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[ CAS No. 109-11-5 ] {[proInfo.proName]}

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3d Animation Molecule Structure of 109-11-5
Chemical Structure| 109-11-5
Chemical Structure| 109-11-5
Structure of 109-11-5 * Storage: {[proInfo.prStorage]}
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Quality Control of [ 109-11-5 ]

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Alternatived Products of [ 109-11-5 ]

Product Details of [ 109-11-5 ]

CAS No. :109-11-5 MDL No. :MFCD00631009
Formula : C4H7NO2 Boiling Point : -
Linear Structure Formula :- InChI Key :VSEAAEQOQBMPQF-UHFFFAOYSA-N
M.W : 101.10 Pubchem ID :66953
Synonyms :

Calculated chemistry of [ 109-11-5 ]

Physicochemical Properties

Num. heavy atoms : 7
Num. arom. heavy atoms : 0
Fraction Csp3 : 0.75
Num. rotatable bonds : 0
Num. H-bond acceptors : 2.0
Num. H-bond donors : 1.0
Molar Refractivity : 27.23
TPSA : 38.33 Ų

Pharmacokinetics

GI absorption : Low
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) : -7.48 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.06
Log Po/w (XLOGP3) : -0.8
Log Po/w (WLOGP) : -1.25
Log Po/w (MLOGP) : -1.19
Log Po/w (SILICOS-IT) : 0.84
Consensus Log Po/w : -0.27

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 2.0
Bioavailability Score : 0.55

Water Solubility

Log S (ESOL) : 0.04
Solubility : 110.0 mg/ml ; 1.09 mol/l
Class : Highly soluble
Log S (Ali) : 0.47
Solubility : 301.0 mg/ml ; 2.98 mol/l
Class : Highly soluble
Log S (SILICOS-IT) : -0.59
Solubility : 25.8 mg/ml ; 0.255 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.25

Safety of [ 109-11-5 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P264-P280-P302+P352-P337+P313-P305+P351+P338-P362+P364-P332+P313 UN#:N/A
Hazard Statements:H315-H319 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 109-11-5 ]

* 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 [ 109-11-5 ]
  • Downstream synthetic route of [ 109-11-5 ]

