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[ CAS No. 31560-06-2 ] {[proInfo.proName]}

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Chemical Structure| 31560-06-2
Chemical Structure| 31560-06-2
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Quality Control of [ 31560-06-2 ]

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Product Details of [ 31560-06-2 ]

CAS No. :31560-06-2 MDL No. :MFCD01569249
Formula : C5H10ClNO Boiling Point : No data available
Linear Structure Formula :- InChI Key :-
M.W : 135.59 Pubchem ID :-
Synonyms :

Calculated chemistry of [ 31560-06-2 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 8
Num. arom. heavy atoms : 0
Fraction Csp3 : 1.0
Num. rotatable bonds : 0
Num. H-bond acceptors : 2.0
Num. H-bond donors : 1.0
Molar Refractivity : 36.69
TPSA : 21.26 ?2

Pharmacokinetics

GI absorption : High
BBB permeant : No
P-gp substrate : No
CYP1A2 inhibitor : No
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -6.78 cm/s

Lipophilicity

Log Po/w (iLOGP) : 0.0
Log Po/w (XLOGP3) : 0.49
Log Po/w (WLOGP) : 0.17
Log Po/w (MLOGP) : 0.21
Log Po/w (SILICOS-IT) : 1.01
Consensus Log Po/w : 0.38

Druglikeness

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

Water Solubility

Log S (ESOL) : -0.99
Solubility : 13.9 mg/ml ; 0.102 mol/l
Class : Very soluble
Log S (Ali) : -0.51
Solubility : 42.3 mg/ml ; 0.312 mol/l
Class : Very soluble
Log S (SILICOS-IT) : -0.51
Solubility : 41.8 mg/ml ; 0.308 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 2.75

Safety of [ 31560-06-2 ]

Signal Word:Warning Class:
Precautionary Statements:P261-P280-P305+P351+P338 UN#:
Hazard Statements:H302-H315-H319-H332-H335 Packing Group:
GHS Pictogram:

Application In Synthesis of [ 31560-06-2 ]

* 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 [ 31560-06-2 ]

