[ CAS No. 374706-07-7 ] {[proInfo.proName]}

Name: 374706-07-7|1-(2,3-Dihydrobenzofuran-6-yl)ethanone|95%
Brand: Ambeed
SKU: A109421
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Quality Control of [ 374706-07-7 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 374706-07-7 ]

SDS Specification

Alternatived Products of [ 374706-07-7 ]

Product Details of [ 374706-07-7 ]

CAS No. :	374706-07-7	MDL No. :	MFCD01548979
Formula :	C₁₀H₁₀O₂	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	FGMNFKJFNHRARH-UHFFFAOYSA-N
M.W :	162.19	Pubchem ID :	45086222
Synonyms :

Calculated chemistry of [ 374706-07-7 ]

Physicochemical Properties

Num. heavy atoms :	12
Num. arom. heavy atoms :	6
Fraction Csp3 :	0.3
Num. rotatable bonds :	1
Num. H-bond acceptors :	2.0
Num. H-bond donors :	0.0
Molar Refractivity :	45.98
TPSA :	26.3 Å²

Pharmacokinetics

GI absorption :	High
BBB permeant :	Yes
P-gp substrate :	No
CYP1A2 inhibitor :	Yes
CYP2C19 inhibitor :	No
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-6.15 cm/s

Lipophilicity

Log Po/w (iLOGP) :	2.0
Log Po/w (XLOGP3) :	1.61
Log Po/w (WLOGP) :	1.82
Log Po/w (MLOGP) :	1.35
Log Po/w (SILICOS-IT) :	2.81
Consensus Log Po/w :	1.92

Druglikeness

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

Water Solubility

Log S (ESOL) :	-2.16
Solubility :	1.11 mg/ml ; 0.00686 mol/l
Class :	Soluble
Log S (Ali) :	-1.77
Solubility :	2.73 mg/ml ; 0.0168 mol/l
Class :	Very soluble
Log S (SILICOS-IT) :	-3.01
Solubility :	0.157 mg/ml ; 0.000968 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	0.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	1.78

Safety of [ 374706-07-7 ]

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

Application In Synthesis of [ 374706-07-7 ]

* 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 [ 374706-07-7 ]
Downstream synthetic route of [ 374706-07-7 ]

[ 374706-07-7 ] Synthesis Path-Upstream 1~3

1
[ 97674-02-7 ]
[ 189035-22-1 ]
[ 374706-07-7 ]

Yield	Reaction Conditions	Operation in experiment
73.7%	With bis-triphenylphosphine-palladium(II) chloride In toluene at 90℃; for 16 h;	The title compound was prepared according to procedures reported in the literature and known by persons skill in the art, using 6-bromo-2,3-dihydro-1-benzofuran (1 g, 5.03 mmol) as starting material. In a preferred method, 6-bromo-2,3-dihydro-1-benzofuran (1 g, 5.03 mmol) in toluene (10 mL) was degassed for 30 min. To this solution, 1-ethoxyvinyl tributyltin (2.012 g, 5.53 mmol) and bis(triphenylphosphine)palladium dichloride (0.35 g, 0.50 mmol) were added at rt and stirred for 16 hours at 90 °C. The reaction mixture was cooled to rt and filtered through celite. After evaporation of the solvent, 6 N HCl solution in water (10 mL) was added and the mixture was stirred for 1 hour at rt. It was concentrated and neutralized with sat. NaHCO₃. The desired product was extracted with DCM (50 mL), dried over Na₂SO₄ and concentrated. The crude product was purified by flash chromatography to give the title compound. Yield: 73.7percent (0.6 g, pale yellow solid). ¹H NMR (400 MHz, DMSO-d₆): δ 7.48 (d, J = 7.64 Hz, 1H), 7.37-7.35 (d, J = 7.68 Hz, 1H), 7.26 (s, 1H), 4.58 (t, J = 8.76 Hz, 2H), 3.24 (t, J = 8.76 Hz, 2H), 2.53 (s, 3H). LCMS: (Method A) 163.2 (M+H), Rt. 3.01 min, 97.60percent (Max).

