[ CAS No. 287944-05-2 ] {[proInfo.proName]}

Name: 287944-05-2|4,4,5,5-Tetramethyl-2-(1,2,3,6-tetrahydro-[1,1'-biphenyl]-4-yl)-1,3,2-dioxaborolane|95%
Brand: Ambeed
SKU: A516688
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Quality Control of [ 287944-05-2 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 287944-05-2 ]

SDS Specification

Alternatived Products of [ 287944-05-2 ]

Product Details of [ 287944-05-2 ]

CAS No. :	287944-05-2	MDL No. :	MFCD11520534
Formula :	C₁₈H₂₅BO₂	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	DRSHTDMLLXFEMB-UHFFFAOYSA-N
M.W :	284.20	Pubchem ID :	11289092
Synonyms :

Calculated chemistry of [ 287944-05-2 ]

Physicochemical Properties

Num. heavy atoms :	21
Num. arom. heavy atoms :	6
Fraction Csp3 :	0.56
Num. rotatable bonds :	2
Num. H-bond acceptors :	2.0
Num. H-bond donors :	0.0
Molar Refractivity :	88.64
TPSA :	18.46 Å²

Pharmacokinetics

GI absorption :	High
BBB permeant :	Yes
P-gp substrate :	Yes
CYP1A2 inhibitor :	No
CYP2C19 inhibitor :	No
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	Yes
CYP3A4 inhibitor :	Yes
Log Kp (skin permeation) :	-5.04 cm/s

Lipophilicity

Log Po/w (iLOGP) :	0.0
Log Po/w (XLOGP3) :	4.21
Log Po/w (WLOGP) :	4.51
Log Po/w (MLOGP) :	3.18
Log Po/w (SILICOS-IT) :	3.13
Consensus Log Po/w :	3.01

Druglikeness

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

Water Solubility

Log S (ESOL) :	-4.33
Solubility :	0.0132 mg/ml ; 0.0000464 mol/l
Class :	Moderately soluble
Log S (Ali) :	-4.31
Solubility :	0.014 mg/ml ; 0.0000493 mol/l
Class :	Moderately soluble
Log S (SILICOS-IT) :	-5.18
Solubility :	0.00188 mg/ml ; 0.00000662 mol/l
Class :	Moderately soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	1.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	4.06

Safety of [ 287944-05-2 ]

Signal Word:	Warning	Class:	N/A
Precautionary Statements:	P261-P280-P305+P351+P338	UN#:	N/A
Hazard Statements:	H302-H315-H319-H332-H335	Packing Group:	N/A
GHS Pictogram:

Application In Synthesis of [ 287944-05-2 ]

* 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 [ 287944-05-2 ]
Downstream synthetic route of [ 287944-05-2 ]

[ 287944-05-2 ] Synthesis Path-Upstream 1~6

1
[ 122948-47-4 ]
[ 73183-34-3 ]
[ 287944-05-2 ]

Reference： [1] Bioorganic and Medicinal Chemistry Letters, 2012, vol. 22, # 24, p. 7376 - 7380
[2] Journal of the American Chemical Society, 2017, vol. 139, # 25, p. 8621 - 8627
[3] Patent: WO2012/129074, 2012, A1, . Location in patent: Page/Page column 32

2
[ 61676-62-8 ]
[ 86724-17-6 ]
[ 287944-05-2 ]

Reference： [1] Journal of the American Chemical Society, 2008, vol. 130, # 26, p. 8481 - 8490
[2] Synthetic Communications, 2008, vol. 38, # 22, p. 3984 - 3995

3
[ 25015-63-8 ]
[ 4994-16-5 ]
[ 287944-05-2 ]

Reference： [1] Synthesis, 2000, # 6, p. 778 - 780

4
[ 4894-75-1 ]
[ 287944-05-2 ]

Reference： [1] Patent: WO2012/129074, 2012, A1,
[2] Bioorganic and Medicinal Chemistry Letters, 2012, vol. 22, # 24, p. 7376 - 7380

5
[ 73183-34-3 ]
[ 287944-05-2 ]

Reference： [1] Chemical Communications, 2018, vol. 54, # 39, p. 4991 - 4994

6
[ 122948-47-4 ]
[ 25015-63-8 ]
[ 4994-16-5 ]
[ 287944-05-2 ]

Reference： [1] Synthesis, 2000, # 6, p. 778 - 780

[ 287944-05-2 ] Synthesis Path-Downstream 1~23

1
[ 122948-47-4 ]
[ 25015-63-8 ]
[ 4994-16-5 ]
[ 287944-05-2 ]

