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[ CAS No. 127-17-3 ] {[proInfo.proName]}

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Chemical Structure| 127-17-3
Chemical Structure| 127-17-3
Structure of 127-17-3 * Storage: {[proInfo.prStorage]}
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Product Details of [ 127-17-3 ]

CAS No. :127-17-3 MDL No. :MFCD00002585
Formula : C3H4O3 Boiling Point : -
Linear Structure Formula :- InChI Key :LCTONWCANYUPML-UHFFFAOYSA-N
M.W : 88.06 Pubchem ID :1060
Synonyms :
Acetylformic acid

Calculated chemistry of [ 127-17-3 ]

Physicochemical Properties

Num. heavy atoms : 6
Num. arom. heavy atoms : 0
Fraction Csp3 : 0.33
Num. rotatable bonds : 1
Num. H-bond acceptors : 3.0
Num. H-bond donors : 1.0
Molar Refractivity : 18.51
TPSA : 54.37 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) : -7.07 cm/s

Lipophilicity

Log Po/w (iLOGP) : 0.25
Log Po/w (XLOGP3) : -0.33
Log Po/w (WLOGP) : -0.34
Log Po/w (MLOGP) : -0.96
Log Po/w (SILICOS-IT) : -0.48
Consensus Log Po/w : -0.37

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 2.0
Bioavailability Score : 0.56

Water Solubility

Log S (ESOL) : -0.11
Solubility : 68.0 mg/ml ; 0.773 mol/l
Class : Very soluble
Log S (Ali) : -0.35
Solubility : 39.3 mg/ml ; 0.446 mol/l
Class : Very soluble
Log S (SILICOS-IT) : 0.51
Solubility : 286.0 mg/ml ; 3.25 mol/l
Class : Soluble

Medicinal Chemistry

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

Safety of [ 127-17-3 ]

Signal Word:Danger Class:8
Precautionary Statements:P280-P305+P351+P338-P310 UN#:3265
Hazard Statements:H227-H314 Packing Group:
GHS Pictogram:

Application In Synthesis of [ 127-17-3 ]

* 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 [ 127-17-3 ]
  • Downstream synthetic route of [ 127-17-3 ]

