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[ CAS No. 3197-44-2 ] {[proInfo.proName]}

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3d Animation Molecule Structure of 3197-44-2
Chemical Structure| 3197-44-2
Chemical Structure| 3197-44-2
Structure of 3197-44-2 * Storage: {[proInfo.prStorage]}
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Product Details of [ 3197-44-2 ]

CAS No. :3197-44-2 MDL No. :MFCD11036292
Formula : C6H13NO Boiling Point : -
Linear Structure Formula :- InChI Key :PRAYXGYYVXRDDW-ZCFIWIBFSA-N
M.W : 115.17 Pubchem ID :6950192
Synonyms :

Calculated chemistry of [ 3197-44-2 ]

Physicochemical Properties

Num. heavy atoms : 8
Num. arom. heavy atoms : 0
Fraction Csp3 : 1.0
Num. rotatable bonds : 1
Num. H-bond acceptors : 2.0
Num. H-bond donors : 2.0
Molar Refractivity : 36.72
TPSA : 32.26 Ų

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) : -6.99 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.61
Log Po/w (XLOGP3) : 0.02
Log Po/w (WLOGP) : -0.26
Log Po/w (MLOGP) : 0.21
Log Po/w (SILICOS-IT) : 0.96
Consensus Log Po/w : 0.51

Druglikeness

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

Water Solubility

Log S (ESOL) : -0.5
Solubility : 36.4 mg/ml ; 0.316 mol/l
Class : Very soluble
Log S (Ali) : -0.25
Solubility : 64.9 mg/ml ; 0.563 mol/l
Class : Very soluble
Log S (SILICOS-IT) : -0.86
Solubility : 15.8 mg/ml ; 0.137 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.56

Safety of [ 3197-44-2 ]

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

Application In Synthesis of [ 3197-44-2 ]

* 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.

  • Upstream synthesis route of [ 3197-44-2 ]
  • Downstream synthetic route of [ 3197-44-2 ]

