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[ CAS No. 188975-30-6 ] {[proInfo.proName]}

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Chemical Structure| 188975-30-6
Chemical Structure| 188975-30-6
Structure of 188975-30-6 * Storage: {[proInfo.prStorage]}
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Product Details of [ 188975-30-6 ]

CAS No. :188975-30-6 MDL No. :MFCD09997709
Formula : C6H7F3O4S Boiling Point : -
Linear Structure Formula :- InChI Key :QXCAHEXKUMUTRF-UHFFFAOYSA-N
M.W : 232.18 Pubchem ID :11356703
Synonyms :

Calculated chemistry of [ 188975-30-6 ]

Physicochemical Properties

Num. heavy atoms : 14
Num. arom. heavy atoms : 0
Fraction Csp3 : 0.67
Num. rotatable bonds : 3
Num. H-bond acceptors : 7.0
Num. H-bond donors : 0.0
Molar Refractivity : 39.69
TPSA : 60.98 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) : -6.84 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.52
Log Po/w (XLOGP3) : 1.24
Log Po/w (WLOGP) : 3.5
Log Po/w (MLOGP) : 0.28
Log Po/w (SILICOS-IT) : 0.89
Consensus Log Po/w : 1.48

Druglikeness

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

Water Solubility

Log S (ESOL) : -1.86
Solubility : 3.19 mg/ml ; 0.0137 mol/l
Class : Very soluble
Log S (Ali) : -2.12
Solubility : 1.77 mg/ml ; 0.00761 mol/l
Class : Soluble
Log S (SILICOS-IT) : -1.32
Solubility : 11.1 mg/ml ; 0.048 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 2.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 3.14

Safety of [ 188975-30-6 ]

Signal Word:Danger Class:8
Precautionary Statements:P264-P270-P271-P280-P303+P361+P353-P304+P340-P305+P351+P338-P310-P330-P331-P363-P403+P233-P501 UN#:3265
Hazard Statements:H302-H314 Packing Group:
GHS Pictogram:

Application In Synthesis of [ 188975-30-6 ]

* 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 [ 188975-30-6 ]
  • Downstream synthetic route of [ 188975-30-6 ]