[ 127-17-3 ] Synthesis Path-Upstream   1~70

  • 1
  • [ 932-32-1 ]
  • [ 127-17-3 ]
  • [ 16136-58-6 ]
Reference: [1] Angewandte Chemie - International Edition, 2004, vol. 43, # 34, p. 4526 - 4528
  • 2
  • [ 77287-34-4 ]
  • [ 23147-58-2 ]
  • [ 1455-77-2 ]
  • [ 120-89-8 ]
  • [ 849585-22-4 ]
  • [ 73-40-5 ]
  • [ 110-15-6 ]
  • [ 120-73-0 ]
  • [ 144-62-7 ]
  • [ 113-00-8 ]
  • [ 127-17-3 ]
  • [ 57-13-6 ]
  • [ 302-72-7 ]
  • [ 18588-61-9 ]
Reference: [1] Chemistry - A European Journal, 2018, vol. 24, # 32, p. 8126 - 8132
  • 3
  • [ 290-37-9 ]
  • [ 127-17-3 ]
  • [ 22047-25-2 ]
Reference: [1] Journal of Organic Chemistry, 1991, vol. 56, # 8, p. 2866 - 2869
  • 4
  • [ 77287-34-4 ]
  • [ 156-81-0 ]
  • [ 849585-22-4 ]
  • [ 617-48-1 ]
  • [ 2491-15-8 ]
  • [ 110-15-6 ]
  • [ 108-53-2 ]
  • [ 71-30-7 ]
  • [ 113-00-8 ]
  • [ 127-17-3 ]
  • [ 66-22-8 ]
  • [ 66224-66-6 ]
  • [ 56-40-6 ]
  • [ 302-72-7 ]
  • [ 18514-52-8 ]
YieldReaction ConditionsOperation in experiment
0.18 mg With ferric sulfate nonahydrate In water at 80℃; for 24 h; General procedure: To model the chemical environment on the outer side of thetubular structures, NH2CHO (200 μL) was mixed with thesodium silicate solution (2.0 mL) in the presence of preformedMSH [ZnCl2, FeCl2·4H2O, CuCl2·2H2O, Fe2(SO4)3·9H2O,and MgSO4] (2.0percent w/w) at 80 °C for 24 h. In two selectedcases [FeCl2 and Fe2(SO4)3·9H2O], NH2CHO (200 μL) wasmixed with the sodium silicate solution (2.0 mL) in the presence of selected growing MSH (starting from 2.0percent w/w ofthe corresponding salt’s pellet) at 80 °C for 24 h. For the innerenvironment, NH2CHO (200 μL) was mixed with distilledwater (2.0 mL) in the presence of selected MSH (2.0percent w/w) at80 °C for 24 h. The reaction of NH2CHO (10percent v/v) with thesodium silicate solution (pH 12) without MSH membranes wasalso analyzed under similar experimental conditions. Theproducts were analyzed by gas chromatography associatedwith mass spectrometry (GC-MS) after treatment with N,Nbis-trimethylsilyl trifluoroacetamide in pyridine (620 μL) at 60°C for 4 h in the presence of betulinol (CAS Registry Number473-98-3) as the internal standard (0.2 mg). Mass spectrometrywas performed by the following program: injection temperature280 °C, detector temperature 280 °C, gradient 100 °C for 2min, and 10 °C/min for 60 min. To identify the structure of theproducts, two strategies were followed. First, the spectra werecompared with commercially available electron mass spectrumlibraries such as NIST (Fison, Manchester, U.K.). Second, GCMSanalysis was repeated with standard compounds. Allproducts have been recognized with a similarity index (SI)greater than 98percent compared to that of the reference standards.The analysis was limited to products of ≥1 ng/mL, and theyield was calculated as micrograms of product per startingformamide. For further experimental details, see the SupportingInformation.
Reference: [1] Biochemistry, 2016, vol. 55, # 19, p. 2806 - 2811
  • 5
  • [ 77287-34-4 ]
  • [ 156-81-0 ]
  • [ 849585-22-4 ]
  • [ 617-48-1 ]
  • [ 2491-15-8 ]
  • [ 110-15-6 ]
  • [ 108-53-2 ]
  • [ 71-30-7 ]
  • [ 113-00-8 ]
  • [ 127-17-3 ]
  • [ 66-22-8 ]
  • [ 66224-66-6 ]
  • [ 56-40-6 ]
  • [ 302-72-7 ]
YieldReaction ConditionsOperation in experiment
0.12 mg With magnesium sulfate In water at 80℃; for 24 h; General procedure: To model the chemical environment on the outer side of thetubular structures, NH2CHO (200 μL) was mixed with thesodium silicate solution (2.0 mL) in the presence of preformedMSH [ZnCl2, FeCl2·4H2O, CuCl2·2H2O, Fe2(SO4)3·9H2O,and MgSO4] (2.0percent w/w) at 80 °C for 24 h. In two selectedcases [FeCl2 and Fe2(SO4)3·9H2O], NH2CHO (200 μL) wasmixed with the sodium silicate solution (2.0 mL) in the presence of selected growing MSH (starting from 2.0percent w/w ofthe corresponding salt’s pellet) at 80 °C for 24 h. For the innerenvironment, NH2CHO (200 μL) was mixed with distilledwater (2.0 mL) in the presence of selected MSH (2.0percent w/w) at80 °C for 24 h. The reaction of NH2CHO (10percent v/v) with thesodium silicate solution (pH 12) without MSH membranes wasalso analyzed under similar experimental conditions. Theproducts were analyzed by gas chromatography associatedwith mass spectrometry (GC-MS) after treatment with N,Nbis-trimethylsilyl trifluoroacetamide in pyridine (620 μL) at 60°C for 4 h in the presence of betulinol (CAS Registry Number473-98-3) as the internal standard (0.2 mg). Mass spectrometrywas performed by the following program: injection temperature280 °C, detector temperature 280 °C, gradient 100 °C for 2min, and 10 °C/min for 60 min. To identify the structure of theproducts, two strategies were followed. First, the spectra werecompared with commercially available electron mass spectrumlibraries such as NIST (Fison, Manchester, U.K.). Second, GCMSanalysis was repeated with standard compounds. Allproducts have been recognized with a similarity index (SI)greater than 98percent compared to that of the reference standards.The analysis was limited to products of ≥1 ng/mL, and theyield was calculated as micrograms of product per startingformamide. For further experimental details, see the SupportingInformation.
Reference: [1] Biochemistry, 2016, vol. 55, # 19, p. 2806 - 2811
  • 6
  • [ 77287-34-4 ]
  • [ 51953-18-5 ]
  • [ 156-81-0 ]
  • [ 120-89-8 ]
  • [ 108-53-2 ]
  • [ 71-30-7 ]
  • [ 144-62-7 ]
  • [ 113-00-8 ]
  • [ 127-17-3 ]
  • [ 66-22-8 ]
  • [ 56-06-4 ]
  • [ 66224-66-6 ]
  • [ 57-13-6 ]
  • [ 56-40-6 ]
YieldReaction ConditionsOperation in experiment
