361456-68-0|Benzo[d][1,3]dioxol-4-ylboronic acid| Ambeed

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Quality Control of [ 361456-68-0 ] Purity: 97% SDS Specification

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Product Details of [ 361456-68-0 ]

CAS No. :	361456-68-0
Formula :	C₇H₇BO₄
M.W :	165.94
SMILES Code :	OB(C1=C2OCOC2=CC=C1)O
MDL No. :	MFCD03095113
InChI Key :	BEIKNVAUEWMMAZ-UHFFFAOYSA-N
Pubchem ID :	4192659

Safety of [ 361456-68-0 ]

GHS Pictogram:
Signal Word:	Warning
Hazard Statements:	H302-H315-H319-H335
Precautionary Statements:	P261-P305+P351+P338

Computational Chemistry of [ 361456-68-0 ] Show Less

Physicochemical Properties

Num. heavy atoms	12
Num. arom. heavy atoms	6
Fraction Csp3	0.14
Num. rotatable bonds	1
Num. H-bond acceptors	4.0
Num. H-bond donors	2.0
Molar Refractivity	42.33
TPSA ? Topological Polar Surface Area: Calculated from Ertl P. et al. 2000 J. Med. Chem.	58.92 Å²

Lipophilicity

Log P_o/w (iLOGP)? iLOGP: in-house physics-based method implemented from Daina A et al. 2014 J. Chem. Inf. Model.	0.0
Log P_o/w (XLOGP3)? XLOGP3: Atomistic and knowledge-based method calculated by XLOGP program, version 3.2.2, courtesy of CCBG, Shanghai Institute of Organic Chemistry	0.64
Log P_o/w (WLOGP)? WLOGP: Atomistic method implemented from Wildman SA and Crippen GM. 1999 J. Chem. Inf. Model.	-0.9
Log P_o/w (MLOGP)? MLOGP: Topological method implemented from Moriguchi I. et al. 1992 Chem. Pharm. Bull. Moriguchi I. et al. 1994 Chem. Pharm. Bull. Lipinski PA. et al. 2001 Adv. Drug. Deliv. Rev.	-0.57
Log P_o/w (SILICOS-IT)? SILICOS-IT: Hybrid fragmental/topological method calculated by FILTER-IT program, version 1.0.2, courtesy of SILICOS-IT, http://www.silicos-it.com	-0.69
Consensus Log P_o/w? Consensus Log P_o/w: Average of all five predictions	-0.31

Water Solubility

Log S (ESOL):? ESOL: Topological method implemented from Delaney JS. 2004 J. Chem. Inf. Model.	-1.58
Solubility	4.4 mg/ml ; 0.0265 mol/l
Class? Solubility class: Log S scale Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly	Very soluble
Log S (Ali)? Ali: Topological method implemented from Ali J. et al. 2012 J. Chem. Inf. Model.	-1.45
Solubility	5.85 mg/ml ; 0.0353 mol/l
Class? Solubility class: Log S scale Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly	Very soluble
Log S (SILICOS-IT)? SILICOS-IT: Fragmental method calculated by FILTER-IT program, version 1.0.2, courtesy of SILICOS-IT, http://www.silicos-it.com	-1.03
Solubility	15.4 mg/ml ; 0.0927 mol/l
Class? Solubility class: Log S scale Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly	Soluble

Pharmacokinetics

GI absorption? Gatrointestinal absorption: according to the white of the BOILED-Egg	High
BBB permeant? BBB permeation: according to the yolk of the BOILED-Egg	No
P-gp substrate? P-glycoprotein substrate: SVM model built on 1033 molecules (training set) and tested on 415 molecules (test set) 10-fold CV: ACC=0.72 / AUC=0.77 External: ACC=0.88 / AUC=0.94	No
CYP1A2 inhibitor? Cytochrome P450 1A2 inhibitor: SVM model built on 9145 molecules (training set) and tested on 3000 molecules (test set) 10-fold CV: ACC=0.83 / AUC=0.90 External: ACC=0.84 / AUC=0.91	No
CYP2C19 inhibitor? Cytochrome P450 2C19 inhibitor: SVM model built on 9272 molecules (training set) and tested on 3000 molecules (test set) 10-fold CV: ACC=0.80 / AUC=0.86 External: ACC=0.80 / AUC=0.87	No
CYP2C9 inhibitor? Cytochrome P450 2C9 inhibitor: SVM model built on 5940 molecules (training set) and tested on 2075 molecules (test set) 10-fold CV: ACC=0.78 / AUC=0.85 External: ACC=0.71 / AUC=0.81	No
CYP2D6 inhibitor? Cytochrome P450 2D6 inhibitor: SVM model built on 3664 molecules (training set) and tested on 1068 molecules (test set) 10-fold CV: ACC=0.79 / AUC=0.85 External: ACC=0.81 / AUC=0.87	No
CYP3A4 inhibitor? Cytochrome P450 3A4 inhibitor: SVM model built on 7518 molecules (training set) and tested on 2579 molecules (test set) 10-fold CV: ACC=0.77 / AUC=0.85 External: ACC=0.78 / AUC=0.86	No
Log Kp (skin permeation)? Skin permeation: QSPR model implemented from Potts RO and Guy RH. 1992 Pharm. Res.	-6.86 cm/s

