[ CAS No. 190661-29-1 ] {[proInfo.proName]}

Name: 190661-29-1|(2-(Benzyloxy)phenyl)boronic acid|97%
Brand: Ambeed
SKU: A326788
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2D 3D

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Quality Control of [ 190661-29-1 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 190661-29-1 ]

SDS Specification

Alternatived Products of [ 190661-29-1 ]

Product Details of [ 190661-29-1 ]

CAS No. :	190661-29-1	MDL No. :	MFCD01632206
Formula :	C₁₃H₁₃BO₃	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	MCAIDINWZOCYQK-UHFFFAOYSA-N
M.W :	228.05	Pubchem ID :	2773253
Synonyms :

Calculated chemistry of [ 190661-29-1 ]

Physicochemical Properties

Num. heavy atoms :	17
Num. arom. heavy atoms :	12
Fraction Csp3 :	0.08
Num. rotatable bonds :	4
Num. H-bond acceptors :	3.0
Num. H-bond donors :	2.0
Molar Refractivity :	67.25
TPSA :	49.69 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) :	-6.07 cm/s

Lipophilicity

Log Po/w (iLOGP) :	0.0
Log Po/w (XLOGP3) :	2.29
Log Po/w (WLOGP) :	0.79
Log Po/w (MLOGP) :	1.54
Log Po/w (SILICOS-IT) :	0.77
Consensus Log Po/w :	1.08

Druglikeness

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

Water Solubility

Log S (ESOL) :	-2.95
Solubility :	0.253 mg/ml ; 0.00111 mol/l
Class :	Soluble
Log S (Ali) :	-2.97
Solubility :	0.244 mg/ml ; 0.00107 mol/l
Class :	Soluble
Log S (SILICOS-IT) :	-3.96
Solubility :	0.0251 mg/ml ; 0.00011 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	1.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	2.14

Safety of [ 190661-29-1 ]

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 [ 190661-29-1 ]

* 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 [ 190661-29-1 ]
Downstream synthetic route of [ 190661-29-1 ]

[ 190661-29-1 ] Synthesis Path-Upstream 1~9

1
[ 190661-29-1 ]
[ 946-80-5 ]
[ 368-21-8 ]

Reference： [1] Tetrahedron Letters, 2009, vol. 50, # 27, p. 3936 - 3938

2
[ 31575-75-4 ]
[ 190661-29-1 ]

Yield	Reaction Conditions	Operation in experiment
47%	Stage #1: With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 0.5 h; Stage #2: With Triisopropyl borate In tetrahydrofuran; hexane at -78 - 20℃; for 4 h; Stage #3: With hydrogenchloride In tetrahydrofuran; hexane; water	1) 19.93 ml of BuLi (1.6M in hexane) (31.9 mM, 1 equivalent) is added, at -78° C. by syringe, to a solution of 8.4 g of bromo derivative (N8) (31.9 mM, 1 equivalent) in 50 ml of THF, and the mixture is stirred for 30 minutes at -78° C. A solution containing the lithiated derivative is thus obtained, and is added via a dropping funnel, at -78° C., to a solution of 30 g of B(OiPr)₃(159.5 mM, 5 equivalents) in 50 ml of THF. The mixture is then stirred, while allowing to warm to room temperature, for 4 hours. The resulting mixture is poured into 20 ml of 3N HCl, extracted twice with 50 ml of EtOAc, washed with water, dried over MgSO₄and evaporated to dryness. The 8.53 g of crude product are obtained, and are purified on silica, eluting with 9/1 cyclohexane/EtOAc. 3.6 g (47percent) of pure product are thus obtained.

Reference： [1] Organic Letters, 2004, vol. 6, # 24, p. 4595 - 4597
[2] Patent: US2005/154048, 2005, A1, . Location in patent: Page/Page column 17

3
[ 688-74-4 ]
[ 31575-75-4 ]
[ 190661-29-1 ]