[ 3197-44-2 ] Synthesis Path-Upstream   1~17

  • 1
  • [ 154499-13-5 ]
  • [ 3197-44-2 ]
YieldReaction ConditionsOperation in experiment
65% With hydrogen In ethyl acetate at 18 - 25℃; for 7 h; Palladium on carbon (500 mg of 10percent) was added to a solution of benzyl (2R)-2-(hydroxymethyl)piperidine-1-carboxylate (5.00 g, 20.06 mmol) in ethyl acetate (70 ml) and the reaction mixture stirred at room temperature under an atmosphere of hydrogen for 4 hours. The mixture was filtered and a new portion of catalyst (300 mg) was added to the filtrate. The mixture was then stirred under an atmosphere of hydrogen for a further 3 hours. The mixture was filtered and the filtrate evaporated to leave a brown oil. The crude product was purified by kugelrohr distillation to give (2R)-piperidin-2-ylmethanol (1.51 g, 65percent yield):1H NMR (CDCl3): 3.53-3.48 (m, 1H), 3.36-3.31 (m, 1H), 3.02 (d, 1H), 2.61-2.53 (m, 2H), 2.35 (s, 2H), 1.75-1.73 (m, 1H), 1.56-1.47 (m, 2H), 1.40-1.25 (m, 2H), 1.14-1.03 (m, 1H
Reference: [1] Bioorganic and Medicinal Chemistry Letters, 2005, vol. 15, # 3, p. 809 - 812
[2] Heterocycles, 2003, vol. 60, # 1, p. 57 - 71
[3] Patent: US2010/168143, 2010, A1, . Location in patent: Page/Page column 12-13
  • 2
  • [ 134441-61-5 ]
  • [ 3197-44-2 ]
YieldReaction ConditionsOperation in experiment
100% With trifluoroacetic acid In dichloromethane at 20℃; for 1 h; Trifluoroacetic acid (3 ml) was carefully added to a stirring solution of tert-butyl (2R)-2- (hydroxymethyl) PIPERIDINE-L-CARBOXYLATE (1.15 g, obtained as described in TETRAHEDRON, 5 8 (2002), 1343-1354) in DCM (3 ml) and stirred at room temperature for 1 hour. Volatiles were removed IN VACUO and the oil thus obtained dissolved in methanol (60 ml), and neutralized by addition of MP-Carbonate resin (polymer supported carbonate reagent ex. Argonaut Technologies Inc.) (approximately I g) whilst stirring at room temperature for 2 hours. The resin was filtered, washed with methanol (3 x 30 ml) and the filtrate concentrated. The resulting oil was dissolved in DCM (30 ml) and dried (MgSO4) before filtration and solvent removal to afford a grey oil (615 mg, 100percent); NMR spectrum (DMSO-D6) 1.44-1. 51 (m, 2H), 1.61 (m, 1H), 1.70-1. 78 (m, 3H), 2.84 (m, 1H), 3.03 (m, 1H), 3.21 (d, 1H), 3.49 (m, 1H), 3.57 (dd, 1H), 5.01 (bs, 1H), 7.65 (bs, 1H) ; Mass spectrum M+ 116.
100% With trifluoroacetic acid In dichloromethane at 20℃; for 1 h; Trifluoroacetic acid (3 ml) was carefully added to a stirred solution of tert-butyl (2R)-2- (hydroxymethyl)piperidine-l-carboxylate (1.15 g, obtained as described in Tetrahedron, 58 (2002), 1343 - 1354) in DCM (3 ml). The reaction mixture was then stirred at room temperature for 1 hour. Volatiles were removed in vacuo and the oil thus obtained dissolved in methanol (60 ml), and neutralized by addition of MP-Carbonate resin (polymer supported carbonate reagent ex. Argonaut Technologies Inc.) (approximately Ig) whilst stirring at room temperature for 2 hours. The resin was filtered, washed with methanol (3 x 30 ml) and the filtrate concentrated. The resulting oil was dissolved in DCM (30 ml) and dried (MgSO4) before filtration and solvent removal to afford a grey oil (615 mg, 100percent); NMR spectrum 1.44 - 1.51 (m, 2H), 1.61 (m, IH), 1.70 - 1.78 (m, 3H), 2.84 (m, IH), 3.03 (m, IH), 3.21 (d, IH), 3.49 (m, IH), 3.57 (dd, IH), 5.01 (bs, IH), 7.65 (bs, IH); Mass spectrum M+ 116.