Reference： [1] Patent: WO2017/144635, 2017, A1, . Location in patent: Page/Page column 32; 33

2
[ 108-24-7 ]
[ 374706-07-7 ]

Reference： [1] Patent: WO2006/137796, 2006, A1, . Location in patent: Page/Page column 86

3
[ 189035-22-1 ]
[ 374706-07-7 ]

Reference： [1] Patent: WO2006/137796, 2006, A1,

[ 374706-07-7 ] Synthesis Path-Downstream 1~12

1
[ 108-24-7 ]
bromo(2,3-dihydro-1-benzofuran-6-yl)magnesium [ No CAS ]
[ 374706-07-7 ]

Yield	Reaction Conditions	Operation in experiment
		-(2,3-Dihydro-benzofuran-6-yI)-ethanoneA solution of bromo(2,3-dihydro-l-benzofuran-6-yl)magnesium (prepared from 6-bromo-2,3~ dihydro-benzofuran (2.50 g, 12,56 rnmol) and Mg (0.336 g, 13.8 mmol)) in THF (10 mL) was dropwise added to a solution of acetic anhydride (2.40 mL, 25.4 rnmol) in Et20 (10 mL) held at -780C. The reaction mixture was stirred at -78C for Ih before the temperature was allowed to reach -1O0C over a period of Ih. The reaction mixture was quenched by the addition of NH4C1 (aq, saturated, 20 mL) and the resulting mixture was extracted twice with Et2O (2x10 mL). The organic extracts were pooled, washed with NaOH (aq, 5%, 10 mL) and brine (10 mL), dried over MgSO4 and concentrated under reduced pressure. The residue was purified by preparative HPLC using a gradient of 20-50% MeCN in a 0. IM ammonium acetate buffer as eluent. Freeze-drying of the pure fractions gave the desired product.1H-NMR (CDC13, 400 MHz): δ 2.5 (s, 3H), 3.2 (t, 2H), 4.6 (t, 2H), 7.5-7.7 (m, 3H).

Reference： [1]Patent: WO2006/137796,2006,A1 .Location in patent: Page/Page column 86

2
[ 374706-07-7 ]
[ 917815-17-9 ]

Yield	Reaction Conditions	Operation in experiment
	With bromine; In methanol; at 0 - 25℃; for 3h;	2-Bromo-l-(2,3-dihydro-benzofuran-6-yl)-ethanoneBr2 (0.36 ml, 7.01 mmol) was added dropwise to a stirring solution of l-(2,3-dihydro- benzofuran-6-yl)-ethanone (1.13 g, 6.97 mmol) in MeOH (20 mL) held at 00C. The reaction mixture was slowly allowed to reach room temperature. After 3 h, the reaction was quenched by the addition of NaHCO3 (aq, saturated)(until pH=8). Most of the methanol was removed under reduced pressure and the residue was extracted twice with EtOAc (2x20 mL). The organic extracts were pooled, washed with brine (10 mL), dried over MgSO4 and concentrated under reduced pressure. The residue was purified by preparative HPLC using a gradient of 40-70% MeCN in a 0.1M ammonium acetate buffer as eluent. The fractions containing the desired product were pooled and most of the MeCN was removed under EPO <DP n="89"/>reduced pressure. The residue was extracted with EtOAc (2x20 mL) and the combined organic layers was washed with brine, dried over MgSO4 and concentrated. The obtained was finely washed MeOH to give the title compound.1H-NMR (CDC13, 400 MHz): δ 3.25 (t, 2H), 4.39 (s, 2H), 4.61 (t, 2H), 7.24-7.36 (m, 2H), 7.45-7.52 (m, IH).-

Reference： [1]Patent: WO2006/137796,2006,A1 .Location in patent: Page/Page column 86-87

Yield	Reaction Conditions	Operation in experiment
73.7%		General procedure: 6-Bromo quinoxaline (2.0 g, 9.5 mmol) in toluene (20 ml.) was degassed for 30 min. To this solution, 1-ethoxy vinyl tributyltin (3.8 g, 10.5 mmol) and bis(triphenylphosphine)palladium dichloride (0.67 g, 0.95 mmol) were added at rt and stirred for 16 hours at 90 C. The reaction mixture was cooled to rt and filtered through celite. After evaporation of the solvent, 6 N HCI solution in water (20 ml.) was added and the mixture was stirred for 1 hour at rt. It was concentrated and neutralized with sat. NaHCO3. The desired product was extracted with DCM (100 mL,), dried over Na2SO4 and concentrated. The crude product was purified by flash column chromatography to afford the title compound (brown solid). 1H NMR (400 MHz, DMSO-d6): δ 9.06-9.04 (m, 2H), 8.70 (d, J=2.4 Hz, 1H), 8.28 (t, J = 2.8 Hz, 1H), 8.16 (d, J = 11.6 Hz, 1H), 2.97 (s, 3H). LCMS: (Method A) 173 (M+H), Rt. 2.25 min, 99.06% (Max).

