction solution, and the aqueous layer was admixed with water and extracted with methylene chloride. The resulting extract was combined with the methylene chloride layer separated previously, and the combined solution was washed with saturated saline, dried over K2 CO3 and freed of the solvent by distillation. The residue was purified on a column of silica gel (7734, n-hexane:ethyl acetate=20:1 to 5:1). Yield of 8.6 g or 17.9%.
With sodium hydroxide;Adogen 464; In dichloromethane; water; at 20℃; Step 15.1 : 3-Benzyloxy-pyridine; 9.5 g (10 mMol) 3-Hydroxy-pyridine and 9.45 ml (10 mMol) benzylchloride are dissolved in 50 ml CH2CI2 at rt. 0.5 g Adogen 464 (Aldrich 63393-96-4) are added followed by dropwise addition of 50 ml of aq. NaOH solution (40 %wt). The resulting yellow solution is stirred overnight, leading to formation of a white precipitate. The insolubles are filtered off and the filtrated is diluted with CH2CI2 and H2O. The phases are separated and the aq. phase is repeatedly extracted with CH2CI2. Combined organic extracts are dried, concentrated and the residual crude product is purified by flash chromatography (SiO2, CH2CI2/Me0H 95:5) to give the title compound as a yellow oil: MS: [M+1]+ = 186; 1H MNR (CDCI3): δ ppm 8.42 (s, 1 H), 8.26 (s, 1 H), 7.55-7.38 (m, 5H), 7.30-7.19 (m, 2H), 5.17 (s, 2H).
  • 5
  • [ 76509-17-6 ]
  • [ 105-36-2 ]
  • 3-(benzyloxy)-1-(2-ethoxy-2-oxoethyl)pyridin-1-ium bromide [ No CAS ]
  • 6
  • [ 76509-17-6 ]
  • [ 36016-40-7 ]
  • 2,4,6-trimethyl-benzenesulfonate-1-amino-3-benzyloxy-pyridinium [ No CAS ]
YieldReaction ConditionsOperation in experiment
In methanol; dichloromethane; ethyl acetate; EXAMPLE 2 Production of N-amino-3-benzyloxypyridinium mesitylenesulfonate (3) A solution of O-mesitylenesulfonylhydroxylamine (13.7 g, 44.6 mmole, purity of 70%) in methylene chloride (150 ml) was added dropwise to a solution of <strong>[76509-17-6]3-benzyloxypyridine</strong> (8.25 g, 44.6 mmole) in methylene chloride (150 ml) under ice-cooling, with stirring. The reaction solution was returned to room temperature, stirred for 1 hours and concentrated to one-quarter of the original volume at 20 to 30 C., and ether was added to the concentrate, thereby white crystals were precipitated. This product was used in the next reaction, without being purified. Yield of 14.9 g or 83.3%. The product was recrystallized from a mixed solution of methanol and ethyl acetate to give white flaky crystals having a melting point of 105 to 108 C. Elemental analysis, for C21 H24 O4 N2 S: Calcd.: C, 62.99; H, 6.04; N, 7.00. Found: C, 62.85; H, 6.03; N, 6.71.
In dichloromethane; at 20℃; for 2h; Step 15.4: 2,4,6-Trimethyl-benzenesulfonate-1 -amino-3-benzyloxy-pyridinium; 8.75 g (40.6 mMol) O-Mesitylenesulfonylacetohydroxylamine and 4.2 g (22.7 mMol) 3- benzyloxy-pyridine are dissolved in 70 ml CH2CI2 and stirred for 2 h at rt. The reaction mixture is diluted with ether leading to precipitation of the product which is isolated by filtration, washed with ether and dried to give the title compound as a white powder: 1H MNR <n="70"/>(CDCI3): δ ppm 9.01 (s, 1 H), 8.76 (d, 1 H), 7.58 (dd, 1 H), 7.41 (d, 1 H), 7.40-7.38 (m, 5 H), 6.84 (s, 2H), 5.18 (s, 2H), 2.74 (s, 6H), 2.22 (s, 3H).