[ 109-11-5 ] Synthesis Path-Upstream   1~12

  • 1
  • [ 141-43-5 ]
  • [ 105-39-5 ]
  • [ 109-11-5 ]
YieldReaction ConditionsOperation in experiment
52%
Stage #1: With sodium In isopropyl alcohol at 50℃; for 5 h;
Stage #2: at 0 - 80℃;
To a solution of ethanolamine (197 mmol, 1.1 equiv) in i-PrOH (100 mL) was portionwise added small pieces ofsodium (197 mmol, 1.1 equiv). The mixture was heated at 50 °C for 5 h, and the resulting yellow solution was cooled in an ice-water bath. Ethyl chloroacetate (179 mmol, 1.0equiv) was dropwise added at 0 °C, and the resulting yellow suspension was heated at 80 °C for 2 h. Insoluble materials were removed by paper filtration and washed with i-PrOH. The combined filtrate and washings were concentrated in vacuo, and the resulting brown solids were recrystallized from iPrOH/EtOAc to afford 3-morpholinone in 52percent yield.
36%
Stage #1: With sodium In 1,4-dioxane; isopropyl alcohol at 50℃; Inert atmosphere
Stage #2: at -10 - 80℃; for 10 h; Inert atmosphere
Under nitrogen, Na (45.26 g, 1.97 mol)Was added in portions to a mixed solution of dioxane and isopropanol, and the temperature was raised to 50 ° C to promote the dissolution of Na(Na dissolves very slowly, generally takes 4 to 5 hours).After all the Na is dissolved,Dropping amino ethanol (98ml, 1.67mo) 1, drop Bi, 50 ° C stirring 30 ~ 40min.Was transferred to cold water, controlled at -10 ° C, and ethyl chloroacetate (182 ml, 1.75mo 1) was added dropwise. Drop 10 ° C stirring 30 ~ 40min.Gradually heated to 80 ° C, the reaction about 10h, finished, hot filter, the filtrate evaporated to dry yellow oily liquid, dissolved with ethyl acetate, standing, the above clear ethyl acetate layer out of cooling crystallization,To be precipitated after the white needle-like crystals after filtration, to obtain moles of crude ketone. The remaining yellow oil was recrystallized again as described above in a yield of 36percent
500 mg
Stage #1: With sodium hydride In 1,4-dioxane at 0 - 20℃; for 0.5 h; Inert atmosphere
Stage #2: at 0 - 20℃; for 1.16667 h; Reflux; Inert atmosphere
under a nitrogen atmosphere, sodium hydride (60 wt percent, 1.2 g) and a solution of dioxane (25 ml) was cooled to 0 °C, ethanolamine (1.5 ml) was added at room temperature and stirred for 30 minutes. This reaction liquid is cooled to 0 °C, after 30 minutes stirring at room temperature ethyl chloroacetate (2.7 ml) was added, this reaction mixture was further stirred and heated for 40 minutes under reflux condition. After cooling the reaction liquid, solid is removed by filtration. Under a reduced pressure by concentrating somas, refining residues is obtained in column chromatography (ethyl acetate: methanol = 19:1), obtained as a colorless solid morpholin-3-one (500 mg).
Reference: [1] Tetrahedron, 2015, vol. 71, # 37, p. 6349 - 6353
[2] Patent: CN104513239, 2017, B, . Location in patent: Paragraph 0197; 0238; 0249; 0250
[3] Chemical Communications, 2012, vol. 48, # 1, p. 145 - 147
[4] Patent: US5002937, 1991, A,
[5] Patent: WO2006/63113, 2006, A2, . Location in patent: Page/Page column 98-99
[6] Patent: WO2006/63293, 2006, A2, . Location in patent: Page/Page column 43
[7] Patent: JP2015/13809, 2015, A, . Location in patent: Paragraph 0097
  • 2
  • [ 6320-16-7 ]
  • [ 109-11-5 ]
YieldReaction ConditionsOperation in experiment
10% With sodium hydride In tetrahydrofuran at 20 - 60℃; for 6 h; Inert atmosphere; Cooling with ice Under an argon atmosphere, to a solution of 2-chloro-N-(2-hydroxyethyl)acetamide (3.2 g, 23 mmol) in tetrahydrofuran (64 ml) was added sodium hydride (1.2 g, 30 mmol) under ice-cooling, and the mixture was stirred for 1 hr. Then, the mixture was stirred at room temperature for 1 hr, and further at 60° C. for 4 hr. After cooling, water (540 μl) was added, and the reaction mixture was dried over magnesium sulfate. Magnesium sulfate was removed by filtration, and the filtrate was concentrated under reduced pressure. The residue was purified by silica gel chromatography to give the title compound (232 mg, yield 10percent).1H-NMR (400 MHz, DMSO-d6) δ: 3.20-3.23 (m, 2H), 3.70-3.73 (m, 2H), 3.96 (s, 2H), 7.88-8.07 (brs, 1H).
