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[ CAS No. 870778-88-4 ]

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2D
Chemical Structure| 870778-88-4
Chemical Structure| 870778-88-4
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Product Details of [ 870778-88-4 ]

CAS No. :870778-88-4MDL No. :MFCD07369736
Formula : C10H15BO4 Boiling Point : -
Linear Structure Formula :-InChI Key :-
M.W :210.04Pubchem ID :-
Synonyms :

Computed Properties of [ 870778-88-4 ]

TPSA : - H-Bond Acceptor Count : -
XLogP3 : - H-Bond Donor Count : -
SP3 : - Rotatable Bond Count : -

Safety of [ 870778-88-4 ]

Signal Word:WarningClass:
Precautionary Statements:P261-P264-P271-P280-P302+P352-P304+P340+P312-P305+P351+P338-P332+P313-P337+P313-P403+P233-P405-P501UN#:
Hazard Statements:H315-H319-H335Packing Group:
GHS Pictogram:

Application In Synthesis of [ 870778-88-4 ]

  • Downstream synthetic route of [ 870778-88-4 ]

[ 870778-88-4 ] Synthesis Path-Downstream   1~7

  • 1
  • [ 90-11-9 ]
  • [ 870778-88-4 ]
  • [ 1246888-95-8 ]
  • 2
  • [ 870778-88-4 ]
  • [ 67061-69-2 ]
  • [ 1353974-87-4 ]
YieldReaction ConditionsOperation in experiment
71% With potassium phosphate;dicyclohexyl-(2',6'-dimethoxybiphenyl-2-yl)-phosphane; palladium diacetate; In tetrahydrofuran; toluene; at 110℃; for 8h;Inert atmosphere; Example 6Synthesis of compound XX-8[0103][Chem. 15] [0104] In a 50-mL reaction container, XX-4 (177.05 mg,0.50 mmol) and 2-isopropoxy-6-methoxyphenylboronic acid (420 mg, 2.0 mmol) were mixed in a toluene/tetrahydrofuran (6 mL/3 mL) mixture solvent, and dissolved oxygen was removed by nitrogen. Then, Pd(OAc)2 (2.3 mg, 0.01 mmol), 2- dicyclohexylphosphino-2 ' , 6 ' -dimethoxybiphenyl (S-Phos) (10.3 mg, 0.025 mmol), and tripotassium phosphate (575.7 mg, 2.5 mmol) were added to the mixture under a nitrogen atmosphere, followed by heating to reflux at 110C for 8 hours. The reaction solution was cooled to room temperature,concentrated under reduced pressure, and subjected to silica gel chromatography (mobile phase: hexane/chloroform = 1/2) for isolation and purification to obtain XX-8 (187 mg, yield: 71%) as a white solid powder.[0105] Mass-spectrometry (MS) and nuclear magnetic resonance spectrometry (NMR) of compound XX-8 gave the results that the molecular weight and the ratio ofintegrated values of NMR peaks well agreed with thestructure of compound XX-8. Specifically, 524 as M+ of this compound was confirmed by matrix-assisted laser desorption- ionization mass spectrometry (MALDI-MS) . The measurement results of nuclear magnetic resonance spectrometry are shown below :XH-NMR (CDCI3) ? (ppm) : 7.72 (s, 2H) , 7.22 (t, 2H) , 6.68 (d, 2H) , 6.65 (d, 2H) , 4.59 (m, 2H), 3.88 (s, 6H) , 1.36 (s, 6H) , 1.35 (s, 6H) .13C-NMR (CDCI3) ? (ppm): 157.98, 156.07, 139.80, 134.87,131.70, 128.52, 122.26, 114.16, 107.54, 104.23, 71.62, 55.98, 22.15.
