[ CAS No. 192804-36-7 ] {[proInfo.proName]}

Name: 192804-36-7|(4-(((Benzyloxy)carbonyl)amino)phenyl)boronic acid|98%
Brand: Ambeed
SKU: A214124
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Quality Control of [ 192804-36-7 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 192804-36-7 ]

SDS Specification

Alternatived Products of [ 192804-36-7 ]

Product Details of [ 192804-36-7 ]

CAS No. :	192804-36-7	MDL No. :	MFCD02093055
Formula :	C₁₄H₁₄BNO₄	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	KYCQBMOJDXVNIC-UHFFFAOYSA-N
M.W :	271.08	Pubchem ID :	2773322
Synonyms :

Calculated chemistry of [ 192804-36-7 ]

Physicochemical Properties

Num. heavy atoms :	20
Num. arom. heavy atoms :	12
Fraction Csp3 :	0.07
Num. rotatable bonds :	6
Num. H-bond acceptors :	4.0
Num. H-bond donors :	3.0
Molar Refractivity :	76.54
TPSA :	78.79 Å²

Pharmacokinetics

GI absorption :	High
BBB permeant :	No
P-gp substrate :	No
CYP1A2 inhibitor :	No
CYP2C19 inhibitor :	No
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-6.6 cm/s

Lipophilicity

Log Po/w (iLOGP) :	0.0
Log Po/w (XLOGP3) :	1.9
Log Po/w (WLOGP) :	0.77
Log Po/w (MLOGP) :	1.26
Log Po/w (SILICOS-IT) :	-0.11
Consensus Log Po/w :	0.77

Druglikeness

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

Water Solubility

Log S (ESOL) :	-2.77
Solubility :	0.465 mg/ml ; 0.00172 mol/l
Class :	Soluble
Log S (Ali) :	-3.18
Solubility :	0.18 mg/ml ; 0.000665 mol/l
Class :	Soluble
Log S (SILICOS-IT) :	-3.95
Solubility :	0.0303 mg/ml ; 0.000112 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	1.0 alert
Leadlikeness :	0.0
Synthetic accessibility :	2.46

Safety of [ 192804-36-7 ]

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 [ 192804-36-7 ]

* 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 [ 192804-36-7 ]

[ 192804-36-7 ] Synthesis Path-Downstream 1~33

1
[ 161365-25-9 ]
[ 192804-36-7 ]
[(3aR,4R,5R,7aR)-7-(4-Benzyloxycarbonylamino-phenyl)-4-(tert-butyl-dimethyl-silanyloxy)-2,2-dimethyl-3a,4,5,7a-tetrahydro-benzo[1,3]dioxol-5-yl]-carbamic acid benzyl ester [ No CAS ]

Reference： [1]Journal of Organic Chemistry,1997,vol. 62,p. 6046 - 6050

2
[ 1072-83-9 ]
[ 192804-36-7 ]
2-acetyl-N-(p-benzyloxycarbonylaminophenyl)pyrrole [ No CAS ]

Reference： [1]Journal of Organic Chemistry,2002,vol. 67,p. 1699 - 1702

3
[ 119671-47-5 ]
[ 192804-36-7 ]
C₂₃H₂₂N₂O₅ [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2007,vol. 50,p. 1958 - 1972

4
[ 138647-49-1 ]
[ 192804-36-7 ]
[ 873454-39-8 ]

Yield	Reaction Conditions	Operation in experiment
	With potassium carbonate;tetrakis(triphenylphosphine) palladium(0); In N,N-dimethyl-formamide; at 100℃; for 3.0h;	A solution of 4-trifluoromethanesulfonyloxy-3,6-dihydro-2H-pyridine-1-carboxylic acid tert-butyl ester (0.92 g) obtained in Example (228a), tetrakis triphenylphosphine palladium (160 mg), potassium carbonate (1.3 g) and <strong>[192804-36-7](4-benzyloxycarbonylaminophenyl)boric acid</strong> (0.80 g) in dimethylformamide (50 mL) was heated at 100C for three hours. The reaction mixture was diluted with ethyl acetate and washed with saturated brine and dried over sodium sulfate and concentrated. The residue was purified by column chromatography (hexane: ethyl acetate 2:1) and 442 mg of the title compound was obtained as a pink solid. MS(ES+) m/z:409 (M + H)+.

