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[ CAS No. 1186377-08-1 ] {[proInfo.proName]}

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Chemical Structure| 1186377-08-1
Chemical Structure| 1186377-08-1
Structure of 1186377-08-1 * Storage: {[proInfo.prStorage]}
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Product Details of [ 1186377-08-1 ]

CAS No. :1186377-08-1 MDL No. :MFCD16996402
Formula : C16H21BO6 Boiling Point : -
Linear Structure Formula :- InChI Key :ZDIIHFUQYYAUAD-UHFFFAOYSA-N
M.W : 320.15 Pubchem ID :68648457
Synonyms :

Calculated chemistry of [ 1186377-08-1 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 23
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.5
Num. rotatable bonds : 5
Num. H-bond acceptors : 6.0
Num. H-bond donors : 0.0
Molar Refractivity : 85.48
TPSA : 71.06 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : Yes
P-gp substrate : Yes
CYP1A2 inhibitor : No
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -6.4 cm/s

Lipophilicity

Log Po/w (iLOGP) : 0.0
Log Po/w (XLOGP3) : 2.61
Log Po/w (WLOGP) : 1.56
Log Po/w (MLOGP) : 1.4
Log Po/w (SILICOS-IT) : 1.78
Consensus Log Po/w : 1.47

Druglikeness

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

Water Solubility

Log S (ESOL) : -3.33
Solubility : 0.149 mg/ml ; 0.000465 mol/l
Class : Soluble
Log S (Ali) : -3.75
Solubility : 0.0567 mg/ml ; 0.000177 mol/l
Class : Soluble
Log S (SILICOS-IT) : -4.13
Solubility : 0.0238 mg/ml ; 0.0000745 mol/l
Class : Moderately soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 2.0 alert
Leadlikeness : 0.0
Synthetic accessibility : 3.48

Safety of [ 1186377-08-1 ]

Signal Word:Warning Class:
Precautionary Statements:P261-P264-P270-P271-P280-P301+P312-P302+P352-P304+P340-P305+P351+P338-P330-P332+P313-P337+P313-P362-P403+P233-P405-P501 UN#:
Hazard Statements:H302-H315-H319-H335 Packing Group:
GHS Pictogram:

Application In Synthesis of [ 1186377-08-1 ]

* 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.

  • Downstream synthetic route of [ 1186377-08-1 ]

