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[ CAS No. 149771-43-7 ] {[proInfo.proName]}

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Chemical Structure| 149771-43-7
Chemical Structure| 149771-43-7
Structure of 149771-43-7 * Storage: {[proInfo.prStorage]}
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Product Details of [ 149771-43-7 ]

CAS No. :149771-43-7 MDL No. :MFCD24465640
Formula : C18H26N2O2 Boiling Point : -
Linear Structure Formula :- InChI Key :IOPMFGUNMBWHIS-UHFFFAOYSA-N
M.W :302.41 Pubchem ID :15740907
Synonyms :

Calculated chemistry of [ 149771-43-7 ]

Physicochemical Properties

Num. heavy atoms : 22
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.61
Num. rotatable bonds : 5
Num. H-bond acceptors : 3.0
Num. H-bond donors : 0.0
Molar Refractivity : 95.39
TPSA : 32.78 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) : -5.99 cm/s

Lipophilicity

Log Po/w (iLOGP) : 3.74
Log Po/w (XLOGP3) : 3.04
Log Po/w (WLOGP) : 2.36
Log Po/w (MLOGP) : 2.66
Log Po/w (SILICOS-IT) : 2.15
Consensus Log Po/w : 2.79

Druglikeness

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

Water Solubility

Log S (ESOL) : -3.5
Solubility : 0.0952 mg/ml ; 0.000315 mol/l
Class : Soluble
Log S (Ali) : -3.39
Solubility : 0.122 mg/ml ; 0.000403 mol/l
Class : Soluble
Log S (SILICOS-IT) : -3.56
Solubility : 0.0831 mg/ml ; 0.000275 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 0.0
Synthetic accessibility : 3.93

Safety of [ 149771-43-7 ]

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:

Application In Synthesis of [ 149771-43-7 ]

* 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 [ 149771-43-7 ]
  • Downstream synthetic route of [ 149771-43-7 ]

[ 149771-43-7 ] Synthesis Path-Upstream   1~13

  • 1
  • [ 149771-43-7 ]
  • [ 149771-44-8 ]
YieldReaction ConditionsOperation in experiment
92% With hydrogen In ethanol 3,8-Diaza-bicyclo[3.2.1]octane-8-carboxylic acid tert-butyl ester (Intermediate); A mixture of 3-benzyl-3,8-diaza-bicyclo[3.2.1]octane-8-carboxylic acid te/if-butyl ester (13.0 g, 43.0 mmol), palladium on carbon (4.0 g, 5percent) and ethanol (100 ml, 99percent) was stirred under hydrogen. The mixture was filtered on celite, dried and evaporated. A white powder was isolated. Yield 8.4 g (92percent). Mp 103.4-106°C.
Reference: [1] Journal of Medicinal Chemistry, 1998, vol. 41, # 5, p. 674 - 681
[2] Patent: US2002/128271, 2002, A1,
[3] Patent: EP1213289, 2002, A1, . Location in patent: Page 13
[4] Patent: WO2006/106090, 2006, A1, . Location in patent: Page/Page column 16
[5] Tetrahedron Letters, 2002, vol. 43, # 5, p. 899 - 902
[6] Farmaco, 1993, vol. 48, # 3, p. 387 - 396
[7] Farmaco, 1998, vol. 53, # 8-9, p. 557 - 562
[8] Patent: US9404081, 2016, B2, . Location in patent: Page/Page column 179
  • 2
  • [ 24424-99-5 ]
  • [ 67571-90-8 ]
  • [ 149771-43-7 ]
YieldReaction ConditionsOperation in experiment
65% With triethylamine In dichloromethane at 0℃; for 3 h; 3-Benzyl-3,8-diaza-bicyclo[3.2.1]octane-8-carboxylic acid tert-butyl ester (Intermediate); A mixture of 3-benzyl-3,8-diaza-bicyclo[3.2.1]octane (13.5 g, 66.7 mmol), triethylamine (6.75 g, 66.7 mmol), di-tert-butyl-dicarbonate (boc-anyhdride) (14.56 g, 66.7 mmol) and dichloromethane (100 ml) was stirred with ice-cooling for 3 h. The crude mixture was washed with water (150 ml). The water phase was extracted with dichloromethane (50 ml). The combined organic phase was dried and evaporated. Yield 13 g (65percent). Mp 58-60°C.
Reference: [1] Journal of Medicinal Chemistry, 1998, vol. 41, # 5, p. 674 - 681
[2] Farmaco, 1993, vol. 48, # 3, p. 387 - 396
[3] Patent: EP1213289, 2002, A1, . Location in patent: Page 12
[4] Patent: WO2006/106090, 2006, A1, . Location in patent: Page/Page column 16
[5] Farmaco, 1998, vol. 53, # 8-9, p. 557 - 562
[6] Tetrahedron Letters, 2002, vol. 43, # 5, p. 899 - 902
[7] Patent: US2004/23971, 2004, A1,
[8] Patent: US9404081, 2016, B2, . Location in patent: Page/Page column 178-179
  • 3
  • [ 100-52-7 ]
  • [ 149771-44-8 ]
  • [ 149771-43-7 ]
Reference: [1] Patent: US9404081, 2016, B2, . Location in patent: Page/Page column 179
  • 4
  • [ 24424-99-5 ]
  • [ 144-55-8 ]
  • [ 67571-90-8 ]
  • [ 149771-43-7 ]
Reference: [1] Patent: US2002/128271, 2002, A1,
  • 5
  • [ 54221-37-3 ]
  • [ 149771-43-7 ]
Reference: [1] Tetrahedron Letters, 2002, vol. 43, # 5, p. 899 - 902
[2] Chinese Chemical Letters, 2011, vol. 22, # 5, p. 523 - 526
[3] Patent: US9404081, 2016, B2,
  • 6
  • [ 52321-06-9 ]
  • [ 149771-43-7 ]
Reference: [1] Tetrahedron Letters, 2002, vol. 43, # 5, p. 899 - 902
[2] Patent: US9404081, 2016, B2,
  • 7
  • [ 37061-44-2 ]
  • [ 149771-43-7 ]
Reference: [1] Tetrahedron Letters, 2002, vol. 43, # 5, p. 899 - 902
[2] Patent: US9404081, 2016, B2,
  • 8
  • [ 96483-83-9 ]
  • [ 149771-43-7 ]
Reference: [1] Tetrahedron Letters, 2002, vol. 43, # 5, p. 899 - 902
[2] Patent: US9404081, 2016, B2,
  • 9
  • [ 885277-59-8 ]
  • [ 149771-43-7 ]
Reference: [1] Chinese Chemical Letters, 2011, vol. 22, # 5, p. 523 - 526
  • 10
  • [ 92197-46-1 ]
  • [ 149771-43-7 ]
Reference: [1] Chinese Chemical Letters, 2011, vol. 22, # 5, p. 523 - 526
  • 11
  • [ 17740-40-8 ]
  • [ 149771-43-7 ]
Reference: [1] Chinese Chemical Letters, 2011, vol. 22, # 5, p. 523 - 526
  • 12
  • [ 1384448-78-5 ]
  • [ 149771-43-7 ]
Reference: [1] Patent: US9404081, 2016, B2,
  • 13
  • [ 1279821-96-3 ]
  • [ 100-46-9 ]
  • [ 149771-43-7 ]
Reference: [1] Chinese Chemical Letters, 2011, vol. 22, # 5, p. 523 - 526
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