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[ CAS No. 3279-76-3 ] {[proInfo.proName]}

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Chemical Structure| 3279-76-3
Chemical Structure| 3279-76-3
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Product Details of [ 3279-76-3 ]

CAS No. :3279-76-3 MDL No. :MFCD00006279
Formula : C6H7NO Boiling Point : -
Linear Structure Formula :- InChI Key :JEAVIRYCMBDJIU-UHFFFAOYSA-N
M.W : 109.13 Pubchem ID :76772
Synonyms :

Calculated chemistry of [ 3279-76-3 ]

Physicochemical Properties

Num. heavy atoms : 8
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.17
Num. rotatable bonds : 0
Num. H-bond acceptors : 1.0
Num. H-bond donors : 1.0
Molar Refractivity : 32.03
TPSA : 32.86 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : Yes
P-gp substrate : No
CYP1A2 inhibitor : No
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -6.55 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.37
Log Po/w (XLOGP3) : 0.58
Log Po/w (WLOGP) : 0.68
Log Po/w (MLOGP) : 0.59
Log Po/w (SILICOS-IT) : 2.0
Consensus Log Po/w : 1.04

Druglikeness

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

Water Solubility

Log S (ESOL) : -1.44
Solubility : 3.99 mg/ml ; 0.0366 mol/l
Class : Very soluble
Log S (Ali) : -0.84
Solubility : 15.7 mg/ml ; 0.144 mol/l
Class : Very soluble
Log S (SILICOS-IT) : -2.25
Solubility : 0.608 mg/ml ; 0.00557 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.23

Safety of [ 3279-76-3 ]

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 [ 3279-76-3 ]

* 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 [ 3279-76-3 ]
  • Downstream synthetic route of [ 3279-76-3 ]

