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[ CAS No. 134003-84-2 ] {[proInfo.proName]}

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Chemical Structure| 134003-84-2
Chemical Structure| 134003-84-2
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Product Details of [ 134003-84-2 ]

CAS No. :134003-84-2 MDL No. :MFCD01321293
Formula : C10H18N2O2 Boiling Point : -
Linear Structure Formula :- InChI Key :UXAWXZDXVOYLII-HTQZYQBOSA-N
M.W : 198.26 Pubchem ID :11860399
Synonyms :

Calculated chemistry of [ 134003-84-2 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 14
Num. arom. heavy atoms : 0
Fraction Csp3 : 0.9
Num. rotatable bonds : 3
Num. H-bond acceptors : 3.0
Num. H-bond donors : 1.0
Molar Refractivity : 61.2
TPSA : 41.57 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) : -7.0 cm/s

Lipophilicity

Log Po/w (iLOGP) : 2.46
Log Po/w (XLOGP3) : 0.72
Log Po/w (WLOGP) : 0.21
Log Po/w (MLOGP) : 0.86
Log Po/w (SILICOS-IT) : 0.39
Consensus Log Po/w : 0.93

Druglikeness

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

Water Solubility

Log S (ESOL) : -1.32
Solubility : 9.38 mg/ml ; 0.0473 mol/l
Class : Very soluble
Log S (Ali) : -1.17
Solubility : 13.4 mg/ml ; 0.0674 mol/l
Class : Very soluble
Log S (SILICOS-IT) : -1.09
Solubility : 16.0 mg/ml ; 0.0809 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 3.65

Safety of [ 134003-84-2 ]

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 [ 134003-84-2 ]

* 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 [ 134003-84-2 ]
  • Downstream synthetic route of [ 134003-84-2 ]

[ 134003-84-2 ] Synthesis Path-Upstream   1~7

  • 1
  • [ 134003-83-1 ]
  • [ 134003-84-2 ]
YieldReaction ConditionsOperation in experiment
93.4% With hydrogen In ethanol for 16 h; Example 15B
tert-butyl (1R,4R)-2,5-diazabicyclo[2.2.1]heptane-2-carboxylate
The product from Example 15A (2 g, 6.9 mmol) in 50 mL of EtOH was treated with 10percent Pd/C (150 mg) under an H2 atmosphere (1 atm) for 16 hours.
The mixture was filtered and the solvent was evaporated under reduced pressure to yield 1.28 g (93.4 percent) of the title compound. 1H NMR (DMSO-d6, MHz) δ 1.39 (s, 9H), 1.54 (d, J=5.6 Hz, 1H), 1.58 (t, J=9.5 Hz, H), 2.70-2.81 (M, 2H), 3.50 (dd, J=1.02, 10.50, 1H), 3.17 (m, 1H), 3.50 (s, 1H), 4.17 (d, J=10.17 Hz, H); MS (DCI/NH3) m/z 199 (M+H)+, 216 (M+NH4)+.
93.4% With hydrogen In ethanol for 16 h; The product from Example 15A (2 g, 6.9 mmol) in 50 mL of EtOH was treated with 10percent Pd/C (150 mg) under an H2 atmosphere (1 atm) for 16 hours. The mixture was filtered and the solvent was evaporated under reduced pressure to yield 1.28 g (93.4percent) of the title compound. 1H NMR (DMSO-d6, MHz) δ 1.39 (s, 9H), 1.54 (d, J=5.6 Hz, 1H), 1.58 (t, J=9.5 Hz, H), 2.70-2.81 (M, 2H), 3.50 (dd, J=1.02, 10.50, 1H), 3.17 (m, 1H), 3.50 (s, 1H), 4.17 (d, J=10.17 Hz, H); MS (DCIINH3) m/z 199 (M+H)+, 216 (M+NH4)+.
93.4% With hydrogen In ethanol for 16 h; Example 25B
tert-butyl(1R,4R)-2,5-diazabicyclo[2.2.1]heptane-2-carboxylate
The product from Example 25A (2 g, 6.9 mmol) in 50 mL of EtOH was treated with 10percent Pd/C (150 mg) under an H2 atmosphere (1 atm) for 16 hours.
The mixture was filtered and the solvent was evaporated under reduced pressure to yield 1.28 g (93.4percent) of the title compound. 1H NMR (DMSO-d6, MHz) δ 1.39 (s, 9H), 1.54 (d, J=5.6 Hz, 1H), 1.58 (t, J=9.5 Hz, H), 2.70-2.81 (M, 2H), 3.50 (dd, J=1.02, 10.50. 1H), 3.17 (m, 1H), 3.50 (s, 1H), 4.17 ppm (d, J=10.17 Hz, H); MS (DCl/NH3) m/z 199 (M+H)+, 216 (M+NH4)+.
Reference: [1] Patent: EP1147112, 2003, B1, . Location in patent: Page/Page column 19
[2] Patent: US2003/225268, 2003, A1, . Location in patent: Page 21
[3] Patent: US2005/101602, 2005, A1, . Location in patent: Page/Page column 37
[4] RSC Advances, 2015, vol. 5, # 14, p. 10386 - 10392
[5] Journal of Medicinal Chemistry, 2007, vol. 50, # 15, p. 3627 - 3644
  • 2
  • [ 326596-46-7 ]
  • [ 134003-84-2 ]
YieldReaction ConditionsOperation in experiment
66% With ammonia In water at 65℃; for 16 h; Step B: (2R,5R)-2,5-Diaza-bicyclo[2.2.1]heptane-2-carboxylic acid tert-butyl ester. A heterogeneous mixture of (4S,2R)-4-methanesulfonyloxy-2-methanesulfonyloxymethyl-pyrrolidine-1-carboxylic acid tert-butyl ester (1 g, 2.7 mmol) in ammonium hydroxide (27 wt percent solution in water, 10 mL) was warmed to 65° C. in a sealed tube for 16 h during which time the mixture became homogeneous. The aqueous was extracted with CH2Cl2 (2.x.) and the combined organics were dried over Na2SO4, filtered, and concentrated to provide the title compound as a yellow solid that was used directly in subsequent steps (350 mg, 66percent). MS (ESI): mass calcd. for C10H18N2O2, 198.1; m/z found, 199.0 [M+H]+. 1H NMR (400 MHz, CDCl3): 4.48-4.27 (m, 1H), 3.70 (s, 1H), 3.41-3.30 (m, 1H), 3.22-3.11 (m, 1H), 3.08-2.95 (m, 2H), 1.80-1.65 (m, 2H), 1.48 (s, 9H).
Reference: [1] Patent: US2009/111794, 2009, A1, . Location in patent: Page/Page column 15
  • 3
  • [ 24424-99-5 ]
  • [ 134003-84-2 ]
Reference: [1] Journal of Medicinal Chemistry, 2007, vol. 50, # 15, p. 3627 - 3644
  • 4
  • [ 116258-17-4 ]
  • [ 134003-84-2 ]
Reference: [1] Journal of Medicinal Chemistry, 2007, vol. 50, # 15, p. 3627 - 3644
  • 5
  • [ 51-35-4 ]
  • [ 134003-84-2 ]
Reference: [1] RSC Advances, 2015, vol. 5, # 14, p. 10386 - 10392
  • 6
  • [ 31560-19-7 ]
  • [ 134003-84-2 ]
Reference: [1] RSC Advances, 2015, vol. 5, # 14, p. 10386 - 10392
  • 7
  • [ 31560-25-5 ]
  • [ 134003-84-2 ]
Reference: [1] RSC Advances, 2015, vol. 5, # 14, p. 10386 - 10392
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