[ 188975-30-6 ] Synthesis Path-Upstream   1~14

  • 1
  • [ 29943-42-8 ]
  • [ 37595-74-7 ]
  • [ 188975-30-6 ]
YieldReaction ConditionsOperation in experiment
40%
Stage #1: With lithium diisopropyl amide In tetrahydrofuran at -70℃; for 0.5 h;
Stage #2: at -70 - 20℃; for 18 h;
LDA/THF (31.5 ml of 1.92M solution) was slowly added to a stirred solution of tetrahydro-4H-pyran-4-one (5.5 g) in THF (30ml) at -70° C., under argon. The mixture was stirred for 30 minutes at -70° C. and then a solution of N-phenyl triflimide (21.6 g) in THF (30 mls) was added. The mixture was allowed to warm to ambient temperature and stirred for 18 hours. The reaction mixture was evaporated and subjected to chromatography by MPLC on Alumina (ICN, N32-63, using as eluant a mixture of ethyl acetate (5percent) and iso-hexane). The product was distilled by Kugelruhr (100° C./10 mm). Remaining traces of the triflimide reagent were removed by a second MPLC (Silica, using as eluant a mixture of ethyl acetate (5percent) and iso-hexane) followed by a second Kugelruhr distillation, giving the title compound as a colourless oil in 40percent yield (5.1 g), which was stored at -20° C. NMR (300 MHz, CDCl3): δ: 2.24(m,2H), 3.90(m,2H), 4.25(m,2H), 5.82(m,1H).
35.7%
Stage #1: With lithium hexamethyldisilazane In tetrahydrofuran at -78℃; for 1 h; Inert atmosphere
Stage #2: at 15℃; for 16 h; Inert atmosphere
Example 47A
3,6-dihydro-2H-pyran-4-yl trifluoromethanesulfonate
To a solution of dihydro-2H-pyran-4(3H)-one (1.8 g, 18.0 mol) in THF (20 ml) was added LiHMDS (1 M, 21.6 ml, 21.6 mmol) at -78° C. under N2 atmosphere.
After stirring for 1 h at -78° C., (CF3SO2)2NPh (6.4 g, 18.0 mmol) was added in portions.
The mixture was stirred at 15° C. for 16 h and quenched with aq NH4Cl solution (20 mL).
The aqueous layer was extracted with EtOAc (30 mL*2).
The combined organic layers were washed with water, brine, dried over Na2SO4 and concentrated under vacuum.
The residue was purified by column chromatograph to provide the title compound as a colorless oil (1.5 g, yield: 35.7percent). LCMS (ESI) m/z: 233 (M+1).
15.1%
Stage #1: With n-butyllithium; diisopropylamine In tetrahydrofuran; hexane at -78℃; for 0.5 h; Inert atmosphere
Stage #2: at -78 - 20℃; for 0.166667 h;
Under an atmosphere of nitrogen, to a solution of diisopropylamine (CAN 180-18-9, 2.42 g, 0.024 mol) in THF (40 mL) was added n-butyl lithium (10.4 mL, 2.5 M solution in hexane, 26 mmol) at -78° C. The reaction mixture was reacted for 30 min at -50° C. Then tetrahydropyran-4-one (CAN 29943-42-8, 2 g, 0.020 mol) in THF (10 mL) was added dropwise to the above solution at -78° C. The reaction mixture was reacted for 30 min at -78° C. Then trifluoro-N-phenyl-N-(trifluoromethylsulfonyl)methanesulfonamide (CAN 37595-74-7, 7.85 g, 0.022 mol) in THF (50 mL) was added dropwise to the above solution at -78° C. The reaction mixture was stirred for 10 min at room temperature. The reaction mixture was quenched with a saturated solution of sodium bicarbonate (10 mL) and extracted with ethyl acetate (3.x.30 mL). The combined organic extracts were washed with citric acid (50 mL) and sodium hydroxide solution (1 N, 50 mL), dried over anhydrous sodium sulfate and evaporated. The residue was purified by column chromatography (silica gel, 10 g, 1percent ethyl acetate in petroleum ether) to yield the title compound (0.7 g, 3 mmol, 15.1percent) as yellow oil. 1H NMR (300 MHz, d6-DMSO): 6.05-6.03 (m, 1H), 4.17 (d, J=3 Hz, 2H), 3.78 (t, J=4.5 Hz, 2H), 2.38 (t, J=3 Hz, 2H).
15.1%
Stage #1: With n-butyllithium; diisopropylamine In tetrahydrofuran; hexane at -78℃; for 0.5 h; Inert atmosphere
Stage #2: at -78 - 20℃; for 0.166667 h;
Under an atmosphere of nitrogen, to a solution of diisopropylamine (CAN 180-18-9, 2.42 g, 0.024 mol) in THF (40 mL) was added w-butyl lithium (10.4 mL, 2.5 M solution in hexane, 26 mmol) at -78°C. The reaction mixture was reacted for 30 min at -50°C. Then tetrahydropyran-4-one (CAN 29943-42-8, 2 g, 0.020 mol) in THF (10 mL) was added dropwise to the above solution at -78°C. The reaction mixture was reacted for 30 min at - 78°C. Then trifluoro-N-phenyl-N-(trifluoromethylsulfonyl) methanesulfonamide (CAN 37595-74-7, 7.85 g, 0.022 mol) in THF (50 mL) was added dropwise to the above solution at -78°C. The reaction mixture was stirred for 10 min at room temperature. The reaction mixture was quenched with a saturated solution of sodium bicarbonate (10 mL) and extracted with ethyl acetate (3 x 30 mL). The combined organic extracts were washed with citric acid (50 mL) and sodium hydroxide solution (1 N, 50 mL), dried over anhydrous sodium sulfate and evaporated. The residue was purified by column chromatography(silica gel, 10 g, 1percent ethyl acetate in petroleum ether) to yield the title compound (0.7 g, 3 mmol, 15.1percent) as yellow oil. 1H NMR (300 MHz , (f-DMSO): 6.05 - 6.03 (m, 1H), 4.17 (d, J = 3 Hz, 2H), 3.78 (t, J = 4.5 Hz, 2H), 2.38 (t, J = 3 Hz, 2H).

