[ CAS No. 2879-20-1 ] {[proInfo.proName]}

Name: 2879-20-1|1-(2,3-Dihydrobenzo[b][1,4]dioxin-6-yl)ethanone|98%
Brand: Ambeed
SKU: A235779
Price: 6.0 USD
Availability: InStock
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3d Animation Molecule Structure of 2879-20-1

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Quality Control of [ 2879-20-1 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 2879-20-1 ]

SDS Specification

Alternatived Products of [ 2879-20-1 ]

Product Details of [ 2879-20-1 ]

CAS No. :	2879-20-1	MDL No. :	MFCD00006823
Formula :	C₁₀H₁₀O₃	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	HGVWMTAIIYNQSI-UHFFFAOYSA-N
M.W :	178.18	Pubchem ID :	76143
Synonyms :

Calculated chemistry of [ 2879-20-1 ]

Physicochemical Properties

Num. heavy atoms :	13
Num. arom. heavy atoms :	6
Fraction Csp3 :	0.3
Num. rotatable bonds :	1
Num. H-bond acceptors :	3.0
Num. H-bond donors :	0.0
Molar Refractivity :	47.51
TPSA :	35.53 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) :	-7.0 cm/s

Lipophilicity

Log Po/w (iLOGP) :	2.08
Log Po/w (XLOGP3) :	0.54
Log Po/w (WLOGP) :	1.66
Log Po/w (MLOGP) :	0.74
Log Po/w (SILICOS-IT) :	2.45
Consensus Log Po/w :	1.49

Druglikeness

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

Water Solubility

Log S (ESOL) :	-1.56
Solubility :	4.9 mg/ml ; 0.0275 mol/l
Class :	Very soluble
Log S (Ali) :	-0.86
Solubility :	24.7 mg/ml ; 0.139 mol/l
Class :	Very soluble
Log S (SILICOS-IT) :	-2.76
Solubility :	0.308 mg/ml ; 0.00173 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	0.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	2.06

Safety of [ 2879-20-1 ]

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

Application In Synthesis of [ 2879-20-1 ]

* 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 [ 2879-20-1 ]
Downstream synthetic route of [ 2879-20-1 ]

[ 2879-20-1 ] Synthesis Path-Upstream 1~8

1
[ 7338-03-6 ]
[ 2879-20-1 ]

Yield	Reaction Conditions	Operation in experiment
82%	With Dess-Martin periodane In dichloromethane at 0 - 20℃; for 16 h; Inert atmosphere	General procedure: Method B: to a solution of compound 4a (1.65 g, 9.94 mmol) inanhydrous CH2Cl2 (100 mL) stirred at 0 C under argon was addedDess-Martin reagent (5.06 g,11.93 mmol). The mixture was allowedto warm to room temperature after 10 min and stirred for 16 h. Thereaction was quenched with a saturated sodium bicarbonate solution and salts were filtered off. The filtrate was extracted withCH2Cl2. The combined organic layers were dried over MgSO4,filtered and evaporated under reduced pressure. Purification bysilica column chromatography using CH2Cl2 as eluent gave thedesired ketone 5a (1.42 g, 87percent) as a pale yellow solid.

Reference： [1] European Journal of Medicinal Chemistry, 2015, vol. 105, p. 80 - 105

2
[ 493-09-4 ]
[ 75-36-5 ]
[ 2879-20-1 ]

Reference： [1] Farmaco, 1996, vol. 51, # 3, p. 215 - 217
[2] European Journal of Medicinal Chemistry, 1997, vol. 32, # 6, p. 529 - 534
[3] Tetrahedron, 2007, vol. 63, # 2, p. 474 - 491

3
[ 1197-09-7 ]
[ 106-93-4 ]
[ 2879-20-1 ]

Reference： [1] DRP/DRBP Org.Chem., [2] Fortschr. Teerfarbenfabr. Verw. Industriezweige, vol. 21, p. 693
[3] Patent: US1964973, 1932, ,
[4] Tetrahedron Letters, 1997, vol. 38, # 25, p. 4459 - 4462

4
[ 493-09-4 ]
[ 2879-20-1 ]

Reference： [1] Journal of the Chemical Society, 1957, p. 3445
[2] Journal of the American Chemical Society, 1949, vol. 71, p. 2050,2052[3] Journal of the American Chemical Society, 1950, vol. 72, p. 3795
[4] Patent: US2383874, 1942, ,

5
[ 29668-44-8 ]
[ 2879-20-1 ]