4
[ 374706-07-7 ]
[ 33513-42-7 ]
2,4-bis(2,3-dihydrobenzofuran-6-yl)pyridine [ No CAS ]

Reference： [1]Advanced Synthesis and Catalysis,2017,vol. 359,p. 78 - 88

5
[ 374706-07-7 ]
1-(2,3-dihydrobenzofuran-6-yl)ethan-1-ol [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With methanol; sodium tetrahydroborate; at 0℃; for 1.5h;	The title compound was prepared according to procedures reported in the literature and known by persons skill in the art, using <strong>[374706-07-7]1-(2,3-dihydrobenzofuran-6-yl)ethan-1-one</strong> (0.6 g, 3.7 mmol) as starting material. In a preferred method, to a stirred solution of <strong>[374706-07-7]1-(2,3-dihydrobenzofuran-6-yl)ethan-1-one</strong> (0.6 g, 3.7 mmol) in methanol (10 mL), sodium borohydride (281 mg, 7.4 mmol) was added slowly at 0 C and stirred 1.5 h. The completion of the reaction was monitored by TLC and the solvents were evaporated at 45 C under vacuum. The residue was diluted with EtOAc (25 mL) and washed with water (25 mL), brine solution (25 mL) and dried over Na2SO4. After evaporation of the solvent, the title compound was isolated and used without further purification. Yield: 88.30% (0.53 g, colourless liquid). 1H NMR (400 MHz, DMSO-d6): δ 7.1 1 (d, J = 7.6 Hz, 1H), 6.77-6.75 (m, 1 H), 6.71 (s, 1H), 5.04 (d, J = 4.4 Hz, 1H), 4.63-4.61 (m, 1H), 4.48 (t, J = 8.8 Hz, 2H), 3.1 1 (t, J = 8.8 Hz, 2H), 1 .25 (d, J = 6.4 Hz, 3H). LCMS: (Method A) 147.0 (M-17H), Rt. 2.64 min, 89.95% (Max).

Reference： [1]Patent: WO2017/144635,2017,A1 .Location in patent: Page/Page column 32; 33

6
[ 97674-02-7 ]
[ 189035-22-1 ]
[ 374706-07-7 ]

Yield	Reaction Conditions	Operation in experiment
73.7%	With bis-triphenylphosphine-palladium(II) chloride; In toluene; at 90℃; for 16h;	The title compound was prepared according to procedures reported in the literature and known by persons skill in the art, using <strong>[189035-22-1]6-bromo-2,3-dihydro-1-benzofuran</strong> (1 g, 5.03 mmol) as starting material. In a preferred method, <strong>[189035-22-1]6-bromo-2,3-dihydro-1-benzofuran</strong> (1 g, 5.03 mmol) in toluene (10 mL) was degassed for 30 min. To this solution, 1-ethoxyvinyl tributyltin (2.012 g, 5.53 mmol) and bis(triphenylphosphine)palladium dichloride (0.35 g, 0.50 mmol) were added at rt and stirred for 16 hours at 90 C. The reaction mixture was cooled to rt and filtered through celite. After evaporation of the solvent, 6 N HCl solution in water (10 mL) was added and the mixture was stirred for 1 hour at rt. It was concentrated and neutralized with sat. NaHCO3. The desired product was extracted with DCM (50 mL), dried over Na2SO4 and concentrated. The crude product was purified by flash chromatography to give the title compound. Yield: 73.7% (0.6 g, pale yellow solid). 1H NMR (400 MHz, DMSO-d6): delta 7.48 (d, J = 7.64 Hz, 1H), 7.37-7.35 (d, J = 7.68 Hz, 1H), 7.26 (s, 1H), 4.58 (t, J = 8.76 Hz, 2H), 3.24 (t, J = 8.76 Hz, 2H), 2.53 (s, 3H). LCMS: (Method A) 163.2 (M+H), Rt. 3.01 min, 97.60% (Max).

Reference： [1]Patent: WO2017/144635,2017,A1 .Location in patent: Page/Page column 32; 33

7
[ 374706-07-7 ]
(R)-3-cyclohexyl-2-[2-(2-{4-[(2R,3R)-3-[2-(2,3-dihydro-benzofuran-6-yl)-2-hydroxy-ethylsulfanyl]-1-(4-fluoro-phenyl)-4-oxo-azetidin-2-yl]-phenoxy}-acetylamino)-acetylamino]-propionic acid [ No CAS ]