  • 7
  • [ 17747-43-2 ]
  • [ 100-39-0 ]
  • [ 76509-17-6 ]
  • 8
  • [ 372-47-4 ]
  • [ 100-51-6 ]
  • [ 76509-17-6 ]
  • 9
  • [ 626-60-8 ]
  • [ 100-51-6 ]
  • [ 76509-17-6 ]
  • 11
  • [ 76509-17-6 ]
  • (1R,3R,4S,8S)-5-Methylene-3-p-tolyl-7-aza-tricyclo[5.3.0.04,8]decane [ No CAS ]
  • 12
  • [ 76509-17-6 ]
  • (2S,3R,6R,8S)-3-Butyl-4-p-tolyl-1-aza-tricyclo[4.4.0.02,8]dec-4-ene [ No CAS ]
  • 13
  • [ 76509-17-6 ]
  • (2S,5S,6R,8S)-5-Butyl-4-p-tolyl-1-aza-tricyclo[4.4.0.02,8]dec-3-ene [ No CAS ]
  • 14
  • [ 76509-17-6 ]
  • (2R,4R,5S,6R,8S)-5-Butyl-4-p-tolyl-1-aza-tricyclo[4.4.0.02,8]decane [ No CAS ]
  • 15
  • [ 76509-17-6 ]
  • (2R,4S,5S,6R,8S)-5-Butyl-4-p-tolyl-1-aza-tricyclo[4.4.0.02,8]decane [ No CAS ]
  • 16
  • [ 76509-17-6 ]
  • [ 202069-85-0 ]
  • 17
  • [ 76509-17-6 ]
  • [ 202069-66-7 ]
  • 18
  • [ 76509-17-6 ]
  • C16H17NO [ No CAS ]
  • 19
  • [ 76509-17-6 ]
  • (2S,6R,8S)-4-p-Tolyl-1-aza-tricyclo[4.4.0.02,8]dec-3-en-5-one [ No CAS ]
  • 20
  • [ 76509-17-6 ]
  • (2S,6R,8S)-4-p-Tolyl-1-aza-tricyclo[4.4.0.02,8]dec-3-en-5-ol [ No CAS ]
  • 21
  • [ 76509-17-6 ]
  • (1S,3S,4R,8R)-5-Methylene-3-phenyl-7-aza-tricyclo[5.3.0.04,8]decan-2-ol [ No CAS ]
  • 22
  • [ 76509-17-6 ]
  • Acetic acid (2S,6R,8S)-4-p-tolyl-1-aza-tricyclo[4.4.0.02,8]dec-3-en-5-yl ester [ No CAS ]
  • 23
  • [ 76509-17-6 ]
  • (1S,3S,4R,8R)-5-Methylene-3-p-tolyl-7-aza-tricyclo[5.3.0.04,8]decan-2-ol [ No CAS ]
  • 24
  • [ 76509-17-6 ]
  • (1S,3S,4R,8R)-3-(4-Chloro-phenyl)-5-methylene-7-aza-tricyclo[5.3.0.04,8]decan-2-ol [ No CAS ]
  • 25
  • [ 76509-17-6 ]
  • (2S,3S,6R,8S)-3-Butyl-4-p-tolyl-1-aza-tricyclo[4.4.0.02,8]dec-4-ene [ No CAS ]
  • 26
  • [ 76509-17-6 ]
  • (2S,5R,6R,8S)-5-Butyl-4-p-tolyl-1-aza-tricyclo[4.4.0.02,8]dec-3-ene [ No CAS ]
  • 27
  • [ 76509-17-6 ]
  • thiocarbonic acid <i>O</i>-(5-methylene-3-<i>p</i>-tolyl-7-aza-tricyclo[5.3.0.04,8]dec-2-yl) ester <i>O</i>-phenyl ester [ No CAS ]
  • 28
  • [ 76509-17-6 ]
  • (1R,5R,6S)-6-Benzenesulfonyl-8-(2-bromo-allyl)-3-p-tolyl-8-aza-bicyclo[3.2.1]oct-3-en-2-one [ No CAS ]
  • 29
  • [ 76509-17-6 ]
  • (1S,5S,7R)-7-Benzenesulfonyl-8-(2-bromo-allyl)-3-p-tolyl-8-aza-bicyclo[3.2.1]oct-3-en-2-one [ No CAS ]
  • 30
  • [ 76509-17-6 ]
