[ CAS No. 27762-64-7 ] {[proInfo.proName]}

Name: 27762-64-7|(Cyclohexylmethyl)boronic acid|95%
Brand: Ambeed
SKU: A208899
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Quality Control of [ 27762-64-7 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 27762-64-7 ]

SDS Specification

Alternatived Products of [ 27762-64-7 ]

Product Details of [ 27762-64-7 ]

CAS No. :	27762-64-7	MDL No. :	MFCD09878538
Formula :	C₇H₁₅BO₂	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	STYXWXRMARWJRD-UHFFFAOYSA-N
M.W :	142.00	Pubchem ID :	10964611
Synonyms :

Calculated chemistry of [ 27762-64-7 ]

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 :	40.46 Å²

Pharmacokinetics

GI absorption :	High
BBB permeant :	Yes
P-gp substrate :	No
CYP1A2 inhibitor :	No
CYP2C19 inhibitor :	No
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-5.56 cm/s

Lipophilicity

Log Po/w (iLOGP) :	0.0
Log Po/w (XLOGP3) :	2.26
Log Po/w (WLOGP) :	1.04
Log Po/w (MLOGP) :	0.57
Log Po/w (SILICOS-IT) :	-0.33
Consensus Log Po/w :	0.71

Druglikeness

Lipinski :	0.0
Ghose :	None
Veber :	0.0
Egan :	0.0
Muegge :	1.0
Bioavailability Score :	0.55

Water Solubility

Log S (ESOL) :	-2.01
Solubility :	1.38 mg/ml ; 0.00972 mol/l
Class :	Soluble
Log S (Ali) :	-2.75
Solubility :	0.255 mg/ml ; 0.00179 mol/l
Class :	Soluble
Log S (SILICOS-IT) :	-0.59
Solubility :	36.8 mg/ml ; 0.259 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	1.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	2.33

Safety of [ 27762-64-7 ]

Signal Word:	Warning	Class:	N/A
Precautionary Statements:	P261-P305+P351+P338	UN#:	N/A
Hazard Statements:	H315-H319-H335	Packing Group:	N/A
GHS Pictogram:

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.

Upstream synthesis route of [ 27762-64-7 ]
Downstream synthetic route of [ 27762-64-7 ]

[ 27762-64-7 ] Synthesis Path-Upstream 1~1

1
[ 16940-66-2 ]
[ 16963-29-4 ]
[ 109-63-7 ]
[ 27762-64-7 ]

Reference： [1] Journal of the American Chemical Society, 1993, vol. 115, # 2, p. 440 - 444

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

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

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

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

Reference： [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.

Reference： [1]Patent: US2003/195192,2003,A1

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

Reference： [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 ]

Reference： [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.

Reference： [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 ]

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

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

Reference： [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 ]

Reference： [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 ]

Reference： [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 ]

Reference： [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).

Reference： [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 ]