[ 1186377-08-1 ] Synthesis Path-Downstream   1~22

  • 1
  • [ 1186377-08-1 ]
  • [ 1351221-58-3 ]
YieldReaction ConditionsOperation in experiment
55% With hydrogenchloride; water at 60℃; for 4h;
  • 2
  • [ 5372-81-6 ]
  • [ 1186377-08-1 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1.1: sulfuric acid; sodium nitrite / water / 1 h / 0 - 5 °C 1.2: 0.33 h / 60 °C 2.1: 1,3-bis[(diphenylphosphino)propane]dichloronickel(II); N-Methyldicyclohexylamine / toluene / 12 h / Reflux; Inert atmosphere
  • 3
  • [ 165534-79-2 ]
  • [ 25015-63-8 ]
  • [ 1186377-08-1 ]
YieldReaction ConditionsOperation in experiment
71% With 1,3-bis[(diphenylphosphino)propane]dichloronickel(II); N-Methyldicyclohexylamine In toluene for 12h; Reflux; Inert atmosphere;
71% With 1,3-bis[(diphenylphosphino)propane]dichloronickel(II) In toluene for 12h; Reflux;
  • 4
  • [ 18643-86-2 ]
  • [ 73183-34-3 ]
  • [ 1186377-08-1 ]
YieldReaction ConditionsOperation in experiment
81% With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; potassium acetate; In 1,4-dioxane; at 100℃; for 3h;Inert atmosphere; To a stirred solution of dimethyl 2-bromobenzene-1 ,4-dicarboxylate (15.8 g, 57.9 mmol) in 1 ,4 dioxane (140 mL) was added fused potassium acetate (17.2 g, 174 mmol), 4,4,5,5-tetramethyl-2- (4,4,5,5-tetramethyl-1 ,3,2-dioxaborolan-2-yl)-1 ,3,2-dioxaborolane (19.1 g, 75.2 mmol) and finally [1 , 1 - Bis(diphenylphosphino) ferrocene]-dichloropalladium(ll) dichloromethane adduct (2.41 g, 2.89 mmol) under nitrogen. The reaction mixture was heated at 100C for 3 h. The reaction mixture was cooled to ambient temperature and diluted with water (100 mL) and then extracted with ethyl acetate (3 x 200 mL). Combined organic layer was washed with water (3 x 200 mL) followed by brine wash (200 mL). Organic layer was dried over sodium sulfate, filtered and evaporated completely to give crude compound. This crude obtained was purified by flash chromatography using 10% ethyl acetate in hexane as eluent to afford desired compound dimethyl 2-(4,4,5,5-tetramethyl-1 ,3,2-dioxaborolan-2- yl)benzene-1 ,4-dicarboxylate (15 g, 81 % of theoretical yield). H NMR (400 MHz, CHLOROFORM-c/) δ ppm 1.41 - 1.45 (m, 15 H) 3.94 (s, 6 H) 8.00 (s, 1 H) 8.05 - 8.13 (m, 1 H) 8.16 (s, 1 H)
With potassium acetate;(1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; In 1,4-dioxane; at 80℃;Inert atmosphere; Step 2[00263] Bis-(pinacolato)diboron (4.93 g, 19.40 mmol), 1 , 1*-Bis(diphenyl phosphino)ferrocene]dichloropalladium (II) (0.72 g, 0.88 mmol), potassium acetate (5.19 g, 17.65 mmol) were dissolved in dioxane (40 ml) and flushed with argon. A solution of <strong>[18643-86-2]dimethyl 2-bromoterephthalate</strong> (CV) (4.82 g, 17.65 mmol) in dioxane (15 mL) was then added and the reaction mixture was heated at 80C overnight. The solids were filtered off and washed with EtOAc. The combined organic phases were concentrated under vacuum and the residue was dissolved in EtOAc, washed with water, dried over anhydrous MgS04 and concentrated to give 8.01 g of a black oil. The oil was purified by silica gel chromatography (DCM/MeOH 1000: 1→500: 1→200: 1→100: 1) to give dimethyl 2-(4,4,5,5-tetramethyl-l,3,2-dioxaborolan-2- yl)terephthalate (CVI) (2.60 g, 8.12 mmol, 51% purity, 23% yield). ESIMS found for Ci6H2iB06 mlz 243.3 (M+Na).
  • 5
  • [ 586-35-6 ]
  • [ 1186377-08-1 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: potassium carbonate / N,N-dimethyl-formamide / 20 °C 2: potassium acetate / (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / 1,4-dioxane / 80 °C / Inert atmosphere
Multi-step reaction with 3 steps 1: thionyl chloride / 5 h / 100 °C 2: triethylamine / 2 h / 0 - 20 °C / Inert atmosphere 3: potassium acetate; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2 / 1,4-dioxane / 3 h / 100 °C / Inert atmosphere
  • 6
  • [ 1186377-08-1 ]
  • [ 947162-87-0 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1.1: diisobutylaluminium hydride / dichloromethane / 2 h / -10 - 0 °C / Inert atmosphere 1.2: 0.08 h 2.1: hydrogenchloride / water / 60 °C
  • 7
  • [ 1186377-08-1 ]
  • [ 1393477-21-8 ]
YieldReaction ConditionsOperation in experiment
Stage #1: dimethyl 2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzene-1,4-dicarboxylate With diisobutylaluminium hydride In dichloromethane at -10 - 0℃; for 2h; Inert atmosphere; Stage #2: With hydrogenchloride In water for 0.0833333h; Step 3[00264] Dimethyl 2-(4,4,5,5-tetramethyl-l,3,2-dioxaborolan-2-yl)terephthalate (CVI) (2.60 g, 8.12 mmol) was dissolved in DCM (25 mL), flushed with argon and cooled to -10°C. A 1 M solution of diisobutylaluminum hydride in DCM (48.73 mL, 48.73 mmol) was then added dropwise and the reaction was stirred at 0°C for 2 h. 1 N aqueous HCI (50 mL) was carefully added and stirred for 5 minutes. The reaction was extracted with DCM and the combined extracts were washed with brine, dried over anhydrous MgS04 and concentrated to give (2- (4,4,5,5-tetramethyl-l,3,2-dioxaborolan-2-yl)-l,4-phenylene)dimethanol (CVII) (2.0 g, 7.57 mmol). The crude product was used without further purification for step 4.