Reference: [1] Journal of Organic Chemistry, 2014, vol. 79, # 6, p. 2781 - 2791
[2] Patent: US6365751, 2002, B1, . Location in patent: Referential example 3
[3] Patent: US6350775, 2002, B1, . Location in patent: Page column 28
[4] ACS Medicinal Chemistry Letters, 2016, vol. 7, # 7, p. 666 - 670
[5] Patent: US2017/29430, 2017, A1, . Location in patent: Paragraph 0472
[6] Patent: US2012/316147, 2012, A1, . Location in patent: Page/Page column 31-32
[7] Patent: WO2012/168350, 2012, A1, . Location in patent: Page/Page column 76
[8] Patent: US2008/318935, 2008, A1, . Location in patent: Page/Page column 64-65
[9] Patent: US2010/184777, 2010, A1, . Location in patent: Page/Page column 11
[10] Patent: WO2015/153720, 2015, A1, . Location in patent: Page/Page column 241
[11] Patent: WO2017/59085, 2017, A1, . Location in patent: Page/Page column 241
[12] Journal of the American Chemical Society, 2018, vol. 140, # 7, p. 2446 - 2449
[13] Patent: WO2008/76425, 2008, A1, . Location in patent: Page/Page column 57
  • 2
  • [ 29943-42-8 ]
  • [ 145100-51-2 ]
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YieldReaction ConditionsOperation in experiment
53%
Stage #1: With n-butyllithium; diisopropylamine In tetrahydrofuran; hexane at -78 - 0℃; for 2 h; Inert atmosphere
Stage #2: at 0℃; for 3.25 h; Inert atmosphere
In a 50 mL round-bottomed flask under nitrogen, a solution of n-butyllithium (1.45 M in hexanes, 1.90 mL, 2.76 mmol) was added dropwise to a solution of diisopropylamine (0.39 mL, 2.74 mmol) in THF (5 mL) at 0 °C and the resulting mixture was stirred for 15 min. The reaction mixture was then cooled to -78 °C and a solution of dihydro-2H-pyran-4(3H)-one (0.23 mL, 2.481 mmol) in THF (7.5 mL) was slowly added and the mixture was at -78 °C for another 2 h. To this mixture was added a solution of 2- (N,N-bis(trifluoromethylsulfonyl)amino)-5-chloropyridine (1.082 g, 2.76 mmol) in THF (5 ml) over 15 min and the mixture was then allowed to warm to 0 °C and stirred for 3 h. The reaction was then quenched with water (15 mL) and the mixture was extracted with Et2O (x3). The combined organic extract was washed successively with 15percent aqueous NaOH and brine and then it was dried over anhydrous Na2SO4, filtered and concentrated. The crude product was chromatographed on a silica gel column (22 mm x 80 mm) which was eluted with 0 to 20percent EtOAc in hexanes. This afforded 3,6-dihydro-2H-pyran-4-yl trifluoromethanesulfonate (0.307 g, 53percent) as a colorless oil which was used as such in the following step. 1H NMR (400 MHz, acetone-d6): δ ppm 6.01 (tt, J= 2.8, 1.5 Hz, 1 H) 4.25 (q, J= 3.0 Hz, 2 H) 3.88 (t, J= 5.5 Hz, 2 H) 2.48 (ttd, J= 5.5, 2.8, 1.4 Hz, 2 H). In a 25 mL round-bottomed flask, the obtained 3,6-dihydro-2H-pyran-4-yl trifluoromethanesulfonate (0.307 g, 1.322 mmol) and potassium fluoride (0.270 g, 4.65 mmol) were added to a solution of (3-(hydroxymethyl)phenyl)boronic acid (0.250 g, 1.645 mmol) in THF (7.5 ml) and the flask was evacuated and purged with nitrogen three times. Bis(diphenylphosphino)ferrocene-palladium(II) dichloride dichloromethane complex (0.024 g, 0.029 mmol) was then added in one portion and the mixture was stirred at room temperature for 66 h. The resulting mixture was diluted with ethyl acetate, filtered through CELITE® and concentrated. The residue was purified on the ISCO using a REDISEP® Gold 24 g column (elution with hexanes-EtOAc) to give the title compound (0.131 g, 52percent) as yellowish oil. LC (Method B): 1.614 min. LCMS (APCI): calcd for C12H13O [M+H]+- H20 m/z 173.096, found 173.2. 1H NMR (400 MHz, acetone-d6): δ ppm 7.46 (s, 1H) 7.22-7.36 (m, 3H) 6.21 (tt, J= 3.0, 1.5 Hz, 1H) 4.64 (d, J= 5.9 Hz, 2H) 4.24 (q, J= 3.0 Hz, 2H) 4.17 (t, J= 5.7 Hz, 1H) 3.86 (t, J= 5.5 Hz, 2H) 2.49 (ttd, J= 5.4, 2.8, 1.6 Hz, 2H).
