27762-64-7|(Cyclohexylmethyl)boronic acid| Ambeed

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Quality Control of [ 27762-64-7 ] Purity: 95% SDS Specification

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Product Details of [ 27762-64-7 ]

CAS No. :	27762-64-7
Formula :	C₇H₁₅BO₂
M.W :	142.00
SMILES Code :	OB(CC1CCCCC1)O
MDL No. :	MFCD09878538
InChI Key :	STYXWXRMARWJRD-UHFFFAOYSA-N
Pubchem ID :	10964611

Safety of [ 27762-64-7 ]

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

Computational Chemistry of [ 27762-64-7 ] Show Less

Physicochemical Properties

Num. heavy atoms	10
Num. arom. heavy atoms	0
Fraction Csp3	1.0
Num. rotatable bonds	2
Num. H-bond acceptors	2.0
Num. H-bond donors	2.0
Molar Refractivity	42.78
TPSA ? Topological Polar Surface Area: Calculated from Ertl P. et al. 2000 J. Med. Chem.	40.46 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	2.26
Log P_o/w (WLOGP)? WLOGP: Atomistic method implemented from Wildman SA and Crippen GM. 1999 J. Chem. Inf. Model.	1.04
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	-0.33
Consensus Log P_o/w? Consensus Log P_o/w: Average of all five predictions	0.71

Water Solubility

Log S (ESOL):? ESOL: Topological method implemented from Delaney JS. 2004 J. Chem. Inf. Model.	-2.01
Solubility	1.38 mg/ml ; 0.00972 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.	-2.75
Solubility	0.255 mg/ml ; 0.00179 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	-0.59
Solubility	36.8 mg/ml ; 0.259 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	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.	-5.56 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)	2.33

Application In Synthesis of [ 27762-64-7 ]

* 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 [ 27762-64-7 ]

[ 27762-64-7 ] Synthesis Path-Downstream 1~23

1
[ 623-00-7 ]
[ 27762-64-7 ]
[ 98446-82-3 ]

References: [1]Tetrahedron,2004,vol. 60,p. 3813 - 3818.

2
[ 99-90-1 ]
[ 27762-64-7 ]
[ 68266-59-1 ]

References: [1]Tetrahedron,2004,vol. 60,p. 3813 - 3818.

3
[ 613660-80-3 ]
[ 27762-64-7 ]
[ 613661-03-3 ]

Yield	Reaction Conditions	Operation in experiment
	With sodium carbonate; trifluoroacetic acid;tetrakis(triphenylphosphine)palladium (0); In methanol; diethyl ether; dichloromethane; water; acetonitrile;	EXAMPLE 44 2-(cyclohexylmethyl)-5-[(2-methylpyrrolidin-1-yl)carbonyl]pyridine A solution of Example 31 (1 mmol), <strong>[27762-64-7]cyclohexylmethylboronic acid</strong> (2.0 mmol), and tetrakis(triphenylphosphine)palladium (0) (0.05 mmol) in dichloromethane (1.5 mL) and methanol (0.25 mL) is treated with 2M sodium carbonate (0.5 mL), heated to 87 C. overnight, and concentrated. The concentrate is dissolved in diethyl ether, washed three times with water, dried (Na2SO4), filtered, and concentrated. The concentrate is purified by HPLC using a C-18 column and a solvent system increasing in gradient over 50 minutes from 5% to 100% acetonitrile/water containing 0.01% TFA and lyophilized to provide the desired product as the trifluoroacetate salt.

References: [1]Patent: US2003/195192,2003,A1 .

4
[ 504-63-2 ]
[ 27762-64-7 ]
[ 102746-89-4 ]

References: [1]Journal of the American Chemical Society,1993,vol. 115,p. 440 - 444.

5
[ 16940-66-2 ]
[ 16963-29-4 ]
[ 109-63-7 ]
[ 27762-64-7 ]

References: [1]Journal of the American Chemical Society,1993,vol. 115,p. 440 - 444.

6
[ 20419-68-5 ]
[ 27762-64-7 ]
[ 1246532-61-5 ]

Yield	Reaction Conditions	Operation in experiment
	With potassium carbonate;tetrakis(triphenylphosphine) palladium(0); In 1,4-dioxane; for 24h;Inert atmosphere; Reflux;	[00552] 2-Chloro-6-cyclohexylmethyl-9-(tetrahydro-pyran-2-yl)-purine (84):Compound 84 was synthesized using Suzuki cross-coupling reaction conditions as described in Tetrahedron, 2002, 58: 1465. To a suspension of 83 (75 mg, 0.28 mmol), the boronic acid (39 mg, 0.28 mmol), K2CO3 (110 mg, 0.82 mmol) in 1,4-dioxane (3mL) was added Pd(PPh3)4 under nitrogen. The reaction was heated to reflux for 24 hours. The reaction was concentrated and purified via silica gel column chromatorgraphy (Hex: ethyl acetate) to afford the desired product 84 (49 mg) as a light yellowish oil.

References: [1]Bioorganic and Medicinal Chemistry Letters,2012,vol. 22,p. 4377 - 4385.
[2]Patent: WO2010/111406,2010,A2 .Location in patent: Page/Page column 125.