[ 31560-06-2 ] Synthesis Path-Downstream   1~10

  • 1
  • [ 934989-28-3 ]
  • [ 31560-06-2 ]
  • C24H25F2NO3 [ No CAS ]
YieldReaction ConditionsOperation in experiment
To the stirred solution of Q-2 (1.0 g) in CH2CI2 (10 mL) was added (IS, 4S)-2-oxa-5- azabicyclo[2.2.1 ]heptane HCl salt (1.23 g), DIPEA (1.58 mL) and molecular sieves (2g). After stirring for 30 minutes, Na(OAc)3BH (1.92 g) was added. The reaction suspension was stirred at room temperature overnight. After filtration, the filtrate was washed with saturated NaHCO3, brine and concentrated. The resulting residue was purified by a flash column chromatography on silica gel to give a racemic mixture of Q-3. ESI-MS calc. for C24H25F2NO3: 413; Found: 414 (M+H).
  • 2
  • [ 934989-28-3 ]
  • [ 31560-06-2 ]
  • C25H29F2NO3 [ No CAS ]
YieldReaction ConditionsOperation in experiment
To the stirred solution of 47-2 (1.0 g) in CH2CI2 (10 mL) was added (IS, 4S)-2-oxa-5- azabicyclo[2.2.1]heptane HCl salt (1.23 g), DlPEA (1.58 mL) and molecular sieves (2g). After stirring for 30 minutes, Na(OAc)3BH (1.92 g) was added. The reaction suspension was stirred at room temperature overnight. After filtration, the filtrate was washed with saturated NaHCO3, brine and concentrated. The resulting residue was purified by a flash column chromatography on silica gel to give a racemic mixture of 47-3. ESI-MS calc. for C24H25F2NO3: 413; Found: 414 (M+H).
  • 3
  • [ 944154-58-9 ]
  • [ 31560-06-2 ]
  • [ 944154-60-3 ]
YieldReaction ConditionsOperation in experiment
70% Example 1; 9beta-13-O-[(2R,3S)-3-(tert-butyloxycarbonylamino)-2-hydroxyl-3-phenyl propionyl]-10-deacetyl-9-dihydro-9,10-O-[2-N-(2S,4S)-2-oxa-5-aza-bicyclo[2.2.1 ] hept-5-ylmethyl] baccatinIII ; [Show Image] The resulting compound from step 7, 9beta-13-O-[(2R,3S)-3-(tert-butyloxycarbonyl amino)-2-hydroxyl-3-phenylpropionyl]-10-deacetyl-9-dihydro-9,10-O-acetaldehyde baccatin H(0.545g, 0.63mmol, 1.0eq) was dissolved in 30ml anhydrous methanol in a 100ml three-neck flask to form a solution under an argon atmosphere. And then, a minor amount of drying molecular sieve (4A) and (S,S)-2-oxa-5-aza-bicyclo[2.2.1] heptane hydrochloride (0.568g, 4.16mmol, 6.6eq) were added into the solution during stirring at room temperature to form a mixture. Upon completion of the addition, the mixture was stirred for 30 minutes at room temperature. Sodium cyanoborohydride (0.261g, 4.16mmol, 6.6eq) was added into the mixture. Upon completion of the addition, the mixture was stirred for 1.5 hours at room temperature. It is shown that the starting materials are completely reacted during the reaction according to the Point-plate tracking (dichloromethane: ethyl acetate: methanol = 10:10:1). The resulting mixture was quenched with 70ml saturated sodium bicarbonate solution, extracted with ethyl acetate (100 ml.x.4) to form the organic extracts. The combined organic extracts were washed with 25ml water and 25ml saturated brine, dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure to form a residue. The residue was purified by silica gel column chromatography with hexane: dichloromethane: ethyl acetate: methanol =20:10:10:2 as eluents firstly, then with dichloromethane: ethyl acetate: methanol =30:10:2 to provide 9beta-13-O-[(2R,3S)-3-(tert-butyloxycarbonylamino)-2-hydroxyl-3-phenylpropionyl] -10-deacetyl-9-dihydro-9,10-O-[2-N-(2S,4S)-2-Oxa-5-aza-bicyclo[2.2.1]hept-5-ylm ethyl] baccatinIII I (0.412 g, white-like solid) with a yield of 70percent. Rf=0.29(dichloromethane: ethyl acetate: methanol = 10:10:1(V/V)) MW=933, ESI-MS:[M+H]+=933.9. 