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[ CAS No. 10602-06-9 ] {[proInfo.proName]}

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Chemical Structure| 10602-06-9
Chemical Structure| 10602-06-9
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Product Details of [ 10602-06-9 ]

CAS No. :10602-06-9 MDL No. :MFCD08703579
Formula : C10H8O2 Boiling Point : -
Linear Structure Formula :- InChI Key :DDXZMLZQQWVSRX-UHFFFAOYSA-N
M.W : 160.17 Pubchem ID :11275159
Synonyms :

Calculated chemistry of [ 10602-06-9 ]

Physicochemical Properties

Num. heavy atoms : 12
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.1
Num. rotatable bonds : 2
Num. H-bond acceptors : 2.0
Num. H-bond donors : 0.0
Molar Refractivity : 45.66
TPSA : 26.3 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) : -5.4 cm/s

Lipophilicity

Log Po/w (iLOGP) : 2.4
Log Po/w (XLOGP3) : 2.65
Log Po/w (WLOGP) : 1.53
Log Po/w (MLOGP) : 2.47
Log Po/w (SILICOS-IT) : 2.34
Consensus Log Po/w : 2.28

Druglikeness

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

Water Solubility

Log S (ESOL) : -2.74
Solubility : 0.291 mg/ml ; 0.00182 mol/l
Class : Soluble
Log S (Ali) : -2.85
Solubility : 0.224 mg/ml ; 0.0014 mol/l
Class : Soluble
Log S (SILICOS-IT) : -2.54
Solubility : 0.457 mg/ml ; 0.00285 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 1.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.87

Safety of [ 10602-06-9 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P280-P305+P351+P338 UN#:N/A
Hazard Statements:H302-H315-H319-H332-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 10602-06-9 ]

* 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 [ 10602-06-9 ]
  • Downstream synthetic route of [ 10602-06-9 ]

[ 10602-06-9 ] Synthesis Path-Upstream   1~10

  • 1
  • [ 67-56-1 ]
  • [ 914943-91-2 ]
  • [ 10602-06-9 ]
YieldReaction ConditionsOperation in experiment
96%
Stage #1: With trifluoroacetic acid In dichloromethane at 20℃; for 3 h;
Stage #2: at 65℃; for 20 h;
terf-Butyl 3-ethynylbenzoate (117) (1.50 g, 9.37 mmoi) was dissolved in dry DCM (70 mL) and TFA (35.9 mL, 488 mmoi) was added carefully. The reaction was stirred at room temperature for 3 hours, concentrated in vacuo and toluene was added and then removed in vacuo to give a pale yellow solid. This material was dissolved in methanol (50 mL) and cone. H2S04 (-1 mL) was added and the resulting solution was stirred at 85 °C for 20 hours. Upon cooling to room temperature, the volatiies were removed in vacuo and the residue was diluted with EtOAc (200 mL) and sat. aq. NaHCO3 (100 mL) was added slowly. The layers were separated and the aqueous layer was extracted with EtOAc (200 mL), the organic layers were combined and washed with water (100 mL), brine (100 mL), dried ( gS04), filtered and concentrated in vacuo to give the title compound (131) (1.136 g, 96percent yield over 2 steps) as a pale yellow solid; 1H NMR (400 MHz, CDCI3) δ 8.17 (t, J = 1.5 Hz, 1 H), 8.03 - 8.00 (m, 1 H), 7.66 (dt, J = 7.7, 1.4 Hz, 1 H), 7.41 (td, J = 7.8, 0.4 Hz, 1 H), 3.93 (s, 3H), 3.12 (s, 1 H). LCMS Method C: rt 5.84 min.
Reference: [1] Patent: WO2014/27199, 2014, A1, . Location in patent: Page/Page column 75
[2] Patent: WO2012/110773, 2012, A1, . Location in patent: Page/Page column 73
  • 2
  • [ 77123-59-2 ]
  • [ 10602-06-9 ]
Reference: [1] Journal of Medicinal Chemistry, 2013, vol. 56, # 8, p. 3281 - 3295
[2] Organic Letters, 2013, vol. 15, # 4, p. 936 - 939
[3] Tetrahedron, 2000, vol. 56, # 3, p. 407 - 415
[4] Journal of Organic Chemistry, 1981, vol. 46, # 11, p. 2280 - 2286
[5] Journal of Medicinal Chemistry, 2010, vol. 53, # 3, p. 994 - 1003
[6] Journal of the American Chemical Society, 2013, vol. 135, # 22, p. 8400 - 8408
[7] Molecules, 2018, vol. 23, # 8,
  • 3
  • [ 33577-97-8 ]
  • [ 10602-06-9 ]
Reference: [1] Journal of Organic Chemistry, 1985, vol. 50, # 10, p. 1763 - 1765
[2] Journal of Medicinal Chemistry, 2004, vol. 47, # 6, p. 1475 - 1486
  • 4
  • [ 618-89-3 ]
  • [ 10602-06-9 ]
Reference: [1] Journal of Medicinal Chemistry, 2004, vol. 47, # 6, p. 1475 - 1486
[2] Journal of Organic Chemistry, 1985, vol. 50, # 10, p. 1763 - 1765
[3] Journal of Organic Chemistry, 1981, vol. 46, # 11, p. 2280 - 2286
[4] Journal of the American Chemical Society, 2013, vol. 135, # 22, p. 8400 - 8408
[5] Molecules, 2018, vol. 23, # 8,
  • 5
  • [ 618-91-7 ]
  • [ 10602-06-9 ]
Reference: [1] Tetrahedron, 2000, vol. 56, # 3, p. 407 - 415
[2] Organic Letters, 2013, vol. 15, # 4, p. 936 - 939
[3] Journal of Medicinal Chemistry, 2013, vol. 56, # 8, p. 3281 - 3295
  • 6
  • [ 618-51-9 ]
  • [ 10602-06-9 ]
Reference: [1] Patent: WO2012/110773, 2012, A1,
[2] Patent: WO2014/27199, 2014, A1,
  • 7
  • [ 173406-17-2 ]
  • [ 10602-06-9 ]
Reference: [1] Patent: WO2012/110773, 2012, A1,
[2] Patent: WO2014/27199, 2014, A1,
  • 8
  • [ 1393900-84-9 ]
  • [ 10602-06-9 ]
Reference: [1] Patent: WO2012/110773, 2012, A1,
[2] Patent: WO2014/27199, 2014, A1,
  • 9
  • [ 6929-96-0 ]
  • [ 922-67-8 ]
  • [ 10602-06-9 ]
  • [ 3034-86-4 ]
Reference: [1] Liebigs Annales, 1996, # 5, p. 815 - 824
  • 10
  • [ 10602-06-9 ]
  • [ 10601-99-7 ]
Reference: [1] Journal of Organic Chemistry, 1966, vol. 31, p. 2585 - 2593
[2] Journal of Medicinal Chemistry, 2015, vol. 58, # 23, p. 9228 - 9237
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