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Chemical Structure| 10602-04-7
Chemical Structure| 10602-04-7
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Product Details of [ 10602-04-7 ]

CAS No. :10602-04-7 MDL No. :MFCD05664205
Formula : C9H8O Boiling Point : -
Linear Structure Formula :- InChI Key :QCZORVSTESPHCO-UHFFFAOYSA-N
M.W : 132.16 Pubchem ID :11170993
Synonyms :

Calculated chemistry of [ 10602-04-7 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 10
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.11
Num. rotatable bonds : 1
Num. H-bond acceptors : 1.0
Num. H-bond donors : 1.0
Molar Refractivity : 40.5
TPSA : 20.23 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) : -6.07 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.84
Log Po/w (XLOGP3) : 1.46
Log Po/w (WLOGP) : 1.09
Log Po/w (MLOGP) : 2.1
Log Po/w (SILICOS-IT) : 2.31
Consensus Log Po/w : 1.76

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 2.0
Bioavailability Score : 0.55

Water Solubility

Log S (ESOL) : -1.96
Solubility : 1.46 mg/ml ; 0.011 mol/l
Class : Very soluble
Log S (Ali) : -1.49
Solubility : 4.27 mg/ml ; 0.0323 mol/l
Class : Very soluble
Log S (SILICOS-IT) : -2.27
Solubility : 0.703 mg/ml ; 0.00532 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 1.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.58

Safety of [ 10602-04-7 ]

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

Application In Synthesis of [ 10602-04-7 ]

* 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 [ 10602-04-7 ]
  • Downstream synthetic route of [ 10602-04-7 ]

[ 10602-04-7 ] Synthesis Path-Upstream   1~22

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Reference: [1] Journal of Organic Chemistry, 2009, vol. 74, # 3, p. 1337 - 1340
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  • [ 275386-60-2 ]
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YieldReaction ConditionsOperation in experiment
100% With tetrabutyl ammonium fluoride In tetrahydrofuran at 0 - 20℃; for 3 h; To a solution of (4-bromophenyl) methanol (935mg, 5mmol) in dry TEA was added Pd (PPh3) 2Cl2 (175mg, 0.25mmol) , CuI (48mg, 0.25mmol) and P (t-Bu) 3 (51mg, 0.25mmol) under N2 atmosphere. The reaction mixture was stirred for 5mins, followed by addition of ethynyltrimethylsilane (980mg, 10mmol) dropwise. The reaction mixture was then microwaved at 130 for 4hrs. The reaction mixture was cooled to room temperature, filtered over celite. Solvents were removed from the filtrate in vacuo, then the residue was extracted by EtOAc/H2O 3 times. The organic layer was combined, washed with brine, dried over Na2SO4 and further pufrified by silica gel column chromatography (PE/EA4/1) to give 670mg of (4- ( (trimethylsilyl) ethynyl) phenyl) methanol as a brown oil (66) .[0633]To a solution of (4- ( (trimethylsilyl) ethynyl) phenyl) methanol (250mg, 1.23mmol) in THF was added TBAF (500mg, 2.45mmol) in portions at 0. The reaction mixture was stirred at 0 to room temperature for 3hrs. Solvents were removed from the mixture in vacuo, and the residue was extracted by EtOAc/H2O 3 times. The organic layer was combined, washed with brine, dried over Na2SO4 and further pufrified by silica gel column chromatography (PE/EA4/1) to give 170mg of (4-ethynylphenyl) methanol as a brown oil (100) . 1H NMR (400Hz, CDCl3) δ7.45-7.49 (m, 2H) , 7.21-7.26 (m, 2H) , 4.69 (s, 1H) , 4.65 (s, 2H) .
100% With potassium carbonate In methanol at 20℃; for 2 h; Part C; Synthesis of (4-EthvnvI-phenyl)-methanoI4-[(Trimethylsilyl)ethynyl-phenyl]methanol (0.47 g, 2.30 mmol) was treated with potassium carbonate (0.34 g, 2.47 mmol) in 10 ml of methanol under argon at room temperature for 2 h. The solution was quenched with half saturated aqueous ammonium chloride solution (30 ml) and extracted with ether (2 x 25 ml). The combined organic layers were washed with saturated brine (2 x 20 ml), dried over MgSO4, filtered and concentrated under reduced pressure giving the product as a pale yellow oil in quantitative yield. The material was used in the next step without any further purification. IH-NMR (CDCl3, 200 MHz): δ[ppm] = 1.67 (tr, IH, J = 5.9 Hz), 4.71 (d, 2H, J = 5.9 Hz), 7.32 (d, 2H, J = 8.5 Hz), 7.50 (d, 2H, J = 8.5 Hz)
88% With tetrabutyl ammonium fluoride In tetrahydrofuran Example 4
Synthesis of (4-Ethynylphenyl)methanol (4)
3 (65 mg, 0.318 mmol) was dissolved in 1 ml of THF. TBAF (0.35 ml, 0.35 mmol) was added and the mixture was stirred at room temperature for 30 min.
The solvent was removed under reduced pressure and the residue was purified by flash chromatography (AcOEt/Hexane 3:7) to afford 4 (37 mg, 0.28 mmol, 88percent yield) as a colorless solid.
87% With tetrabutyl ammonium fluoride In tetrahydrofuran at 20℃; for 2 h; To a solution of (4-((trimethylsilyl)ethynyl)phenyl)methanol (2.96 g, 14.47 mmol) in THF (29 mL) was added tetrabutylammonium fluoride solution (15.92 ml, 1M in THF). After addition, the reaction was stirred at ambient temperature for 2 h. All the volatile solvent was removed under reduced pressure, and the residue was dissolved in DCM (20 ml). Water (15 mL) was added, and the aqueous layer was extracted with DCM (15 mL X 2). The combined organic layer was washed with brine (30 mL), dried over Na2SO4, and filtered. The organic layer was concentrated under reduced pressure and the residue was purified by silica gel chromatography, by column chromatography with hexane/ethyl acetate (3/1, v/v) to obtain the compound 56 as a white solid (1.66 mg, 87percent yield): 1H NMR (400 MHz, CDCl3) _ 7.41 (d, J = 8.3 Hz, 2H), 7.17 (d, J = 8.6 Hz, 2H), 4.48 (s, 2H), 3.59 (s, 1H), 3.09 (s, 1H); 13C NMR (100 MHz, CDCl3) _ 141.5, 132.2, 126.7, 121.0, 83.5, 77.4, 64.3.
37 mg With tetrabutyl ammonium fluoride In tetrahydrofuran at 20℃; for 0.5 h; 3 (65 mg, 0.318 mmol) was dissolved in 1 ml of THF. TBAF (0.35 ml, 0.35 mmol) was added and the mixture was stirred at room temperature for 30 min. The solvent was removed under reduced pressure and the residue was purified by flash chromatography (AcOEt/Hexane 3:7) to afford 4 (37 mg, 0.28 mmol, 88percent yield) as a colorless solid.

