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[ CAS No. 80866-88-2 ] {[proInfo.proName]}

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Chemical Structure| 80866-88-2
Chemical Structure| 80866-88-2
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Product Details of [ 80866-88-2 ]

CAS No. :80866-88-2 MDL No. :MFCD00007098
Formula : C8H9NO4 Boiling Point : -
Linear Structure Formula :- InChI Key :AADYWCBPJZAJNU-UHFFFAOYSA-N
M.W : 183.16 Pubchem ID :602961
Synonyms :

Calculated chemistry of [ 80866-88-2 ]

Physicochemical Properties

Num. heavy atoms : 13
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.25
Num. rotatable bonds : 3
Num. H-bond acceptors : 4.0
Num. H-bond donors : 1.0
Molar Refractivity : 47.88
TPSA : 75.28 Ų

Pharmacokinetics

GI absorption : High
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) : -6.82 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.48
Log Po/w (XLOGP3) : 0.84
Log Po/w (WLOGP) : 0.94
Log Po/w (MLOGP) : 0.11
Log Po/w (SILICOS-IT) : -0.47
Consensus Log Po/w : 0.58

Druglikeness

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

Water Solubility

Log S (ESOL) : -1.65
Solubility : 4.12 mg/ml ; 0.0225 mol/l
Class : Very soluble
Log S (Ali) : -2.0
Solubility : 1.82 mg/ml ; 0.00991 mol/l
Class : Soluble
Log S (SILICOS-IT) : -1.74
Solubility : 3.36 mg/ml ; 0.0184 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 2.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.86

Safety of [ 80866-88-2 ]

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 [ 80866-88-2 ]

* 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 [ 80866-88-2 ]
  • Downstream synthetic route of [ 80866-88-2 ]

[ 80866-88-2 ] Synthesis Path-Upstream   1~2

  • 1
  • [ 80866-88-2 ]
  • [ 80410-57-7 ]
YieldReaction ConditionsOperation in experiment
100% With dipyridinium dichromate In dichloromethane at 20℃; for 17 h; A dispersion of (3-methoxy-4-nitrophenyl)methanol (43) (1.4 mmol) and pyridinium dichromate (2.3 mmol) in dry DCM(38 mL) was stirred 17 hours at room temperature and a mixture of celite and silica was added.
The dispersion was filtered and washed with DCM (3x10 mL).
The solvent of the resulting solution was evaporated under vacuum to give a brown residue (1.3 mmol, quantitative yield).
1H NMR (400 MHz, CDCl3) δ 10.05 (s, 1H), 7.92 (d, J = 8.1 Hz, 1H), 7.60 (d, J = 1.3 Hz, 1H), 7.54 (dd, J = 8.1, 1.5 Hz, 1H), 4.03 (s, 3H).
79.71% With manganese(IV) oxide In dichloromethane at 40℃; for 12 h; 3-Methoxy-4-nitrobenzyl alcohol (4.70g, 25.66mmol) was added to DCM (50mL), and MnO2 (13.39g, 153.96mmol) was added to the mixture and the reaction mixture was warmed to 40°C and stirred for 12 hours. TLC showed the reaction was complete, the reaction mixture was filtered and the filtrate was concentrated to deliver the title compound (yellow solid, 3.90g, yield 79.71percent).
1H NMR (300 MHz, CDCl3): δ 10.0-10.20 (m, 1 H), 7.87 - 8.05 (m, 1 H), 7.47 - 7.72 (m, 2 H), 3.96 - 4.14 (m, 3 H).
74% With dipyridinium dichromate In dichloromethane at 20℃; for 2 h; molecular sieve Step 1 : To a solution of 3-methoxy-4-nitrobenzyl alcohol (5g) in DCM ( 100 mL) was added PDC (1 .5 eq) and molecular sieves (6.0 g). The mixture was stirred at room temperature for 2h and diluted with Et20 (100 mL). The mixture was filtered through a Celite pad and solvent was evaporated. The residue was washed with a small amount MeOH to give off white solid (3.7 g, yield 74percent).
74% With dipyridinium dichromate In dichloromethane at 20℃; for 2 h; To a solution of 3-methoxy-4-nitrobenzyl alcohol (5g) in DCM (100 mL) was added PDC (1.5 eq) and molecular sieves (6.0 g). The mixture was stirred at room temperature for 2h and diluted with Et.20 (100 mL). The mixture was filtered through a Celite pad and solvent was evaporated. The residue was washed with a small amount MeOH to give off white solid (3.7 g, yield 74percent).

Reference: [1] Patent: EP2853565, 2015, A1, . Location in patent: Paragraph 0220
[2] Bioorganic and Medicinal Chemistry, 2000, vol. 8, # 10, p. 2417 - 2425
[3] Angewandte Chemie - International Edition, 2018, vol. 57, # 24, p. 7040 - 7045[4] Angew. Chem., 2018, vol. 130, # 24, p. 7158 - 7163,6
[5] Patent: EP3290419, 2018, A1, . Location in patent: Paragraph 0176; 0177
[6] Patent: WO2012/151561, 2012, A1, . Location in patent: Page/Page column 71
[7] Patent: WO2013/169401, 2013, A1, . Location in patent: Page/Page column 84
[8] Journal of Fluorine Chemistry, 2007, vol. 128, # 12, p. 1461 - 1468
  • 2
  • [ 80866-88-2 ]
  • [ 148459-54-5 ]
YieldReaction ConditionsOperation in experiment
15% With hydrogen In methanol A solution of 3-methoxy-4-nitrobenzyl alcohol (5 g, 27 mmol) in methanol (250 mL) was added to a flask containing 10percent Pd-C (5 molpercent). The mixture was stirred under hydrogen atmosphere for overnight. The reaction mixture was then filtered through a plug of celite and the filtrate was concentrated. The crude product was purified on silica gel column eluting with EtOAc/hexanes to give pure product as a colorless oil (0.5 g, 15percent).
Reference: [1] Bulletin de la Societe Chimique de France, 1993, vol. 130, # 1, p. 93 - 95
[2] Patent: WO2005/97752, 2005, A1, . Location in patent: Page/Page column 124-125
[3] Tetrahedron, 2004, vol. 60, # 19, p. 4295 - 4302
[4] Patent: US5994368, 1999, A,
[5] Patent: US6008229, 1999, A,
[6] Patent: US6083961, 2000, A,
[7] Patent: US6344462, 2002, B1, . Location in patent: Page column 22
[8] Patent: WO2012/97683, 2012, A1, . Location in patent: Page/Page column 90
[9] Patent: US2014/171429, 2014, A1, . Location in patent: Paragraph 0375
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