[ 3279-76-3 ] Synthesis Path-Upstream   1~26

  • 1
  • [ 63071-03-4 ]
  • [ 3279-76-3 ]
Reference: [1] Heterocycles, 1993, vol. 36, # 2, p. 323 - 328
[2] Journal of Organic Chemistry, 1993, vol. 58, # 17, p. 4742 - 4744
  • 2
  • [ 1824-81-3 ]
  • [ 3279-76-3 ]
Reference: [1] Zhurnal Russkago Fiziko-Khimicheskago Obshchestva, 1920, vol. 50, p. 536[2] Chem. Zentralbl., 1923, vol. 94, # III, p. 1022
[3] Organic Syntheses, 2002, vol. 78, p. 51 - 51
  • 3
  • [ 66909-37-3 ]
  • [ 3279-76-3 ]
Reference: [1] Chemische Berichte, 1940, vol. 73, p. 156
[2] Journal of Organic Chemistry, 1954, vol. 19, p. 183,191
  • 4
  • [ 109-06-8 ]
  • [ 3279-76-3 ]
Reference: [1] Zhurnal Russkago Fiziko-Khimicheskago Obshchestva, 1920, vol. 50, p. 536[2] Chem. Zentralbl., 1923, vol. 94, # III, p. 1022
[3] Fortschr. Teerfarbenfabr. Verw. Industriezweige, vol. 14, p. 516
  • 5
  • [ 4775-98-8 ]
  • [ 3279-76-3 ]
Reference: [1] Journal of the Chemical Society, 1952, p. 3261,3264
[2] Chemische Berichte, 1936, vol. 69, p. 2059
  • 6
  • [ 18368-63-3 ]
  • [ 3279-76-3 ]
Reference: [1] Yakugaku Zasshi, 1955, vol. 75, p. 1233[2] Chem.Abstr., 1956, p. 8664
  • 7
  • [ 854389-41-6 ]
  • [ 3279-76-3 ]
Reference: [1] Chemische Berichte, 1941, vol. 74, p. 1111,1114
  • 8
  • [ 3424-43-9 ]
  • [ 3279-76-3 ]
Reference: [1] Journal of Organic Chemistry, 1954, vol. 19, p. 183,191
[2] Journal of Organic Chemistry, 1954, vol. 19, p. 183,191
  • 9
  • [ 4027-39-8 ]
  • [ 3279-76-3 ]
Reference: [1] Journal of Organic Chemistry, 1954, vol. 19, p. 183,191
[2] Journal of Organic Chemistry, 1954, vol. 19, p. 183,191
  • 10
  • [ 31163-12-9 ]
  • [ 3279-76-3 ]
Reference: [1] Journal of Organic Chemistry, 1954, vol. 19, p. 183,191
  • 11
  • [ 18613-73-5 ]
  • [ 3279-76-3 ]
Reference: [1] Chemische Berichte, 1941, vol. 74, p. 1111,1114
  • 12
  • [ 128702-09-0 ]
  • [ 3279-76-3 ]
  • [ 100-52-7 ]
  • [ 100-51-6 ]
Reference: [1] Journal of the Chemical Society, Perkin Transactions 2: Physical Organic Chemistry (1972-1999), 1990, # 3, p. 499 - 503
  • 13
  • [ 3279-76-3 ]
  • [ 18368-57-5 ]
Reference: [1] Angewandte Chemie, International Edition, 2015, vol. 54, # 1, p. 280 - 284[2] Angewandte Chemie, 2015, vol. 127, # 1, p. 282 - 286,5
  • 14
  • [ 3279-76-3 ]
  • [ 18368-63-3 ]
Reference: [1] Journal of the Chemical Society, 1954, p. 2693,2697
[2] Doklady Akademii Nauk SSSR, 1952, vol. 84, p. 289,292[3] Chem.Abstr., 1953, p. 3309
  • 15
  • [ 3279-76-3 ]
  • [ 5315-25-3 ]
  • [ 3430-15-7 ]
Reference: [1] Recueil des Travaux Chimiques des Pays-Bas, 1934, vol. 53, p. 417,420
  • 16
  • [ 3279-76-3 ]
  • [ 5315-25-3 ]
Reference: [1] Recueil des Travaux Chimiques des Pays-Bas, 1934, vol. 53, p. 417,420
  • 17
  • [ 103548-82-9 ]
  • [ 612-60-2 ]
  • [ 3279-76-3 ]
Reference: [1] Canadian Journal of Chemistry, 1986, vol. 64, p. 837 - 840
  • 18
  • [ 3279-76-3 ]
  • [ 74-88-4 ]
  • [ 63071-03-4 ]
YieldReaction ConditionsOperation in experiment
80% With silver carbonate In chloroform at 20℃; for 48.5 h; In the dark Step A.
2-Methoxy-6-methyl-pyridine.
To a mixture of 6-methyl-pyridin-2-ol (10.0 g, 91.6 mmol) and Ag2CO3 (34.5 g, 125.1 mmol) in CHCl3 (300 mL) was added Mel (64.4 mL, 1.04 mol) over 30 min.
The mixture was stirred for 48 h at rt in the dark, then was filtered through a pad of SiO2, washing with Et2O.
The filtrate was concentrated to provide the title compound (9.03 g, 80percent). MS (ESI): mass calcd. for C7H9NO, 123.07; m/z found, 124.3 [M+H]+. 1H NMR (CDCl3): 7.46-7.41 (m, 1H), 6.70 (d, J=7.2, 1H), 6.53 (d, J=8.2, 1H), 3.91 (s, 3H), 2.44 (s, 3H).
