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[ CAS No. 16665-38-6 ] {[proInfo.proName]}

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Chemical Structure| 16665-38-6
Chemical Structure| 16665-38-6
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Product Details of [ 16665-38-6 ]

CAS No. :16665-38-6 MDL No. :MFCD07774100
Formula : C7H9NO2 Boiling Point : -
Linear Structure Formula :- InChI Key :GBMRUSRMPOUVEK-UHFFFAOYSA-N
M.W : 139.15 Pubchem ID :10820596
Synonyms :

Calculated chemistry of [ 16665-38-6 ]

Physicochemical Properties

Num. heavy atoms : 10
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.29
Num. rotatable bonds : 2
Num. H-bond acceptors : 3.0
Num. H-bond donors : 1.0
Molar Refractivity : 36.86
TPSA : 42.35 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) : -7.17 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.51
Log Po/w (XLOGP3) : -0.03
Log Po/w (WLOGP) : 0.43
Log Po/w (MLOGP) : -0.39
Log Po/w (SILICOS-IT) : 1.17
Consensus Log Po/w : 0.54

Druglikeness

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

Water Solubility

Log S (ESOL) : -1.0
Solubility : 14.0 mg/ml ; 0.101 mol/l
Class : Very soluble
Log S (Ali) : -0.41
Solubility : 54.2 mg/ml ; 0.39 mol/l
Class : Very soluble
Log S (SILICOS-IT) : -1.95
Solubility : 1.55 mg/ml ; 0.0111 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.54

Safety of [ 16665-38-6 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P280-P305+P351+P338 UN#:N/A
Hazard Statements:H302 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 16665-38-6 ]

* 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 [ 16665-38-6 ]
  • Downstream synthetic route of [ 16665-38-6 ]

[ 16665-38-6 ] Synthesis Path-Upstream   1~2

  • 1
  • [ 16665-38-6 ]
  • [ 16744-81-3 ]
YieldReaction ConditionsOperation in experiment
62.9% With manganese(IV) oxide In ethyl acetate at 80℃; for 2 h; 4-Methoxypyridine-2-carbaldehyde, used as starting material was prepared as follows:- Manganese(IV) oxide (2.412 mL, 139.42 mmol, 4eq) was added portionwise to (4- methoxypyridin-2-yl)methanol (4.85g, 34.85 mmol, leq) in ethyl acetate (15OmL). The resulting mixture was stirred at 80 0C for 2 h. The hot reaction mixture was filtered through celite. The resulting mixture was evaporated to dryness to afford desired A- methoxypyridine-2-carbaldehyde (3.01 g, 21.93 mmol, 62.9 percent). IH NMR (400.132 MHz, DMSO) δ 3.93 (3H, s), 7.27 (IH, m), 7.44 (IH, d), 8.63 (IH, d), 9.96 (IH, s)
46% With manganese(IV) oxide In chloroform for 2.5 h; Reflux A suspension of 17 (420 mg, 3.02 mmol) and MnO2 (3.2 g) in dry CHCl3 (5 mL) was refluxed for 2.5 hr. After removal of MnO2 by filtration, the filtrate was concentrated under reduced pressure to give 18 (193 mg, 46 percent) as a pale yellow solid.
193 mg With manganese(IV) oxide In ethyl acetate for 3 h; Reflux Manganese dioxide (696 mg) was added to a solution of (4-methoxypyridin-2-yl)methanol (278 mg) obtained in Reference Example 21-6 (3) in ethyl acetate (5 mL), followed by refluxing for 1 hour. Manganese dioxide (696 mg) was added thereto, followed by refluxing for 2 hours. The reaction mixture was cooled to room temperature, the insoluble materials were filtered off, and the solvent was distilled off under reduced pressure. The obtained residues were purified by silica gel column chromatography (ethyl acetate), whereby 4-methoxypicolinic aldehyde (193 mg) was obtained as a colorless oily material
Reference: [1] Patent: WO2009/56886, 2009, A1, . Location in patent: Page/Page column 54
[2] Chemical and Pharmaceutical Bulletin, 1990, vol. 38, # 9, p. 2446 - 2458
[3] Inorganic Chemistry, 2013, vol. 52, # 11, p. 6481 - 6501
[4] Bulletin of the Chemical Society of Japan, 2015, vol. 88, # 6, p. 784 - 791
[5] Yakugaku Zasshi, 1957, vol. 77, p. 11,13[6] Chem.Abstr., 1957, p. 8745
[7] Inorganic Chemistry, 2015, vol. 54, # 21, p. 10141 - 10152
[8] Patent: US2016/168139, 2016, A1, . Location in patent: Paragraph 0970; 0981; 0982
  • 2
  • [ 16665-38-6 ]
  • [ 62734-08-1 ]
Reference: [1] Journal of Medicinal Chemistry, 1995, vol. 38, # 25, p. 4906 - 4916
[2] Journal of Medicinal Chemistry, 1992, vol. 35, # 6, p. 1049 - 1057
[3] Patent: US4560693, 1985, A,
[4] Patent: US4562197, 1985, A,
[5] Journal of Organic Chemistry, 2013, vol. 78, # 22, p. 11508 - 11512
[6] Patent: US4083983, 1978, A,
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