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[ CAS No. 3616-59-9 ] {[proInfo.proName]}

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Chemical Structure| 3616-59-9
Chemical Structure| 3616-59-9
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Product Details of [ 3616-59-9 ]

CAS No. :3616-59-9 MDL No. :MFCD00034483
Formula : C10H21NO3 Boiling Point : -
Linear Structure Formula :- InChI Key :SZCDHXBTGQLOBZ-UHFFFAOYSA-N
M.W : 203.28 Pubchem ID :248492
Synonyms :

Calculated chemistry of [ 3616-59-9 ]

Physicochemical Properties

Num. heavy atoms : 14
Num. arom. heavy atoms : 0
Fraction Csp3 : 1.0
Num. rotatable bonds : 6
Num. H-bond acceptors : 4.0
Num. H-bond donors : 0.0
Molar Refractivity : 58.14
TPSA : 30.93 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : No
P-gp substrate : Yes
CYP1A2 inhibitor : No
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -7.19 cm/s

Lipophilicity

Log Po/w (iLOGP) : 2.83
Log Po/w (XLOGP3) : 0.49
Log Po/w (WLOGP) : 0.34
Log Po/w (MLOGP) : 0.2
Log Po/w (SILICOS-IT) : 1.35
Consensus Log Po/w : 1.04

Druglikeness

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

Water Solubility

Log S (ESOL) : -1.01
Solubility : 19.7 mg/ml ; 0.097 mol/l
Class : Very soluble
Log S (Ali) : -0.71
Solubility : 39.7 mg/ml ; 0.195 mol/l
Class : Very soluble
Log S (SILICOS-IT) : -1.59
Solubility : 5.23 mg/ml ; 0.0257 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 1.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 2.45

Safety of [ 3616-59-9 ]

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

Application In Synthesis of [ 3616-59-9 ]

* 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 [ 3616-59-9 ]
  • Downstream synthetic route of [ 3616-59-9 ]

[ 3616-59-9 ] Synthesis Path-Upstream   1~3

  • 1
  • [ 110-91-8 ]
  • [ 2032-35-1 ]
  • [ 3616-59-9 ]
YieldReaction ConditionsOperation in experiment
56% at 120℃; for 16 h; Example 28 - Preparation of Cmpd 23; [0206] A useful scheme for the preparation of compounds of the type of Cmpd 23 is provided in Scheme 2 following. Scheme 2Intermediate 7 Intermediate 8Cmpd 23 Intermediate 9[0207] A detailed description of the preparation of Intermediates 7-9 and Cmpd 23 follows. Preparation of Intermediate 7Intermediate 7[0208] A mixture of 2-bromoacetaldehyde diethyl acetal (4.5 g, 22.9 mmol), morpholine (2.0 g, 22.9 mmol) and K2C03 (6.34 g, 45.9 mmol, 2 eq) was stirred at 120 °C for 16 h. The reaction mixture was cooled to RT, diluted with water (50 mL) and extracted with DCM (3 x 50 mL). The organic layer was washed with saturated aqueous NaHC03 (50 mL), brine (50 mL), dried over Na2S04, filtered and concentrated to get crude a residue. The crude compound was purified by column chromatography over silica gel (100-200 mesh) by using a gradient mixture of 0-50percent EtOAc-hexane as the eluent to afford Intermediate 7 (2.6 g, 56percent) as a pale yellow liquid. 1H NMR: (CDC13) δ 4.64 (t, J= 5.3 Hz, 1H), 3.63-3.70 (m, 6H), 3.50-3.58 (m, 2H), 2.52-2.55 (m, 6H), 1.20 (t, J= 7.0 Hz, 6H); TLC: 60percent EtOAc in hexane: Rf: 0.50.
56% at 120℃; for 16 h; A mixture of 2-bromoacetaldehyde diethyl acetal (4.5 g, 22.9 mmol), morpholine (2.0 g, 22.9 mmol) and K2CO3 (6.34 g, 45.9 mmol, 2 eq) was stirred at 120°C. for 16 h. The reaction mixture was cooled to RT, diluted with water (50 mL) and extracted with DCM (350 mL). The organic layer was washed with saturated aqueous NaHCO3 (50 mL), brine (50 mL), dried over Na2SO4, filtered and concentrated to get crude a residue. The crude compound was purified by column chromatography over silica gel (100-200 mesh) by using a gradient mixture of 0-50percent EtOAc-hexane as the eluent to afford Intermediate 7 (2.6 g, 56percent) as a pale yellow liquid. 1H NMR: (CDCl3) δ 4.64 (t, J=5.3 Hz, 1H), 3.63-3.70 (m, 6H), 3.50-3.58 (m, 2H), 2.52-2.55 (m, 6H), 1.20 (t, J=7.0 Hz, 6H); TLC: 60percent EtOAcin hexane: Rf: 0.50.
14% With potassium carbonate In N,N-dimethyl-formamide at 120℃; for 5 h; Synthesis of compound 62.2. Morpholine (2.0g, 2.19mmol, l .Oeq), bromoacetaldehyde diethyl acetal (4.5g, 2.54mmol, 1.16eq) and dry K2CO3 (6.04g, 4.38mmol, 2.0 eq) were mixed in dry dimethylformamide and heated at 120 °C for 5h. After completion of reaction, reaction mixture was diluted with ethyl acetate (200ml) and washed with water (200ml x2) and then with brine (100ml). Organic layer was dried over sodium sulphate and concentrated under reduced pressure at 45°C. Crude was purified by column chromatography to afford compound 62.2 (0.650g, 14percent). 1H NMR (400 MHz, CDC13): δ 4.660-4.686 (t, 1H), 3.686-3.738 (m, 6H), 3.528-3.3.581 (m, 2H), 3.554-3.577 (t, 6H), 1.216-1.252 (t, 6H).
Reference: [1] Patent: WO2011/126903, 2011, A2, . Location in patent: Page/Page column 78
[2] Patent: US2017/326125, 2017, A1, . Location in patent: Paragraph 0297-0298
[3] Patent: WO2015/131080, 2015, A1, . Location in patent: Paragraph 00472; 00473
[4] Comptes Rendus Hebdomadaires des Seances de l'Academie des Sciences, 1959, vol. 248, p. 2015
[5] Organic and Biomolecular Chemistry, 2011, vol. 9, # 17, p. 5930 - 5933
  • 2
  • [ 621-62-5 ]
  • [ 3616-59-9 ]
Reference: [1] Journal of the American Chemical Society, 1949, vol. 71, p. 2272
[2] Patent: US2830050, 1955, ,
  • 3
  • [ 3616-59-9 ]
  • [ 21977-09-3 ]
Reference: [1] Organic and Biomolecular Chemistry, 2011, vol. 9, # 17, p. 5930 - 5933
[2] Patent: WO2011/126903, 2011, A2, . Location in patent: Page/Page column 79
[3] Patent: WO2015/131080, 2015, A1, . Location in patent: Paragraph 00472; 00474
[4] Patent: US2017/326125, 2017, A1, . Location in patent: Paragraph 0299-0300
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