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Chemical Structure| 1131912-76-9 Chemical Structure| 1131912-76-9

Structure of 1131912-76-9

Chemical Structure| 1131912-76-9

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Product Details of [ 1131912-76-9 ]

CAS No. :1131912-76-9
Formula : C11H21BO3
M.W : 212.09
SMILES Code : CC1(C)OB(OC1(C)C)C1CCOCC1
MDL No. :MFCD11506065
InChI Key :NLSMOSUUBUCSPL-UHFFFAOYSA-N
Pubchem ID :42614649

Safety of [ 1131912-76-9 ]

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

Computational Chemistry of [ 1131912-76-9 ] Show Less

Physicochemical Properties

Num. heavy atoms 15
Num. arom. heavy atoms 0
Fraction Csp3 1.0
Num. rotatable bonds 1
Num. H-bond acceptors 3.0
Num. H-bond donors 0.0
Molar Refractivity 60.9
TPSA ?

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

27.69 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

1.84
Log Po/w (WLOGP)?

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

2.26
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.

0.93
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

1.34
Consensus Log Po/w?

Consensus Log Po/w: Average of all five predictions

1.27

Water Solubility

Log S (ESOL):?

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

-2.25
Solubility 1.2 mg/ml ; 0.00565 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.

-2.04
Solubility 1.93 mg/ml ; 0.00908 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

-2.38
Solubility 0.876 mg/ml ; 0.00413 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

No
Log Kp (skin permeation)?

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

-6.29 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)

3.14

Application In Synthesis of [ 1131912-76-9 ]

* 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 [ 1131912-76-9 ]

