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[ CAS No. 86-86-2 ]

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Chemical Structure| 86-86-2
Chemical Structure| 86-86-2
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Product Details of [ 86-86-2 ]

CAS No. :86-86-2 MDL No. :MFCD00004047
Formula : C12H11NO Boiling Point : -
Linear Structure Formula :- InChI Key :XFNJVKMNNVCYEK-UHFFFAOYSA-N
M.W :185.22 Pubchem ID :6861
Synonyms :

Calculated chemistry of [ 86-86-2 ]

Physicochemical Properties

Num. heavy atoms : 14
Num. arom. heavy atoms : 10
Fraction Csp3 : 0.08
Num. rotatable bonds : 2
Num. H-bond acceptors : 1.0
Num. H-bond donors : 1.0
Molar Refractivity : 56.63
TPSA : 43.09 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : Yes
P-gp substrate : No
CYP1A2 inhibitor : Yes
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -6.3 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.4
Log Po/w (XLOGP3) : 1.59
Log Po/w (WLOGP) : 1.87
Log Po/w (MLOGP) : 2.24
Log Po/w (SILICOS-IT) : 2.45
Consensus Log Po/w : 1.91

Druglikeness

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

Water Solubility

Log S (ESOL) : -2.39
Solubility : 0.76 mg/ml ; 0.00411 mol/l
Class : Soluble
Log S (Ali) : -2.11
Solubility : 1.45 mg/ml ; 0.00783 mol/l
Class : Soluble
Log S (SILICOS-IT) : -4.07
Solubility : 0.0158 mg/ml ; 0.0000855 mol/l
Class : Moderately soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.02

Safety of [ 86-86-2 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P280-P305+P351+P338-P310 UN#:N/A
Hazard Statements:H302-H315-H319-H332-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 86-86-2 ]

* 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 [ 86-86-2 ]
  • Downstream synthetic route of [ 86-86-2 ]

[ 86-86-2 ] Synthesis Path-Upstream   1~7

  • 1
  • [ 5121-00-6 ]
  • [ 86-86-2 ]
YieldReaction ConditionsOperation in experiment
72% With ammonium hydroxide In tetrahydrofuran at 0 - 20℃; for 0.166667 h; 1-naphthaleneacetic acid (93.5 mg, 0.50 mmol) was added to methylene chloride (0.8 mL)And a catalytic amount of DMF were added and while stirring,Further oxalyl chloride (135.6 mg, 1.00 mmol, 2.00 eq.) Was added dropwise,Followed by stirring at room temperature for 15 minutes. After concentrating the resulting solution under vacuum,Was dissolved in tetrahydrofuran (0.8 mL).Ammonia water (28percent, 450.4 mg, 7.50 mmol, 15.0 eq.) At 0 ° C. was added to the solution,It was then stirred at room temperature for 10 minutes. After concentrating the resulting solution under vacuum,Silica gel column chromatography (chloroform / methanol(10/1, Rf = 0.50)) to obtain the target substance (Y-015) as a white solid (yield 72percent).
Reference: [1] Patent: JP2015/89885, 2015, A, . Location in patent: Paragraph 0146; 0147; 0162-0164
[2] Chimica e l'Industria (Milan, Italy), 1955, vol. 37, p. 857,860
[3] Bulletin de la Societe Chimique de France, 1965, p. 861 - 868
[4] Journal of Medicinal Chemistry, 2009, vol. 52, # 10, p. 3366 - 3376
[5] Chemistry Letters, 2015, vol. 44, # 5, p. 621 - 623
[6] ACS Medicinal Chemistry Letters, 2017, vol. 8, # 3, p. 287 - 292
  • 2
  • [ 86-87-3 ]
  • [ 86-86-2 ]
YieldReaction ConditionsOperation in experiment
88%
Stage #1: With thionyl chloride In dichloromethane at 0℃; for 2 h;
Stage #2: With ammonium hydroxide In tetrahydrofuran at 0 - 20℃;
To a solution of 2—(naphthalen-1—yl)acetic acid (1.50 g, 8.01 mmcl, 1.00 equiv.) in dry CH2C12 (10.0 mL, 0.801 H) was added thionyl chloride (6.73 mL, 92.6 rnmol, 11.5 equiv.) at 0 °C, then the reaction was refluxed for 2 h. The solvent was evaporated and the residue wasazeotroped with toluene (2 xlO.0 mL) . To the crude acyl chloride was added THF (30.0 mL) and NHsH2O (30.0 mL) under vigorous stirring at 0 °C. After the reaction mixture was stirred at room temperature for overnight, the solvent was removed. The residue was purified by column chromatography using with EtOAc:hexane (1 :2 (v/v)) to afford thetitle compound as a white solid (1.31 g, 7.07 mmcl, 88percent yield)NMR Spectroscopy: 1H NMR (700 MHz, (CD3)2S0, 25 °C, 5): 8.08 (d, J =8.3 Hz, 1H), 7.92 (d, J = 7.7 Hz, lH), 7.81 (d, J = 7.7 Hz, 1H), 7.56—7.49 (m, 3H), 7.45—7.41 (m, 2H), 6.99 (s, 1H), 3.86 (s, 2H). C NMR(175 MHz, (CD)2SO, 25 °C, 5): 172.1, 133.3, 132.9, 132.0, 128.3,127.8, 126.9, 125.9, 125.5, 125.5, 124.2. The 1H NMR data were in goodagreement with values reported in the literature (Tu, T. et al. 2012)
Reference: [1] Patent: WO2018/132636, 2018, A1, . Location in patent: Page/Page column 66; 67
[2] Chemische Berichte, 1883, vol. 16, p. 639
[3] Bioorganic and Medicinal Chemistry Letters, 2008, vol. 18, # 7, p. 2390 - 2394
[4] ACS Medicinal Chemistry Letters, 2017, vol. 8, # 3, p. 287 - 292
  • 3
  • [ 132-75-2 ]
  • [ 86-86-2 ]
Reference: [1] Green Chemistry, 2012, vol. 14, # 4, p. 921 - 924
[2] Journal of Organic Chemistry, 1950, vol. 15, p. 548,549[3] Organic Syntheses, 1963, vol. Coll. Vol. IV, p. 760,762
[4] Patent: US2331711, 1942, ,
  • 4
  • [ 90-15-3 ]
  • [ 79-07-2 ]
  • [ 86-86-2 ]
Reference: [1] Journal of Medicinal Chemistry, 2013, vol. 56, # 20, p. 7851 - 7861
  • 5
  • [ 941-98-0 ]
  • [ 86-86-2 ]
Reference: [1] Journal fuer Praktische Chemie (Leipzig), 1910, vol. <2> 81, p. 387
  • 6
  • [ 26153-26-4 ]
  • [ 86-86-2 ]
Reference: [1] Chemische Berichte, 1883, vol. 16, p. 639
  • 7
  • [ 352352-80-8 ]
  • [ 86-86-2 ]
Reference: [1] Chemische Berichte, 1883, vol. 16, p. 639
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