Reference： [1]Patent: EP1764360,2007,A1 .Location in patent: Page/Page column 89; 165

5
[ 109911-38-8 ]
[ 192804-36-7 ]
[ 1123215-72-4 ]

Reference： [1]Journal of Medicinal Chemistry,2009,vol. 52,p. 1081 - 1099

6
[ 1122-91-4 ]
[ 192804-36-7 ]
[ 939758-25-5 ]

Reference： [1]Organic and Biomolecular Chemistry,2009,vol. 7,p. 4309 - 4316

7
[ 108-05-4 ]
[ 192804-36-7 ]
[ 227778-64-5 ]

Reference： [1]European Journal of Organic Chemistry,2010,p. 2270 - 2274

8
[ 111-34-2 ]
[ 192804-36-7 ]
[ 72531-10-3 ]

Reference： [1]European Journal of Organic Chemistry,2010,p. 2270 - 2274

9
[ 141-32-2 ]
[ 192804-36-7 ]
[ 1228345-84-3 ]

Reference： [1]European Journal of Organic Chemistry,2010,p. 2270 - 2274

10
[ 16212-05-8 ]
[ 192804-36-7 ]
[ 1260118-74-8 ]

Reference： [1]Angewandte Chemie - International Edition,2010,vol. 49,p. 8938 - 8941

11
[ 930-30-3 ]
[ 192804-36-7 ]
[ 1350445-11-2 ]

Yield	Reaction Conditions	Operation in experiment
80%	acetylacetonatobis-(ethylene)rhodium(I); (+)-2,2'-O,O-(1,1'-binaphthyl)-dioxo-N,N-diethylphospholidine; In 1,4-dioxane; water; at 20 - 105℃; for 0.666667h;Inert atmosphere;	Intermediate (9)[4-((S)-3-Oxo-cyclopentyl)-phenyl]-carbamic acid benzyl esterIn a 50 mL round bottom flask was charged with Rh(acac)(C-2H )2 (acetylacetonatobis-(ethylene)rhodium(l), CAS 12082-47-2) (54 mg, 0.21 mmol, 3 mol%) and (S)-(+)-(3,5-dioxa-4-phospha-cyclohepta[2,1 -a:3,4- a']dinaphthalen-4-yl)- diethylamine (from Strem Chemicals, Inc. CAS: 252288-04-3) (210 mg, 0.542 mmol, 7.5 mol%). To this was added 18 mL of dioxane and 1 .8 mL of water. The flask was purged with N2/vacuum cycle 3 times. The solution was stirred at rt for 5 min. 4- Benzyloxycarbonylamino-boronic acid (CAS 192804-36-7) (5.39 g, 19.8 mmol, 2.28 equiv.) was added in powder form and the solution was heated in a pre-heated oil bath set at 105C externally and was kept at that temperature for 5 min to ensure the inside and outside temperature was in equilibrium. To this was added slowly cyclopentenone (710 mg, 8.66 mmol, 1 equiv.) in liquid neat form drop-wise, and the resulting mixture was stirred at 105C (external temperature) for 35 min. The reaction was cooled to rt and quenched with NaHCO3 aq (15 mL) and EtOAc 20 mL. The two layers were separated and the aqueous layer was extracted with EtOAc (2X20 mL). The combined extracts were washed with NaHCO3 aq. (10 mL), and brine (10 mL), and dried (K2CO3). The solution was filtered through a silica gel pad, eluted with EtOAc. The filtrate was concentrated to dryness. The residue was dissolved in 30% EtOAc in heptane and loaded onto a 50 g silica gel column, eluted with 30% EtOAc in heptane to obtain a crude product. This was crystallized from 30% EtOAc in heptane to obtain 2.15 g (80% yield) of the title compound as a very white crystalline material, m.p. 96.3-98.5C.LC/MS: RT =3.20 min. MS (ESI) m/z = 310 (M+H+)[a]D = -28.4 in chloroform (c = 0.5 g/100 mL); Chiral HPCL: ee = 57.3%. Chiral HPLC conditions: Agilent 1200 HPLC system; CHIRALCEL OD-H, 150 mm x 4.6 mm ID, 5 micron; Heptane : Ethanol = 50:50; Flow rate: 0.70 mL/min; Detection: UV 220 nm; injection volume: 10 mu.1H NMR (300MHz, CDCI3) delta: 7.37 (m, 5H), 7.26-7.18 (m, 4H), 6.62 (s, 1 H), 5.21 (s, 2H), 3.38 (m, 1 H), 2.65 (dd, 7.5 Hz, 18.3 Hz, 1 H), 2.50-2.23 (m, 4H), 1 .95 (m, 1 H).

Reference： [1]Patent: WO2011/143150,2011,A1 .Location in patent: Page/Page column 41-42

12
[ 192804-36-7 ]
[ 865869-24-5 ]
[ 1350445-16-7 ]