  • 8
  • [ 1186377-08-1 ]
  • [ 1393477-22-9 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1.1: diisobutylaluminium hydride / dichloromethane / 2 h / -10 - 0 °C / Inert atmosphere 1.2: 0.08 h 2.1: hydrogenchloride / water / 60 °C 3.1: triethylamine / dichloromethane / 20 °C
  • 9
  • [ 1186377-08-1 ]
  • [ 1393477-23-0 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1.1: diisobutylaluminium hydride / dichloromethane / 2 h / -10 - 0 °C / Inert atmosphere 1.2: 0.08 h 2.1: hydrogenchloride / water / 60 °C 3.1: triethylamine / dichloromethane / 20 °C 4.1: sodium iodide; sodium azide / N,N-dimethyl-formamide / 60 °C
  • 10
  • [ 591-50-4 ]
  • [ 1186377-08-1 ]
  • [ 84269-70-5 ]
YieldReaction ConditionsOperation in experiment
83% With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In water; toluene for 18h; Reflux; Inert atmosphere;
  • 11
  • [ 108-86-1 ]
  • [ 1186377-08-1 ]
  • [ 84269-70-5 ]
YieldReaction ConditionsOperation in experiment
45% With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In water; toluene for 18h; Reflux; Inert atmosphere;
  • 12
  • [ 636-98-6 ]
  • [ 1186377-08-1 ]
  • [ 1451870-46-4 ]
YieldReaction ConditionsOperation in experiment
71% With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In water; toluene for 18h; Reflux; Inert atmosphere;
  • 13
  • [ 1003-09-4 ]
  • [ 1186377-08-1 ]
  • [ 1451870-49-7 ]
YieldReaction ConditionsOperation in experiment
42% With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In water; toluene for 18h; Reflux; Inert atmosphere;
  • 14
  • [ 3034-53-5 ]
  • [ 1186377-08-1 ]
  • [ 1451870-52-2 ]
YieldReaction ConditionsOperation in experiment
58% With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In water; toluene for 18h; Reflux; Inert atmosphere;
  • 15
  • [ 1186377-08-1 ]
  • methyl 1-hydroxy-3H-2,1-benzoxaborole-6-carboxylate [ No CAS ]
YieldReaction ConditionsOperation in experiment
88% With sodium tetrahydroborate In methanol at 0 - 20℃; for 12h; 6 Example P6: Preparation of methyl 1-hvdroxy-3H-2, 1-benzoxaborole-6-carboxylate: To a stirred solution of dimethyl 2-(4,4,5,5-tetramethyl-1 ,3,2-dioxaborolan-2-yl)benzene-1 ,4- dicarboxylate (17 g, 53.1 1 mmol) in methanol (170 mL) was added sodium borohydride (4.2 g, 106.2 mmol) in portions at 0°C. The reaction mixture was then allowed to stir at ambient temperature for 12 h. The reaction mixture was diluted with water (100 mL) and evaporated under reduced pressure. The residual mass was diluted with 2N HCI to pH 2 and stirred for 4 h. Precipitation of fine white solid occurred, which was collected by filtration and washed with water and dried under vacuum to afford methyl 1-hydroxy-3H-2, 1-benzoxaborole-6-carboxylate (9 g, 88% of theoretical yield) as a white solid. H NMR (400 MHz, DMSO-c/6) δ ppm 3.33 (s, 3 H) 3.88 (s, 3 H) 5.07 (s, 2 H) 7.56 (dd, J=8.03, 0.75 Hz, 1 H) 8.07 (d, J=8.13 Hz, 1 H) 8.41 (s, 1 H) 9.39 (s, 1 H) LC-MS- M+H- 193 (RT;1 .40-1.42)
  • 16
  • [ 1186377-08-1 ]
  • [ 1221343-14-1 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: sodium tetrahydroborate / methanol / 12 h / 0 - 20 °C 2: sodium hydroxide / water / 12 h / 50 °C
  • 17
  • [ 1186377-08-1 ]
  • ethyl 1-hydroxy-3H-2,1-benzoxaborole-6-carboxylate [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: sodium tetrahydroborate / methanol / 12 h / 0 - 20 °C 2: sodium hydroxide / water / 12 h / 50 °C 3: sulfuric acid / Reflux
  • 18
  • [ 1186377-08-1 ]
  • 3-thienylmethyl 1-hydroxy-3H-2,1-benzoxaborole-6-carboxylate [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: sodium tetrahydroborate / methanol / 12 h / 0 - 20 °C 2: sodium hydroxide / water / 12 h / 50 °C 3: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; dmap / dichloromethane / 5 h / 20 °C
  • 19
  • [ 1186377-08-1 ]
  • N-[(4-chlorophenyl)methyl]-1-hydroxy-3H-2,1-benzoxaborole-6-carboxamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: sodium tetrahydroborate / methanol / 12 h / 0 - 20 °C 2: sodium hydroxide / water / 12 h / 50 °C 3: triethylamine; HATU / dichloromethane / 12 h / 20 °C
  • 20
  • [ 1186377-08-1 ]
  • 1-hydroxy-N-methoxy-N-methyl-3H-2,1-benzoxaborole-6-carboxamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: sodium tetrahydroborate / methanol / 12 h / 0 - 20 °C 2: sodium hydroxide / water / 12 h / 50 °C 3: triethylamine; 2,4,6-tripropyl-1,3,5,2,4,6-trioxatriphosphinane-2,4,6-trioxide / dichloromethane / 3 h / 20 °C
  • 21
  • [ 553-94-6 ]
  • [ 1186377-08-1 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1: potassium permanganate / water / 12 h / 70 °C 2: thionyl chloride / 5 h / 100 °C 3: triethylamine / 2 h / 0 - 20 °C / Inert atmosphere 4: potassium acetate; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2 / 1,4-dioxane / 3 h / 100 °C / Inert atmosphere
  • 22
  • [ 13815-89-9 ]
  • [ 1186377-08-1 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: triethylamine / 2 h / 0 - 20 °C / Inert atmosphere 2: potassium acetate; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2 / 1,4-dioxane / 3 h / 100 °C / Inert atmosphere
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