  • (1S,3S,4R,8S,9R)-9-Benzenesulfonyl-3-(4-chloro-phenyl)-5-methylene-7-aza-tricyclo[5.3.0.04,8]decan-2-ol [ No CAS ]
  • 31
  • [ 76509-17-6 ]
  • (1S,3S,4R,8S,9R)-9-Benzenesulfonyl-3-(4-chloro-phenyl)-5-methylene-7-aza-tricyclo[5.3.0.04,8]decan-2-one [ No CAS ]
  • 32
  • [ 76509-17-6 ]
  • (1S,3S,4R,8S,9R)-9-Benzenesulfonyl-5-methylene-3-p-tolyl-7-aza-tricyclo[5.3.0.04,8]decan-2-ol [ No CAS ]
  • 33
  • [ 76509-17-6 ]
  • (1S,3S,4R,8S,9R)-9-Benzenesulfonyl-5-methylene-3-p-tolyl-7-aza-tricyclo[5.3.0.04,8]decan-2-one [ No CAS ]
  • 34
  • [ 76509-17-6 ]
  • (1R,5R,6S)-6-Benzenesulfonyl-8-(2-bromo-allyl)-3-(4-chloro-phenyl)-8-aza-bicyclo[3.2.1]oct-3-en-2-one [ No CAS ]
  • 35
  • [ 76509-17-6 ]
  • (1S,5S,7R)-7-Benzenesulfonyl-8-(2-bromo-allyl)-3-(4-chloro-phenyl)-8-aza-bicyclo[3.2.1]oct-3-en-2-one [ No CAS ]
  • 36
  • [ 76509-17-6 ]
  • 1-(2-bromo-allyl)-4-(4-chloro-phenyl)-3-hydroxy-pyridinium; bromide [ No CAS ]
  • 37
  • [ 76509-17-6 ]
  • 1-(2-bromo-allyl)-3-hydroxy-4-<i>p</i>-tolyl-pyridinium; bromide [ No CAS ]
  • 38
  • [ 76509-17-6 ]
  • [ 184473-24-3 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: 95 percent / CH2Cl2 / 1 h / 0 °C 2: 17 percent / K2CO3 / dimethylformamide / 0 deg C, 10 min; RT, overnight 3: 88 percent / 47percent HBr / 0.17 h / Heating
  • 39
  • [ 76509-17-6 ]
  • [ 141032-72-6 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: 95 percent / CH2Cl2 / 1 h / 0 °C 2: 59 percent / K2CO3 / dimethylformamide / 0 deg C, 10 min; RT, overnight 3: 47percent HBr / 0.17 h / Heating
  • 42
  • [ 76509-17-6 ]
  • [ 187030-98-4 ]
  • 43
  • [ 76509-17-6 ]
  • 8-methyl-3-phenyl-7-exo-(phenylsulfonyl)-8-azabicyclo[3.2.1]oct-3-en-2-one [ No CAS ]
  • 44
  • [ 76509-17-6 ]
  • Thiocarbonic acid O-((1S,2S,3R,4S,5S,6R)-4-butyl-6-cyano-8-methyl-3-phenyl-8-aza-bicyclo[3.2.1]oct-2-yl) ester O-phenyl ester [ No CAS ]
  • 45
  • [ 76509-17-6 ]
  • 1-methyl-4-phenyl-3-hydroxypyridinium iodide [ No CAS ]
  • 46
  • [ 76509-17-6 ]
  • 2α-hydroxy-8-methyl-3-phenyl-8-azabicyclo[3.2.1]octane-3-ene-6-exo-carbonitrile [ No CAS ]
  • 47
  • [ 76509-17-6 ]
  • 2β-hydroxy-8-methyl-3-phenyl-8-azabicyclo[3.2.1]octane-3-ene-6-exo-carbonitrile [ No CAS ]
  • 48
  • [ 76509-17-6 ]
  • 8-methyl-2-oxo-3-phenyl-8-azabicyclo[3.2.1]oct-3-ene-7-exo-carbonitrile [ No CAS ]
