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Product Details of [ 142009-99-2 ]

CAS No. :142009-99-2 MDL No. :MFCD06658335
Formula : C13H17NO Boiling Point : -
Linear Structure Formula :- InChI Key :NMCDGVLRNAILQW-UHFFFAOYSA-N
M.W : 203.28 Pubchem ID :15932625
Synonyms :

Calculated chemistry of [ 142009-99-2 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 15
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.46
Num. rotatable bonds : 3
Num. H-bond acceptors : 2.0
Num. H-bond donors : 1.0
Molar Refractivity : 61.14
TPSA : 29.1 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : Yes
P-gp substrate : No
CYP1A2 inhibitor : No
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : Yes
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -6.46 cm/s

Lipophilicity

Log Po/w (iLOGP) : 2.35
Log Po/w (XLOGP3) : 1.52
Log Po/w (WLOGP) : 2.14
Log Po/w (MLOGP) : 1.93
Log Po/w (SILICOS-IT) : 2.87
Consensus Log Po/w : 2.16

Druglikeness

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

Water Solubility

Log S (ESOL) : -2.16
Solubility : 1.42 mg/ml ; 0.00698 mol/l
Class : Soluble
Log S (Ali) : -1.74
Solubility : 3.7 mg/ml ; 0.0182 mol/l
Class : Very soluble
Log S (SILICOS-IT) : -4.18
Solubility : 0.0133 mg/ml ; 0.0000655 mol/l
Class : Moderately soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.26

Safety of [ 142009-99-2 ]

Signal Word:Warning Class:
Precautionary Statements:P273-P233-P260-P261-P264-P271-P280-P302+P352-P304-P304+P340-P305+P351+P338-P312-P321-P332+P313-P337+P313-P340-P362-P403-P403+P233-P405-P501 UN#:
Hazard Statements:H315-H319-H335-H411 Packing Group:
GHS Pictogram:

Application In Synthesis of [ 142009-99-2 ]

* 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 [ 142009-99-2 ]