800 mg
Stage #1: With lithium hexamethyldisilazane In tetrahydrofuran at -78℃; for 1 h;
Stage #2: Cooling
A solution of LiHMDS (1.0 M in THF, 11 mL, 11 mmol) was added dropwise to a cooled solution of 4-tetrahydropyranone (1 g, 10 mmol) in dry THF (5 mL) at -78° C. and the resulting reaction was maintained at -78° C. for 1 h.
A solution of 2-[N,N-bis(trifluoromethanesulfonyl)amino]-5-chloropyridine (3.93 g, 10 mmol) in dry THF (6 mL) was added dropwise and the reaction maintained overnight, allowing the cooling bath to expire.
The reaction was quenched with water (10 mL) and partitioned with DCM.
The layers were separated and the aqueous portion was extracted with DCM (2*).
The combined organic portions were dried (Na2SO4) and evaporated.
The crude residue was purified by flash chromatography (neutral alumina, 80:20 DCM-hexanes) to provide 800 mg of 3,6-dihydro-2H-pyran-4-yl trifluoromethanesulfonate as a colorless oil: 1H NMR (400 MHz, CDCl3) δ 5.82-5.81 (m, 1H), 4.27-4.25 (m, 2H), 3.91-3.88 (m, 2H), 2.48-2.45 (m, 2H).
Reference: [1] Patent: WO2013/163241, 2013, A1, . Location in patent: Paragraph 00181
[2] Patent: US2013/210818, 2013, A1, . Location in patent: Paragraph 0351
[3] Patent: WO2008/153858, 2008, A1, . Location in patent: Page/Page column 307
[4] Patent: WO2009/115572, 2009, A2, . Location in patent: Page/Page column 105
  • 3
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Reference: [1] Journal of the American Chemical Society, 2009, vol. 131, # 28, p. 9612 - 9613
  • 4
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  • [ 84302-42-1 ]
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Reference: [1] Patent: WO2010/13161, 2010, A1, . Location in patent: Page/Page column 49-50
[2] Patent: WO2010/29461, 2010, A1, . Location in patent: Page/Page column 40
  • 5
  • [ 29943-42-8 ]
  • [ 456-64-4 ]
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Reference: [1] Patent: WO2016/34673, 2016, A1, . Location in patent: Page/Page column 101
  • 6
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  • [ 107-83-5 ]
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Reference: [1] Patent: US5981528, 1999, A,
  • 7
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  • [ 358-23-6 ]
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Reference: [1] Angewandte Chemie - International Edition, 2017, vol. 56, # 5, p. 1338 - 1341[2] Angew. Chem., 2017, vol. 129, # 5, p. 1358 - 1361,4
  • 8
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Reference: [1] Patent: US5968962, 1999, A,
  • 9
  • [ 73183-34-3 ]
  • [ 188975-30-6 ]
  • [ 287944-16-5 ]
YieldReaction ConditionsOperation in experiment
81% With potassium acetate In 1,4-dioxane at 80℃; A 250 ml_ round bottom flask containing trifluoro-methanesulfonic acid 3, 6- dihydro-2H-pyran-4-yl ester (2.7 g, 11.6 mmol), PdCI2(dppf) (440 mg, 0.6 mmol) and potassium acetate (3g, 36 mmol) in dioxane (20 mL) was flushed with Ar three times. The reaction mixture was heated at 80 °C for overnight. After the reaction was cooled to room temperature, the reaction mixture was filter through a column packed with celite and the filtrate was concentrated. The residue was purified using column chromatography (10 percent hexane in dichloromethane) and product was obtained as white solid (2g, 81 percent yield).