Reference： [1] European Journal of Medicinal Chemistry, 2015, vol. 105, p. 80 - 105

6
[ 493-09-4 ]
[ 108-24-7 ]
[ 2879-20-1 ]

Reference： [1] Bioorganic and Medicinal Chemistry Letters, 2015, vol. 25, # 13, p. 2668 - 2674

7
[ 2879-20-1 ]
[ 4442-54-0 ]

Reference： [1] Patent: WO2004/26829, 2004, A2, . Location in patent: Page/Page column 76-77
[2] Journal of the Chemical Society, 1957, p. 3445
[3] Patent: US2383874, 1942, ,

8
[ 2879-20-1 ]
[ 57672-33-0 ]

Reference： [1] Journal of the Chemical Society, 1957, p. 3445

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[ 2879-20-1 ]

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Yield	Reaction Conditions	Operation in experiment
67%	With copper(ll) bromide; In chloroform; at 70℃; for 20h;	To a solution of <strong>[2879-20-1]1-(2,3-dihydrobenzo[b][1,4]dioxin-6-yl)ethan-1-one</strong> (5.0g, 28.0mmol, 1.0 equiv.) in chloroform (100mL), CuBr2 (10.7g, 47.7mmol, 1.7 equiv.) was added in one aliquot. The reaction mixture was stirred at 70C for 20h. After cooling the mixture to room temperature, the excess CuBr2 and CuBr (formed as side product) were filtered off. The product was purified by flash chromatograph using DCM/Hex (4:1, v/v) as mobile phase. Yield, 67%. 1H NMR (400MHz, CDCl3) delta 4.27-4.29 (m, 2H), 4.31-4.34 (m, 2H), 4.37 (s, 2H), 6.91-6.93 (m, 1H), 7.49-7.52 (m, 2H) ppm. 13C NMR (100MHz, CDCl3) delta 30.89, 64.18, 64.85, 117.63, 118.53, 123.29, 127.73, 143.63, 148.91, 189.92ppm. HRMS (ESI) m/z calculated for C10H10O3Br [M+H]+ 256.9808, found 256.9799.
28%	With phenyltrimethylammonium bromide dibromide; In tetrahydrofuran; at 0 - 20℃; for 16h;Inert atmosphere;	General procedure: Method G: a solution of compound 5a (210 mg, 1.28 mmol) inanhydrous THF (5 mL) was stirred at 0 C under argon beforeaddition of phenyltrimethylammonium tribromide (481 mg,1.28 mmol). The mixture was then stirred for 15 min at 0 C andwarmed to room temperature. The reaction mixture was stirred for16 h and evaporated to dryness. The residue was suspended inwater and extracted with EtOAc. The combined organic layers werewashed with water and brine, dried over MgSO4, filtered, andevaporated under reduced pressure. A purification by silica columnchromatography using petroleum ether/CH2Cl2 (9:1 v/v) as eluentgave the desired bromoethanone 12a (239 mg, 77%) as a whitesolid.
		a 2-Bromo-<strong>[2879-20-1]1-(2,3-dihydro-1,4-benzodioxin-6-yl)ethan-1-one</strong> By using <strong>[2879-20-1]1-(2,3-dihydro-1,4-benzodioxin-6-yl)ethan-1-one</strong> (1.42 g, 7.97 mmol), the title compound was obtained as pale yellow solid by similar procedures to those of Example 38a (2.05 g, yield: 100%). 1H-NMR(CDCl3): 7.50-7.54(2H,m), 6.93(1H,m), 4.37(2H,s), 4.32-4.35(2H,m), 4.27-4.31(2H,m)