[ 142009-99-2 ] Synthesis Path-Downstream   1~100

  • 1
  • [ 131511-13-2 ]
  • [ 142009-99-2 ]
YieldReaction ConditionsOperation in experiment
95.6% With hydrogenchloride; In water; at 20℃; for 22h; Loaded with N-benzyl-1,4-dioxaspiro[4.5]silane-8-amine (16g, 64.69mmol, 1eq.)Of single-mouth bottle with 2mol/L HCl(81ml, 161.72mmol, 2.5eq.), stirred at room temperature overnight (12h),TLC (DCM:MeOH=25:1, 2 times) about half of the raw materials remained.After adding 2mol/L HCl (16ml, 0.5 eq.) for 10hTLC showed that the reaction was basically complete. Under the ice bath, Add NaOH (8g, about 3eq.) in water (about 24ml) solution,Adjust pH 910 with 2mol/L NaOH solution.Extract with dichloromethane (150+75+30 ml). The organic phase is combined,Wash with saturated sodium chloride (30ml), dry with anhydrous magnesium sulfate, filter with suction,The filtrate was evaporated under reduced pressure to obtain 12.57g of light brown liquid.The yield was 95.6%.
  • 2
  • [ 142009-99-2 ]
  • [ 162338-03-6 ]
  • 3
  • [ 867-13-0 ]
  • [ 142009-99-2 ]
  • [ 172947-72-7 ]
  • 4
  • [ 7677-24-9 ]
  • [ 142009-99-2 ]
  • 4-Benzylamino-1-trimethylsilanyloxy-cyclohexanecarbonitrile [ No CAS ]
  • 4-Benzylamino-1-trimethylsilanyloxy-cyclohexanecarbonitrile [ No CAS ]
  • 5
  • [ 24424-99-5 ]
  • [ 142009-99-2 ]
  • [ 188562-91-6 ]
YieldReaction ConditionsOperation in experiment
62.5% With dmap; triethylamine; In dichloromethane; for 13h; 500ml three-necked bottle with thermometer and constant pressure dropping funnel4-(benzylamino)cyclohexane-1-one(35.7g, 175.61mmol, 1eq.), DCM (300ml),TEA (21.32g, 210.73mmol, 1.2eq.), DMAP (215mg, 1.76mmol, 0.01eq.),Stir in ice water bath. (Boc)2O (40.24 g,184.39mmol, 1.05eq.) in DCM (50ml).After adding, remove the ice water bath and stir. Overnight (13h),TLC (DCM:MeOH=100:1 and DCM:MeOH=10:1)Shows that the reaction is complete. Add water (200ml), mix, stand still, separate the layers, and extract the aqueous phase with dichloromethane (100+100ml).Combine the organic phases, wash with water (100ml), wash with citric acid solution (100ml),Wash with saturated sodium chloride (100ml), dry with anhydrous magnesium sulfate, filter with suction, and distill off the filtrate under reduced pressure.51.68g of yellow liquid was obtained. Silica gel column chromatography purification (DCM:PEDCM), 33.3g off-white solid was obtained, the yield was 62.5%.
  • 6
  • [ 7677-24-9 ]
  • [ 142009-99-2 ]
  • [ 422507-45-7 ]
  • 7
  • [ 7677-24-9 ]
  • [ 142009-99-2 ]
  • [ 187807-19-8 ]
  • 8
  • [ 17853-42-8 ]
  • [ 142009-99-2 ]
  • 4-[N-benzyl-N-(2-bromo-3-methyl-2-butenyl)amino]cyclohexanone [ No CAS ]
  • 9
  • 1,2-dibromo-2-butene [ No CAS ]
  • [ 142009-99-2 ]
  • [ 583887-17-6 ]
  • 10
  • [ 85970-82-7 ]
  • [ 142009-99-2 ]
  • [ 290301-57-4 ]
  • 11
  • [ 133834-87-4 ]
  • [ 142009-99-2 ]
  • [ 290301-49-4 ]
  • 12
  • [ 147644-04-0 ]
  • [ 142009-99-2 ]
  • [ 583887-16-5 ]
  • 13
  • [ 142009-99-2 ]
  • [ 178877-39-9 ]
  • [ 290301-46-1 ]
  • 14
  • [ 142009-99-2 ]
  • [ 222421-23-0 ]
  • 4-[N-benzyl-N-(Z)-(3-iodo-2-methyl-2-propenyl)amino]cyclohexanone [ No CAS ]
  • 15
  • 4-(benzylimino)cyclohexanone [ No CAS ]
  • [ 142009-99-2 ]