Reference: [1] Patent: US2011/306599, 2011, A1, . Location in patent: Page/Page column 35
  • 3
  • [ 75-39-8 ]
  • [ 105-39-5 ]
  • [ 109-11-5 ]
Reference: [1] Patent: WO2006/55951, 2006, A2, . Location in patent: Page/Page column 44
  • 4
  • [ 1366074-90-9 ]
  • [ 109-11-5 ]
Reference: [1] Bulletin of the Korean Chemical Society, 2012, vol. 33, # 2, p. 739 - 741
[2] Bulletin of the Korean Chemical Society, 2012, vol. 33, # 1, p. 333 - 336
  • 5
  • [ 105-39-5 ]
  • [ 109-11-5 ]
Reference: [1] Patent: US2007/259924, 2007, A1, . Location in patent: Page/Page column 24
  • 6
  • [ 929-06-6 ]
  • [ 109-11-5 ]
Reference: [1] ChemCatChem, 2015, vol. 7, # 5, p. 865 - 871
  • 7
  • [ 110-91-8 ]
  • [ 109-11-5 ]
Reference: [1] Chemistry of Heterocyclic Compounds, 2003, vol. 39, # 4, p. 478 - 484
[2] Journal of the American Chemical Society, 2014, vol. 136, # 8, p. 2998 - 3001
[3] Angewandte Chemie - International Edition, 2016, vol. 55, # 25, p. 7212 - 7217[4] Angew. Chem., 2016, vol. 128, # 25, p. 7328 - 7333,6
  • 8
  • [ 141-43-5 ]
  • [ 96-32-2 ]
  • [ 109-11-5 ]
Reference: [1] Helvetica Chimica Acta, 1976, vol. 59, p. 1566 - 1583
  • 9
  • [ 31250-08-5 ]
  • [ 1074-82-4 ]
  • [ 109-11-5 ]
Reference: [1] Suomen Kemistilehti B, 1945, vol. 18, p. 40,42
  • 10
  • [ 7397-62-8 ]
  • [ 109-11-5 ]
Reference: [1] Angewandte Chemie, 1967, vol. 79, p. 188
  • 11
  • [ 141-43-5 ]
  • [ 79-04-9 ]
  • [ 109-11-5 ]
Reference: [1] Journal of Agricultural and Food Chemistry, 2001, vol. 49, # 1, p. 138 - 141
  • 12
  • [ 109-11-5 ]
  • [ 24424-99-5 ]
  • [ 142929-48-4 ]
YieldReaction ConditionsOperation in experiment
76% With dmap In tetrahydrofuran at 20℃; for 24 h; Step 1: 7¾ri-butyl 3-oxomorpholine- -carboxylate [00197] Morpholin-3-one (35g, 346.2 mmol) was slurried in dry THF (350ml). Tert- butoxycarbonyl tert- butyl carbonate (105.8g, 11 1.4 mmol) was added, followed by DMAP (4.2g, 34.6 mmol). The mixture began to degass rapidly over 30 minutes. The resulting orange solution was stirred at ambient temperature for 24hrs. The mixture was then cooled in an ice bath and imidazole (23.57g, 346.2 mmol) was added. After stirring for 30 minutes ethyl acetate (500ml) was added. The organic phase was separated and washed with 1percent (v/v) HC1 (500ml), then sat NaHC03 (500ml), then brine (200ml), dried (MgS04), filtered and concentrated. The crude was purified through a plug of silica gel, eluting with ethyl acetate. The filtrate was evaporated to give an oil. 40/60 pet ether (200ml) was added slowly with stirring to generate a white solid. The mixture was aged for 30 minutes, cooled briefly in an ice bath and filtered, washing with 40/60 pet ether. Tert-butyl 3-oxomorpholine-4- carboxylate was obtained as a white solid which was dried under vacuum (52.7g, 76percent); lH- NMR (CDCI3) 1.47 (9H, s), 3.68 (2H, m), 3.82 (2H, m), 4.15 (2H, s); MS ES(+) 145.8 (M+ - tBu).
66% With dmap In tetrahydrofuran at 20℃; Inert atmosphere Morpholmn-3-one (8.00 g, 79.2 mmcl) was dissolved in dry THE (100 mL), and then (Boc)20 (25.9 g, 0.119 mol) and DMAP (966 mg, 7.92 mmol) were added. The mixture was stirred at room temperature under N2 atmosphere overnight. Imidazole (5.39 g, 79.2 mmol) was added. After stirred for 30 mm EtOAc (150 mL) was added. The organic layer was washed with brine (100 mL), dried over Na2SO4, filtered and concentrated in vacuo to give oil whichwas solidified after standing. The solid was washed with PE (100 mL)to afford the desired compound (10.5 g, yield 66percent) as a white solid.1H NMR (300 MHz, CDCI3): 64.20 (s, 2H), 3.88-3.85 (m, 2H), 3.74-3.70 (m, 2H), 1.51 (s, 9H).LC-MS (mobile phase: from 95percent water and 5percent CH3CN to 5percent water and 95percent CH3CN in 3.0mm, purity is >95percent, Rt = 1.56 mm; MS Calcd.: 201; MS Found: 202 [M+H] 146 [M-56+H].
Reference: [1] Patent: WO2013/49719, 2013, A1, . Location in patent: Paragraph 00197
[2] Patent: WO2017/12576, 2017, A1, . Location in patent: Page/Page column 177
[3] Journal of Medicinal Chemistry, 1992, vol. 35, # 16, p. 2928 - 2938
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