  • 49
  • [ 76509-17-6 ]
  • 8-methyl-2-oxo-3-phenyl-8-azabicyclo[3.2.1]oct-3-ene-6-endo-carbonitrile [ No CAS ]
  • 50
  • [ 76509-17-6 ]
  • 8-methyl-2-oxo-3-phenyl-8-azabicyclo[3.2.1]oct-3-ene-7-exo-carbonitrile [ No CAS ]
  • 51
  • [ 76509-17-6 ]
  • 8-methyl-2-oxo-3-phenyl-8-azabicyclo[3.2.1]oct-3-ene-7-endo-carbonitrile [ No CAS ]
  • 52
  • [ 76509-17-6 ]
  • 2-exo-butyl-8-methyl-3-endo-phenyl-8-azabicyclo[3.2.1]octane-7β-carbonitrile [ No CAS ]
  • 53
  • [ 76509-17-6 ]
  • 6-endo-carboethoxy-3-phenyltrop-3-en-2-one [ No CAS ]
  • 54
  • [ 76509-17-6 ]
  • 6-exo-carboethoxy-3-phenyltrop-3-en-2-one [ No CAS ]
  • 55
  • [ 76509-17-6 ]
  • 4β-butyl-2β-hydroxy-8-methyl-3α-phenyl-8-azabicyclo[3.2.1]octane-6-exo-carbonitrile [ No CAS ]
  • 56
  • [ 76509-17-6 ]
  • 4β-butyl-2α-hydroxy-8-methyl-3α-phenyl-8-azabicyclo[3.2.1]octane-6-endo-carbonitrile [ No CAS ]
  • 57
  • [ 76509-17-6 ]
  • 4β-butyl-2α-hydroxy-8-methyl-3α-phenyl-8-azabicyclo[3.2.1]octane-6-exo-carbonitrile [ No CAS ]
  • 58
  • [ 76509-17-6 ]
  • 7-exo-carboethoxy-3-phenyl-3-en-2-one [ No CAS ]
  • 59
  • [ 76509-17-6 ]
  • 7-endo-carboethoxy-3-phenyl-3-en-2-one [ No CAS ]
  • 60
  • [ 76509-17-6 ]
  • 4β-butyl-8-methyl-2-oxo-3α-phenyl-8-azabicyclo[3.2.1]octane-6-endo-carbonitrile [ No CAS ]
  • 61
  • [ 76509-17-6 ]
  • 4β-butyl-8-methyl-2-oxo-3α-phenyl-8-azabicyclo[3.2.1]octane-6-exo-carbonitrile [ No CAS ]
  • 62
  • [ 76509-17-6 ]
  • (1S,4S,5S,6R)-4-Butyl-8-methyl-3-phenyl-2-trimethylsilanyloxy-8-aza-bicyclo[3.2.1]oct-2-ene-6-carbonitrile [ No CAS ]
  • 63
  • [ 76509-17-6 ]
  • (1S,4S,5S,6S)-4-Butyl-8-methyl-3-phenyl-2-trimethylsilanyloxy-8-aza-bicyclo[3.2.1]oct-2-ene-6-carbonitrile [ No CAS ]
  • 64
  • [ 76509-17-6 ]
  • 8-methyl-3-phenyl-6-exo-(phenylsulfonyl)-8-azabicyclo[3.2.1]oct-3-en-2-one [ No CAS ]
  • 65
  • [ 76509-17-6 ]
  • 8-methyl-3-phenyl-6-endo-(phenylsulfonyl)-8-azabicyclo[3.2.1]oct-3-en-2-one [ No CAS ]
  • 66
  • [ 76509-17-6 ]
  • 4-benzyl-3-hydroxypyridine [ No CAS ]
  • 67
  • [ 76509-17-6 ]
  • 4-(p-trifluoromethylbenzyl)-3-hydroxypyridine [ No CAS ]
  • 68
  • [ 76509-17-6 ]
  • [ 177559-90-9 ]
  • 69
  • [ 76509-17-6 ]
  • [ 1027055-67-9 ]
  • 70
  • [ 76509-17-6 ]
  • [ 1028264-80-3 ]
  • 71
  • [ 76509-17-6 ]
  • [ 177559-92-1 ]