  • 16
  • [ 62-53-3 ]
  • [ 142009-99-2 ]
  • N-benzyl-4-phenylimino-1-cyclohexylamine [ No CAS ]
  • 17
  • [ 142009-99-2 ]
  • 2-benzyl-4-methyl-2-azabicyclo[4.3.1]dec-4-en-7-one [ No CAS ]
  • 18
  • [ 142009-99-2 ]
  • 4-[benzyl-(2-methyl-allyl)-amino]-cyclohexanone [ No CAS ]
  • 19
  • [ 142009-99-2 ]
  • 2-benzyl-2-azabicyclo[4.3.1]dec-4-en-7-one [ No CAS ]
  • 20
  • [ 142009-99-2 ]
  • 2-benzyl-4-ethyl-2-azabicyclo[3.3.1]non-3-en-6-one [ No CAS ]
  • 21
  • [ 142009-99-2 ]
  • [ 290301-47-2 ]
  • 22
  • [ 142009-99-2 ]
  • 4-(N-benzyl-N-propargylamino)cyclohexanone [ No CAS ]
  • 23
  • [ 142009-99-2 ]
  • 2-benzyl-4-methylene-2-azabicyclo[3.3.1]nonan-6-one [ No CAS ]
  • 24
  • [ 142009-99-2 ]
  • 2-benzyl-4-[(E)-ethylidene]-2-azabicyclo[3.3.1]nonan-6-one [ No CAS ]
  • 25
  • [ 142009-99-2 ]
  • 4-(N-benzyl-N-but-2-ynyl)cyclohexanone [ No CAS ]
  • 30
  • [ 142009-99-2 ]
  • (1RS,2SR,5RS)-6-benzyl-6-azabicyclo[3.2.1]octane-2-carbonitrile [ No CAS ]
  • 31
  • [ 142009-99-2 ]
  • (1RS,2RS,5RS)-6-benzyl-6-azabicyclo[3.2.1]octane-2-carbonitrile [ No CAS ]
  • 32
  • [ 142009-99-2 ]
  • (1RS,6RS,7SR)-2-benzyl-5-oxo-2-azabicyclo[4.3.1]decane-7-carbonitrile [ No CAS ]
  • 33
  • [ 142009-99-2 ]
  • (1RS,6RS,7RS)-2-benzyl-5-oxo-2-azabicyclo[4.3.1]decane-7-carbonitrile [ No CAS ]
  • 34
  • [ 142009-99-2 ]
  • [ 422507-39-9 ]
  • 35
  • [ 142009-99-2 ]
  • N-benzyl-N-carboxymethyl-N-[4-cyanocyclohex-3-en-1-yl]ammonium chloride [ No CAS ]
  • 37
  • [ 142009-99-2 ]
  • [ 192373-28-7 ]
  • 38
  • [ 142009-99-2 ]
  • C22H36N2O4Si [ No CAS ]
  • 39
  • [ 142009-99-2 ]
  • Benzyl-(2,4-dioxo-1,3-diaza-spiro[4.5]dec-8-yl)-carbamic acid tert-butyl ester [ No CAS ]
  • 40
  • [ 142009-99-2 ]
  • 4-(Benzyl-tert-butoxycarbonyl-amino)-1-(9H-fluoren-9-ylmethoxycarbonylamino)-cyclohexanecarboxylic acid [ No CAS ]
  • 41
  • [ 142009-99-2 ]
  • [ 192373-17-4 ]
  • 42
  • [ 142009-99-2 ]
  • C37H46N2O6Si [ No CAS ]
  • 43
  • [ 100-46-9 ]
  • chloride of/the/ 2-nitro-toluene-sulfonic acid-(4) [ No CAS ]
  • [ 142009-99-2 ]
  • 44
  • [ 142009-99-2 ]
  • [ 187807-23-4 ]
  • 46
  • [ 142009-99-2 ]
  • 4-(N-benzyl-N-methylamino)-1-cyclohexene [ No CAS ]
  • 47
  • [ 142009-99-2 ]
  • [ 422507-12-8 ]
  • 48
  • [ 142009-99-2 ]
  • [ 187807-24-5 ]
  • 49
  • [ 142009-99-2 ]
  • [ 188562-95-0 ]
  • 50
  • [ 142009-99-2 ]
  • 5-(Benzyl-tert-butoxycarbonyl-amino)-cyclohex-1-enecarboxylic acid methyl ester [ No CAS ]
  • 51
  • [ 142009-99-2 ]
  • [ 188562-97-2 ]
  • 52
  • [ 142009-99-2 ]
  • [ 188562-93-8 ]
  • 53
  • [ 142009-99-2 ]
  • 4-benzylamino-1-cyclohexenecarbonitrile trifluoroacetate [ No CAS ]
  • 54
  • [ 142009-99-2 ]
  • 4-Benzylamino-cyclohex-1-enecarboxylic acid methyl ester; compound with trifluoro-acetic acid [ No CAS ]
  • 55
  • [ 142009-99-2 ]
  • 2-(7-Benzyl-7-aza-bicyclo[2.2.1]hept-1-yl)-ethanol [ No CAS ]
  • 56
  • [ 142009-99-2 ]
  • (4-Benzylamino-cyclohex-1-enyl)-acetic acid ethyl ester [ No CAS ]
  • 58
  • [ 100-46-9 ]
  • sodium arsenic ate [ No CAS ]
  • [ 142009-99-2 ]
  • 59
  • [ 142009-99-2 ]
  • N-benzyl-7-azabicyclo[2.2.1]heptane [ No CAS ]
  • 61
  • [ 15861-49-1 ]
  • [ 142009-99-2 ]
  • [ 1186383-03-8 ]
