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[ CAS No. 128372-89-4 ] {[proInfo.proName]}

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Chemical Structure| 128372-89-4
Chemical Structure| 128372-89-4
Structure of 128372-89-4 * Storage: {[proInfo.prStorage]}
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Product Details of [ 128372-89-4 ]

CAS No. :128372-89-4 MDL No. :MFCD17169880
Formula : C10H15NO3 Boiling Point : -
Linear Structure Formula :- InChI Key :VOVJZEJLJABSJY-UHFFFAOYSA-N
M.W : 197.23 Pubchem ID :66598173
Synonyms :

Calculated chemistry of [ 128372-89-4 ]

Physicochemical Properties

Num. heavy atoms : 14
Num. arom. heavy atoms : 0
Fraction Csp3 : 0.6
Num. rotatable bonds : 3
Num. H-bond acceptors : 3.0
Num. H-bond donors : 0.0
Molar Refractivity : 56.32
TPSA : 46.61 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : Yes
P-gp substrate : No
CYP1A2 inhibitor : Yes
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -6.47 cm/s

Lipophilicity

Log Po/w (iLOGP) : 2.35
Log Po/w (XLOGP3) : 1.46
Log Po/w (WLOGP) : 1.33
Log Po/w (MLOGP) : 0.66
Log Po/w (SILICOS-IT) : 0.74
Consensus Log Po/w : 1.31

Druglikeness

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

Water Solubility

Log S (ESOL) : -1.78
Solubility : 3.24 mg/ml ; 0.0164 mol/l
Class : Very soluble
Log S (Ali) : -2.05
Solubility : 1.78 mg/ml ; 0.00901 mol/l
Class : Soluble
Log S (SILICOS-IT) : -0.93
Solubility : 23.2 mg/ml ; 0.118 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 3.14

Safety of [ 128372-89-4 ]

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 [ 128372-89-4 ]

* 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 [ 128372-89-4 ]
  • Downstream synthetic route of [ 128372-89-4 ]