  • 72
  • [ 76509-17-6 ]
  • 6-benzyloxy-1,3-dicarbethoxy-2-mercaptoindolizine [ No CAS ]
  • 73
  • [ 76509-17-6 ]
  • [ 177559-88-5 ]
  • 74
  • [ 76509-17-6 ]
  • [ 177559-89-6 ]
  • 75
  • [ 76509-17-6 ]
  • [ 177559-86-3 ]
  • 76
  • [ 76509-17-6 ]
  • 2-(8-(carboxymethyloxy)-2-methylthio-3-(o-phenylbenzyl)indolizin-lyl)-glyoxylamide [ No CAS ]
  • 77
  • [ 76509-17-6 ]
  • [ 177559-91-0 ]
  • 78
  • [ 76509-17-6 ]
  • [ 1025963-82-9 ]
  • 79
  • [ 76509-17-6 ]
  • [ 177558-34-8 ]
  • 81
  • [ 76509-17-6 ]
  • [ 83431-03-2 ]
  • 82
  • [ 76509-17-6 ]
  • [ 101925-24-0 ]
  • 83
  • [ 76509-17-6 ]
  • [ 101925-25-1 ]
  • 84
  • [ 76509-17-6 ]
  • [ 101925-22-8 ]
  • 89
  • [ 109-00-2 ]
  • [ 100-39-0 ]
  • [ 76509-17-6 ]
YieldReaction ConditionsOperation in experiment
84% With sodium hydride; In DMF (N,N-dimethyl-formamide); at 0 - 20℃; 60% NaH (4.42 g, 111 mmol) was added to a solution of Compound A (10.0 g, 105 mmol) in DMF (100 ml) at 0C, subsequently benzyl bromide (13.7 ml, 115 mmol) was added to the mixture. Then, the mixture was stirred at room temperature overnight. The reaction mixture was poured into ice-water, and extracted with diethyl ether. The extract was washed with water, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (hexane: ethyl acetate=97:3-50:50) to give Compound B (16.3 g, 84%) as a liquid. MS: 186 [M+H]+, APCI (MeOH)
59% With tetrabutylammomium bromide; potassium hydroxide; In tetrahydrofuran; for 12h;Reflux; General procedure: Five grams (52.6 mmol) 3-hydroxypyridine, 5.9 g (110 mmol) pulverized potassium hydroxideand 0.85 g (2.6 mmol) nBu4NBr were dissolved in 150 mL of dried THF. After addition of 84 mmol ofthe respective alkyl halogenide the mixture was stirred for 12 h under reflux. The reaction was finishedwith the addition of 200 mL water and extraction with each 100 mL of hydrochloric acid (10%) fortwo times. The unified water phases were alkalined with a 10 M sodium hydroxide solution and thenextracted with each 75 mL of chloroform for three times. After removal of the solvent of the unifiedorganic layers in vacuum, the raw product was purified using column chromatography technique oversilica gel and an eluent mixture of cyclohexane and ethyl acetate in a relation of 1:1.