Druglikeness

Lipinski? Lipinski (Pfizer) filter: implemented from Lipinski CA. et al. 2001 Adv. Drug Deliv. Rev. MW ≤ 500 MLOGP ≤ 4.15 N or O ≤ 10 NH or OH ≤ 5	0.0
Ghose? Ghose filter: implemented from Ghose AK. et al. 1999 J. Comb. Chem. 160 ≤ MW ≤ 480 -0.4 ≤ WLOGP ≤ 5.6 40 ≤ MR ≤ 130 20 ≤ atoms ≤ 70	None
Veber? Veber (GSK) filter: implemented from Veber DF. et al. 2002 J. Med. Chem. Rotatable bonds ≤ 10 TPSA ≤ 140	0.0
Egan? Egan (Pharmacia) filter: implemented from Egan WJ. et al. 2000 J. Med. Chem. WLOGP ≤ 5.88 TPSA ≤ 131.6	0.0
Muegge? Muegge (Bayer) filter: implemented from Muegge I. et al. 2001 J. Med. Chem. 200 ≤ MW ≤ 600 -2 ≤ XLOGP ≤ 5 TPSA ≤ 150 Num. rings ≤ 7 Num. carbon > 4 Num. heteroatoms > 1 Num. rotatable bonds ≤ 15 H-bond acc. ≤ 10 H-bond don. ≤ 5	1.0
Bioavailability Score? Abbott Bioavailability Score: Probability of F > 10% in rat implemented from Martin YC. 2005 J. Med. Chem.	0.55

Medicinal Chemistry

PAINS? Pan Assay Interference Structures: implemented from Baell JB. & Holloway GA. 2010 J. Med. Chem.	0.0 alert
Brenk? Structural Alert: implemented from Brenk R. et al. 2008 ChemMedChem	1.0 alert: heavy_metal
Leadlikeness? Leadlikeness: implemented from Teague SJ. 1999 Angew. Chem. Int. Ed. 250 ≤ MW ≤ 350 XLOGP ≤ 3.5 Num. rotatable bonds ≤ 7	No; 1 violation:MW<1.0
Synthetic accessibility? Synthetic accessibility score: from 1 (very easy) to 10 (very difficult) based on 1024 fragmental contributions (FP2) modulated by size and complexity penaties, trained on 12'782'590 molecules and tested on 40 external molecules (r² = 0.94)	2.69

Application In Synthesis of [ 361456-68-0 ]

* 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 [ 361456-68-0 ]

[ 361456-68-0 ] Synthesis Path-Downstream 1~34

1
[ 3610-42-2 ]
[ 361456-68-0 ]
[ 74-88-4 ]
[2-(5-benzo[1,3]dioxol-4-yl-1<i>H</i>-indol-3-yl)-ethyl]-dimethyl-amine [ No CAS ]

References: [1]Organic Letters,2002,vol. 4,p. 4033 - 4035.

2
[ 361456-68-0 ]
1-((Z)-4-Chloro-but-2-enyloxy)-hept-2-yne [ No CAS ]
5-{1-[4-Vinyl-dihydro-furan-(3E)-ylidene]-pentyl}-benzo[1,3]dioxole [ No CAS ]

References: [1]Organic Letters,2003,vol. 5,p. 3645 - 3648.

3
[ 361456-68-0 ]
5-cyano-2-methylphenyl halide [ No CAS ]
3-benzo[1,3]dioxol-4-yl-4-methyl-benzonitrile [ No CAS ]

References: [1]Bioorganic and Medicinal Chemistry Letters,2004,vol. 14,p. 5371 - 5376.

4
[ 361456-68-0 ]
[ 796841-87-7 ]

References: [1]Bioorganic and Medicinal Chemistry Letters,2004,vol. 14,p. 5371 - 5376.

5
[ 361456-68-0 ]
3-Benzo[1,3]dioxol-4-yl-4-[3-(4-cyano-benzyl)-3H-imidazol-4-ylmethoxymethyl]-benzonitrile [ No CAS ]

References: [1]Bioorganic and Medicinal Chemistry Letters,2004,vol. 14,p. 5371 - 5376.