YieldReaction ConditionsOperation in experiment
90% 2-(4-tolylsulfanyl)-phenyl bromide (419 g, 1.5mol) was dissolved in heptanes (900 mL) and dry tetrahydrofuran (243 mL, 3 mol,) and after 0.5 h the reaction mixture was cooled down to -15 C under an atmosphere of nitrogen. To this mixture was added /? -butyl lithium in heptanes 2.7 M (583 mL, 1.6 mol) while maintaining the temperature in the range -15 C to 0 C. Once the addition was complete the reaction mixture was cooled to around -15 C before a solution of N-benzyl-4-piperidone (278 mL, 1.5mol) in dry tetrahydrofuran (450 mL) was added at such a rate that the temperature did not rise above - 15 C. Once the addition was complete the reaction was allowed to warm to room temperature.The reaction was quenched with water (1 L), and ethyl acetate (1 L) and aqueous sodium hydroxide solution (1 M, 300 mL) added. The pH was maintained between 10 and 12. The phases were separated, the water phase was extracted with ethyl acetate (1 L), and the organic phases combined. The solvents were removed by vacuum distillation (max. temperature 50 C). Once the distillation was complete, tetrahydrofuran (2.25 L) was added and the solvents removed by vacuum distillation (max. temperature 50 C). Once the distillation was complete, tetrahydrofuran (2 L) was added. Hydrogen chloride gas (85 g, 2.33 mol,) was bubbled into the solution and the product precipitated by addition to diethyl ether (9 L) with stirring. The precipitate was filtered off and washed with diethyl ether (1.2 L) and the precipitate dried in a vacuum oven over night (T = 50 C) to obtain the title compound at 574 g (90% yield).
  • 62
  • [ 4746-97-8 ]
  • [ 100-46-9 ]
  • [ 142009-99-2 ]
YieldReaction ConditionsOperation in experiment
69.9% Step A: 4-(Benzylamino)cyclohexanone. To a suspension of 1 ,4- dioxaspiro[4.5]decan-8-one (l Og, 64.0 mmol) in DCE (200 mL) was addedphenylmethanamine (7.34 mL, 67.2 mmol), AcOH (3.67 mL, 64.0 mmol) and sodium triacetoxyborohydride (19.00 g, 90 mmol). The reaction was stirred at RT for 16 hours and then the mixture was diluted with IN NaOH (100 mL) and DCM (250 mL). The organic layer was collected, dried over sodium sulfate and concentrated under reduced pressure. The residue was suspended in acetone (66.7 mL) and treated with HC1 (2N aqueous) (64.0 mL, 128 mmol), and the mixture was stirred at RT for 16 hours. The reaction mixture was concentrated to half its volume and diluted with 1 N aqueous NaOH (100 mL) and DCM (300 mL). The layers were separated, and the organic portion was dried over sodium sulfate and concentrated under reduced pressure to afford a white solid. The solid was purified by silica gel chromatography (5-10% MeOH/DCM) to afford 4- (benzylamino)cyclohexanone (9.1 g, 69.9 % yield). MS m/z = 204.2 [M+H]. Calc'd for Ci3H17NO: 203.1.
  • 63
  • [ 773837-37-9 ]
  • [ 142009-99-2 ]
  • [ 1357922-30-5 ]
YieldReaction ConditionsOperation in experiment