1.6 mg With copper(II) choride dihydrate In water at 80℃; for 24 h; General procedure: To model the chemical environment on the outer side of thetubular structures, NH2CHO (200 μL) was mixed with thesodium silicate solution (2.0 mL) in the presence of preformedMSH [ZnCl2, FeCl2·4H2O, CuCl2·2H2O, Fe2(SO4)3·9H2O,and MgSO4] (2.0percent w/w) at 80 °C for 24 h. In two selectedcases [FeCl2 and Fe2(SO4)3·9H2O], NH2CHO (200 μL) wasmixed with the sodium silicate solution (2.0 mL) in the presence of selected growing MSH (starting from 2.0percent w/w ofthe corresponding salt’s pellet) at 80 °C for 24 h. For the innerenvironment, NH2CHO (200 μL) was mixed with distilledwater (2.0 mL) in the presence of selected MSH (2.0percent w/w) at80 °C for 24 h. The reaction of NH2CHO (10percent v/v) with thesodium silicate solution (pH 12) without MSH membranes wasalso analyzed under similar experimental conditions. Theproducts were analyzed by gas chromatography associatedwith mass spectrometry (GC-MS) after treatment with N,Nbis-trimethylsilyl trifluoroacetamide in pyridine (620 μL) at 60°C for 4 h in the presence of betulinol (CAS Registry Number473-98-3) as the internal standard (0.2 mg). Mass spectrometrywas performed by the following program: injection temperature280 °C, detector temperature 280 °C, gradient 100 °C for 2min, and 10 °C/min for 60 min. To identify the structure of theproducts, two strategies were followed. First, the spectra werecompared with commercially available electron mass spectrumlibraries such as NIST (Fison, Manchester, U.K.). Second, GCMSanalysis was repeated with standard compounds. Allproducts have been recognized with a similarity index (SI)greater than 98percent compared to that of the reference standards.The analysis was limited to products of ≥1 ng/mL, and theyield was calculated as micrograms of product per startingformamide. For further experimental details, see the SupportingInformation.
Reference: [1] Biochemistry, 2016, vol. 55, # 19, p. 2806 - 2811
  • 7
  • [ 77287-34-4 ]
  • [ 51953-18-5 ]
  • [ 1455-77-2 ]
  • [ 120-89-8 ]
  • [ 849585-22-4 ]
  • [ 73-40-5 ]
  • [ 328-42-7 ]
  • [ 2491-15-8 ]
  • [ 110-15-6 ]
  • [ 71-30-7 ]
  • [ 120-73-0 ]
  • [ 144-62-7 ]
  • [ 113-00-8 ]
  • [ 127-17-3 ]
  • [ 66-22-8 ]
  • [ 56-06-4 ]
  • [ 66224-66-6 ]
  • [ 57-13-6 ]
  • [ 56-40-6 ]
  • [ 302-72-7 ]
  • [ 18588-61-9 ]
Reference: [1] Chemistry - A European Journal, 2018, vol. 24, # 32, p. 8126 - 8132
  • 8
  • [ 77287-34-4 ]
  • [ 51953-18-5 ]
  • [ 1455-77-2 ]
  • [ 120-89-8 ]
  • [ 73-40-5 ]
  • [ 328-42-7 ]
  • [ 2491-15-8 ]
  • [ 110-15-6 ]
  • [ 71-30-7 ]
  • [ 120-73-0 ]
  • [ 144-62-7 ]
  • [ 113-00-8 ]
  • [ 127-17-3 ]
  • [ 66-22-8 ]
  • [ 66224-66-6 ]
  • [ 57-13-6 ]
  • [ 56-40-6 ]
  • [ 302-72-7 ]
Reference: [1] Chemistry - A European Journal, 2018, vol. 24, # 32, p. 8126 - 8132
  • 9
  • [ 77287-34-4 ]
  • [ 23147-58-2 ]
  • [ 1455-77-2 ]
  • [ 120-89-8 ]
  • [ 849585-22-4 ]
  • [ 73-40-5 ]
  • [ 110-15-6 ]
  • [ 120-73-0 ]
  • [ 144-62-7 ]
  • [ 113-00-8 ]
  • [ 127-17-3 ]
  • [ 57-13-6 ]
  • [ 302-72-7 ]
  • [ 18588-61-9 ]
Reference: [1] Chemistry - A European Journal, 2018, vol. 24, # 32, p. 8126 - 8132
  • 10
  • [ 119-65-3 ]
  • [ 127-17-3 ]
  • [ 58022-21-2 ]
YieldReaction ConditionsOperation in experiment
76% With ammonium peroxydisulfate; [Ir(2-(2,4-difluorophenyl)-5-methylpyridine)24,4′-di-tert-butyl-2,2′-bipyridine]PF6 In dimethyl sulfoxide at 20℃; for 12 h; Inert atmosphere; Irradiation; Green chemistry General procedure: Heterocycle (0.10mmol, 1 equiv)ammonium persulfate (0.20 mmol, 2equiv),[Ir{dF(CF3ppy)}2(dtbbpy)]PF6 ( 0.2 molpercent),α-keto acids(1.0mmol10equiv)wereplaced in a dry glass tube.Then, anhydrous DMSO1mLwereinjected into the tubeby syringe under a N2 atmosphere.The solution was then stirred at roomtemperatureunder the irradiation of 15W blue LEDs strip for 12h.After completion of thereaction,then saturated Na2CO3solution was added to adjust pH to basic.Thecombined organic layer was washed with brine and then dried overanhydrousNa2SO4.The desired products were obtained in thecorresponding yields afterpurification by flashchromatography on silica gel eluting with petroleum andethylacetate.
70% With dipotassium peroxodisulfate In water at 100℃; Sealed tube General procedure: To a solution of isoquinoline 1a (0.5 mmol) in water (2 mL) was added keto acid 2a (1.25 mmol), followed by K2S2O8 (1.5 mmol). The reaction mixture contained in a sealed tube was heated at 100 °C for 4-6 h. The contents were then cooled in an ice-bath and quenched with the saturated solution of sodium bicarbonate. The resulting mixture was extracted with ethyl acetate (2 × 10 mL) The organic phase was washed with water, dried over anhydrous sodium sulphate and evaporated under diminished pressure to afford the crude residue. The residue was finally purified by column chromatography to obtain the pure acylated product 3a.
Reference: [1] Organic Letters, 2017, vol. 19, # 21, p. 5772 - 5775
[2] Synlett, 2018, vol. 29, # 14, p. 1881 - 1886
[3] Tetrahedron Letters, 2017, vol. 58, # 24, p. 2347 - 2350
  • 11
  • [ 127-17-3 ]
  • [ 3034-19-3 ]
  • [ 6960-42-5 ]
Reference: [1] Tetrahedron Letters, 2008, vol. 49, # 6, p. 984 - 986
  • 12
  • [ 95-81-8 ]
  • [ 127-17-3 ]
  • [ 18474-59-4 ]
Reference: [1] Journal of Medicinal Chemistry, 2005, vol. 48, # 14, p. 4511 - 4525
  • 13
  • [ 29289-13-2 ]
  • [ 127-17-3 ]
  • [ 10241-97-1 ]
Reference: [1] Bioorganic and Medicinal Chemistry Letters, 2003, vol. 13, # 24, p. 4385 - 4388
  • 14
  • [ 63069-48-7 ]
  • [ 127-17-3 ]
  • [ 10517-21-2 ]
Reference: [1] ChemMedChem, 2018, vol. 13, # 12, p. 1181 - 1192
  • 15
  • [ 66416-72-6 ]
  • [ 127-17-3 ]
  • [ 7254-19-5 ]
Reference: [1] Bioorganic and Medicinal Chemistry Letters, 2003, vol. 13, # 24, p. 4385 - 4388
  • 16
  • [ 123-30-8 ]
  • [ 127-17-3 ]
  • [ 50741-53-2 ]
Reference: [1] Justus Liebigs Annalen der Chemie, 1957, vol. 607, p. 92,101
[2] Arkiv foer Kemi, 1953, vol. 5, p. 251,252[3] Justus Liebigs Annalen der Chemie, 1952, vol. 578, p. 188,193
  • 17
  • [ 64-17-5 ]
  • [ 123-30-8 ]
  • [ 127-17-3 ]
  • [ 50741-53-2 ]
Reference: [1] Justus Liebigs Annalen der Chemie, 1957, vol. 607, p. 92,101
  • 18
  • [ 64-17-5 ]
  • [ 127-17-3 ]
  • [ 658-27-5 ]
  • [ 348-37-8 ]
Reference: [1] Bioorganic and Medicinal Chemistry Letters, 2016, vol. 26, # 18, p. 4403 - 4407
  • 19
  • [ 64-17-5 ]
  • [ 127-17-3 ]
  • [ 14763-20-3 ]
  • [ 27034-51-1 ]
Reference: [1] Bioorganic and Medicinal Chemistry Letters, 2016, vol. 26, # 18, p. 4403 - 4407
  • 20
  • [ 64-17-5 ]
  • [ 127-17-3 ]
  • [ 1073-69-4 ]
  • [ 4792-67-0 ]
Reference: [1] Bioorganic and Medicinal Chemistry Letters, 2016, vol. 26, # 18, p. 4403 - 4407
  • 21
  • [ 91004-61-4 ]
  • [ 127-17-3 ]
  • [ 58457-37-7 ]