6
[ 6698-13-1 ]
[ 5419-55-6 ]
[ 361456-68-0 ]

Yield	Reaction Conditions	Operation in experiment
69%	With n-butyllithium; In tetrahydrofuran; hexanes; at -78 - 20℃; for 3.0h;	PREPARATION 531,3-Benzodioxole-4-boronic acid nBuLi (2.5M in hexanes, 2.38 mL, 5.97 mmol) was dropwise added to a solution of 4- bromo-1 ,3-benzodioxole (1 g, 4.97 mmol) and triisopropyl borate (1.49 mL, 6.47 mmol) in 50 mL of dry tetrahydrofuran at -78 0C under argon. The reaction was maintained at that temperature for 3 hours, then warmed up to room temperature and cooled back to 0 0C immediately. The solution was acidified to pH=2 with HCI 2N and neutralized to pH=7 with NaOH 2N, it was then extracted with ethyl acetate (3 x 25 ml), the organic solution was washed with brine, dried over sodium sulphate and the solvent removed under reduced pressure to yield the title compound (570 mg, 69%) as a white solid. 1H-NMR delta (CD3OD): 5.92 (s, 2H), 6.80-6.86 (m, 3H).
69%		nBuLi (2.5M in hexanes, 2.38 mL, 5.97 mmol) was dropwise added to a solution of 4- bromo-1 ,3-benzodioxole (1 g, 4.97 mmol) and triisopropyl borate (1.49 mL, 6.47 mmol) in 50 mL of dry tetrahydrofuran at -78 0C under argon. The reaction was maintained at that temperature for 3 hours, then warmed up to room temperature and cooled back to 0 0C immediately. The solution was acidified to pH=2 with HCI 2N and neutralized to pH=7 with NaOH 2N, it was then extracted with ethyl acetate (3 x 25 ml), the organic solution was washed with brine, dried over sodium sulphate and the solvent removed under reduced pressure to yield the title compound (570 mg, 69%) as a white solid. H1-NMR delta (CD3OD): 5.92 (s, 2H), 6.80-6.86 (m, 3H).

References: [1]Patent: WO2008/17461,2008,A1 .Location in patent: Page/Page column 60.
[2]Patent: WO2007/96072,2007,A2 .Location in patent: Page/Page column 34.

7
[ 1189852-16-1 ]
[ 76-05-1 ]
[ 361456-68-0 ]
N-(7-(benzo[d][1,3]dioxol-5-yl)-2-methylpyrazolo[1,5-d]pyrimidin-5-yl)-4-(2-hydroxypropan-2-yl)benzamide trifluoroacetate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
8%		N-(7-chloro-2-methylpyrazolo[ 1 ,5-alpha]pyrimidin-5-yl)-4-(2-hydroxypropan-2- yl)benzamide (2F, 0.07g, 1.0 equivalent) and benzo[d][l,3]dioxol-5-ylboronic acid (2.0 equivalents) and PdCl2(dppf)/DCM (0.10 equivalent) in 2N Na2CO3 (0.2 M), dioxane (0.1M) and DMF (0.5M) was heated at 120 0C for 10 minutes in the microwave. After cooling to room temperature, the mixture was added water and EtOAc; and extracted with EtOAc twice and the combined organic layers were dried over Na2SO4. Then the solvent was removed in vacuo and the crude mixture was purified by preparatory HPLC (40-55% ACN/water, TFA mode) to afford the TFA salt of the titled compound, which was further purified by EtOAc wash and filtered to afford the titled compound 232 (8%) as a white solid. 1H NMR (400 MHz, DMSO- J6) delta ppm 1.46 (s, 6 H) 2.41 (s, 3 H) 5.19 (s, 1 H) 6.18 (s, 2 H) 6.37 (s, 1 H) 7.17 (d, J=8.34 Hz, 1 H) 7.58 - 7.64 (m, 3 H) 7.70 (d, J=1.52 Hz, 1 H) 7.94 (s, 1 H) 8.01 (d, J=8.59 Hz, 2 H) 11.16 (s, 1 H); ESI- MS: m/z 431.2 (M+H)+.

References: [1]Patent: WO2009/123986,2009,A1 .Location in patent: Page/Page column 299.