Reference: [1] Angewandte Chemie - International Edition, 2004, vol. 43, # 29, p. 3814 - 3818
[2] Patent: WO2018/14802, 2018, A1, . Location in patent: Paragraph 0364
[3] Patent: WO2008/31157, 2008, A1, . Location in patent: Page/Page column 65
[4] Chemistry - A European Journal, 2013, vol. 19, # 29, p. 9452 - 9456
[5] Synthesis (Germany), 2014, vol. 46, # 3, p. 348 - 356
[6] Patent: US2013/266644, 2013, A1, . Location in patent: Page/Page column
[7] Patent: WO2018/160967, 2018, A1, . Location in patent: Page/Page column 87-88
[8] Chirality, 2015, vol. 27, # 8, p. 454 - 458
[9] Macromolecules, 2005, vol. 38, # 15, p. 6367 - 6373
[10] Tetrahedron Letters, 2000, vol. 41, # 17, p. 3123 - 3126
[11] Journal of the American Chemical Society, 2005, vol. 127, # 43, p. 15257 - 15264
[12] Journal of Medicinal Chemistry, 2010, vol. 53, # 2, p. 699 - 714
[13] Patent: CN105622638, 2016, A, . Location in patent: Paragraph 0328
[14] Patent: US9758545, 2017, B2, . Location in patent: Page/Page column 19; 20; 26; 27
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YieldReaction ConditionsOperation in experiment
90% at 0 - 20℃; for 2 h; A solution of 543 4-ethynylbenzaldehyde (3.8 g, 29.23 mmol) in 124 methanol (80 mL) at 0° C. was charged with 246 sodium borohydride (2.2 g, 58.46 mmol) portionwise. The reaction mixture allowed to attain room temperature and stirred for 2 h. The reaction mixture was concentrated in vacuo, quenched with saturated ammonium chloride solution and extracted with ethyl acetate The combined organic layers were dried over anhydrous Na2SO4, filtered and concentrated in vacuo to afford 3.47 g, 90percent yield, of the title compound as light yellow oil.1H NMR (400 MHz, CDCl3) δ=7.49 (d, J=7.83 Hz, 2H), 7.33 (d, J=7.82 Hz, 2H), 4.71 (s, 2H), 3.07 (s, 1H).
66.7% at 20℃; for 8 h; The p-alkynylbenzaldehyde (390 mg, 3 mmol) was dissolved in 15 mL of dry EtOH.Sodium borohydride (567 mg, 15 mmol) was dissolved in a small amount of dry EtOH, slowly added dropwise to the reaction system, and reacted at room temperature for 8 h.After the reaction was completed, H2O was added dropwise to the system to quench the unreacted sodium borohydride, then the solvent was deconcentrated, extracted with DCM, and washed three times with saturated NaCl.The organic phase was dried over anhydrous Na2SO4, filtered, concentrated and purified by column eluting with MeOH and DCM (volume ratio 1:3) to give 264 mg of compound 1 as a pale yellow solid. The yield was 66.7percent.
61%
Stage #1: With sodium tetrahydroborate In methanol at 0 - 20℃; for 1.08333 h;
Stage #2: With ammonium chloride In methanol
To a solution of 4-Ethynyl-benzaldehyde (1.8 g, 13.8 mmol) in methanol (40 mL) was added NaBH4; (1.04 g, 27.1 mmol) at 0 °C over a period of 5 min. The reaction mixture was allowed to stir at 25 °C over a period of 60 min. The reaction mixture quenched with saturated ammonium chloride and the solvent was evaporated under reduced pressure. The crude product was diluted with ethyl acetate (200 mL) washed with water (2X 50 mL) dried over sodium sulphate and it was evaporated under reduced pressure to give (4-Ethynyl-phenyl)-methanol as a light yellow oil (1.1 g, 61 percent)
61%
Stage #1: With sodium tetrahydroborate In methanol at 0 - 25℃; for 1.08333 h;
Stage #2: With ammonium chloride In methanol
To a solution of 4-Ethynyl-benzaldehyde (1.8 g, 13.8 mmol) in methanol (40 mL) was added NaBH4 (1.04 g, 27.1 mmol) at 0° C. over a period of 5 min.
The reaction mixture was allowed to stir at 25° C. over a period of 60 min.
The reaction mixture quenched with saturated ammonium chloride and the solvent was evaporated under reduced pressure.
The crude product was diluted with ethyl acetate (200 mL) washed with water (2*50 mL) dried over sodium sulphate and it was evaporated under reduced pressure to give (4-Ethynyl-phenyl)-methanol as a light yellow oil (1.1 g, 61percent).