1H-NMR(CD3Cl3, 400MHz): delta8.1(d, J=7.5Hz, 2H, Ar-H), 7.7-7.5(t, J=7.0Hz, 1H, Ar-H), 7.5-7.2(m, 7H), 6.1-6.0(m, 2H), 5.7-5.6(d, J=9.4Hz, 1H), 5.3(d, J=9.4Hz, 1H), 5.2(d, J=7.0Hz, 1H), 5.1(s, 1H), 5.0-4.9(b, 1H), 4.7-4.6(d, J=8.2Hz, 1H), 4.6(b, 1H), 4.4(b, 1H), 4.4-4.2(dd, AB-type, J=8.4Hz, 2H), 4.2-4.0(m, 2H), 4.0(d, J=7.9Hz, 1H), 3.8(d, J=7.1Hz, 1H), 3.7-3.6(d, J=7.8Hz, 1H), 3.6(b, 1H), 3.1-3.0(m, 2H), 3.0-2.9(m, 1H), 2.9(d, J=4.7Hz, 1H), 2.7(m, J=10.2Hz, 1H), 2.4(dd, J=9.7Hz, J'=14.6Hz, 1H), 2.3(s, 3H, CH3), 2.3-2.2(m, 1H), 2.2-2.0(m, 2H), 1.9(b, 1H), 1.9-1.8(m, 1H), 1.8-1.7(m, 1H), 1.65(s, 3H, CH3), 1.60(s, 3H, CH3), 1.55(s, 3H, CH3), 1.4(s, 9H, t-Bu), 1.3(s, 3H, CH3).
  • 4
  • [ 1075757-45-7 ]
  • [ 31560-06-2 ]
  • 5-fluoro-N4-[(1S)-1-(5-fluoropyridin-2-yl)ethyl]-N2-(5-methoxy-1H-pyrazol-3-yl)-6-(2-oxa-5-azabicyclo[2.2.1]hept-5-yl)pyrimidine-2,4-diamine [ No CAS ]
YieldReaction ConditionsOperation in experiment
30% With N-ethyl-N,N-diisopropylamine; In butan-1-ol; at 150℃; for 4h;Microwave irradiation; Example 85-Fluoro-N4-r(y)-l-(5-fluoro-pyridin-2-yl)-ethyl1-N2-(5-methoxy-lH-pyrazol-3-yl)-6-(2-oxa-5- aza-bicvclo[2.2.11hept-5-yl)-pyrimidine-2,4-diamineA mixture of 6-chloro-5-fluoro-lambda^-[(S)-l-(5-fluoro-pyridin-2-yl)-ethyl]-N -(5-methoxy-lH- pyrazol-3-yl)-pyrimidine-2,4-diamine (Example 7, 70mg, 0.18 mmol), (l1S',41S)-2-oxa-5-aza- bicyclo[2.2.1]heptane hydrochloride (40mg, 0.3 mmol) and DIPEA (0.088ml, 0.5 mmol) in n- BuOH (0.8 ml) was heated in a microwave reactor at 1500C for 4 hours. Evaporation of the solvents under reduced pressure gave a residue. This residue was purified by silica gel chromatography (ISCO, DCMZMeOHZNH4OH: IOOZOZO tol00Z4Z0.4) to afford the title compound (24mg, 30percent). 1H NMR (CDCl3) delta 8.40 (s, IH), 7.37 (m, IH), 7.28 (m, IH), 5.96 (m, IH), 5.26 (m, IH), 5.10 (s, IH), 4.86 (br, IH), 4.59(s, IH), 3.85 (s, 3H), 3.80 (m, 2H), 3.46 (m, 3H), 1.83 (s, 2H), 1.54 (d, 3H). LCMS: 445 [M+H].
  • 5
  • [ 1108184-21-9 ]
  • [ 31560-06-2 ]
  • [ 1108184-22-0 ]
YieldReaction ConditionsOperation in experiment
39% With potassium carbonate; potassium iodide; In N,N-dimethyl-formamide; at 90℃; for 19h; 5-Bromo-1-(2-chloroethyl)-1H-indazole (183 mg, 0.703 mmol) was added to a suspension of <strong>[31560-06-2](1S,4S)-(+)-5-aza-2-oxabicyclo[2.2.1]heptane hydrochloride</strong> (286 mg, 2.11 mmol), K2CO3 (485 mg, 3.52 mmol) and KI (117 mg, 0.703 mmol) in DMF (10 mL) under N2. The resulting suspension was stirred at 90° C. for 19 h. The suspension was cooled, and H2O (10 mL) was added. The aqueous solution was extracted with EtOAc, and the combined organic extracts were washed with brine. The organic solution was dried over Na2SO4 and concentrated under reduced pressure to afford clear viscous oil. Flash chromatography on silica gel (100:0 to 0:100 hexanes/(9:0.9:0.1 CH2Cl2/MeOH/NH4OH)) gave the title compound (88 mg, 39percent) as a clear oil: 1H NMR (300 MHz, CDCl3) delta 7.95-7.92 (m, 1H), 7.87-7.84 (m, 1H), 7.45 (dd, J=8.7, 1.8 Hz, 1H), 7.34 (d, J=8.7 Hz, 1H), 4.43 (t, J=6.7 Hz, 2H), 4.34 (br s, 1H), 3.92 (d, J=7.8 Hz, 1H), 3.56 (dd, J=7.8, 1.5 Hz, 1H), 3.34 (br s, 1H), 3.15-3.01 (m, 2H), 2.92 (d, J=21.9 Hz, 1H), 2.81 (dd, J=9.9, 1.5 Hz, 1H), 2.47 (br d, J=9.9 Hz, 1H), 1.79-1.60 (m, 1H).
  • 6
  • [ 1195778-76-7 ]
  • [ 31560-06-2 ]
  • [ 1195779-88-4 ]
YieldReaction ConditionsOperation in experiment