Reference： [1]Synthesis,2000,p. 778 - 780

2
[ 25015-63-8 ]
4-iodo-1,2,3,6-tetrahydro-1,1'-biphenyl [ No CAS ]
[ 4994-16-5 ]
[ 287944-05-2 ]

Reference： [1]Synthesis,2000,p. 778 - 780

3
[ 21040-45-9 ]
[ 287944-05-2 ]
4-cinnamyl-1,2,3,6-tetrahydro-1,1'-biphenyl [ No CAS ]

Reference： [1]Tetrahedron Letters,2003,vol. 44,p. 4311 - 4314

5
[ 61676-62-8 ]
[ 86724-17-6 ]
[ 287944-05-2 ]

Reference： [1]Journal of the American Chemical Society,2008,vol. 130,p. 8481 - 8490
[2]Synthetic Communications,2008,vol. 38,p. 3984 - 3995

6
[ 181658-26-4 ]
[ 287944-05-2 ]
[ 1041003-01-3 ]

Reference： [1]Journal of the American Chemical Society,2008,vol. 130,p. 8481 - 8490

7
[ 287944-05-2 ]
C₂₀H₁₇NO₃ [ No CAS ]
C₂₀H₁₇NO₃ [ No CAS ]

Reference： [1]Angewandte Chemie - International Edition,2012,vol. 51,p. 7799 - 7803

8
[ 287944-05-2 ]
[ 1402704-13-5 ]

Reference： [1]Angewandte Chemie - International Edition,2012,vol. 51,p. 7799 - 7803

9
[ 287944-05-2 ]
[ 1402704-33-9 ]

Reference： [1]Angewandte Chemie - International Edition,2012,vol. 51,p. 7799 - 7803

10
[ 122948-47-4 ]
[ 73183-34-3 ]
[ 287944-05-2 ]

Yield	Reaction Conditions	Operation in experiment
71.9%	With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; potassium acetate; In N,N-dimethyl-formamide; at 85℃; for 18.0h;Sealed tube; Inert atmosphere;	1F. 4,4,5,5-tetramethyl-2-(1,2,3,6-tetrahydro-[1,1'-biphenyl]-4-yl)-1,3,2-dioxaborolane In a sealed tube 1E (0.3 g, 0.979 mmol), BISPIN (0.373 g, 1.469 mmol) and potassium acetate (0.288 g, 2.94 mmol) in DMF (5.0 mL) purged with Argon for 20 min. To this PdCl2(dppf)-CH2Cl2 Adduct (0.040 g, 0.049 mmol) was added and purged with Argon for 5 min. The reaction mixture was heated at 85 C. for 18 h. Reaction mixture was cooled to room temperature and it was filtered through a pad of Celite. The pad of Celite was rinsed with dichloromethane (340 mL) and the filtrate was concentrated under reduced pressure to get residue which was diluted with dichloromethane (50 mL) and water (50 mL). Aqueous layer was extracted with DCM (250 mL). The combined organic layer was washed with brine (50 mL), dried over anhydrous sodium sulphate and concentrated under reduced pressure. Purification via flash chromatography gave 1F (colorless liquid, 0.2 g, 0.704 mmol, 71.9% yield). 1H NMR (300 MHz, CDCl3) delta 7.16-7.32 (m, 5H), 6.65-6.66 (m, 1H), 2.74-2.82 (m, 1H), 2.17-2.44 (m, 4H), 1.93-2.04 (m, 1H), 1.67-1.72 (m, 1H), 1.28 (s, 12H).
	With potassium acetate;(1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; In 1,4-dioxane; at 80℃; for 2.0h;Inert atmosphere;	A mixture of trifluoro-methanesulfonic acid 4-phenyl-cyclohex-l-enyl ester (5.8 g),bis(pinacolato)diboron (5.3 g), potassium acetate (5.58 g) and [1 ,1 '- bis(diphenylphosphine)ferrocene]dichloropalladium(II) (0.77 g) in 1 ,4-dioxane (150 mL) was degassed then heated to 80 C for 2 hours. The reaction mixture was filtered and the resulting filtrate concentrated under reduced pressure. The resulting residue was purified by column chromatography on silica gel, eluting with a mixture of diethyl ether and cyclohexane (0: 1 to 1 :20 by volume) to afford the title compound (4.0 g). NMR (CDC13): delta 7.30-7.28 (2 H, m), 7.24-7.15 (3 H, m), 6.65-6.64 (1 H, m), 2.82-2.71 (1 H, m), 2.40-2.36 (2 H, m), 2.23-2.22 (2 H, m), 1.95-1.94 (1 H, m), 1.70-1.68 (1 H, m), 1.43 (3 H, s), 1.28 (9 H, s).

