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[ CAS No. 51814-19-8 ] {[proInfo.proName]}

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Chemical Structure| 51814-19-8
Chemical Structure| 51814-19-8
Structure of 51814-19-8 * Storage: {[proInfo.prStorage]}
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Product Details of [ 51814-19-8 ]

CAS No. :51814-19-8 MDL No. :MFCD09878816
Formula : C15H17NO5 Boiling Point : -
Linear Structure Formula :- InChI Key :FRNZCPLVDNHRIH-UHFFFAOYSA-N
M.W : 291.30 Pubchem ID :15043278
Synonyms :

Calculated chemistry of [ 51814-19-8 ]

Physicochemical Properties

Num. heavy atoms : 21
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.4
Num. rotatable bonds : 7
Num. H-bond acceptors : 5.0
Num. H-bond donors : 0.0
Molar Refractivity : 77.72
TPSA : 72.91 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : No
P-gp substrate : No
CYP1A2 inhibitor : No
CYP2C19 inhibitor : Yes
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -6.9 cm/s

Lipophilicity

Log Po/w (iLOGP) : 2.34
Log Po/w (XLOGP3) : 1.66
Log Po/w (WLOGP) : 0.85
Log Po/w (MLOGP) : 0.93
Log Po/w (SILICOS-IT) : 1.63
Consensus Log Po/w : 1.48

Druglikeness

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

Water Solubility

Log S (ESOL) : -2.44
Solubility : 1.05 mg/ml ; 0.00362 mol/l
Class : Soluble
Log S (Ali) : -2.8
Solubility : 0.457 mg/ml ; 0.00157 mol/l
Class : Soluble
Log S (SILICOS-IT) : -3.07
Solubility : 0.249 mg/ml ; 0.000853 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 2.0 alert
Leadlikeness : 0.0
Synthetic accessibility : 3.06

Safety of [ 51814-19-8 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P305+P351+P338 UN#:N/A
Hazard Statements:H315-H319-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 51814-19-8 ]

* 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 [ 51814-19-8 ]
  • Downstream synthetic route of [ 51814-19-8 ]

[ 51814-19-8 ] Synthesis Path-Upstream   1~5

  • 1
  • [ 51814-17-6 ]
  • [ 51814-19-8 ]
YieldReaction ConditionsOperation in experiment
72%
Stage #1: With sodium ethanolate In ethanol for 2 h; Heating / reflux
Stage #2: at 0℃;
Reference Example 63
Ethyl 1-benzyloxycarbonyl-4-oxopyrrolidine-3-carboxylate
To a solution of ethyl 3-[N-benzyloxycarbonyl-N-(ethoxycarbonyl methyl)amino]ethylpropionate (26.8 g, 79.5 mmol) in ethanol (200 mL), sodium ethoxide (20percent solution in ethanol, 40.6 mL, 119.3 mmol) was added, and the mixture was heated under reflux for 2 hours.
After concentrating the reaction mixture under reduced pressure, the residue was dissolved in water (100 mL).
Concentrated hydrochloric acid was added to this solution in an ice bath for acidification, and the solution was extracted with chloroform (100 mL*3).
The extract was washed with saturated aqueous solution of sodium chloride (100 mL), and dried with anhydrous sodium sulfate.
After the filtration, the filtrate was concentrated under reduced pressure, and the residue was purified by silica gel column chromatography (hexane:ethyl acetate, 2:1) to obtain 16.7 g (72percent) of the title compound as a pale brown oily product.
1H-NMR (400 MHz, CDCl3)δ ppm: 1.25-1.33 (3H, m), 3.87-4.37 (7H, m), 5.16-5.22 (2H, m), 7.23-7.41 (5H, m).
MS (ESI) m/z: 314 (M+Na)+.
Reference: [1] Patent: US2006/264428, 2006, A1, . Location in patent: Page/Page column 47-48
[2] Patent: WO2006/123792, 2006, A1, . Location in patent: Page/Page column 109-110
[3] Bioorganic and Medicinal Chemistry Letters, 2004, vol. 14, # 5, p. 1273 - 1277
[4] Patent: EP1992613, 2008, A1, . Location in patent: Page/Page column 12
[5] Archiv der Pharmazie, 2008, vol. 341, # 12, p. 780 - 786
[6] Patent: CN103922987, 2016, B, . Location in patent: Paragraph 0047-0049
  • 2
  • [ 1145-81-9 ]
  • [ 140-88-5 ]
  • [ 51814-19-8 ]
Reference: [1] Journal of the Chemical Society, Chemical Communications, 1992, # 24, p. 1767 - 1769
[2] Patent: US6423843, 2002, B1,
  • 3
  • [ 140-88-5 ]
  • [ 51814-19-8 ]
Reference: [1] Patent: CN103922987, 2016, B,
[2] Patent: CN103922987, 2016, B,
  • 4
  • [ 501-53-1 ]
  • [ 51814-19-8 ]
Reference: [1] Patent: CN103922987, 2016, B,
[2] Patent: CN103922987, 2016, B,
  • 5
  • [ 51814-19-8 ]
  • [ 130312-02-6 ]
Reference: [1] Archiv der Pharmazie, 2008, vol. 341, # 12, p. 780 - 786
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