100% With trifluoroacetic acid In dichloromethane at 20℃; for 1 h; The (2R)-piperidin-2-ylmethanol used as starting material was prepared as follows: Trifluoroacetic acid (3 ml) was carefully added to a stirring solution of tert-butyl (2R)-2- (hydroxymethyl)piperidine-l-carboxylate (1.15 g, obtained as described in Tetrahedron, 58 (2002), 1343 - 1354) in DCM (3 ml) and stirred at room temperature for 1 hour. Volatiles were removed in vacuo and the oil thus obtained dissolved in methanol (60 ml), and neutralized by addition of MP-Carbonate resin (polymer supported carbonate reagent ex. Argonaut Technologies Inc.) (approximately 1 g) whilst stirring at room temperature for 2 hours. The resin was filtered, washed with methanol (3 x 30 ml) and the filtrate concentrated. The resulting oil was dissolved in DCM (30 ml) and dried (MgSO4) before filtration and solvent removal to afford a grey oil (615 mg, 100percent); NMR spectrum 1.44 - 1.51 (m, 2H), 1.61 (m, IH), 1.70 - 1.78 (m, 3H), 2.84 (m, IH), 3.03 (m, IH), 3.21 (d, IH), 3.49 (m, IH), 3.57 (dd, IH), 5.01 (bs, IH), 7.65 (bs, IH): Mass spectrum M+ 116.
Reference: [1] Patent: WO2005/26152, 2005, A1, . Location in patent: Page/Page column 121-122
[2] Patent: WO2006/92573, 2006, A1, . Location in patent: Page/Page column 68
[3] Patent: WO2006/92574, 2006, A1, . Location in patent: Page/Page column 66
[4] RSC Advances, 2015, vol. 5, # 62, p. 50580 - 50590
  • 3
  • [ 1723-00-8 ]
  • [ 3197-44-2 ]
Reference: [1] Journal of the American Chemical Society, 1995, vol. 117, # 36, p. 9369 - 9370
[2] Journal of Organic Chemistry, 1997, vol. 62, # 15, p. 5023 - 5033
[3] Journal of the American Chemical Society, 1999, vol. 121, # 4, p. 700 - 709
[4] Tetrahedron, 2013, vol. 69, # 48, p. 10311 - 10315
  • 4
  • [ 18650-38-9 ]
  • [ 3197-44-2 ]
Reference: [1] Journal of Organic Chemistry, 2005, vol. 70, # 11, p. 4248 - 4256
  • 5
  • [ 1353042-37-1 ]
  • [ 3197-44-2 ]
Reference: [1] RSC Advances, 2015, vol. 5, # 62, p. 50580 - 50590
  • 6
  • [ 1120-80-5 ]
  • [ 3197-44-2 ]
Reference: [1] Agricultural and Biological Chemistry, 1986, vol. 50, # 12, p. 3107 - 3112
[2] Agricultural and Biological Chemistry, 1986, vol. 50, # 12, p. 3107 - 3112
  • 7
  • [ 6140-65-4 ]
  • [ 3197-44-2 ]
Reference: [1] Agricultural and Biological Chemistry, 1986, vol. 50, # 12, p. 3107 - 3112
[2] Agricultural and Biological Chemistry, 1986, vol. 50, # 12, p. 3107 - 3112
  • 8
  • [ 113965-39-2 ]
  • [ 3197-44-2 ]
Reference: [1] Agricultural and Biological Chemistry, 1986, vol. 50, # 12, p. 3107 - 3112
  • 9
  • [ 28697-07-6 ]
  • [ 3197-44-2 ]
Reference: [1] Bioorganic and Medicinal Chemistry Letters, 2005, vol. 15, # 3, p. 809 - 812
  • 10
  • [ 160885-25-6 ]
  • [ 3197-44-2 ]
Reference: [1] RSC Advances, 2015, vol. 5, # 62, p. 50580 - 50590
  • 11
  • [ 189188-59-8 ]
  • [ 3197-44-2 ]
Reference: [1] RSC Advances, 2015, vol. 5, # 62, p. 50580 - 50590
  • 12
  • [ 182969-96-6 ]
  • [ 3197-44-2 ]
Reference: [1] RSC Advances, 2015, vol. 5, # 62, p. 50580 - 50590
  • 13
  • [ 4043-87-2 ]
  • [ 41373-39-1 ]
  • [ 3197-44-2 ]
Reference: [1] Synlett, 2008, # 5, p. 702 - 706
  • 14
  • [ 35677-83-9 ]
  • [ 3197-44-2 ]
Reference: [1] Chemische Berichte, 1957, vol. 90, p. 2036
  • 15
  • [ 141-78-6 ]
  • [ 3433-37-2 ]
  • [ 41373-39-1 ]
  • [ 111555-84-1 ]
  • [ 136982-28-0 ]
  • [ 3197-44-2 ]
Reference: [1] Tetrahedron Letters, 1991, vol. 32, # 33, p. 4197 - 4198
  • 16
  • [ 4043-87-2 ]
  • [ 41373-39-1 ]
  • [ 3197-44-2 ]
Reference: [1] Synlett, 2008, # 5, p. 702 - 706
  • 17
  • [ 141-78-6 ]
  • [ 3433-37-2 ]
  • [ 41373-39-1 ]
  • [ 111555-84-1 ]
  • [ 136982-28-0 ]
  • [ 3197-44-2 ]
Reference: [1] Tetrahedron Letters, 1991, vol. 32, # 33, p. 4197 - 4198
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