Yield	Reaction Conditions	Operation in experiment
63.3%	Stage #1: With iodine; magnesium In tetrahydrofuran at 47℃; for 2 h; Inert atmosphere Stage #2: at -30 - 20℃; for 4 h; Inert atmosphere Stage #3: With hydrogenchloride; water In tetrahydrofuran at 20℃; for 0.5 h;	Magnesium shavings(0.22 g, 9.13 mmol) and one crystal of iodine were added to a flask slowly and heated to 35 °C under a nitrogen atmosphere, and then 3–5 drops of solution of compound 1 (2.00 g, 7.61 mmol) in dry THF (12 mL) were added. After keeping the reaction mixture at 47 °C for 5 min without stirring, the rest of the mixture was added dropwise into the flask with stirring, during which the iodine started to fade. Simultaneously, the flask was replenished with dry THF (4 mL). The reaction mixture was kept at 47 °C for 2 h, and then cooled to room temperature. Finally, it was added dropwise over a period of 30 min to a stirred solution of tri-n-butylborate (3.50 g, 15.21 mmol) inTHF (7 mL) at –30 °C. 2 h later, the solution was warmed to room temperature and stirred for a further 2 h. The reaction was quenched by adding 37percent HCl aqueous (4 mL). 30 min later, the solution was extracted with ether. The combined ether extracts were then extracted with 1 M NaOH (45 mL). A grey white precipitate then formed which was removed by filtration. The resulting precipitate, namely a basic salt was reacted with 37percent HCl aqueous once again to obtain a white precipitate, which was then collected by vacuum filtration and washed with a little cold water and dried to afford 2 (1.10 g, 63.3percent); m.p. 108–109 °C; IR (KBr, νmax/cm–1): 3400, 1341, 759; 1H NMR: δ 7.89 (d, 1H, J = 7.29 Hz), 7.48–7.39 (m, 6H), 7.10–7.06 (m, 1H), 7.01(d, 1H, J = 8.22 Hz), 5.74 (s, 2H), 5.17 (s, 2H); LC-MS (ESI): calcd forC13H11BO3([M-2H]+): 226.1; found: 226.2.
63.3%	Stage #1: With iodine; magnesium In tetrahydrofuran at 35 - 47℃; for 0.0833333 h; Inert atmosphere Stage #2: With hydrogenchloride In tetrahydrofuran at -30℃; for 5 h;	Preparation of 2-benzyloxy-phenyl boronic acid: Magnesium turnings (0.22g, 9.12mmol) and a fine iodine added to the reaction vessel, N₂Under protection, at room temperature to 35 , then a few drops of 2-benzyloxy-bromobenzene (2.00g, 7.60mmol) and anhydrous tetrahydrofuran (12mL) mixture solution, heated to 47 deg.] C water bath, incubated for about 5min , the color of iodine began to disappear, indicating the successful initiation, then began stirring, and a solution of the remaining mixture to the reactor while additional anhydrous tetrahydrofuran 1.5 mL, insulation reaction 2h, obtained2-benzyloxy-magnesium bromide Grignard reagent, by acid titration in a yield of 99.2percent..Preparation of 2-benzyloxy-phenyl boronic acid: Magnesium turnings (0.22g, 9.12mmol) and a fine iodine added to the reaction vessel, N₂Under protection, at room temperature to 35 , then a few drops of 2-benzyloxy-bromobenzene (2.00g, 7.60mmol) and anhydrous tetrahydrofuran (12mL) mixture solution, heated to 47 deg.] C water bath, incubated for about 5min , the color of iodine began to disappear, indicating the successful initiation, then began stirring, and a solution of the remaining mixture to the reactor while additional anhydrous tetrahydrofuran 1.5 mL, insulation reaction 2h, obtained.Mixed solution prepared Grignard reagent was slowly added dropwise tributyl borate (3.50g, 15.21mmol) and anhydrous tetrahydrofuran (7mL) composition, stirring, temperature control at -30 , heat the reaction 2h, then quickly warmed to room temperature and stirring was continued for 2h, was slowly added a solution of hydrochloric acid, to pH = about 2, 1h, the organic phase was separated, the aqueous layer was extracted with ethyl acetate, the combined organic phase was concentrated under reduced pressure, and water was added to the concentrate, and treated with sodium hydroxide solution to adjust pH = 12, and practically about 50 steam distillation under reduced pressure to a yellow oil block appears flask, filtered hot, the filtrate was acidified to about pH = 2, the yellow oil was extracted with hot block, the mother liquor combined and concentrated , placed in an ice water bath cooling, crystallization, drying to a constant weight to give a white solid 1.13g, yield 63.3percent.

Reference： [1] Journal of Chemical Research, 2015, vol. 39, # 10, p. 586 - 589
[2] Patent: CN105566231, 2016, A, . Location in patent: Paragraph 0032; 0039; 0040; 0041

4
[ 5419-55-6 ]
[ 31575-75-4 ]
[ 190661-29-1 ]

Reference： [1] Patent: US2002/156018, 2002, A1,
[2] Patent: US5998470, 1999, A,

5
[ 95-56-7 ]
[ 190661-29-1 ]

Reference： [1] Organic Letters, 2004, vol. 6, # 24, p. 4595 - 4597
[2] Journal of Chemical Research, 2015, vol. 39, # 10, p. 586 - 589
[3] Patent: CN105566231, 2016, A,

6
[ 100-39-0 ]
[ 190661-29-1 ]

Reference： [1] Bioorganic and Medicinal Chemistry Letters, 2009, vol. 19, # 2, p. 497 - 501
[2] Journal of Chemical Research, 2015, vol. 39, # 10, p. 586 - 589
[3] Patent: CN105566231, 2016, A,

7
[ 946-80-5 ]
[ 190661-29-1 ]

Reference： [1] Bioorganic and Medicinal Chemistry Letters, 2009, vol. 19, # 2, p. 497 - 501

8
[ 142523-69-1 ]
[ 190661-29-1 ]