Reference: [1] Farmaco, 1992, vol. 47, # 12, p. 1513 - 1528
  • 22
  • [ 100-48-1 ]
  • [ 127-17-3 ]
  • [ 37398-49-5 ]
Reference: [1] Journal of Organic Chemistry, 1991, vol. 56, # 8, p. 2866 - 2869
  • 23
  • [ 100-54-9 ]
  • [ 127-17-3 ]
  • [ 52689-19-7 ]
YieldReaction ConditionsOperation in experiment
21%
Stage #1: With ammonium peroxydisulfate; sulfuric acid; silver nitrate In dichloromethane; water at 0 - 40℃; for 1.5 h;
Stage #2: With sodium hydroxide In dichloromethane; water at 0℃;
Method B; 1) 2-Acetyl-5-cyanopyridine; Ammonium peroxodisulfate (10.3 g) was gradually added to a solution of 3-cyanopyridine (3.12 g), pyruvic acid (6.23 ml), and silver nitrate (1.27 g) in a mixture of dichloromethane (150 ml) and water (150 ml) at room temperature. Sulfuric acid (3.2 ml) was gradually added to the reaction liquid under ice cooling, and the mixture was stirred at 40°C for 1.5 hours. To the reaction liquid was added 1N aqueous sodium hydroxide to make the solution basic under ice cooling, and the solution was extracted with dichloromethane. The organic layer was dried over anhydrous sodium sulfate. After filtration, the solvent was evaporated under reduced pressure, and the residue was purified by column chromatography on silica gel (ethyl acetate-hexane) to give 2-acetyl-5-cyanopyridine (903 mg, 21percent) as a solid. 1H-NMR (400 MHz, CDCl3)δ: 2.75 (3H, s), 8.13-8.16 (2H, m), 8.95 (1H, d, J = 1.2 Hz).
21%
Stage #1: With ammonium peroxydisulfate; silver nitrate In dichloromethane; water
Stage #2: With sulfuric acid In dichloromethane; water at 0 - 40℃; for 1.5 h;
Stage #3: With sodium hydroxide In dichloromethane; water
1)
2-Acetyl-5-cyanopyridine
At room temperature, ammonium peroxodisulfate (10.3 g) was gradually added to 3-cyanopyridine (3.12 g), pyruvic acid (6.23 mL), and silver nitrate (1.27 g) in a mixture of dichloromethane (150 mL) and water (150 mL).
Sulfuric acid (3.2 mL) was gradually added to the reaction mixture under cooling on ice, followed by stirring at 40°C for 1.5 hours.
Subsequently, the reaction mixture was alkalinized with 1M aqueous solution of sodium hydroxide under cooling on ice, and then the resultant mixture was extracted with dichloromethane.
The organic layer was dried over sodium sulfate anhydrate.
After a filtration step, the solvent was evaporated under reduced pressure, and the residue was purified by silica gel column chromatography (ethyl acetate - hexane), to thereby give 2-acetyl-5-cyanopyridine as a solid product (903 mg, 21percent).
1H-NMR(400MHz,CDCl3)δ:2.75(3H,s), 8.13-8.16(2H,m), 8.95(1H,d,J=1.2Hz).
21%
Stage #1: With ammonium peroxydisulfate; sulfuric acid; silver nitrate In dichloromethane; water at 0 - 40℃; for 1.5 h;
Stage #2: With sodium hydroxide In dichloromethane; water at 0℃;
1) 2-Acetyl-5-cyanopyridine Ammonium peroxodisulfate (10.3 g) was slowly added to a mixture of 3-cyanopyridine (3.12 g), pyruvic acid (6.23 mL) and silver nitrate (1.27 g) in dichloromethane (150 mL) and water (150 mL) at room temperature. Under ice cooling, sulfuric acid (3.2 mL) was slowly added to the reaction solution, and then the mixture was stirred for 1.5 hours at 40°C. Under ice cooling, the reaction solution was alkalinized by adding an aqueous 1 M sodium hydroxide solution, and then extracted with dichloromethane. The organic solvent was dried over anhydrous sodium sulfate. After separation by filtration, a residue obtained by evaporating the solvent under reduced pressure was purified by silica gel column chromatography (hexane-ethyl acetate), to obtain 2-acetyl-5-cyanopyridine (903 mg, 21percent) as a solid. 1H-NMR(400MHz, CDCl3)δ: 2.75(3H, s), 8.13-8.16(2H, m), 8.95(1H, d, J=1.2Hz).
Reference: [1] Patent: EP1698626, 2006, A1, . Location in patent: Page/Page column 86-87
[2] Patent: EP1762568, 2007, A1, . Location in patent: Page/Page column 29
[3] Patent: EP1785418, 2007, A1, . Location in patent: Page/Page column 76
  • 24
  • [ 2999-46-4 ]
  • [ 127-17-3 ]
  • [ 32968-44-8 ]
Reference: [1] Chemical Communications, 2015, vol. 51, # 52, p. 10524 - 10527
  • 25
  • [ 77287-34-4 ]
  • [ 51953-18-5 ]
  • [ 156-81-0 ]
  • [ 120-89-8 ]
  • [ 108-53-2 ]
  • [ 71-30-7 ]
  • [ 144-62-7 ]
  • [ 113-00-8 ]
  • [ 127-17-3 ]
  • [ 66-22-8 ]
  • [ 56-06-4 ]
  • [ 66224-66-6 ]
  • [ 57-13-6 ]
  • [ 56-40-6 ]
YieldReaction ConditionsOperation in experiment
1.6 mg With copper(II) choride dihydrate In water at 80℃; for 24 h; General procedure: To model the chemical environment on the outer side of thetubular structures, NH2CHO (200 μL) was mixed with thesodium silicate solution (2.0 mL) in the presence of preformedMSH [ZnCl2, FeCl2·4H2O, CuCl2·2H2O, Fe2(SO4)3·9H2O,and MgSO4] (2.0percent w/w) at 80 °C for 24 h. In two selectedcases [FeCl2 and Fe2(SO4)3·9H2O], NH2CHO (200 μL) wasmixed with the sodium silicate solution (2.0 mL) in the presence of selected growing MSH (starting from 2.0percent w/w ofthe corresponding salt’s pellet) at 80 °C for 24 h. For the innerenvironment, NH2CHO (200 μL) was mixed with distilledwater (2.0 mL) in the presence of selected MSH (2.0percent w/w) at80 °C for 24 h. The reaction of NH2CHO (10percent v/v) with thesodium silicate solution (pH 12) without MSH membranes wasalso analyzed under similar experimental conditions. Theproducts were analyzed by gas chromatography associatedwith mass spectrometry (GC-MS) after treatment with N,Nbis-trimethylsilyl trifluoroacetamide in pyridine (620 μL) at 60°C for 4 h in the presence of betulinol (CAS Registry Number473-98-3) as the internal standard (0.2 mg). Mass spectrometrywas performed by the following program: injection temperature280 °C, detector temperature 280 °C, gradient 100 °C for 2min, and 10 °C/min for 60 min. To identify the structure of theproducts, two strategies were followed. First, the spectra werecompared with commercially available electron mass spectrumlibraries such as NIST (Fison, Manchester, U.K.). Second, GCMSanalysis was repeated with standard compounds. Allproducts have been recognized with a similarity index (SI)greater than 98percent compared to that of the reference standards.The analysis was limited to products of ≥1 ng/mL, and theyield was calculated as micrograms of product per startingformamide. For further experimental details, see the SupportingInformation.