71% With dicyclohexyl-(2',6'-dimethoxybiphenyl-2-yl)-phosphane; potassium phosphate; palladium diacetate; In tetrahydrofuran; toluene; at 110℃; for 8h;Inert atmosphere; <Synthesis Example 4: Synthesis of Exemplified Compound A-12>[0137] In a 50-ml reaction vessel, XX-1 (177.05 mg, 0.50 mmol) and 2-isopropoxy-6-methoxyphenylboronic acid (420 mg, 2.0 mmol) were mixed in a toluene/tetrahydrofuran (6 ml/3 ml) mixed solvent. Dissolved oxygen was removed by nitrogen. [0138] Next, Pd(OAc)2 (2.3 mg, 0.01 mmol), 2-dicyclohexylphosphino-2',6'-dimethoxybiphenyl (S-Phos) (10.3 mg, 0.025 mmol), and tripotassium phosphate (575.7 mg, 2.5 mmol) were added thereto in a nitrogen atmosphere. The mixture was then heated at 110C to perform a reaction for 8 hours. [0139] The reaction solution was cooled to room temperature and then concentrated under reduced pressure. Separation and purification were performed by silica-gel chromatography (mobile phase: hexane/chloroform = 1/2) to give a white solid power A-12 (187 mg, yield: 71%). Measurement by MALDl-MS demonstrated that M+ of this compound was found to be 524.
71% With dicyclohexyl-(2',6'-dimethoxybiphenyl-2-yl)-phosphane; potassium phosphate; palladium diacetate; In tetrahydrofuran; toluene; at 110℃; for 8h;Inert atmosphere; In a 50 ml reaction vessel, 177.05 mg (0.50 mmol) of XX-11, 420 mg (2.0 mmol) of 2-isopropoxy-6-methoxyphenylboronic acid: Were mixed in a mixed solvent of toluene / tetrahydrofuran (6 ml / 3 ml), and dissolved oxygen was removed with nitrogen. Next, Pd (OAc) 2: 2.3 mg (0.01 mmol), 2-dicyclohexylphosphino-2 ', 6'- dimethoxybiphenyl (S-Phos): 10.3 mg (0.0 25 mmol) and tripotassium phosphate: 575.7 mg (2.5 mmol) were added in a nitrogen atmosphere, and the mixture was heated under reflux at 110 C. for 8 hours. The reaction solution was cooled to room temperature, concentrated under reduced pressure and separated and purified by silica gel chromatography (mobile phase: hexane / chloroform = 1/2) to obtain D-16 as a white solid powder (187 mg, yield 71%
  • 3
  • [ 4805-22-5 ]
  • [ 870778-88-4 ]
  • [ 1415917-11-1 ]
YieldReaction ConditionsOperation in experiment
84.1% With dicyclohexyl-(2',6'-dimethoxybiphenyl-2-yl)-phosphane; potassium phosphate; palladium diacetate; In tetrahydrofuran; toluene; at 110℃; for 8h;Inert atmosphere; In a 50-mL reaction container, 326.3 mg (1.01 mmol) of XX-4 (2, 5-dibromobithiophene) and 749.8 mg (3.57 mmol) of 2-isopropoxy-6-methoxyphenylboronic acid were mixed in a toluene/tetrahydrofuran (4 mL/4 mL) solvent mixture, and dissolved oxygen was removed by nitrogen. [0119] Subsequently, 5.9 mg (0.026 mmol) of Pd(OAc)2, 21.4 mg (0.052 mmol) of 2-dicyclohexylphosphino-2 ', 6'- dimethoxybiphenyl (S-Phos), and 1123.7 mg (4.88 mmol) of tripotassxum phosphate were added to the mixture under a nitrogen atmosphere, followed by heating to reflux at 110C for 8 hours. [0120] The reaction solution was cooled to room temperature, concentrated under reduced pressure, and subjected to silica gel chromatography (mobile phase: hexane/chloroform = 1/3) for isolation and purification to give compound B-l (418.8 mg, yield: 84.1%) as a white solid powder . [0121] As in Example 1, the structure of compound B-l was confirmed by NMR and MALDI-MS . Specifically, 494 as M+ of this compound was confirmed by MALDI-MS. The measurement results of NMR are shown below: 1NMR (CDCl3) σ (ppm) : 7.48 (d,2H), 7.18 (t,2H), 7.17 (d,2H), 6.65 (d,2H), 6.62 (d,2H), 4.58 (sept,2H), 3.87 (s,6H), 1.36 (s, 12H) . 13C-NMR (CDCl3) σ (ppm): 158.12, 156.14, 137.72, 133.35, 130.02, 128.42, 122.49, 114.24, 107.88, 104.54, 71.88, 56.27, 22.46.