8
[ 1189852-14-9 ]
[ 361456-68-0 ]
[ 1190045-71-6 ]

Yield	Reaction Conditions	Operation in experiment
4%	With sodium hydrogencarbonate;(1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; In 1,4-dioxane; water; at 110℃; for 0.333333h;Microwave irradiation;	A suspension of N-(7-chloro-2-methylpyrazolo[l,5-a]pyrimidin-5-yl)-4-(2- hydroxypropan-2-yl)benzamide (2D, 50 mg, 0.151 mmol), benzo[d][l,3]dioxol-4-ylboronic acid (50 mg, 0.302 mmol), and [l,r-bis(diphenylphosphino)ferrocene]dichloropalladium(II) (9 mg, 12 mumol) in 2:1 1 ,4-dioxane/saturated aqueous NaHCO3 (330 microliters of 1 ,4-dioxane and 670 microliters of saturated aqueous NaHCO3) was prepared in a 2 mL microwave reaction vessel and the sealed reaction vessel warmed to 110 0C for 20 minutes. The reaction mixture was cooled to rt, diluted with methanol, filtered, and purified via preparative HPLC, 5-95% (MeCNZH2O gradient + 0.01% TFA). Lyophilization of the combined fractions gave the titled compound as a yellow solid (2.8 mg, 4%). 1H NMR (400 MHz, DMSO-J6) delta ppm 1.46 (s, 6 H) 5.20 (s, 1 H) 6.18 (s, 2 H) 6.57 (d, J=2.27 Hz, 1 H) 7.17 (d, J=8.34 Hz, 1 H) 7.56 - 7.69 (m, 3 H) 7.72 (d, J=I.77 Hz, 1 H) 7.98 - 8.10 (m, 3 H) 8.19 (d, J=2.27 Hz, I H) 11.23 (s, I H). ESI-MS: m/z 417.0 (M+H)+.

References: [1]Patent: WO2009/123986,2009,A1 .Location in patent: Page/Page column 280.

9
[ 947410-36-8 ]
[ 361456-68-0 ]
[3-amino-2-(1,3-benzodioxol-4-yl)pyridin-4-yl](2,4-difluorophenyl)methanone [ No CAS ]

References: [1]Journal of Medicinal Chemistry,2009,vol. 52,p. 5531 - 5545.

10
[ 1216771-56-0 ]
[ 361456-68-0 ]
[ 1216771-86-6 ]

References: [1]Bioorganic and Medicinal Chemistry,2010,vol. 18,p. 707 - 718.

11
[ 1222470-30-5 ]
[ 361456-68-0 ]
[ 1222470-41-8 ]

References: [1]Angewandte Chemie - International Edition,2010,vol. 49,p. 1825 - 1829.

12
[ 1222470-40-7 ]
[ 361456-68-0 ]
[ 1222470-47-4 ]
(R)-tert-butyl 3-(benzo[d][1,3]dioxol-4-ylmethyl)-1-benzyl-4-oxopyrrolidine-3-carboxylate [ No CAS ]

References: [1]Angewandte Chemie - International Edition,2010,vol. 49,p. 1825 - 1829.

13
C₁₆H₁₃BrN₂O₂ [ No CAS ]
[ 361456-68-0 ]
C₂₃H₁₈N₂O₄ [ No CAS ]

References: [1]Bioorganic and Medicinal Chemistry Letters,2010,vol. 20,p. 5449 - 5453.

14
C₁₅H₁₂BrN₃O₂ [ No CAS ]
[ 361456-68-0 ]
C₂₂H₁₇N₃O₄ [ No CAS ]

References: [1]Bioorganic and Medicinal Chemistry Letters,2010,vol. 20,p. 5449 - 5453.

15
[ 1246241-87-1 ]
[ 361456-68-0 ]
[ 1246241-71-3 ]

References: [1]Bioorganic and Medicinal Chemistry Letters,2010,vol. 20,p. 5449 - 5453.

16
[ 1246241-88-2 ]
[ 361456-68-0 ]
[ 1246241-73-5 ]

References: [1]Bioorganic and Medicinal Chemistry Letters,2010,vol. 20,p. 5449 - 5453.

17
C₁₅H₁₁BrN₂O₂ [ No CAS ]
[ 361456-68-0 ]
C₂₂H₁₆N₂O₄ [ No CAS ]

References: [1]Bioorganic and Medicinal Chemistry Letters,2010,vol. 20,p. 5449 - 5453.

18
C₁₄H₁₀BrN₃O₂ [ No CAS ]
[ 361456-68-0 ]
C₂₁H₁₅N₃O₄ [ No CAS ]

References: [1]Bioorganic and Medicinal Chemistry Letters,2010,vol. 20,p. 5449 - 5453.

19
[ 930-68-7 ]
[ 361456-68-0 ]
(R)-3-(benzo[d][1,3]dioxol-4-yl)cyclohexanone [ No CAS ]
[ 1309435-10-6 ]

References: [1]Organic Letters,2011,vol. 13,p. 3182 - 3185.

20
[ 122079-41-8 ]
[ 361456-68-0 ]
[ 1362110-11-9 ]