[ 1131912-76-9 ] Synthesis Path-Downstream   1~25

  • 2
  • [ 142-68-7 ]
  • [ 73183-34-3 ]
  • [ 1131912-76-9 ]
  • [ 1391850-39-7 ]
  • 3
  • [ 1131912-76-9 ]
  • [ 1394939-89-9 ]
  • [ 1394939-90-2 ]
  • 4
  • [ 1131912-76-9 ]
  • 1-bromo-5-cyclopropyloxy-2-methyl-4-nitrobenzene [ No CAS ]
  • C15H19NO4 [ No CAS ]
  • 5
  • [ 1131912-76-9 ]
  • C26H33ClN6O4S [ No CAS ]
  • 6
  • [ 1131912-76-9 ]
  • 2-cyclopropoxy-4-(tetrahydro-2H-pyran)-5-methyl-aniline [ No CAS ]
  • 7
  • [ 824-75-9 ]
  • [ 1131912-76-9 ]
  • C12H14FNO2 [ No CAS ]
  • 9
  • 1,3-dioxoisoindolin-2-yl tetrahydro-2H-pyran-4-carboxylate [ No CAS ]
  • [ 1131912-76-9 ]
  • 11
  • [ 1131912-76-9 ]
  • 3-benzyl-2-bromo-9-methyl-4H,6H-thieno[2,3-e][1,2,4]triazolo[3,4-c][1,4]oxazepine [ No CAS ]
  • 3-benzyl-9-methyl-2-(tetrahydro-2H-pyran-4-yl)-4H,6H-thieno-[2,3-e][1,2,4]triazolo[3,4-c][1,4]oxazepine [ No CAS ]
  • 12
  • 1,3-dioxoisoindolin-2-yl tetrahydro-2H-pyran-4-carboxylate [ No CAS ]
  • [ 73183-34-3 ]
  • [ 1131912-76-9 ]
YieldReaction ConditionsOperation in experiment
32% With triethylamine; for 1h; General procedure: General Procedure B: NHPI ester (1.0 eq., 0.13 mmol) and B2cat2 (40 mg, 1.25 eq., 0.16 mmol) were carefully weighed into a flame-dried 7 mL vial containing a small magnetic stiffer bar. DMAc (1.3 mL, 0.1 M) was added and then the headspace of thevial was purged with a gentle stream of argon for approximately 10 seconds. The vial was tightly sealed and stirred under blue LED iffadiation for 14 h. Pinacol (63 mg, 0.53 mmol, 4 eq.) was dissolved in Et3N (0.45 mL), added to the reaction mixture and stuffed for 1 h. For workup, the reaction mixture was transfeffed into a vial containing EtOAc (15 mL), H20 (3 mL), NH4Cl (saturated aqueous solution, 3 mL). After vigorouslyshaking and allowing the two layers to separate, the top organic layer was carefully removed with a pipette. This was repeated twice more with EtOAc delta mL). The organic layers were combined and concentrated under reduced pressure. The crude residue was directly purified using a short silica gel column to yield the desired boronic ester. Alternative workup: The crude reaction mixture was diluted with Et20 (10 mL) andwashed with NaOH (aqueous, 0.10 M, 6 mL), and then the aqueous layer was extracted with Et20 (10 mL). The combined organic layers were washed with NaOH (aqueous,0.10 M, 6 mL) and water (6 mL), then dried over MgSO4, filtered and concentrated under reduced pressure to yield the desired boronic ester.
  • 14
  • [ 76-09-5 ]
  • [ 13826-27-2 ]
  • 2,4,6-triphenyl-1-(tetrahydro-2H-pyran-4-yl)pyridin-1-ium tetrafluoroborate [ No CAS ]
  • [ 1131912-76-9 ]
  • 15
  • [ 38041-19-9 ]
  • [ 1131912-76-9 ]
  • 17
  • [ 1131912-76-9 ]
  • [ 591-51-5 ]
  • C17H26BO3(1-)*Li(1+) [ No CAS ]
  • 18
  • [ 1131912-76-9 ]
  • methyl 1-((tetrahydro-2H-pyran-4-yl)methyl)cyclobutane-1-carboxylate [ No CAS ]
  • 19
  • trimethyl((1-phenyl-1-(tetrahydro-2H-pyran-4-yl)ethyl)peroxy)silane [ No CAS ]
  • [ 73183-34-3 ]
  • [ 1131912-76-9 ]
  • 20
  • [ 25637-18-7 ]
  • [ 73183-34-3 ]
  • [ 1131912-76-9 ]
YieldReaction ConditionsOperation in experiment
50% With lithium tert-butoxide; In methanol; water; at 50℃; for 48h;Glovebox; IN a glove box, t-BuOLi (1 mmol, 2 equivalents, 80.1 mg), B2pin2 (2 mmol, 4 equivalents, 507.9 mg), 0.85 mL of solvent methanol, 10 muL of H 2 O were added to the vial containing the stirrer in turn.4-iodotetrahydropyran (0.5 mmol). The capped vial was removed from the glove box and the reaction mixture was stirred at 50 C for 48 hours. After cooling to room temperature, the reaction mixture was transferred to a 100 mL flask by methanol, and then a small amount of silica gel was added thereto. After removing the solvent in a vacuum, the residue was poured onto a silica gel column and purified by column chromatography, and the solvent was a mixture of petroleum ether/ethyl acetate in a volume ratio of 30:1 to 20:1.The desired product, 4-tetrahydropyranylboronic acid pinacol ester, was obtained in a yield of 50%.
  • 21
  • [ 25637-18-7 ]
  • [ 13826-27-2 ]
  • [ 1131912-76-9 ]
  • 22
  • [ 1131912-76-9 ]
  • 2-bromo-N-(cyclopropylmethyl)-5-nitrobenzamide [ No CAS ]
  • 2-(tetrahydro-2H-pyran-4-yl)-N-(cyclopropylmethyl)-5-aminobenzamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
75% With potassium phosphate; palladium on activated charcoal; In 1,4-dioxane; water; at 80℃; for 4h;Inert atmosphere; Interventional 2-bromo-N-(cyclopropylmethyl)-5-nitrobenzamide 50 mg (1 eq) into a 50 mL vial.Tetrahydrofuran-3-boronic acid pinacol ester 52mg (1eq),PdXPhosG2 1mg (0.01eq), Pd/C 22mg (0.12eq),Potassium phosphate 107mg (3eq), then sealed with argon to replace the air in the single-mouth bottle three times, to ensure no oxygen, then add 1-4, dioxane: water = 4:1 (5mL),After the addition was completed, the gas in the three-necked flask was replaced with argon gas, and then the temperature was raised to 80 C, and after reacting for 4 hours,The heating device was turned off, the reaction was allowed to cool to room temperature, and then 106 mg (10 eq) of ammonium formate was dissolved in 2 mL of methanol.After completely dissolved, it is added to the reaction system and reacted at room temperature for 16 hours.The reaction was completely detected by TLC, and then filtered through celite, and the filtrate was concentrated under reduced pressure, and then directly separated by column chromatography.47 mg of a white solid were obtained in a yield of 75%.
  • 23
  • [ 40191-32-0 ]
  • [ 1131912-76-9 ]
  • 24
  • [ 76-09-5 ]
  • [ 13826-27-2 ]
  • 3-chlorobenzoic tetrahydro-2H-pyran-4-carboxylic peroxyanhydride [ No CAS ]
  • [ 1131912-76-9 ]
  • 25
  • [ 25637-16-5 ]
  • [ 76-09-5 ]
  • [ 13826-27-2 ]
  • [ 1131912-76-9 ]
 

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