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Structure of 201733-56-4

Chemical Structure| 201733-56-4

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Product Details of [ 201733-56-4 ]

CAS No. :201733-56-4
Formula : C10H20B2O4
M.W : 225.89
SMILES Code : CC1(C)COB(B2OCC(C)(C)CO2)OC1
MDL No. :MFCD02093062
InChI Key :MDNDJMCSXOXBFZ-UHFFFAOYSA-N
Pubchem ID :2734316

Safety of [ 201733-56-4 ]

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

Computational Chemistry of [ 201733-56-4 ] Show Less

Physicochemical Properties

Num. heavy atoms 16
Num. arom. heavy atoms 0
Fraction Csp3 1.0
Num. rotatable bonds 1
Num. H-bond acceptors 4.0
Num. H-bond donors 0.0
Molar Refractivity 63.4
TPSA ?

Topological Polar Surface Area: Calculated from
Ertl P. et al. 2000 J. Med. Chem.

36.92 Ų

Lipophilicity

Log Po/w (iLOGP)?

iLOGP: in-house physics-based method implemented from
Daina A et al. 2014 J. Chem. Inf. Model.

0.0
Log Po/w (XLOGP3)?

XLOGP3: Atomistic and knowledge-based method calculated by
XLOGP program, version 3.2.2, courtesy of CCBG, Shanghai Institute of Organic Chemistry

2.18
Log Po/w (WLOGP)?

WLOGP: Atomistic method implemented from
Wildman SA and Crippen GM. 1999 J. Chem. Inf. Model.

1.19
Log Po/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.

-0.21
Log Po/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

-0.36
Consensus Log Po/w?

Consensus Log Po/w: Average of all five predictions

0.56

Water Solubility

Log S (ESOL):?

ESOL: Topological method implemented from
Delaney JS. 2004 J. Chem. Inf. Model.

-2.55
Solubility 0.64 mg/ml ; 0.00283 mol/l
Class?

Solubility class: Log S scale
Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly

Soluble
Log S (Ali)?

Ali: Topological method implemented from
Ali J. et al. 2012 J. Chem. Inf. Model.

-2.59
Solubility 0.582 mg/ml ; 0.00258 mol/l
Class?

Solubility class: Log S scale
Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly

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

-2.12
Solubility 1.72 mg/ml ; 0.00762 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

Yes
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

Yes
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

Yes
Log Kp (skin permeation)?

Skin permeation: QSPR model implemented from
Potts RO and Guy RH. 1992 Pharm. Res.

-6.13 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

0.0
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)

3.42

Application In Synthesis of [ 201733-56-4 ]

* 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 [ 201733-56-4 ]