84.1% With dicyclohexyl-(2',6'-dimethoxybiphenyl-2-yl)-phosphane; potassium phosphate; palladium diacetate; In tetrahydrofuran; toluene; at 110℃; for 8h;Inert atmosphere; <Synthesis Example 7: Synthesis of Exemplified Compound B-7>0149] In a 50-ml reaction vessel, XX-7 (2,5-dibromobithiophene) (326.3 mg, 1.01 mmol) and 2-isopropoxy-6-methoxyphenylboronic acid (749.8 mg, 3.57 mmol) were mixed in a toluene/tetrahydrofuran (4 ml/4 ml) mixed solvent. Dissolved oxygen was removed by nitrogen. [0150] Next, Pd(OAc)2 (5.9 mg, 0.026 mmol), 2-dicyclohexylphosphino-2',6'-dimethoxybiphenyl (S-Phos) (21.4 mg, 0.052 mmol), and tripotassium phosphate (1123.7 mg, 4.88 mmol) were added thereto in a nitrogen atmosphere. The mixture was then heated and refluxed at 110C to perform a reaction for 8 hours. [0151] The reaction solution was cooled to room temperature and then concentrated under reduced pressure. Separation and purification were performed by silica-gel chromatography (mobile phase: hexane/chloroform = 1/3) to give a white solid power B-7 (418.8 mg, yield: 84.1%). Measurement by MALDl-MS demonstrated that M+ of this compound was found to be 494.2.
  • 4
  • [ 870778-88-4 ]
  • [ 174508-31-7 ]
  • [ 1415917-07-5 ]
YieldReaction ConditionsOperation in experiment
54% With dicyclohexyl-(2',6'-dimethoxybiphenyl-2-yl)-phosphane; potassium phosphate; palladium diacetate; In tetrahydrofuran; toluene; at 110℃; for 7h;Inert atmosphere; In a 50-mL reaction container, 500 mg (1.67 mmol) of XX-2 (2, 5-dibromo-ethylenedioxythiophene) and 1.05 g (5.0 mmol) of 2-isopropoxy-6-methoxyphenylboronic acid were mixed in a toluene/tetrahydrofuran (10 mL/5 mL) solvent mixture, and dissolved oxygen was removed by nitrogen. Subsequently, 19 mg (0.083 mmol) of Pd(0Ac)2, 89 mg (0.22 mmol) of 2- dicyclohexylphosphino-2', 6 ' -dimethoxybiphenyl (S-Phos) , and 1.92 g (8.35 mmol) of tripotassium phosphate were added to the mixture under a nitrogen atmosphere, followed by heating to reflux at 110C for 7 hours. The reaction solution was cooled to room temperature, concentrated under reduced pressure, and subjected to silica gel chromatography (mobile phase: hexane/ethyl acetate = 4/3) for isolation and purification to give compound A-ll (420 mg, yield: 54%) as a white solid powder. [0112] As in Example 1, the structure of compound A-ll was confirmed by NMR and MALDI-MS. Specifically, 470 as M+ of this compound was confirmed by MALDI-MS. The measurement results of NMR are shown below: 1H-NMR (CDCl3) (ppm) : 7.21 (t,2H), 6.63 (d,2H), 6.60 (d,2H), 4.41 (m,2H), 4.20 (s,4H), 3.81 (s,6H), 1.25 (s,6H), 1.24 (s, 6H) . 13C-NMR (CDCl3) sigma (ppm): 159.01, 157.52, 138.10, 129.20, 112.07, 108.96, 108.36, 104.53, 71.80, 64.49, 56.06, 22.23