Reference: [1] Biochemistry, 2016, vol. 55, # 19, p. 2806 - 2811
  • 26
  • [ 77287-34-4 ]
  • [ 51953-18-5 ]
  • [ 1455-77-2 ]
  • [ 120-89-8 ]
  • [ 849585-22-4 ]
  • [ 73-40-5 ]
  • [ 328-42-7 ]
  • [ 2491-15-8 ]
  • [ 110-15-6 ]
  • [ 71-30-7 ]
  • [ 120-73-0 ]
  • [ 144-62-7 ]
  • [ 113-00-8 ]
  • [ 127-17-3 ]
  • [ 66-22-8 ]
  • [ 56-06-4 ]
  • [ 66224-66-6 ]
  • [ 57-13-6 ]
  • [ 56-40-6 ]
  • [ 302-72-7 ]
  • [ 18588-61-9 ]
Reference: [1] Chemistry - A European Journal, 2018, vol. 24, # 32, p. 8126 - 8132
  • 27
  • [ 77287-34-4 ]
  • [ 51953-18-5 ]
  • [ 120-89-8 ]
  • [ 73-40-5 ]
  • [ 328-42-7 ]
  • [ 110-15-6 ]
  • [ 144-62-7 ]
  • [ 127-17-3 ]
  • [ 56-06-4 ]
  • [ 57-13-6 ]
  • [ 18588-61-9 ]
  • [ 18514-52-8 ]
Reference: [1] Chemistry - A European Journal, 2018, vol. 24, # 32, p. 8126 - 8132
  • 28
  • [ 127-17-3 ]
  • [ 95-54-5 ]
  • [ 939-70-8 ]
Reference: [1] Bioorganic and Medicinal Chemistry Letters, 2018, vol. 28, # 9, p. 1621 - 1628
  • 29
  • [ 39856-58-1 ]
  • [ 127-17-3 ]
  • [ 17288-35-6 ]
Reference: [1] Patent: EP1479680, 2004, A1, . Location in patent: Page 48
  • 30
  • [ 302-72-7 ]
  • [ 1068-84-4 ]
  • [ 302-84-1 ]
  • [ 5735-66-0 ]
  • [ 64-19-7 ]
  • [ 127-17-3 ]
  • [ 56-40-6 ]
Reference: [1] Tetrahedron Letters, 1983, vol. 24, # 44, p. 4839 - 4842
  • 31
  • [ 127-17-3 ]
  • [ 103-67-3 ]
  • [ 600-21-5 ]
Reference: [1] Tetrahedron Letters, 1979, p. 4183 - 4184
  • 32
  • [ 338-69-2 ]
  • [ 1821-02-9 ]
  • [ 2013-12-9 ]
  • [ 127-17-3 ]
Reference: [1] Journal of Molecular Catalysis B: Enzymatic, 2013, vol. 94, p. 15 - 22
  • 33
  • [ 328-42-7 ]
  • [ 338-69-2 ]
  • [ 1783-96-6 ]
  • [ 127-17-3 ]
Reference: [1] Journal of Molecular Catalysis B: Enzymatic, 2013, vol. 94, p. 15 - 22
  • 34
  • [ 127-17-3 ]
  • [ 1113-59-3 ]
Reference: [1] Journal of Organic Chemistry, 1982, vol. 47, # 19, p. 3765 - 3766
[2] Journal of Medicinal Chemistry, 2006, vol. 49, # 2, p. 511 - 522
[3] Helvetica Chimica Acta, 1946, vol. 29, p. 415,431
[4] Journal of Biological Chemistry, 1946, vol. 164, p. 437
[5] Journal of the Chemical Society, 1923, vol. 123, p. 2208
[6] Synthesis, 2006, # 15, p. 2563 - 2567
  • 35
  • [ 127-17-3 ]
  • [ 1113-59-3 ]
Reference: [1] Patent: US4457936, 1984, A,
  • 36
  • [ 123-54-6 ]
  • [ 1113-59-3 ]
  • [ 600-35-1 ]
  • [ 858451-26-0 ]
  • [ 64-19-7 ]
  • [ 127-17-3 ]
Reference: [1] Indian Journal of Chemistry, Section A: Inorganic, Physical, Theoretical & Analytical, 1980, vol. 19, # 1, p. 1 - 6
  • 37
  • [ 7732-18-5 ]
  • [ 7726-95-6 ]
  • [ 127-17-3 ]
  • [ 1113-59-3 ]
  • [ 600-35-1 ]
  • [ 858451-26-0 ]
Reference: [1] Chemische Berichte, 1881, vol. 14, p. 1236 Anm. 1
[2] Bulletin de la Societe Chimique de France, 1874, vol. <2> 21, p. 391,393
[3] Chemische Berichte, 1868, vol. 1, p. 265[4] Justus Liebigs Annalen der Chemie, 1869, vol. 152, p. 264
  • 38
  • [ 77287-34-4 ]
  • [ 2491-15-8 ]
  • [ 113-00-8 ]
  • [ 127-17-3 ]
  • [ 56-40-6 ]
YieldReaction ConditionsOperation in experiment
0.0034 mg With iron(II) chloride tetrahydrate In water at 80℃; for 24 h; General procedure: To model the chemical environment on the outer side of thetubular structures, NH2CHO (200 μL) was mixed with thesodium silicate solution (2.0 mL) in the presence of preformedMSH [ZnCl2, FeCl2·4H2O, CuCl2·2H2O, Fe2(SO4)3·9H2O,and MgSO4] (2.0percent w/w) at 80 °C for 24 h. In two selectedcases [FeCl2 and Fe2(SO4)3·9H2O], NH2CHO (200 μL) wasmixed with the sodium silicate solution (2.0 mL) in the presence of selected growing MSH (starting from 2.0percent w/w ofthe corresponding salt’s pellet) at 80 °C for 24 h. For the innerenvironment, NH2CHO (200 μL) was mixed with distilledwater (2.0 mL) in the presence of selected MSH (2.0percent w/w) at80 °C for 24 h. The reaction of NH2CHO (10percent v/v) with thesodium silicate solution (pH 12) without MSH membranes wasalso analyzed under similar experimental conditions. Theproducts were analyzed by gas chromatography associatedwith mass spectrometry (GC-MS) after treatment with N,Nbis-trimethylsilyl trifluoroacetamide in pyridine (620 μL) at 60°C for 4 h in the presence of betulinol (CAS Registry Number473-98-3) as the internal standard (0.2 mg). Mass spectrometrywas performed by the following program: injection temperature280 °C, detector temperature 280 °C, gradient 100 °C for 2min, and 10 °C/min for 60 min. To identify the structure of theproducts, two strategies were followed. First, the spectra werecompared with commercially available electron mass spectrumlibraries such as NIST (Fison, Manchester, U.K.). Second, GCMSanalysis was repeated with standard compounds. Allproducts have been recognized with a similarity index (SI)greater than 98percent compared to that of the reference standards.The analysis was limited to products of ≥1 ng/mL, and theyield was calculated as micrograms of product per startingformamide. For further experimental details, see the SupportingInformation.
0.0052 mg With zinc(II) chloride In water at 80℃; for 24 h; General procedure: To model the chemical environment on the outer side of thetubular structures, NH2CHO (200 μL) was mixed with thesodium silicate solution (2.0 mL) in the presence of preformedMSH [ZnCl2, FeCl2·4H2O, CuCl2·2H2O, Fe2(SO4)3·9H2O,and MgSO4] (2.0percent w/w) at 80 °C for 24 h. In two selectedcases [FeCl2 and Fe2(SO4)3·9H2O], NH2CHO (200 μL) wasmixed with the sodium silicate solution (2.0 mL) in the presence of selected growing MSH (starting from 2.0percent w/w ofthe corresponding salt’s pellet) at 80 °C for 24 h. For the innerenvironment, NH2CHO (200 μL) was mixed with distilledwater (2.0 mL) in the presence of selected MSH (2.0percent w/w) at80 °C for 24 h. The reaction of NH2CHO (10percent v/v) with thesodium silicate solution (pH 12) without MSH membranes wasalso analyzed under similar experimental conditions. Theproducts were analyzed by gas chromatography associatedwith mass spectrometry (GC-MS) after treatment with N,Nbis-trimethylsilyl trifluoroacetamide in pyridine (620 μL) at 60°C for 4 h in the presence of betulinol (CAS Registry Number473-98-3) as the internal standard (0.2 mg). Mass spectrometrywas performed by the following program: injection temperature280 °C, detector temperature 280 °C, gradient 100 °C for 2min, and 10 °C/min for 60 min. To identify the structure of theproducts, two strategies were followed. First, the spectra werecompared with commercially available electron mass spectrumlibraries such as NIST (Fison, Manchester, U.K.). Second, GCMSanalysis was repeated with standard compounds. Allproducts have been recognized with a similarity index (SI)greater than 98percent compared to that of the reference standards.The analysis was limited to products of ≥1 ng/mL, and theyield was calculated as micrograms of product per startingformamide. For further experimental details, see the SupportingInformation.