[ 201733-56-4 ] Synthesis Path-Downstream   1~12

  • 1
  • [ 2042-37-7 ]
  • [ 201733-56-4 ]
  • [ 214360-47-1 ]
  • 2
  • [ 319474-34-5 ]
  • [ 201733-56-4 ]
  • [ 944956-50-7 ]
YieldReaction ConditionsOperation in experiment
With potassium acetate;dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; In ethanol; for 20h;Heating / reflux; [306] 4-Iodo-7-Azaindole (1.0Og, 4.12mmol), bis(neopentylglycolato)diboron (1.49g, 6.59mmol), potassium acetate (0.65g, 6.59mmol), and l,r-bis(diphenylphosphino)ferrocene dichloro palladium (II) dichloromethane complex (0.09g, 0.12mmol) were added to a round bottom flask. The flask was evacuated and backfilled with N2 (3 x). Anhydrous ethanol (2OmL) was added and the mixture was heated to reflux for 2Oh. After cooling to rt, the reaction mixture was diluted with diethyl ether (35mL) and then filtered through celite. The resulting filtrate was concentrated in vacuo and dissolved in ethyl acetate (5OmL). The solution was washed with water (15mL), brine (15mL), and dried over MgSO4. The filtrate was concentrated to a brown solid which was recrystallized with ethyl acetate to yield the title compound as a tan solid. The mother liquor was concentrated in vacuo and purified by column chromatography (HexanesrEtOAc = 80:20 ? 60:40) to yield the title compound. 1H NMR (400 MHz, DMSO-d6) delta 0.99 (s, 6H), 3.83 (s, 4H), 6.69 (dd, IH3 J= 1.8, 1.0 Hz), 7.30 (d, IH, J = 2.4 Hz), 7.45 (dd, IH3 J= 2.8, 2.4 Hz), 8.18 (d, IH, J= 2.2 Hz), 11.52 (bs, IH).
  • 4
  • [ 1122-91-4 ]
  • [ 201733-56-4 ]
  • [ 128376-65-8 ]
  • 5
  • [ 19936-14-2 ]
  • [ 201733-56-4 ]
  • [ 1467059-89-7 ]
YieldReaction ConditionsOperation in experiment
76% With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate; In 1,4-dioxane; at 110℃; for 2h;Inert atmosphere; A mixture of 5,5,5',5'-tetramethyl-2,2'-bi(1,3,2-dioxaborinane) (16.50 g, 48.33 mmol), oven dried potassium acetate (20.03 g, 204.1 mmol), and <strong>[19936-14-2]1-(4-bromophenyl)cyclobutanol</strong> (10.00 g, 44.03 mmol) in 1,4-dioxane (120 mL) was degassed with N2 for 15 min, then treated with [1,1'-bis(diphenylphosphino)ferrocene]dichloropalladium(II) (2.44 g, 2.99 mmol). The reaction mixture was heated to 110 C. and stirred for 2 hours under N2. The reaction mixture was cooled to room temperature and filtered through celite, eluting with EtOAc. The filtrate was evaporated to give a black oil, which was purified by flash chromatography (0-50% EtOAc/Heptane) three times to afford the title compound (8.68 g, 76%) as a white solid. GC/MS: 259. 1H NMR (400 MHz, CD3Cl) delta 7.83 (d, J=8.05 Hz, 2H), 7.50 (d, J=8.29 Hz, 2H), 3.78 (s, 4H), 2.65-2.52 (m, 2H), 2.38-2.42 (m, 2H), 1.98-2.03 (m, 1H), 1.72-1.80 (m, 1H), 1.03 (s, 6H).
  • 6
  • [ 954238-61-0 ]
  • methyl 2-(((2-amino-5-bromopyridin-3-yl)oxy)methyl)-4-fluorobenzoate [ No CAS ]
  • [ 201733-56-4 ]
  • C27H30FN3O5 [ No CAS ]
YieldReaction ConditionsOperation in experiment
53% Step 1 : To a degassed solution of compound 35 (350 mg, 0.99 mmol), bis(neopentylglycolato)diboron (289 mg, 1.3 mmol) and KOAc (339 mg, 3.4 mmol) in DMSO (10 mL) was added Pd(dppf)CI2 (80 mg, 0.1 mmol). The resulting mixture was stirred at 75 C for 1 h. LCMS analysis indicated that the boronic acid intermediate was formed. After cooling to RT, compound 59 (31 1 mg, 1.03 mmol) and NaHC03 (aq) (1 M solution, 3.0 mL, 3.0 mmol) and dioxane (10 mL) were added. The mixture was degassed, followed by the addition of Pd(dppf)CI2 (80 mg, 0.1 mmol). The resulting mixture was stirred at 80 C for 2 hours and concentrated in vacuo, ethyl acetate (100 mL) and water (150 mL) were added and then partitioned. The aqueous was extracted with EtOAc (2 x 100 mL), and the combined organic layers were washed with brine (400 mL), dried over MgS04, and then concentrated in vacuo. Purification by flash column chromatography over silica gel, which was eluted with 1 % MeOH and 10% heptane in DCM, gave compound 355 as a yellow solid (260 mg, 53% yield). 1 H NMR (400 MHz, CDCI3) δ 8.06 (dd, 1 H), 7.66 (s, 1 H), 7.16 - 7.30 (m, 5 H), 7.05 (ddd, 1 H), 6.86 (d, 1 H), 5.53 (s, 2 H), 4.80 (br s, 2H), 4.33 (br s, 2 H), 3.96 (s, 3 H), 2.63 (br d, 3 H), 1.42 (br d, 9 H). LCMS ES m/z 440 [M-'Bu]+.
  • 7
  • [ 2296-23-3 ]
  • [ 201733-56-4 ]
  • 3-(5,5-dimethyl-1,3,2-dioxaborinan-2-yl)-4-hydroxybenzonitrile [ No CAS ]
  • 8
  • [ 2296-23-3 ]
  • [ 201733-56-4 ]
  • 4-cyano-2-(5,5-dimethyl-1,3,2-dioxaborinan-2-yl)phenyltrifluoromethanesulfonate [ No CAS ]
  • 9
  • [ 1753-75-9 ]
  • [ 201733-56-4 ]
  • 5-(5,5-dimethyl-1,3,2-dioxaborinan-2-yl)benzo[c][1,2,5]thiadiazole [ No CAS ]
  • 10
  • [ 52092-47-4 ]
  • [ 201733-56-4 ]
  • C10H15BN2O2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
68% Under nitrogen protection, 550 mL of dioxane and <strong>[52092-47-4]2-nitro-5-chloropyridine</strong> (15.8 g, were added to the reaction flask in turn. 0.10 mol), neopentyl glycol diborate (22.6 g, 0.10 mol), potassium acetate (14.7 g, 0.15 mol), after stirring uniformly, finally adding catalyst PdCl2dppf (0.74 g, 0.001 mol), slowly heating to 80 -90 ° C, Stir the reaction for 2-3 h. After the end of the GC reaction, the reaction was stopped by cooling, and the reaction solution was filtered through celite to obtain a dark-black reaction solution. After charging at 3 atm of hydrogen, the reaction was carried out at room temperature overnight. After the reaction was completed, the activated carbon was decolorized, and the filtrate was distilled under reduced pressure until no liquid was poured. / heptane mixed solvent was cooled and beaten for half an hour, filtered to obtain an off-white product, heated again with ethanol, and then cooled down, and the filter cake was rinsed with -20 ° C anhydrous ethanol, and dried to obtain an off-white solid 14.0 g. 68percent, HPLC purity 98.9percent
  • 11
  • [ 32412-39-8 ]
  • [ 201733-56-4 ]
  • 1-(5-(5,5-dimethyl-1,3,2-dioxaborinan-2-yl)thiophen-2-yl)propan-1-one [ No CAS ]
  • 12
  • [ 31161-46-3 ]
  • [ 201733-56-4 ]
  • (5-(5,5-dimethyl-1,3,2-dioxaborinan-2-yl)thiophen-2-yl)(phenyl)methanone [ No CAS ]
 

Historical Records

Categories

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[ 201733-56-4 ]

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