[ 128372-89-4 ] Synthesis Path-Upstream   1~12

  • 1
  • [ 128372-89-4 ]
  • [ 20069-09-4 ]
Reference: [1] Organic and Biomolecular Chemistry, 2016, vol. 14, # 31, p. 7585 - 7593
  • 2
  • [ 128372-89-4 ]
  • [ 6052-73-9 ]
Reference: [1] Organic and Biomolecular Chemistry, 2016, vol. 14, # 31, p. 7585 - 7593
[2] Journal of Organic Chemistry, 2010, vol. 75, # 8, p. 2610 - 2618
  • 3
  • [ 1215765-59-5 ]
  • [ 128372-89-4 ]
YieldReaction ConditionsOperation in experiment
88.6% With dihydrogen peroxide In tetrahydrofuran at 0 - 20℃; for 0.75 h; [00333] A solution of 30percent H2O2 (2.2 ml_, 36 mmol) was added to a stirring solution of tert-butyl 2-oxo-3-(phenylselanyl)piperidine-1 -carboxylate (4.27 g, 12 mmol) in THF (20 ml_) at 0 °C. The reaction mixture was stirred 15 min at 0 °C and allowed to warm up to room temperature and kept for 30 min. The reaction mixture was then dissolved in CH2CI2 (200 ml_) and washed with a saturated NaHCO3. The organic phase was dried and condensed to compound tert-butyl 2-oxo-5,6-dihydropyridine-1 (2H)-carboxylate (2.1 g, 88.6percent).
88.6% With dihydrogen peroxide In tetrahydrofuran at 0 - 20℃; for 0.75 h; A solution of 30percent H2O2 (2.2 mL, 36 mmol) was added to a stirring solution of tert-butyl 2-oxo-3-(phenylselanyl)piperidine-1-carboxylate (4.27 g, 12 mmol) in THF (20 mL) at 0° C. The reaction mixture was stirred 15 min at 0° C. and allowed to warm up to room temperature and kept for 30 min. The reaction mixture was then dissolved in CH2Cl2 (200 mL) and washed with a saturated NaHCO3. The organic phase was dried and condensed to compound tert-butyl 2-oxo-5,6-dihydropyridine-1(2H)-carboxylate (2.1 g, 88.6percent).
Reference: [1] Patent: WO2013/13188, 2013, A1, . Location in patent: Paragraph 00333
[2] Patent: US9416132, 2016, B2, . Location in patent: Page/Page column 140; 141
[3] Journal of Organic Chemistry, 2010, vol. 75, # 8, p. 2610 - 2618
[4] Tetrahedron Letters, 2010, vol. 51, # 23, p. 3095 - 3098
  • 4
  • [ 85908-96-9 ]
  • [ 128372-89-4 ]
YieldReaction ConditionsOperation in experiment
38%
Stage #1: With n-butyllithium; diisopropylamine In tetrahydrofuran at -78℃; for 0.25 h;
Stage #2: With mukaiyama’s reagent In tetrahydrofuran for 0.5 h;
Diisopropylamine (1.7 mL, 12.1 mmol) of THF (10 mL)To the solution was added n-butyllithium (6.7 ml, 11.0 mmol) was added dropwise at -78 ° C., and the mixture was stirred for 30 minutes. Compound 34 (2 g, 10.0 mmol) in THF (10 mL) was added dropwise, and the mixture was stirred for 15 minutes. A solution of N-tert-butylbenzenesulfinimidoyl chloride (2.6 g, 12.1 mmol) in THF (5 mL) was added and the mixture was stirred for 30 minutes. Water was added to the reaction solution, the mixture was extracted with ethyl acetate, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The resulting residue was purified by silica gel chromatography (hexane / ethyl acetate) to give Compound 35 (750 mg, yield: 38percent) as an orange solid.
Reference: [1] Journal of the American Chemical Society, 2008, vol. 130, # 23, p. 7449 - 7458
[2] Patent: JP2016/193887, 2016, A, . Location in patent: Paragraph 0146
[3] Tetrahedron Letters, 2005, vol. 46, # 3, p. 407 - 410
[4] Bioorganic and Medicinal Chemistry Letters, 2003, vol. 13, # 11, p. 1939 - 1942
[5] Patent: WO2013/13188, 2013, A1,
[6] Organic and Biomolecular Chemistry, 2016, vol. 14, # 31, p. 7585 - 7593
[7] Patent: US9416132, 2016, B2,
[8] Tetrahedron, 2017, vol. 73, # 27-28, p. 3866 - 3877
  • 5
  • [ 358732-56-6 ]
  • [ 128372-89-4 ]
Reference: [1] Organic and Biomolecular Chemistry, 2016, vol. 14, # 31, p. 7585 - 7593
[2] Bioorganic and Medicinal Chemistry Letters, 2003, vol. 13, # 11, p. 1939 - 1942
  • 6
  • [ 831227-07-7 ]
  • [ 128372-89-4 ]
Reference: [1] Patent: WO2005/7618, 2005, A1, . Location in patent: Page/Page column 14; 15
  • 7
  • [ 675-20-7 ]
  • [ 128372-89-4 ]
Reference: [1] Bioorganic and Medicinal Chemistry Letters, 2003, vol. 13, # 11, p. 1939 - 1942
[2] Organic and Biomolecular Chemistry, 2016, vol. 14, # 31, p. 7585 - 7593
  • 8
  • [ 24424-99-5 ]
  • [ 128372-89-4 ]
Reference: [1] Bioorganic and Medicinal Chemistry Letters, 2003, vol. 13, # 11, p. 1939 - 1942
[2] Organic and Biomolecular Chemistry, 2016, vol. 14, # 31, p. 7585 - 7593
  • 9
  • [ 131667-57-7 ]
  • [ 325486-45-1 ]
  • [ 128372-89-4 ]
Reference: [1] Journal of Organic Chemistry, 2017, vol. 82, # 16, p. 8506 - 8513
  • 10
  • [ 1415686-28-0 ]
  • [ 128372-89-4 ]
Reference: [1] Chemistry of Heterocyclic Compounds, 2016, vol. 52, # 3, p. 183 - 191[2] Khim. Geterotsikl. Soedin., 2016, vol. 52, # 3, p. 183 - 191,9
  • 11
  • [ 3303-84-2 ]
  • [ 128372-89-4 ]
Reference: [1] Patent: WO2016/187393, 2016, A1,
  • 12
  • [ 845267-78-9 ]
  • [ 128372-89-4 ]
Reference: [1] Patent: WO2016/187393, 2016, A1,
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