54% With dicyclohexyl-(2',6'-dimethoxybiphenyl-2-yl)-phosphane; potassium phosphate; palladium diacetate; In tetrahydrofuran; toluene; at 110℃; for 7h;Inert atmosphere; <Synthesis Example 6: Synthesis of Exemplified Compound B-6>0145] In a 50-ml reaction vessel, XX-6 (2,5-dibromoethylenedioxythiophene) (500 mg, 1.67 mmol) and 2-isopropoxy-6-methoxyphenylboronic acid (1.05 g, 5.0 mmol) were mixed in a toluene/tetrahydrofuran (10 ml/5 ml) mixed solvent. Dissolved oxygen was removed by nitrogen. [0146] Next, Pd(OAc)2 (19 mg, 0.083 mmol), 2-dicyclohexylphosphino-2',6'-dimethoxybiphenyl (S-Phos) (89 mg, 0.22 mmol), and tripotassium phosphate (1.92 g, 8.35 mmol) were added thereto in a nitrogen atmosphere. The mixture was then heated and refluxed at 110C to perform a reaction for 7 hours. [0147] The reaction solution was cooled to room temperature and then concentrated under reduced pressure. Separation and purification were performed by silica-gel chromatography (mobile phase: hexane/ethyl acetate = 4/3) to give a white solid power B-6 (420 mg, yield: 54%). Measurement by MALDl-MS demonstrated that M+ of this compound was found to be 470.
54% With dicyclohexyl-(2',6'-dimethoxybiphenyl-2-yl)-phosphane; potassium phosphate; palladium diacetate; In tetrahydrofuran; toluene; at 110℃; for 7h;Inert atmosphere; With a 50-ml reaction container, XX-9(2,5-dibromoethylene dioxythiophene):500mg (1.67mmol), 2-isopropoxy 6-methoxy phenylboronic acid: 1.05 g (5.0mmol) was mixed in toluene / tetrahydrofuran (10-ml/five ml) mixed solvent, and nitrogen removed dissolved oxygen.Next, Pd(OAc) 2:19mg (0.083mmol), 2-dicyclohexyl phosphino 2',6'-dimethoxybiphenyl (S-Phos): 89 mg (0.22mmol) and phosphoric-acid 3 potassium posphate: 1.92 g (8.35mmol) was added under a nitrogen atmosphere, and it heated at reflux at 110 degrees C, and performed the reaction for 7 hours. The reaction solution was concentrated in vacuum after cooling to the room temperature, separation refinement was carried out with silica gel chromatography (mobile phase: hexane/ethyl acetate =4/3), and D-6 of white solid powder was obtained (420 mg, 54% of yield).
  • 5
  • [ 25121-87-3 ]
  • [ 870778-88-4 ]
  • [ 1415917-17-7 ]
YieldReaction ConditionsOperation in experiment
75% With dicyclohexyl-(2',6'-dimethoxybiphenyl-2-yl)-phosphane; potassium phosphate; palladium diacetate; In tetrahydrofuran; toluene; at 110℃; for 8h;Inert atmosphere; <Synthesis Example 9: Synthesis of Exemplified Compound B-11>[0157] In a 50-ml reaction vessel, XX-9 (200 mg, 0.671 mmol) and 2-isopropoxy-6-methoxyphenylboronic acid (563 mg, 2.684 mmol) were mixed in a toluene/tetrahydrofuran (6 ml/3 ml) mixed solvent. Dissolved oxygen was removed by nitrogen. [0158] Next, Pd(OAc)2 (3.0 mg, 0.013 mmol), 2-dicyclohexylphosphino-2',6'-dimethoxybiphenyl (S-Phos) (13.8 mg, 0.034 mmol), and tripotassium phosphate (772 mg, 3.36 mmol) were added thereto in a nitrogen atmosphere. The mixture was then heated and refluxed at 110C to perform a reaction for 8 hours. [0159] The reaction solution was cooled to room temperature and then concentrated under reduced pressure. Separation and purification were performed by silica-gel chromatography (mobile phase: hexane/chloroform = 1/2) to give a white solid power B-11 (235 mg, yield: 75%). Measurement by MALDl-MS demonstrated that M+ of this compound was found to be 468.