85% With sodium hydrogencarbonate; In diethyl ether; water; at 20℃; for 16h; Step B: 4-(Benzylamino)-l-hydroxycyclohexanecarbonitrile. A of <strong>[142009-99-2]4-(benzylamino)cyclohexanone</strong> (5.8 g, 28.5 mmol) in ether (1 12 mL) was cooled to 0C. To this mixture was added NaCN (1.538 g, 31.4 mmol) as a solution in NaHC03 (4.79 g, 57.1 mmol) and water (71.4 mL, 3966 mmol). The reaction mixture was stirred at RT for 16 hours. The resulting mixture was diluted with ether (110 mL) and water (50 mL). The layers were separated, and the organic portion was dried over sodium sulfate and concentrated under reduced pressure to afford 4-(benzylamino)-l- hydroxycyclohexanecarbonitrile as a light yellow solid (5.6 g, 85 % yield). MS m/z = 231.2 [M+H]. Calc'd for Ci4H18N20: 230.1.
  • 68
  • [ 1610517-27-5 ]
  • [ 142009-99-2 ]
  • [ 1610517-26-4 ]
  • 69
  • [ 142009-99-2 ]
  • [ 1610517-30-0 ]
  • 70
  • [ 142009-99-2 ]
  • ethyl (1RS,4SR,5RS)-2-benzyl-4-chloro-3,6-dioxo-2-azabicyclo[3.3.1]nonane-4-carboxylate [ No CAS ]
  • 71
  • [ 142009-99-2 ]
  • ethyl (1RS,4RS,5RS)-2-benzyl-4-chloro-3,6-dioxo-2-azabicyclo[3.3.1]nonane-4-carboxylate [ No CAS ]
  • 72
  • [ 142009-99-2 ]
  • ethyl 2-benzyl-3,6-dioxo-2-azabicyclo[3.3.1]nonane-4-carboxylate [ No CAS ]
  • 74
  • [ 142009-99-2 ]
  • ethyl 3-[benzyl(4-cyanocyclohex-3-en-1-yl)amino]-3-oxopropanoate [ No CAS ]
  • 75
  • [ 142009-99-2 ]
  • ethyl (1RS,4RS,5RS,6SR)-2-benzyl-6-cyano-3-oxo-2-azabicyclo[3.3.1]nonane-4-carboxylate [ No CAS ]
  • C19H22N2O3 [ No CAS ]
  • 76
  • [ 142009-99-2 ]
  • C22H26N2O3 [ No CAS ]
  • 77
  • [ 142009-99-2 ]
  • C20H30N2O [ No CAS ]
  • 78
  • [ 142009-99-2 ]
  • C26H33N3O5S [ No CAS ]
  • 79
  • [ 142009-99-2 ]
  • (4RS,4aSR,6SR,8aRS)-4-allyl-9-benzyl-2-((2-nitrophenyl)sulfonyl)perhydro-6,4-(iminomethano)isoquinoline [ No CAS ]
  • 80
  • [ 142009-99-2 ]
  • (4RS,4aSR,6SR,8aRS)-4-allyl-9-benzylperhydro-6,4-(iminomethano)isoquinoline [ No CAS ]
  • 81
  • [ 142009-99-2 ]
  • (4RS,4aSR,6SR,8aRS)-4-allyl-9-benzyl-2-(undec-10-enoyl)perhydro-6,4-(iminomethano)isoquinoline [ No CAS ]
  • 82
  • [ 142009-99-2 ]
  • (4RS,4aSR,6SR,8aRS)-4-allyl-9-benzyl-2-(dec-9-enoyl)perhydro-6,4-(iminomethano)isoquinoline [ No CAS ]
  • 83
  • [ 142009-99-2 ]
  • (4RS,4aSR,6SR,8aRS)-4-allyl-9-benzyl-2-(non-9-enoyl)perhydro-6,4-(iminomethano)isoquinoline [ No CAS ]
  • 84
  • [ 142009-99-2 ]
  • C29H42N2O [ No CAS ]
  • 85
  • [ 142009-99-2 ]
  • C28H40N2O [ No CAS ]
  • 86
  • [ 142009-99-2 ]
  • C27H38N2O [ No CAS ]
  • 87
  • [ 142009-99-2 ]
  • C22H38N2O [ No CAS ]
  • 88
  • [ 142009-99-2 ]
  • C21H36N2O [ No CAS ]
  • 89
  • [ 142009-99-2 ]
  • C20H34N2O [ No CAS ]
  • 90
  • [ 142009-99-2 ]
  • C22H40N2 [ No CAS ]
  • 91
  • [ 142009-99-2 ]
  • C21H38N2 [ No CAS ]
  • 92
  • [ 142009-99-2 ]
  • C20H36N2 [ No CAS ]
  • 93
  • [ 142009-99-2 ]
  • C16H19NO2 [ No CAS ]
  • 94
  • [ 142009-99-2 ]
  • C19H26N2O [ No CAS ]
  • 95
  • [ 142009-99-2 ]
  • C19H24Cl2N2O [ No CAS ]
  • 96
  • [ 79-36-7 ]
  • [ 142009-99-2 ]
  • C15H17Cl2NO2 [ No CAS ]
  • 97
  • [ 7623-09-8 ]
  • [ 142009-99-2 ]
  • C16H20ClNO2 [ No CAS ]
  • 98
  • [ 142009-99-2 ]
  • [ 7148-74-5 ]
  • C16H20BrNO2 [ No CAS ]
  • 99
  • [ 142009-99-2 ]
  • 1-benzyl-7-methyl-1,3,4,6-tetrahydro-2,6-methanobenzo[b]azocin-5(2H)-one [ No CAS ]
  • 100
  • [ 142009-99-2 ]
  • [ 94-36-0 ]
  • C20H21NO3 [ No CAS ]
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