50.5% With potassium acetate In dimethyl sulfoxide at 80℃; Inert atmosphere Under an atmosphere of nitrogen, a solution of 3,6-dihydro-2H-pyran-4-yl trifluoromethanesulfonate (0.7 g, 3.0 mmol), 4,4,4',4',5,5,5',5'-octamethyl-2,2'-bi(1,3,2-dioxaborolane) (CAN 3183-34-3, 0.84 g, 3.3 mmol), 1,1'-bis(diphenylphosphino) ferrocene-palladium(II)dichloride methylene chloride complex (CAN 95464-05-4, 0.05 g, 0.06 mmol) and potassium acetate (0.89 g, 9.0 mmol) in DMSO (10 mL) was heated to 80° C. overnight. Water (50 mL) was added to the reaction mixture which then was extracted with ethyl acetate (3.x.30 mL). The combined organic extracts were washed with brine, dried over anhydrous sodium sulfate and evaporated. The residue was purified by column chromatography (silica gel, 9 g, 1percent ethyl acetate in petroleum ether) to yield the title compound (0.32 g, 2 mmol, 50.5percent) as colorless oil. 1H NMR (300 MHz, CDCl3): δ 6.53 (s, 1H), 4.20 (t, J=3 Hz, 2H), 3.76 (t, J=6 Hz, 2H), 2.24 (dd, J1=6 Hz, J2=6 Hz, 2H), 1.28 (s, 12H).
50.5% With potassium acetate In dimethyl sulfoxide at 80℃; Inert atmosphere Under an atmosphere of nitrogen, a solution of 3, 6-dihydro-2H-pyran-4-yltrifluoromethanesulfonate (0.7 g, 3.0 mmol), 4,4,4',4',5,5,5',5'-octamethyl-2,2'- bi(l,3,2- dioxaborolane) (CAN 3183-34-3, 0.84 g, 3.3 mmol), 1,1*- bis(diphenylphosphino)ferrocene-palladium(II)dichloride methylene chloride complex (CAN 95464-05-4, 0.05 g, 0.06 mmol) and potassium acetate (0.89 g, 9.0 mmol) in DMSO (10 mL) was heated to 80°C overnight. Water (50 mL) was added to the reaction mixture which then was extracted with ethyl acetate (3><30 mL). The combined organic extracts were washed with brine, dried over anhydrous sodium sulfate and evaporated. The residue was purified by column chromatography (silica gel, 9 g, 1percent ethyl acetate in petroleum ether) to yield the title compound (0.32 g, 2 mmol, 50.5percent) as colorless oil. 1H NMR (300 MHz, CDCh): δ 6.53 (s, 1H), 4.20 (t, J= 3 Hz, 2H), 3.76 (t, J = 6 Hz, 2H), 2.24 (dd, J; = 6 Hz, J 2 = 6 Hz, 2H), 1.28 (s, 12H).
150 mg With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; potassium acetate In 1,4-dioxane at 80℃; Inert atmosphere A mixture of 3,6-dihydro-2H-pyran-4-yl trifluoromethanesulfonate (250 mg, 1.1 mmol), bis(pinacolato)diboron (410 mg, 1.6 mmol), and KOAc (323 mg, 3.3 mmol) dioxane (3 mL) was sparged with Ar for 5 min. Then PdCl2dppf.DCM (45 mg, 0.05 mmol) was added and reaction was sparged again with Ar for 5 min. The reaction was sealed and heated to and maintained at 80° C. for overnight. The reaction mixture was allowed to cool rt and was filtered through Celite, washing the filter cake with EtOAc. The combined filtrate was concentrated and the resulting residue was purified by flash chromatography (SiO2, 100:0-80:20 hexanes-EtOAc) to furnish 150 mg of 2-(3,6-dihydro-2H-pyran-4-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane. LCMS (m/z): 211.0 (MH+), tR=0.89 min; 1H NMR (400 MHz, CDCl3) δ 6.48 (br s, 1H); 4.15-4.14 (app dd, J=2.8, 5.6 Hz, 2H); 3.72-3.69 (app t, 5.2, 2H); 2.19-2.17 (m, 2H); 1.22 (s, 12H).
300 mg With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate In dimethyl sulfoxide at 80℃; Inert atmosphere To a solution of 4.4,4',4',5.5,5',5'-octamethyl-2.2'-bi(1.3,2-dioxaborolane) (993 mg, 3.91 mmol) in DMSO (5 mL) under N2 was added KOAc (959.8 mg, 9.78 mmol) and Pd(dppf)CI2 (71.7 mg, 0.097 mmol). A solution of the triflate intermediate (750 mg) in DMSO (1 mL) was added and the reaction heated at 80 °C overnight. The mixture was diluted with water (20 mL) and extracted with DCM (3 x 20 mL). The combined organic layers were washed with saturated NaHCC>3 (3 x 10 mL) and brine (3 x 10 mL), dried (Na2SO.t) and concentrated. The residue obtained was purified by silica gel chromatography (ethyl acetate /petroleum ether=1 /2) to give the title compound (300 mg) as a white solid which was used without further purification or analysis