Reference： [1] Bioorganic and Medicinal Chemistry Letters, 2009, vol. 19, # 2, p. 497 - 501

9
[ 108-95-2 ]
[ 190661-29-1 ]

Reference： [1] Bioorganic and Medicinal Chemistry Letters, 2009, vol. 19, # 2, p. 497 - 501

[ 190661-29-1 ] Synthesis Path-Downstream 1~88

1
[ 190661-29-1 ]
[ 351002-11-4 ]
8-(2-benzyloxy-phenyl)-2-morpholin-4-yl-chromen-4-one [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2005,vol. 48,p. 7829 - 7846

2
[ 190661-29-1 ]
[ 503467-98-9 ]
7-(2-benzyloxy-phenyl)-2-morpholin-4-yl-chromen-4-one [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2005,vol. 48,p. 7829 - 7846

3
[ 190661-29-1 ]
[ 130735-60-3 ]
6-(2-benzyloxy-phenyl)-2-morpholin-4-yl-chromen-4-one [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2005,vol. 48,p. 7829 - 7846

4
[ 61294-07-3 ]
[ 190661-29-1 ]
1-(2-Benzyloxy-phenyl)-3-[(Z)-3-trifluoromethyl-phenylimino]-1,3-dihydro-indol-2-one [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2006,vol. 16,p. 3950 - 3954

5
[ 190661-29-1 ]
[ 500169-22-2 ]
C₂₈H₂₅NO₃S [ No CAS ]

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

6
[ 190661-29-1 ]
[ 500169-21-1 ]
C₂₈H₂₅NO₃S [ No CAS ]

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

7
[ 119671-47-5 ]
[ 190661-29-1 ]
2-(4-Morpholinyl)-6-(2-(phenylmethoxy)phenyl)-4H-pyran-4-one [ No CAS ]

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

8
[ 81574-69-8 ]
[ 190661-29-1 ]
[ 947499-30-1 ]

Reference： [1]Journal of the American Chemical Society,2007,vol. 129,p. 9304 - 9305

9
[ 95-56-7 ]
[ 190661-29-1 ]

Reference： [1]Organic Letters,2004,vol. 6,p. 4595 - 4597
[2]Journal of Chemical Research,2015,vol. 39,p. 586 - 589
[3]Patent: CN105566231,2016,A

10
[ 100-44-7 ]
N,N-diethyl-glycine-<4-hydroxy-anilide> [ No CAS ]
[ 190661-29-1 ]

Reference： [1]Organic Letters,2004,vol. 6,p. 4595 - 4597

11
[ 190661-29-1 ]
(+/-)-(1S,3S,3aR,8bS)-3a-(4-methoxyphenyl)-3-phenyl-2,3,3a,8b-tetrahydro-1H-benzo[b]cyclopenta[d]furan-1,8b-diol [ No CAS ]

Reference： [1]Organic Letters,2004,vol. 6,p. 4595 - 4597
[2]Organic Letters,2004,vol. 6,p. 4595 - 4597

12
[ 190661-29-1 ]
(+/-)-(1S,3R,3aR,8bS)-3a-(4-methoxyphenyl)-3-phenyl-2,3,3a,8b-tetrahydro-1H-benzo[b]cyclopenta[d]furan-1,8b-diol [ No CAS ]

Reference： [1]Organic Letters,2004,vol. 6,p. 4595 - 4597

13
[ 190661-29-1 ]
(+/-)-(1S,4S)-2-[2-(benzyloxy)phenyl]-3-(4-methoxyphenyl)-4-phenylcyclopent-2-en-1-ol [ No CAS ]

Reference： [1]Organic Letters,2004,vol. 6,p. 4595 - 4597
[2]Organic Letters,2004,vol. 6,p. 4595 - 4597

14
[ 190661-29-1 ]
(+/-)-(1S,4R)-2-[2-(benzyloxy)phenyl]-3-(4-methoxyphenyl)-4-phenylcyclopent-2-en-1-ol [ No CAS ]

Reference： [1]Organic Letters,2004,vol. 6,p. 4595 - 4597

15
[ 190661-29-1 ]
(+/-)-(1S,2S,4R,5S)-1-[2-(benzyloxy)phenyl]-5-(4-methoxyphenyl)-4-phenyl-6-oxabicyclo[3.1.0]hexan-2-ol [ No CAS ]

Reference： [1]Organic Letters,2004,vol. 6,p. 4595 - 4597

16
[ 190661-29-1 ]
(+/-)-(1S,2S,4S,5S)-1-[2-(benzyloxy)phenyl]-5-(4-methoxyphenyl)-4-phenyl-6-oxabicyclo[3.1.0]hexan-2-ol [ No CAS ]

Reference： [1]Organic Letters,2004,vol. 6,p. 4595 - 4597
[2]Organic Letters,2004,vol. 6,p. 4595 - 4597

17
[ 190661-29-1 ]
[ 637328-01-9 ]