Reference: [1] Chemistry - An Asian Journal, 2018, vol. 13, # 22, p. 3491 - 3500
[2] Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999), 1987, p. 1573 - 1578
[3] Journal of the American Chemical Society, 2009, vol. 131, # 2, p. 634 - 643
[4] Patent: US2017/202970, 2017, A1, . Location in patent: Paragraph 0728; 0733; 0734
[5] Patent: CN107365254, 2017, A, . Location in patent: Paragraph 0115; 0126-0128
[6] Patent: WO2011/21209, 2011, A1, . Location in patent: Page/Page column 35; 36
[7] Patent: US2012/101099, 2012, A1, . Location in patent: Page/Page column 12
[8] Green Chemistry, 2009, vol. 11, # 9, p. 1313 - 1316
[9] ChemMedChem, 2011, vol. 6, # 11, p. 2009 - 2018
[10] Journal of the American Chemical Society, 2014, vol. 136, # 6, p. 2520 - 2528
[11] Chemical Communications, 2017, vol. 53, # 30, p. 4215 - 4218
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YieldReaction ConditionsOperation in experiment
67%
Stage #1: With copper(l) iodide; bis(benzonitrile)palladium(II) dichloride; tri-tert-butyl phosphine; triethylamine In tetrahydrofuran at 70℃;
Stage #2: With tetrabutyl ammonium fluoride In tetrahydrofuran at 20℃; for 3 h;
General procedure: 4.1.4.1. General procedure for the coupling of a terminal alkynewith an aryl halide using a palladium-catalyzed cross-coupling (Sonogashira)protocol. To an oven-dried round-bottom flask or screwcap tube equipped with a magnetic stir bar were added the arylhalide, the terminal alkyne, PdCl2(PPh3)2 or PdCl2(PhCN)2 (w2 molpercent per aryl halide), CuI (w4 mol percent per aryl halide), and in the case ofusing PdCl2(PhCN)2, alsow4 mol percent per aryl halide of HP(tert-Bu)3. Asolvent system of TEA and/or THF was added depending on thesubstrates. Upon completion, the reaction was quenched witha saturated solution of NH4Cl. The organic layer was then dilutedwith diethyl ether or CH2Cl2, and washed with water or saturatedNH4Cl (1). The combined aqueous layers were extracted withhexanes, diethyl ether, or CH2Cl2 (2). The combined organic layerswere dried over MgSO4 and filtered, and the solvent was removedfrom the filtrate in vacuo to afford the crude product, which waspurified by column chromatography (silica gel). Eluents and otherslight modifications are described below for each compound.4.1.4.2. General procedure for deprotection of TIPS-protected alkynesusing TBAF. In a round-bottomed flask equipped witha magnetic stir bar, the protected alkyne was dissolved in THF([protected alkyne]0.05e0.1 M). TBAF in THF (1.0 M, 1.1 equiv peralkyne) was added. The mixture was stirred at rt for 0.5 h or untilthe reaction was complete (monitored by TLC). The reaction wasquenched with a saturated solution of NH4Cl. The organic layer wasthen diluted with ethyl acetate. The organic layer was dried overMgSO4 and filtered, and the solvent was removed from the filtratein vacuo to afford the crude product, which was purified by columnchromatography (silica gel).
Reference: [1] Tetrahedron, 2015, vol. 71, # 35, p. 5965 - 5972
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Reference: [1] Angewandte Chemie - International Edition, 2004, vol. 43, # 29, p. 3814 - 3818
[2] Chemistry - A European Journal, 2013, vol. 19, # 29, p. 9452 - 9456
[3] Patent: US2013/266644, 2013, A1,
[4] Synthesis (Germany), 2014, vol. 46, # 3, p. 348 - 356
[5] Patent: CN105622638, 2016, A,
[6] Patent: US9758545, 2017, B2,
[7] Patent: WO2018/14802, 2018, A1,
  • 6
  • [ 38846-64-9 ]
  • [ 63697-96-1 ]
  • [ 10602-04-7 ]