Reference: [1] Biochemistry, 2016, vol. 55, # 19, p. 2806 - 2811
[2] Biochemistry, 2016, vol. 55, # 19, p. 2806 - 2811
  • 39
  • [ 77287-34-4 ]
  • [ 156-81-0 ]
  • [ 849585-22-4 ]
  • [ 617-48-1 ]
  • [ 2491-15-8 ]
  • [ 110-15-6 ]
  • [ 108-53-2 ]
  • [ 71-30-7 ]
  • [ 113-00-8 ]
  • [ 127-17-3 ]
  • [ 66-22-8 ]
  • [ 66224-66-6 ]
  • [ 56-40-6 ]
  • [ 302-72-7 ]
  • [ 18514-52-8 ]
YieldReaction ConditionsOperation in experiment
0.18 mg With ferric sulfate nonahydrate In water at 80℃; for 24 h; General procedure: To model the chemical environment on the outer side of thetubular structures, NH2CHO (200 μL) was mixed with thesodium silicate solution (2.0 mL) in the presence of preformedMSH [ZnCl2, FeCl2·4H2O, CuCl2·2H2O, Fe2(SO4)3·9H2O,and MgSO4] (2.0percent w/w) at 80 °C for 24 h. In two selectedcases [FeCl2 and Fe2(SO4)3·9H2O], NH2CHO (200 μL) wasmixed with the sodium silicate solution (2.0 mL) in the presence of selected growing MSH (starting from 2.0percent w/w ofthe corresponding salt’s pellet) at 80 °C for 24 h. For the innerenvironment, NH2CHO (200 μL) was mixed with distilledwater (2.0 mL) in the presence of selected MSH (2.0percent w/w) at80 °C for 24 h. The reaction of NH2CHO (10percent v/v) with thesodium silicate solution (pH 12) without MSH membranes wasalso analyzed under similar experimental conditions. Theproducts were analyzed by gas chromatography associatedwith mass spectrometry (GC-MS) after treatment with N,Nbis-trimethylsilyl trifluoroacetamide in pyridine (620 μL) at 60°C for 4 h in the presence of betulinol (CAS Registry Number473-98-3) as the internal standard (0.2 mg). Mass spectrometrywas performed by the following program: injection temperature280 °C, detector temperature 280 °C, gradient 100 °C for 2min, and 10 °C/min for 60 min. To identify the structure of theproducts, two strategies were followed. First, the spectra werecompared with commercially available electron mass spectrumlibraries such as NIST (Fison, Manchester, U.K.). Second, GCMSanalysis was repeated with standard compounds. Allproducts have been recognized with a similarity index (SI)greater than 98percent compared to that of the reference standards.The analysis was limited to products of ≥1 ng/mL, and theyield was calculated as micrograms of product per startingformamide. For further experimental details, see the SupportingInformation.
Reference: [1] Biochemistry, 2016, vol. 55, # 19, p. 2806 - 2811
  • 40
  • [ 77287-34-4 ]
  • [ 156-81-0 ]
  • [ 849585-22-4 ]
  • [ 617-48-1 ]
  • [ 2491-15-8 ]
  • [ 110-15-6 ]
  • [ 108-53-2 ]
  • [ 71-30-7 ]
  • [ 113-00-8 ]
  • [ 127-17-3 ]
  • [ 66-22-8 ]
  • [ 66224-66-6 ]
  • [ 56-40-6 ]
  • [ 302-72-7 ]
YieldReaction ConditionsOperation in experiment
0.12 mg With magnesium sulfate In water at 80℃; for 24 h; General procedure: To model the chemical environment on the outer side of thetubular structures, NH2CHO (200 μL) was mixed with thesodium silicate solution (2.0 mL) in the presence of preformedMSH [ZnCl2, FeCl2·4H2O, CuCl2·2H2O, Fe2(SO4)3·9H2O,and MgSO4] (2.0percent w/w) at 80 °C for 24 h. In two selectedcases [FeCl2 and Fe2(SO4)3·9H2O], NH2CHO (200 μL) wasmixed with the sodium silicate solution (2.0 mL) in the presence of selected growing MSH (starting from 2.0percent w/w ofthe corresponding salt’s pellet) at 80 °C for 24 h. For the innerenvironment, NH2CHO (200 μL) was mixed with distilledwater (2.0 mL) in the presence of selected MSH (2.0percent w/w) at80 °C for 24 h. The reaction of NH2CHO (10percent v/v) with thesodium silicate solution (pH 12) without MSH membranes wasalso analyzed under similar experimental conditions. Theproducts were analyzed by gas chromatography associatedwith mass spectrometry (GC-MS) after treatment with N,Nbis-trimethylsilyl trifluoroacetamide in pyridine (620 μL) at 60°C for 4 h in the presence of betulinol (CAS Registry Number473-98-3) as the internal standard (0.2 mg). Mass spectrometrywas performed by the following program: injection temperature280 °C, detector temperature 280 °C, gradient 100 °C for 2min, and 10 °C/min for 60 min. To identify the structure of theproducts, two strategies were followed. First, the spectra werecompared with commercially available electron mass spectrumlibraries such as NIST (Fison, Manchester, U.K.). Second, GCMSanalysis was repeated with standard compounds. Allproducts have been recognized with a similarity index (SI)greater than 98percent compared to that of the reference standards.The analysis was limited to products of ≥1 ng/mL, and theyield was calculated as micrograms of product per startingformamide. For further experimental details, see the SupportingInformation.
Reference: [1] Biochemistry, 2016, vol. 55, # 19, p. 2806 - 2811
  • 41
  • [ 77287-34-4 ]
  • [ 79-14-1 ]
  • [ 849585-22-4 ]
  • [ 2491-15-8 ]
  • [ 144-62-7 ]
  • [ 127-17-3 ]
  • [ 57-13-6 ]
YieldReaction ConditionsOperation in experiment