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2012,vol. 22,p. 7376 - 7380
[2]Patent: US2020/69646,2020,A1 .Location in patent: Paragraph 0325
[3]Journal of the American Chemical Society,2017,vol. 139,p. 8621 - 8627
[4]Patent: WO2012/129074,2012,A1 .Location in patent: Page/Page column 32

11
[ 4894-75-1 ]
[ 287944-05-2 ]

Reference： [1]Patent: WO2012/129074,2012,A1
[2]Bioorganic and Medicinal Chemistry Letters,2012,vol. 22,p. 7376 - 7380
[3]Patent: US2020/69646,2020,A1

12
[ 18493-82-8 ]
[ 287944-05-2 ]
[ 1400901-95-2 ]
[ 1400902-32-0 ]

Reference： [1]Patent: WO2012/129074,2012,A1

13
[ 18493-82-8 ]
[ 287944-05-2 ]
[ 1400902-26-2 ]

Yield	Reaction Conditions	Operation in experiment
	With cesium fluoride;bis(di-tert-?butyl(4-?dimethylaminophenyl)?phosphine)?dichloropalladium(II); In 1,4-dioxane; water; at 140℃; for 0.333333h;microwave reactor;	A mixture of 5-benzyl-6-chloro-l H-pyrimidine-2,4-dione (WO06014394) (1.0 g), 4,4,5,5-tetramethyl-2-(4- phenylcyclohex-l-enyl)-[l ,3,2]dioxaborolane (1.4 g), bis[di-tert-butyl(4- dimethylaminophenyl)phosphine]dichloropalladium(II) (0.06 g) and cesium fluoride (1.92 g) in 1,4-dioxane (18 mL) and water (2 mL) was heated at 140 C in a microwave reactor for 20 minutes. The resulting mixture was diluted with saturated aqueous ammonium chloride and filtered to remove the precipitate. The filtrate was extracted with dichloromethane and the combined organic layers washed with water and brine, then dried over sodium sulfate and concentrated under reduced pressure. The resulting residue was purified by column chromatography on silica gel, eluting with a mixture of methanol and dichloromethane (0:1 to 1 :20 by volume) to afford the title compound 2a as an off-white solid (0.48 g). LCMS (Method A): R, = 3.56 min. (M+H)+ = 359. NMR (DMSO-D6): delta 11.06 (1 H, s), 10.69 (1 H, s), 7.23-7.21 (10 H, m), 5.84-5.79 (1 H, m), 3.61 (2 H, s), 3.57 (1 H, s), 2.77-2.67 (1 H, m), 2.19-2.16 (3 H, m), 1.84-1.81 (1 H, m), 1.68-1.67 (1 H, m).

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2012,vol. 22,p. 7376 - 7380
[2]Patent: WO2012/129074,2012,A1 .Location in patent: Page/Page column 32

14
[ 18493-82-8 ]
[ 287944-05-2 ]
C₂₃H₂₄N₂O₂ [ No CAS ]
C₂₃H₂₄N₂O₂ [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2012,vol. 22,p. 7376 - 7380

15
2-phenylhexa-4,5-dien-1-ol [ No CAS ]
trans-4,4,5,5-tetramethyl-2-[1-(3-phenylcyclobutyl)vinyl]-1,3,2-dioxaborolane [ No CAS ]
4,4,5,5-tetramethyl-2-[1-(3-phenylcyclobutyl)vinyl]-1,3,2-dioxaborolane [ No CAS ]
[ 287944-05-2 ]

Reference： [1]Chemical Communications,2018,vol. 54,p. 4991 - 4994

16
(1-bromohexa-4,5-dien-2-yl)benzene [ No CAS ]
[ 73183-34-3 ]
trans-4,4,5,5-tetramethyl-2-[1-(3-phenylcyclobutyl)vinyl]-1,3,2-dioxaborolane [ No CAS ]
4,4,5,5-tetramethyl-2-[1-(3-phenylcyclobutyl)vinyl]-1,3,2-dioxaborolane [ No CAS ]
[ 287944-05-2 ]

Reference： [1]Chemical Communications,2018,vol. 54,p. 4991 - 4994

17
[ 170011-47-9 ]
[ 287944-05-2 ]