7
ethyl 2-(pyridin-2-yl)-5-thiophene carboxylate [ No CAS ]
[ 27762-64-7 ]
C₁₉H₂₃NO₂S [ No CAS ]

References: [1]Chemical Communications,2015,vol. 51,p. 3166 - 3168.

8
[ 3319-99-1 ]
[ 27762-64-7 ]
C₁₆H₁₉NS [ No CAS ]

References: [1]Chemical Communications,2015,vol. 51,p. 3166 - 3168.

9
1-acetyl-6-bromo-2,3-dihydroquinolin-4(1H)-one [ No CAS ]
[ 27762-64-7 ]
1-acetyl-6-(cyclohexylmethyl)-2,3-dihydroquinolin-4(1H)-one [ No CAS ]

References: [1]Journal of Medicinal Chemistry,2015,vol. 58,p. 8952 - 8969.

10
tert-butyl 6-bromo-4-oxo-3,4-dihydroquinoline-1(2H)-carboxylate [ No CAS ]
[ 27762-64-7 ]
C₂₁H₂₉NO₃ [ No CAS ]

References: [1]Journal of Medicinal Chemistry,2015,vol. 58,p. 8952 - 8969.

11
(R)-N-((R)-7-bromo-1,2,3,4-tetrahydronaphthalen-1-yl)-2-methylpropane-2-sulfinamide [ No CAS ]
[ 27762-64-7 ]
(R)-N-((R)-7-(cyclohexylmethyl)-1,2,3,4-tetrahydronaphthalen-1-yl)-2-methylpropane-2-sulfinamide [ No CAS ]

References: [1]Journal of Medicinal Chemistry,2015,vol. 58,p. 8952 - 8969.

12
(S)-tert-butyl 2-(((6-chloro-5-fluoro-2-methoxypyridin-3-yl)methyl)carbamoyl)pyrrolidine-1-carboxylate [ No CAS ]
[ 27762-64-7 ]
(S)-tert-butyl 2-(((6-(cyclohexylmethyl)-5-fluoro-2-methoxypyridin-3-yl)methyl)carbamoyl)pyrrolidine-1-carboxylate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl; In 1,4-dioxane; water; at 80 - 140℃; for 24h;Inert atmosphere; Microwave irradiation;	(S)-tert-Butyl 2-(((6-chloro-5-fluoro-2-methoxypyridin-3-yl)methyl)carbamoyl)- pyrrolidine-l-carboxylate (250 mg, 0.645 mmol), <strong>[27762-64-7]cyclohexylmethylboronic acid</strong> (101 mg, 0.709 mmol), cesium carbonate (525 mg, 1,612 mmol) and bis(diphenylphospino)- ferrocene-palladium(II)dichloride dichloromethane complex (52.6 mg, 0.064 mmol) were dissolved in dioxane (12 ml) and water (2 ml) and flushed 3x with argon. The re- action mixture was stirred in the microwave at 80C for 10 h, then 130C for 2 h and finally at 140C for 12 h. The reaction mixture was filtered under vacuum over diato- maceous earth, washed and concentrated. The crude product (773.7 mg) was dissolved in DCM. Bulk Isolute Sorbent was added and the product was purified using flash chromatography (4 g column; DCM 100%? DCM:MeOH 0: 100, 18 ml/min) to give (S)-tert-butyl 2-(((6-(cyclohexylmethyl)-5-fluoro-2-methoxypyridin-3-yl)methyl)- carbamoyl)pyrrolidine-l-carboxylate (317.2 mg). The material was used as crude product without further purification. To a solution of (S)-tert-butyl 2-(((6-(cyclohexyl- methyl)-5-fluoro-2-methoxypyridin-3-yl)methyl)carbamoyl)pyrrolidine-l-carboxylate (317 mg, 0.705 mmol) in DCM (5 ml) was added TFA (1,087 ml, 14.10 mmol). The reaction mixture was stirred at room temperature overnight and subsequently concentrated under reduced pressure. The obtained crude product (544 mg) was dissolved in DCM. Bulk Isolute Sorbent was added and the product was purified using flash chromatography (4 g column; DCM 100%? DCM:MeOH 50:50, 18 ml/min) to give 265.7 mg crude product. The title product was obtained by preparative HPLC chromatography on a reversed phase column (26.3 mg, yield 11%) LCMS (ESI+) m/z [M+H]+: 350.40 1H NMR (500 MHz, methanol-^) delta ppm: 7.34 (d, J= 9.1 Hz, 1H), 4.34 (s, 2H), 4.30 - 4.25 (m, 1H), 3.93 (s, 3H), 3.45 - 3.35 (m, 1H), 2.60 - 2.55 (m, 2H), 2.45 - 2.35 (m, 1H), 2.10 - 1.95 (m, 3H), 1.80 - 1.75 (m, 1H), 1.70 - 1.60 (m, 6H), 1.30 - 1.20 (m, 4H), 1.10 - 1.00 (m, 2H).

References: [1]Patent: WO2017/50807,2017,A1 .Location in patent: Page/Page column 225-226.

13
[ 27762-64-7 ]
methyl 2-(chloromethyl)-4-(cyclohexylmethyl)benzoate [ No CAS ]