0.002 mg at 80℃; for 24 h; General procedure: To model the chemical environment on the outer side of thetubular structures, NH2CHO (200 μL) was mixed with thesodium silicate solution (2.0 mL) in the presence of preformedMSH [ZnCl2, FeCl2·4H2O, CuCl2·2H2O, Fe2(SO4)3·9H2O,and MgSO4] (2.0percent w/w) at 80 °C for 24 h. In two selectedcases [FeCl2 and Fe2(SO4)3·9H2O], NH2CHO (200 μL) wasmixed with the sodium silicate solution (2.0 mL) in the presence of selected growing MSH (starting from 2.0percent w/w ofthe corresponding salt’s pellet) at 80 °C for 24 h. For the innerenvironment, NH2CHO (200 μL) was mixed with distilledwater (2.0 mL) in the presence of selected MSH (2.0percent w/w) at80 °C for 24 h. The reaction of NH2CHO (10percent v/v) with thesodium silicate solution (pH 12) without MSH membranes wasalso analyzed under similar experimental conditions. Theproducts were analyzed by gas chromatography associatedwith mass spectrometry (GC-MS) after treatment with N,Nbis-trimethylsilyl trifluoroacetamide in pyridine (620 μL) at 60°C for 4 h in the presence of betulinol (CAS Registry Number473-98-3) as the internal standard (0.2 mg). Mass spectrometrywas performed by the following program: injection temperature280 °C, detector temperature 280 °C, gradient 100 °C for 2min, and 10 °C/min for 60 min. To identify the structure of theproducts, two strategies were followed. First, the spectra werecompared with commercially available electron mass spectrumlibraries such as NIST (Fison, Manchester, U.K.). Second, GCMSanalysis was repeated with standard compounds. Allproducts have been recognized with a similarity index (SI)greater than 98percent compared to that of the reference standards.The analysis was limited to products of ≥1 ng/mL, and theyield was calculated as micrograms of product per startingformamide. For further experimental details, see the SupportingInformation.
Reference: [1] Biochemistry, 2016, vol. 55, # 19, p. 2806 - 2811
  • 42
  • [ 77287-34-4 ]
  • [ 849585-22-4 ]
  • [ 617-48-1 ]
  • [ 2491-15-8 ]
  • [ 110-15-6 ]
  • [ 144-62-7 ]
  • [ 113-00-8 ]
  • [ 127-17-3 ]
  • [ 57-13-6 ]
  • [ 18514-52-8 ]
YieldReaction ConditionsOperation in experiment
0.9 mg at 80℃; for 24 h; General procedure: To model the chemical environment on the outer side of thetubular structures, NH2CHO (200 μL) was mixed with thesodium silicate solution (2.0 mL) in the presence of preformedMSH [ZnCl2, FeCl2·4H2O, CuCl2·2H2O, Fe2(SO4)3·9H2O,and MgSO4] (2.0percent w/w) at 80 °C for 24 h. In two selectedcases [FeCl2 and Fe2(SO4)3·9H2O], NH2CHO (200 μL) wasmixed with the sodium silicate solution (2.0 mL) in the presence of selected growing MSH (starting from 2.0percent w/w ofthe corresponding salt’s pellet) at 80 °C for 24 h. For the innerenvironment, NH2CHO (200 μL) was mixed with distilledwater (2.0 mL) in the presence of selected MSH (2.0percent w/w) at80 °C for 24 h. The reaction of NH2CHO (10percent v/v) with thesodium silicate solution (pH 12) without MSH membranes wasalso analyzed under similar experimental conditions. Theproducts were analyzed by gas chromatography associatedwith mass spectrometry (GC-MS) after treatment with N,Nbis-trimethylsilyl trifluoroacetamide in pyridine (620 μL) at 60°C for 4 h in the presence of betulinol (CAS Registry Number473-98-3) as the internal standard (0.2 mg). Mass spectrometrywas performed by the following program: injection temperature280 °C, detector temperature 280 °C, gradient 100 °C for 2min, and 10 °C/min for 60 min. To identify the structure of theproducts, two strategies were followed. First, the spectra werecompared with commercially available electron mass spectrumlibraries such as NIST (Fison, Manchester, U.K.). Second, GCMSanalysis was repeated with standard compounds. Allproducts have been recognized with a similarity index (SI)greater than 98percent compared to that of the reference standards.The analysis was limited to products of ≥1 ng/mL, and theyield was calculated as micrograms of product per startingformamide. For further experimental details, see the SupportingInformation.
Reference: [1] Biochemistry, 2016, vol. 55, # 19, p. 2806 - 2811
  • 43
  • [ 77287-34-4 ]
  • [ 51953-18-5 ]
  • [ 1455-77-2 ]
  • [ 120-89-8 ]
  • [ 849585-22-4 ]
  • [ 73-40-5 ]
  • [ 328-42-7 ]
  • [ 2491-15-8 ]
  • [ 110-15-6 ]
  • [ 71-30-7 ]
  • [ 120-73-0 ]
  • [ 144-62-7 ]
  • [ 113-00-8 ]
  • [ 127-17-3 ]
  • [ 66-22-8 ]
  • [ 56-06-4 ]
  • [ 66224-66-6 ]
  • [ 57-13-6 ]
  • [ 56-40-6 ]
  • [ 302-72-7 ]
  • [ 18588-61-9 ]
Reference: [1] Chemistry - A European Journal, 2018, vol. 24, # 32, p. 8126 - 8132
  • 44
  • [ 77287-34-4 ]
  • [ 51953-18-5 ]
  • [ 120-89-8 ]
  • [ 849585-22-4 ]
  • [ 73-40-5 ]
  • [ 328-42-7 ]
  • [ 2491-15-8 ]
  • [ 110-15-6 ]
  • [ 71-30-7 ]
  • [ 144-62-7 ]
  • [ 113-00-8 ]
  • [ 127-17-3 ]
  • [ 66-22-8 ]
  • [ 66224-66-6 ]
  • [ 56-40-6 ]
  • [ 18588-61-9 ]
  • [ 18514-52-8 ]
Reference: [1] Chemistry - A European Journal, 2018, vol. 24, # 32, p. 8126 - 8132
  • 45
  • [ 77287-34-4 ]
  • [ 51953-18-5 ]
  • [ 1455-77-2 ]
  • [ 120-89-8 ]
  • [ 73-40-5 ]
  • [ 328-42-7 ]
  • [ 2491-15-8 ]
  • [ 110-15-6 ]
  • [ 71-30-7 ]
  • [ 120-73-0 ]
  • [ 144-62-7 ]
  • [ 113-00-8 ]
  • [ 127-17-3 ]
  • [ 66-22-8 ]
  • [ 66224-66-6 ]
  • [ 57-13-6 ]
  • [ 56-40-6 ]
  • [ 302-72-7 ]
Reference: [1] Chemistry - A European Journal, 2018, vol. 24, # 32, p. 8126 - 8132
  • 46
  • [ 72915-12-9 ]
  • [ 25561-30-2 ]
  • [ 127-17-3 ]
  • [ 354-38-1 ]
  • [ 55982-15-5 ]
Reference: [1] Environmental Science and Technology, 1998, vol. 32, # 16, p. 2357 - 2370
  • 47
  • [ 127-17-3 ]
  • [ 600-35-1 ]
Reference: [1] Gazzetta Chimica Italiana, 1926, vol. 56, p. 253
[2] Gazzetta Chimica Italiana, 1922, vol. 52 II, p. 218
[3] Journal of the Chemical Society [Section] C: Organic, 1966, p. 533 - 540
[4] Journal of the American Chemical Society, 2003, vol. 125, # 42, p. 12759 - 12767
  • 48
  • [ 127-17-3 ]
  • [ 600-35-1 ]
  • [ 858451-26-0 ]
Reference: [1] Chemische Berichte, 1881, vol. 14, p. 1236 Anm. 1
[2] Bulletin de la Societe Chimique de France, 1874, vol. <2> 21, p. 391,393
  • 49
  • [ 127-17-3 ]
  • [ 79-49-2 ]
  • [ 600-35-1 ]
Reference: [1] Justus Liebigs Annalen der Chemie, 1869, vol. 152, p. 260
  • 50
  • [ 123-54-6 ]
  • [ 1113-59-3 ]
  • [ 600-35-1 ]
  • [ 858451-26-0 ]
  • [ 64-19-7 ]
  • [ 127-17-3 ]
Reference: [1] Indian Journal of Chemistry, Section A: Inorganic, Physical, Theoretical & Analytical, 1980, vol. 19, # 1, p. 1 - 6
  • 51
  • [ 7732-18-5 ]
  • [ 7726-95-6 ]
  • [ 127-17-3 ]
  • [ 1113-59-3 ]
  • [ 600-35-1 ]
  • [ 858451-26-0 ]
Reference: [1] Chemische Berichte, 1881, vol. 14, p. 1236 Anm. 1
[2] Bulletin de la Societe Chimique de France, 1874, vol. <2> 21, p. 391,393