75% With dicyclohexyl-(2',6'-dimethoxybiphenyl-2-yl)-phosphane; potassium phosphate; palladium diacetate; In tetrahydrofuran; toluene; at 110℃; for 8h;Inert atmosphere; a 50-ml reaction container -- XX-10:200mg (0.671mmol) and the 2-isopropoxy 6 - methoxy-phenylboronic acid:563mg (2.684mmol) was dissolved into toluene / tetrahydrofuran (6-ml/three ml) mixed solvent, and nitrogen removed dissolved oxygen.Next, Pd(OAc) 2:3.0mg (0.013mmol), 2-dicyclohexyl phosphino 2',6'-dimethoxybiphenyl (S-Phos): 13.8 mg (0.034mmol) and phosphoric-acid 3 potassium: 772 mg (3.36mmol) was added under a nitrogen atmosphere, and it heated at reflux at 110 degrees C, and performed the reaction for 8 hours. The reaction solution was concentrated in vacuum after cooling to the room temperature, separation refinement was carried out with silica gel chromatography (mobile phase: hexane/chloroform =1/2), and D-14 of white solid powder was obtained (235 mg, 75% of yield).
  • 6
  • [ 36848-40-5 ]
  • [ 870778-88-4 ]
  • C32H32N2O4 [ No CAS ]
YieldReaction ConditionsOperation in experiment
75% With dicyclohexyl-(2',6'-dimethoxybiphenyl-2-yl)-phosphane; potassium phosphate; palladium diacetate In 1,4-dioxane; toluene at 110℃; for 8h; Inert atmosphere; 1 The example compound A-21 can be synthesized, for example, by the following procedure. First, a compound XX-2 is synthesized. In a 50-ml reaction chamber, 676 mg (2.0 mmol) of a compound XX-1 and 1.26 g (6.0 mmol) of 2-isopropoxy-6-methoxyphenylboronic acid were mixed together in a mixed solvent of toluene/1,4-dioxane (7 ml/7 ml), and dissolved oxygen was removed by nitrogen. In addition, the compound XX-1 was a compound synthesized in accordance with Tetrahedron Letters, 52, 6484 (2011).Next, 18.0 mg (0.08 mmol) of Pd(OAc)2, 82.1 mg (0.10 mmol) of 2-dicyclohexylphosphino-2′,6′-dimethoxybiphenyl (S-Phos), and 2.30 g (10.0 mmol) of tripotassium phosphate were added in a nitrogen atmosphere, and a reaction was performed by heating and refluxing at 110° C. for 8 hours.After the reaction solution was cooled to room temperature and was then condensed at a reduced pressure, separation and purification were performed by a silica gel chromatography (mobile phase: hexane/chloroform), so that a yellow solid compound XX-2 was obtained (770 mg, yield: 75%).
  • 7
  • [ 36848-40-5 ]
  • [ 870778-88-4 ]
  • C38H46N2O4 [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: palladium diacetate; dicyclohexyl-(2',6'-dimethoxybiphenyl-2-yl)-phosphane; potassium phosphate / toluene; 1,4-dioxane / 8 h / 110 °C / Inert atmosphere 2: sodium dithionite; potassium carbonate / acetonitrile; water / 9 h / 90 °C / Inert atmosphere
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