  • [ 10602-08-1 ]
Reference: [1] Journal of the American Chemical Society, 2000, vol. 122, # 19, p. 4817 - 4818
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  • [ 3034-86-4 ]
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Reference: [1] Patent: CN106883217, 2017, A, . Location in patent: Paragraph 0186
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Reference: [1] Synthesis, 2009, # 12, p. 1963 - 1968
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  • [ 51934-41-9 ]
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Reference: [1] Macromolecules, 2005, vol. 38, # 15, p. 6367 - 6373
[2] Tetrahedron Letters, 2000, vol. 41, # 17, p. 3123 - 3126
[3] Chirality, 2015, vol. 27, # 8, p. 454 - 458
  • 10
  • [ 1122-91-4 ]
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Reference: [1] Russian Chemical Bulletin, 2002, vol. 51, # 1, p. 128 - 134[2] Izvestiya Akademi Nauk, Seriya Khimicheskaya, 2002, # 1, p. 122 - 127
[3] Patent: WO2011/21209, 2011, A1,
[4] Patent: US2012/101099, 2012, A1,
[5] Patent: US2017/202970, 2017, A1,
[6] Patent: CN107365254, 2017, A,
[7] Patent: WO2008/31157, 2008, A1,
  • 11
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Reference: [1] Journal of the American Chemical Society, 2005, vol. 127, # 43, p. 15257 - 15264
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Reference: [1] Journal of the American Chemical Society, 2005, vol. 127, # 43, p. 15257 - 15264
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  • [ 150969-54-3 ]
  • [ 10602-04-7 ]
Reference: [1] Macromolecules, 2005, vol. 38, # 15, p. 6367 - 6373
[2] Tetrahedron Letters, 2000, vol. 41, # 17, p. 3123 - 3126
[3] Chirality, 2015, vol. 27, # 8, p. 454 - 458
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  • [ 175203-59-5 ]
  • [ 10602-04-7 ]
Reference: [1] Russian Chemical Bulletin, 2002, vol. 51, # 1, p. 128 - 134[2] Izvestiya Akademi Nauk, Seriya Khimicheskaya, 2002, # 1, p. 122 - 127
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Reference: [1] Patent: WO2011/21209, 2011, A1,
[2] Patent: US2012/101099, 2012, A1,
[3] Patent: US2017/202970, 2017, A1,
[4] Patent: CN107365254, 2017, A,
[5] Patent: WO2008/31157, 2008, A1,
  • 16
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Reference: [1] Organic and Biomolecular Chemistry, 2008, vol. 6, # 22, p. 4102 - 4104
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Reference: [1] Journal of Organic Chemistry, 1966, vol. 31, p. 2585 - 2593
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Reference: [1] Russian Chemical Bulletin, 2002, vol. 51, # 1, p. 128 - 134[2] Izvestiya Akademi Nauk, Seriya Khimicheskaya, 2002, # 1, p. 122 - 127
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Reference: [1] Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999), 1987, p. 1573 - 1578
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  • [ 619-44-3 ]
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Reference: [1] Patent: CN106883217, 2017, A,
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  • [ 18282-51-4 ]
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Reference: [1] Patent: WO2018/160967, 2018, A1,
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  • [ 63697-96-1 ]
Reference: [1] Russian Chemical Bulletin, 2002, vol. 51, # 1, p. 128 - 134[2] Izvestiya Akademi Nauk, Seriya Khimicheskaya, 2002, # 1, p. 122 - 127
[3] Chemistry - A European Journal, 2013, vol. 19, # 29, p. 9452 - 9456
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