80% With silver carbonate In tetrahydrofuran at 20℃; Darkness 1) 3-Bromo-2-methoxy-5,8-dimethyl-6,7,8,9-tetrahydro-5H-pyrido[2,3-d]azepine A mixture of 2-hydroxy-6-methylpyridine (164 g, 1.47 mol), iodomethane (1.35 kg, 9.53 mol), Ag2CO3 (526 g, 1.91 mol) in THF (10 ml) was strirred overnight at ambient temperature while protecting from light. The mixture was filtered through Celite and the filter cake was washed with THF. The filtrate was concentrated in vacuo until all methyl iodide was removed by HPLC analysis to yield 145.6 g (80percent) of 2-methoxy-6-methylpyridine.
67% With silver carbonate In dichloromethane at 20℃; for 96 h; To a solution of 6-methyl-pyridin-2-ol (2.5 g, 0.023 mol) in CH2CI2 (10 mL) at r. t. , under N2, were added AG2CO3 (6 g, 1.5 eq. ) and Mel (5,6 mL, 4 eq). The solution was stirred at r. t. for 4 days, then AG2CO3 was filtered and washed with CH2CI2, and the organic layer was evaporated to dryness. The crude product was purified by flash chromatography (silica gel, EtOAc/cHex 2: 8) to give the title compound (1.9 mg, 67percent) as a white solid. NMR (APOS;H, CDCl3) : 8 7.4 (t, 1H), 6.6 (d, 1H), 6.5 (d, 1H), 3.8 (s, 3H), 2.4 (s, 3H).
Reference: [1] Tetrahedron Letters, 1997, vol. 38, # 35, p. 6153 - 6156
[2] Synthetic Communications, 1994, vol. 24, # 10, p. 1367 - 1379
[3] Tetrahedron, 2000, vol. 56, # 20, p. 3181 - 3187
[4] Patent: US2006/287292, 2006, A1, . Location in patent: Page/Page column 28
[5] Patent: US2007/281918, 2007, A1, . Location in patent: Page/Page column 13
[6] Patent: WO2004/62665, 2004, A1, . Location in patent: Page/Page column 44
[7] Journal of Medicinal Chemistry, 2003, vol. 46, # 6, p. 921 - 924
[8] Journal of Medicinal Chemistry, 2009, vol. 52, # 9, p. 3084 - 3092
[9] Science China Chemistry, 2012, vol. 55, # 6, p. 1097 - 1100
  • 19
  • [ 3279-76-3 ]
  • [ 420-37-1 ]
  • [ 63071-03-4 ]
YieldReaction ConditionsOperation in experiment
27% With sodium hydroxide In dichloromethane PREPARATION 133
2-Methoxy-6-methylpyridine
Trimethyloxonium tetrafluoroborate (10.0 g, 67.6 mmol) was added portionwise to a suspension of 6-methylpyridin-2-one (7.3 g, 67.0 mmol) in dichloromethane (100 ml), and once addition was complete, the reaction was stirred at room temperature for 24 hours.
Dichloromethane (50 ml) and aqueous sodium hydroxide solution (50 ml, 2N) were added and the layers separated.
The aqueous phase was extracted with dichloromethane (2*50 ml), the combined organic solutions washed with brine (50 ml), dried (MgSO4) and evaporated under reduced pressure.
The crude product was purified by column chromatography on silica gel, using an elution gradient of pentane: dichloromethane (66:34 to 0:100) to afford the title compound (2.25 g, 27percent) as a colourless oil. δ (CDCl3): 2.49 (3H, s), 3.90 (3H, s), 6.38-6.73 (2H, m), 7.23-7.40 (1 H, br d).
Reference: [1] Patent: US6251904, 2001, B1,
  • 20
  • [ 3279-76-3 ]
  • [ 54923-31-8 ]
  • [ 500587-45-1 ]
  • [ 374633-33-7 ]
Reference: [1] Synlett, 2003, # 11, p. 1678 - 1682
  • 21
  • [ 3279-76-3 ]
  • [ 5315-25-3 ]
  • [ 3430-15-7 ]
Reference: [1] Recueil des Travaux Chimiques des Pays-Bas, 1934, vol. 53, p. 417,420
  • 22
  • [ 3279-76-3 ]
  • [ 39745-39-6 ]
Reference: [1] Recueil des Travaux Chimiques des Pays-Bas, 1949, vol. 68, p. 1013,1024
  • 23
  • [ 3279-76-3 ]
  • [ 856834-95-2 ]
Reference: [1] Patent: WO2015/89192, 2015, A1,
[2] Patent: WO2016/37005, 2016, A1,
[3] Patent: WO2008/101682, 2008, A2,
  • 24
  • [ 3279-76-3 ]
  • [ 56100-22-2 ]
Reference: [1] Journal of Organic Chemistry, 1998, vol. 63, # 26, p. 10048 - 10051
[2] Organic Syntheses, 2002, vol. 78, p. 51 - 51
  • 25
  • [ 3279-76-3 ]
  • [ 126717-59-7 ]
Reference: [1] Tetrahedron, 2000, vol. 56, # 20, p. 3181 - 3187
[2] Synthetic Communications, 1994, vol. 24, # 10, p. 1367 - 1379
[3] Synthetic Communications, 1994, vol. 24, # 10, p. 1367 - 1379
[4] Science China Chemistry, 2012, vol. 55, # 6, p. 1097 - 1100
  • 26
  • [ 3279-76-3 ]
  • [ 156094-63-2 ]
Reference: [1] Synthetic Communications, 1994, vol. 24, # 10, p. 1367 - 1379
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