[3] Chemische Berichte, 1868, vol. 1, p. 265[4] Justus Liebigs Annalen der Chemie, 1869, vol. 152, p. 264
  • 52
  • [ 67-56-1 ]
  • [ 127-17-3 ]
  • [ 10076-48-9 ]
Reference: [1] Synthesis, 1983, # 3, p. 201 - 203
[2] Green Chemistry, 2014, vol. 16, # 7, p. 3569 - 3579
  • 53
  • [ 127-17-3 ]
  • [ 149-73-5 ]
  • [ 10076-48-9 ]
Reference: [1] Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999), 1982, # 8, p. 1897 - 1904
[2] Journal of Heterocyclic Chemistry, 1990, vol. 27, # 3, p. 815 - 817
[3] Tetrahedron Letters, 2003, vol. 44, # 15, p. 3081 - 3084
  • 54
  • [ 67-56-1 ]
  • [ 127-17-3 ]
  • [ 77-76-9 ]
  • [ 10076-48-9 ]
Reference: [1] Journal of Organic Chemistry, 1967, vol. 32, p. 1615 - 1617
  • 55
  • [ 67-56-1 ]
  • [ 127-17-3 ]
  • [ 600-22-6 ]
  • [ 10076-48-9 ]
Reference: [1] Tetrahedron Letters, 1998, vol. 39, # 47, p. 8563 - 8566
  • 56
  • [ 462-06-6 ]
  • [ 127-17-3 ]
  • [ 55660-73-6 ]
  • [ 7423-96-3 ]
Reference: [1] ACS Catalysis, 2015, vol. 5, # 12, p. 7503 - 7506
  • 57
  • [ 127-17-3 ]
  • [ 150-78-7 ]
  • [ 1201-38-3 ]
Reference: [1] Synthetic Communications, 1999, vol. 29, # 10, p. 1687 - 1695
  • 58
  • [ 127-17-3 ]
  • [ 1195-49-9 ]
  • [ 82017-30-9 ]
Reference: [1] Justus Liebigs Annalen der Chemie, 1927, vol. 453, p. 197[2] Justus Liebigs Annalen der Chemie, 1927, vol. 455, p. 32
  • 59
  • [ 127-17-3 ]
  • [ 108-90-7 ]
  • [ 7423-93-0 ]
  • [ 615-67-8 ]
Reference: [1] ACS Catalysis, 2015, vol. 5, # 12, p. 7503 - 7506
  • 60
  • [ 367-12-4 ]
  • [ 127-17-3 ]
  • [ 7423-96-3 ]
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[2] Biochemistry, 2010, vol. 49, # 8, p. 1557 - 1559
[3] Journal of the American Chemical Society, 2011, vol. 133, # 40, p. 15942 - 15945
[4] Journal of the American Chemical Society, 2014, vol. 136, # 21, p. 7643 - 7654
  • 61
  • [ 462-06-6 ]
  • [ 127-17-3 ]
  • [ 55660-73-6 ]
  • [ 7423-96-3 ]
Reference: [1] ACS Catalysis, 2015, vol. 5, # 12, p. 7503 - 7506
  • 62
  • [ 372-20-3 ]
  • [ 127-17-3 ]
  • [ 7423-96-3 ]
Reference: [1] Journal of the American Chemical Society, 2016, vol. 138, # 3, p. 926 - 935
  • 63
  • [ 108-86-1 ]
  • [ 127-17-3 ]
  • [ 583-69-7 ]
  • [ 38739-13-8 ]
Reference: [1] ACS Catalysis, 2015, vol. 5, # 12, p. 7503 - 7506
  • 64
  • [ 13534-99-1 ]
  • [ 127-17-3 ]
  • [ 136818-50-3 ]
Reference: [1] Patent: WO2010/5528, 2010, A2, . Location in patent: Page/Page column 86
  • 65
  • [ 127-17-3 ]
  • [ 163444-17-5 ]
  • [ 496946-78-2 ]
YieldReaction ConditionsOperation in experiment
65% With 1,4-diaza-bicyclo[2.2.2]octane; palladium diacetate In N,N-dimethyl-formamide at 105℃; for 10 h; Inert atmosphere A mixture of 2-iodo-4-(trifluoromethyl)aniline (C34) (250 mg, 0.871 mmol), pyruvic acid (0.123 mL,1.74 mmol), (195 mg, 1.74 mmol), and palladium(ll) acetate (10 mg, 44 pmol) in dry N,N-dimethylformamide (10 mL) was degassed viavacuum / nitrogen purges and heated at 105 °C for 10 h. The reaction mixture was allowed to cool to room temperature and was partitioned between ethyl acetate and water. The organic layer was washed with brine, dried over sodium sulfate, and concentrated under vacuum. The residue was purified by silica gel chromatography, eluting with 10percent ethyl acetate in hexane, to give the title compound as a brown solid.Yield: 130 mg, 65percent. LCMS m/z 228.0 (M-H); 1H NMR (400 MHz, DMSO-d6) ö 13.27 (5,1H), 12.20 (5, 1H), 8.09 (5, 1H), 7.61 (d, J=8.7 Hz, 1H), 7.51 (d, J=8.6 Hz, 1H), 7.25 (5,1 H).
1.15 g With 1,4-diaza-bicyclo[2.2.2]octane; palladium diacetate In N,N-dimethyl-formamide at 100℃; for 24 h; Inert atmosphere A mixture of 2.28 g of 2-iodo-4-trifluoromethyla- niline, 2.10 g of pyruvic acid, 2.67 g of DAI3CO, 89mg of palladium (II) acetate, and 25 ml of DMF was stirred for 24 hours at 1000 C. in nitrogen atmosphere. After the reaction mixture was cooled to room temperature, 25 ml of ethyl acetate and 50 ml of 5 M hydrochloric acid were added thereto, and extraction was performed three times by using ethyl acetate. The collected organic layer was washed with water and saturated saline, dried over magnesium sulfate, and then concentrated under reduced pressure. The residues were washed with chloroform, thereby obtaining 1.15 g of 5-trif- luoromethylindole-2-carboxylic acid (hereinafter, described as a “compound 7 of the present invention”).1H-NMR (DMSO-D5) ö: 13.24 (br s, 1H), 12.20 (br s, 1H), 8.08 (s, 1H), 7.60 (d, 1H, J=8.8 Hz), 7.51 (dd, 1H, J8.8, 1.6 Hz), 7.24 (d, 1H, J=1.6 Hz)
Reference: [1] Bioorganic and Medicinal Chemistry Letters, 2010, vol. 20, # 9, p. 2722 - 2725
[2] Patent: WO2015/49616, 2015, A1, . Location in patent: Page/Page column 66; 67
[3] Bioorganic and Medicinal Chemistry Letters, 2003, vol. 13, # 24, p. 4385 - 4388
[4] Patent: US2007/88071, 2007, A1, . Location in patent: Page/Page column 16
[5] Patent: US2015/289512, 2015, A1, . Location in patent: Paragraph 1210; 1211
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Reference: [1] Patent: WO2006/59164, 2006, A2, . Location in patent: Page/Page column 21
[2] Patent: WO2004/104001, 2004, A2, . Location in patent: Page 51
  • 67
  • [ 800402-12-4 ]
  • [ 127-17-3 ]
  • [ 800401-54-1 ]
Reference: [1] Patent: WO2006/59164, 2006, A2, . Location in patent: Page/Page column 24
[2] Patent: WO2006/67532, 2006, A1, . Location in patent: Page/Page column 18
[3] Bioorganic and Medicinal Chemistry Letters, 2011, vol. 21, # 23, p. 7107 - 7112
[4] Patent: WO2004/104001, 2004, A2, . Location in patent: Page 75
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  • [ 800401-68-7 ]
Reference: [1] Patent: WO2006/59164, 2006, A2, . Location in patent: Page/Page column 21
[2] Patent: WO2004/104001, 2004, A2, . Location in patent: Page 36
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Reference: [1] Patent: US2008/125459, 2008, A1, . Location in patent: Page/Page column 16
[2] Patent: US2009/42873, 2009, A1, . Location in patent: Page/Page column 25
[3] Patent: US2010/41634, 2010, A1, . Location in patent: Page/Page column 20
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Reference: [1] Organic and Biomolecular Chemistry, 2015, vol. 13, # 9, p. 2750 - 2755
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