Reference: [1] Patent: WO2008/153858, 2008, A1, . Location in patent: Page/Page column 307
[2] Patent: US2012/316147, 2012, A1, . Location in patent: Page/Page column 32
[3] Patent: WO2012/168350, 2012, A1, . Location in patent: Page/Page column 76; 77
[4] ACS Medicinal Chemistry Letters, 2016, vol. 7, # 7, p. 666 - 670
[5] Patent: US2008/318935, 2008, A1, . Location in patent: Page/Page column 65
[6] Patent: US2010/331293, 2010, A1, . Location in patent: Page/Page column 105
[7] Patent: US2013/210818, 2013, A1, . Location in patent: Paragraph 0353
[8] Patent: WO2016/34673, 2016, A1, . Location in patent: Page/Page column 101-102
[9] Patent: WO2009/115572, 2009, A2, . Location in patent: Page/Page column 105-106
  • 10
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  • [ 188975-30-6 ]
  • [ 1173199-90-0 ]
  • [ 287944-16-5 ]
Reference: [1] Journal of the American Chemical Society, 2009, vol. 131, # 28, p. 9612 - 9613
[2] Journal of the American Chemical Society, 2009, vol. 131, # 28, p. 9612 - 9613
[3] Journal of the American Chemical Society, 2009, vol. 131, # 28, p. 9612 - 9613
[4] Journal of the American Chemical Society, 2009, vol. 131, # 28, p. 9612 - 9613
[5] Journal of the American Chemical Society, 2009, vol. 131, # 28, p. 9612 - 9613
[6] Journal of the American Chemical Society, 2009, vol. 131, # 28, p. 9612 - 9613
  • 11
  • [ 25015-63-8 ]
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Reference: [1] Journal of the American Chemical Society, 2009, vol. 131, # 28, p. 9612 - 9613
  • 12
  • [ 25015-63-8 ]
  • [ 188975-30-6 ]
  • [ 1173199-90-0 ]
  • [ 287944-16-5 ]
Reference: [1] Journal of the American Chemical Society, 2009, vol. 131, # 28, p. 9612 - 9613
[2] Journal of the American Chemical Society, 2009, vol. 131, # 28, p. 9612 - 9613
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Reference: [1] Synthesis, 2000, # 6, p. 778 - 780
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  • [ 1000016-93-2 ]
Reference: [1] Patent: WO2007/149031, 2007, A1,
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