73% With 4-methyl-morpholine; O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate; In N,N-dimethyl-formamide; for 1h; 7H-Indolo[2,1-a][2]benzazepine-10-carboxamide, 6-[1-cyclobutyl-4-((1S,4S)-2-oxa-5-azabicyclo[2.2.1]heptan-5-yl)carbonyl-1H-pyrazol-5-yl]-13-cyclohexyl-3-methoxy-N-[(1-methylethyl)sulfonyl]- A 2 dram vial was charged with 1H-pyrazole-4-carboxylic acid, 1-cyclobutyl-5-[13-cyclohexyl-3-methoxy-10-[[[(1-methylethyl)sulfonyl]amino]carbonyl]-7H-indolo[2,1-a][2]benzazepin-6-yl]-(70 mg, 0.107 mmol), DMF (1 mL), (1S,4S)-2-oxa-5-azabicyclo[2.2.1]heptane, HCl (28.9 mg, 0.213 mmol), 4-methylmorpholine (0.035 mL, 0.320 mmol) and o-Benzotriazol-1-yl-N,N,N',N'-tetramethyluronium tetrafluoroborate (TBTU) (37.6 mg, 0.117 mmol). The rxn was stirred for 1 hour. It was diluted with ether, washed with saturated ammonium chloride then brine, dried (MgSO4) and evaporated giving a yellow foam. The foam was dissolved in DCM, the solution was added to a Thompson silica gel cartridge and it was eluted with ethyl acetate/methanol (0percent to 10percent). The appropriate fractions (TLC) were combined and evaporated giving a light yellow film. The film was dissolved in DCM, re-evaporated, the residue triturated in hexane/ether (5percent) and filtered giving the product (58 mg, 0.078 mmol, 73.0percent yield) as light a yellow powder. HPLC: 99.9percent pure, 22.39 minutes. LCMS: 738.26 at 3.96 minutes, mp: 164-166° C. HRMS: calculate-738.3820, found-738.382.
  • 7
  • [ 1195782-58-1 ]
  • [ 31560-06-2 ]
  • [ 1195780-46-1 ]
YieldReaction ConditionsOperation in experiment
64.8% With 4-methyl-morpholine; O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate; In N,N-dimethyl-formamide; 7H-Indolo[2,1-a][2]benzazepine-10-carboxamide, 6-[1-cyclobutyl-3-methyl-4-((1S,4S)-2-oxa-5-azabicyclo[2.2.1]heptan-5-ylcarbonyl)-1H-pyrazol-5-yl]-13-cyclohexyl-3-methoxy-N-[(1-methylethyl)sulfonyl]- A 2 dram vial was charged with 1H-pyrazole-4-carboxylic acid-5-methyl, 1-cyclobutyl-5-[13-cyclohexyl-3-methoxy-10-[[[(1-methylethyl)sulfonyl]amino]carbonyl]-7H-indolo[2,1-a][2]benzazepin-6-yl]-(70 mg, 0.104 mmol), DMF (1 mL), 4-methylmorpholine (0.023 mL, 0.209 mmol), (1S,4S)-2-oxa-5-azabicyclo[2.2.1]heptane, HCl (16.98 mg, 0.125 mmol) and o-benzotriazol-1-yl-N,N,N',N'-tetramethyluronium tetrafluoroborate (TBTU) (36.9 mg, 0.115 mmol). The rxn was stirred over night. The rxn was diluted with DCM, washed with 0.1 N HCl (aqueous) then brine, dried (MgSO4) and evaporated giving a yellow syrup. The syrup was dissolved in DCM, the solution was added to a Thompson silica gel cartridge and it was eluted with DCM/methanol (0percent to 4percent). The appropriate fractions (TLC) were combined and evaporated giving a light yellow solid. The solid was triturated in ether/hexane and filtered giving the product (53 mg, 0.068 mmol, 64.8percent yield) as a creamy white powder. HPLC: 96.0percent pure, 24.07 minutes. LCMS: 752.20 at 3.83 minutes. LCMS neg/pos: 750.2/752.1 at 2.51 minutes. 1H NMR: (400 Mz, CD3OD) delta 1.18-1.24 (m, 2H), 1.41 (m, 5H), 1.53 (s, 2H), 1.78-1.80 (m, 3H), 1.95 (bs, 3H), 2.05 (m, 3H), 2.31 (s, 3H), 2.47-2.50 (m, 1H), 2.67-2.76 (m, 1H), 2.81 (s, 3 h), 2.87 (s, 3H), 2.94 (s, 2H), 3.31-3.38 (m, 1H), 3.84-3.89 (m, 1H), 3.95 (m, 3H), 4.03-4.12 (m, 2H), 4.55-4.58 (d, J=14 Hz, 1H), 4.82-4.85 (d, J=14 Hz, 2H), 6.71-6.83 (m, 1H), 6.93-6.96 (m, 1H), 7.11-7.12 (d, J=8 Hz, 1H), 7.54-7.72 (m, 3H), 7.86-7.95 (m, 1H) 10.99 (bs, 1H).
  • 8