  • 90
  • [ 76509-17-6 ]
  • [ 131379-16-3 ]
  • C21H19NO3 [ No CAS ]
YieldReaction ConditionsOperation in experiment
31% A solution of phenyl chloroformate (3.45 ml, 27.5 mmol) in THF (20 ml) was added dropwise to a solution of .Compound B (4.63 g, 25.0 ml), lithium chloride (0.21 g, 5.0 mmol) and copper (I) iodide (0.476 g, 2.5 mmol) in THF (500 ml) at-23C. After 20 minutes from completion of the dropwise addition, Compound C (0.5M THF solution, 50 ml, 25.0 mmol) was added dropwise to the mixture at-23C. After 20 minutes from completion of the dropwise addition, a tem- perature of the reaction mixture was gradually raised to room temperature. An aqueous 20% ammonium chloride solution (100 ml) and an aqueous 5% ammonia (20 ml) were added to the mixture, and then, THF was removed under reduced pressure. Diethyl ether was added to the residue, and the mixture was washed with water, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. Toluene (200 ml) was added to the residue, and a solution of o-chloranil (6.15 g, 25.0 mmol) in toluene (50 ml) was added dropwise to the mixture at 0C. After completion of the dropwise addition, the mixture was stirred at room temperature overnight. Diethyl ether was added to the mixture, and the resulting mixture was washed with an aqueous 10% sodium hydroxide solution and water, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (hexane:ethyl acetate=95:5-50:50) to give Compound D (2.61 g, 31%) as powders. MS: 334 [M+H]+, APCI (MeOH) (3)
  • 91
  • [ 76509-17-6 ]
  • [ 75-36-5 ]
  • (3-chlorophenyl)magnesium halide [ No CAS ]
  • [ 1228595-65-0 ]
  • 92
  • [ 76509-17-6 ]
  • [ 75-36-5 ]
  • (4-chlorophenyl)magnesium halide [ No CAS ]
  • [ 1228595-64-9 ]
  • 93
  • [ 76509-17-6 ]
  • [ 75-36-5 ]
  • phenylmagnesium halide [ No CAS ]
  • [ 1029797-91-8 ]
  • 94
  • [ 76509-17-6 ]
  • [ 25015-63-8 ]
  • 3-(benzyloxy)-1-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1,4-dihydropyridine [ No CAS ]
  • 95
  • [ 76509-17-6 ]
  • 3-(benzyloxy)piperidine [ No CAS ]
  • 96
  • [ 76509-17-6 ]
  • [ 1407992-99-7 ]
  • 97
  • [ 76509-17-6 ]
  • [ 1407992-88-4 ]
  • 98
  • [ 76509-17-6 ]
  • [ 1407993-01-4 ]
  • 99
  • [ 76509-17-6 ]
  • [ 1029797-91-8 ]
  • 100
  • [ 76509-17-6 ]
  • [ 1029797-95-2 ]
  • 101
  • [ 76509-17-6 ]
  • [ 75-36-5 ]
  • C14H14NO2(1+)*Cl(1-) [ No CAS ]
YieldReaction ConditionsOperation in experiment
General procedure: First, 10 mmol of the respective pyridine were dissolved in 50 mL of dried THF. After additionof 0.5 mmol of copper(I) iodide and 3 mL of dimethyl sulphide, the mixture was stirred at room temperature until a clear solution resulted. Then, it was cooled down to -20 C. After 15 min, 10 mmolof acetyl chloride were added dropwise and stirring continued for 15 min. Then, 10 mmol of phenylmagnesium chloride were added and stirring followed for additional 15 min. Then, the mixturewarmed up to room temperature. Then, 50 mL of an ammonium chloride solution (20%) were addedand extraction with diethyl ether followed with portions of 50, 25 and again 25 mL. The unified organiclayer was extracted with each 50 mL of a solution of ammonium chloride in ammonia for two times,with 50 mL water, hydrochloric acid (10%) for two times, water and finally a saturated solution ofsodium chloride in water. The organic layer was then dried over sodium sulphate, filtered and finallyremoved under reduced pressure to give an oily substance that partially crystallized from methanol.
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