  • [ 1223404-88-3 ]
  • [ 31560-06-2 ]
  • [ 530-62-1 ]
  • [ 1223404-67-8 ]
YieldReaction ConditionsOperation in experiment
86% Example 92; (lS.4S)-N-(5-((R)-2-(2.5-difluorophenvnpyrrolidin-l-vnpyrazolori.5-alpyrimidin-3- vD-Sigma-oxa-S-azabicvclo^^.?heptane-S-carboxamide; [00515] To a DCM (1.0 niL) solution of (R)-5-(2-(2,5-difluorophenyl)pyrrolidin-l- yl)pyrazolo[l,5-a]pyrimidin-3-amine (Preparation B; 50 mg, 0.16 mmol) was added CDI (51 mg, 0.32 mmol) at ambient temperature in one portion. After stirring 90 minutes, (lS,4S)-2- oxa-5-azabicyclo[2.2.1]heptane hydrochloride (43 mg, 0.32 mmol) was added in one portion, followed by DIEA (0.083 mL, 0.48 mmol). The reaction was stirred for 5 minutes before it was concentrated and directly purified by reverse-phase column chromatography, eluting with 0 to 60% acetonitrile/water to yield the final product as a pale-yellowish powder (60 mg, 86% yield). MS (apci) m/z = 441.2 (M+H).
  • 9
  • [ 1000295-82-8 ]
  • [ 31560-06-2 ]
  • {3-[4-(2-chloro-6-fluoro-phenyl)-piperidin-1-ylmethyl]-1H-indol-2-yl}-(1S,4S)-2-oxa-5-aza-bicyclo[2.2.1]hept-5-yl-methanone [ No CAS ]
YieldReaction ConditionsOperation in experiment
Example 9; {3-[4-(2-Chloro-6-fluoro-phenyl)-piperidin-1-ylmethyl]-1 H-indol-2-yl}-(1S,4S)-2-oxa-5-aza-bicyclo[2.2.1]hept-5-yl-methanone; To a suspension of 204 mg (0.492 mmol) of 3-[4-(2-chloro-6-fluoro-phenyl)- piperidin-1 -ylmethyl]-1 H-indole-2-carboxylic acid ethyl ester (obtained as described in General Preparation 2) in EtOH (2.5 ml_), 1 ml_ of 1 N sodium hydroxide solution was added and the mixture was stirred at 80 °C for 2 h. The solvent was evaporated under reduced pressure and the pale yellow solid obtained (199 mg) was suspended in SOCI2 (2 ml_) and the reaction mixture was stirred at 50 °C for 2 h. Excess SOCI2 was evaporated under reduced pressure and the light brown solid obtained was suspended in dry DMF (1 ml_) and added dropwise at 0°C to a solution of (1 S,4S)-2-Oxa-5-aza-bicyclo[2.2.1 ]heptane hydrochloride (133 mg, 0.98 mmol) and thethylamine (0.34 ml_, 2.45 mmol) in CH2CI2 (3 ml_). The mixture was stirred at room temperature overnight, then it was washed with water (2x5 ml_) and with 1 N NaOH solution (2x5 ml_). Organic layers were collected, dried over Na2SO4 and evaporated under reduced pressure. The crude product obtained was purified by flash chromatography (CH2CI2/MeOH/NH4OH 96:3.5:0.5 to 93:6:1 respectively) yielding 25 mg of the title compound. NMR (300 MHz, CDCI3, delta ppm): 1 1.52 (s br, 1 H); 7.72 (d, 1 H); 7.60 (d br, 1 H); 7.24 (dd, 1 H); 7.13-7.05 (m, 3H); 6.91 (m, 1 H); 4.86 (m, 1 H); 4.62 (m, 1 H); 4.36- 4.05 (m, 2H); 4.00 (d, 1 H); 3.79 (m, 1 H); 3.57 (m, 1 H); 3.26 (m, 3H); 2.88-2.22 (m, 3H); 2.05 (m, 1 H); 1.90 (m, 1 H); 1.77 (m, 4H). ESI Pos, 3.2KV, 20V, 400°C MS (m/z): 468.04 (MH+).
  • 10
  • [ 31560-06-2 ]
  • [ 590-17-0 ]
  • [ 1319197-37-9 ]
YieldReaction ConditionsOperation in experiment
Bromoacetonitrile (0.208 mL, 3.12 mmol) was added to a slurry of (lS,4S)-2-oxa- 5-azabicyclo[2.2.1]heptane hydrochloride (0.353 g, 2.60 mmol) , DMSO (13 mL) and MP-carbonate (3.17 mmol/g, 2.5X, 6.5 mmol, 2.05 g). After shaking overnight, 0.52 mmol trisamine (4.17 mmol/g, 125 mg) was added, and the slurry was shaken for an additional 2 h. The slurry was filtered and the resulting 2-((lS,4S)-2-oxa-5- azabicyclo[2.2.1]heptan-5-yl)acetonitrile/DMSO solution was used directly in the next step.
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