	With N-Bromosuccinimide; toluene-4-sulfonic acid; In acetonitrile; for 1h;Reflux;	General procedure: N-Bromobutanimide (NBS, 356 mg, 2.0 mmol) and 4-Methylbenzenesulfonic acid (PTSA, 344 mg, 2.0 mmol) were added to a well-stirred solution of aryl methyl ketone 8a (240 mg, 2.0 mmol) in anhydrous MeCN (15 mL). The mixture was stirred at room temperature for 1 h, and then refluxed for another 1-2.5 h. After disappearance of aryl methyl ketone 8a (monitored by TLC), the solvent was removed under reduced pressure, then added 50mL water to the mixture, extracted with EtOAc 3 times (3 × 50 mL). The extract was washed with 10% NaCl solution, dried over anhydrous Na2SO4 and concentrated under reduced pressure. The residue was puried by column chromatography on silica gel to yield the desired product 4a as a white solid in 90% yield.
	With phenyltrimethylammonium tribromide; In dichloromethane; at 20℃;	A mixture of <strong>[2879-20-1]1-(2,3-dihydro-1,4-benzodioxin-6-yl)ethanone</strong> (25.0 g, 140 mmol) and phenyltri-methylammonium tribromide (52.7 g, 140 mmol) in dichloromethane (300 ml) was stirred at RT overnight. The ammonium salts were filtered off, and the filter cake was washed with ethyl ace- tate. The filtrate was concentrated under reduced pressure, and the solid product thus obtained was used in the next step without further purification. Yield: 34.35 g (95% of theory). 1H-NMR (400 MHz, CDCIs): d [ppm] = 7.50-7.54 (m, 2H), 6.91-6.95 (m, 1H), 4.37 (s, 2H), 4.27-4.35 (m, 4H).

Physical hazards
Code	Phrase
H200	Unstable explosive
H201	Explosive; mass explosion hazard
H202	Explosive; severe projection hazard
H203	Explosive; fire, blast or projection hazard
H204	Fire or projection hazard
H205	May mass explode in fire
H220	Extremely flammable gas
H221	Flammable gas
H222	Extremely flammable aerosol
H223	Flammable aerosol
H224	Extremely flammable liquid and vapour
H225	Highly flammable liquid and vapour
H226	Flammable liquid and vapour
H227	Combustible liquid
H228	Flammable solid
H229	Pressurized container: may burst if heated
H230	May react explosively even in the absence of air
H231	May react explosively even in the absence of air at elevated pressure and/or temperature
H240	Heating may cause an explosion
H241	Heating may cause a fire or explosion
H242	Heating may cause a fire
H250	Catches fire spontaneously if exposed to air
H251	Self-heating; may catch fire
H252	Self-heating in large quantities; may catch fire
H260	In contact with water releases flammable gases which may ignite spontaneously
H261	In contact with water releases flammable gas
H270	May cause or intensify fire; oxidizer
H271	May cause fire or explosion; strong oxidizer
H272	May intensify fire; oxidizer
H280	Contains gas under pressure; may explode if heated
H281	Contains refrigerated gas; may cause cryogenic burns or injury
H290	May be corrosive to metals
Health hazards
Code	Phrase
H300	Fatal if swallowed
H301	Toxic if swallowed
H302	Harmful if swallowed
H303	May be harmful if swallowed
H304	May be fatal if swallowed and enters airways
H305	May be harmful if swallowed and enters airways
H310	Fatal in contact with skin
H311	Toxic in contact with skin
H312	Harmful in contact with skin
H313	May be harmful in contact with skin
H314	Causes severe skin burns and eye damage
H315	Causes skin irritation
H316	Causes mild skin irritation
H317	May cause an allergic skin reaction
H318	Causes serious eye damage
H319	Causes serious eye irritation
H320	Causes eye irritation
H330	Fatal if inhaled
H331	Toxic if inhaled
H332	Harmful if inhaled
H333	May be harmful if inhaled
H334	May cause allergy or asthma symptoms or breathing difficulties if inhaled
H335	May cause respiratory irritation
H336	May cause drowsiness or dizziness
H340	May cause genetic defects
H341	Suspected of causing genetic defects
H350	May cause cancer
H351	Suspected of causing cancer
H360	May damage fertility or the unborn child
H361	Suspected of damaging fertility or the unborn child
H361d	Suspected of damaging the unborn child
H362	May cause harm to breast-fed children
H370	Causes damage to organs
H371	May cause damage to organs
H372	Causes damage to organs through prolonged or repeated exposure
H373	May cause damage to organs through prolonged or repeated exposure
Environmental hazards
Code	Phrase
H400	Very toxic to aquatic life
H401	Toxic to aquatic life
H402	Harmful to aquatic life
H410	Very toxic to aquatic life with long-lasting effects
H411	Toxic to aquatic life with long-lasting effects
H412	Harmful to aquatic life with long-lasting effects
H413	May cause long-lasting harmful effects to aquatic life
H420	Harms public health and the environment by destroying ozone in the upper atmosphere

Yield	Reaction Conditions	Operation in experiment
	With hydrogenchloride; sodium hydroxide; sodium cyanoborohydride; triethylamine;titanium tetrachloride; In methanol; dichloromethane;	Example 11 1-butyl-2,5-dioxo-3-(2-methylpropyl)-9-(1-(1,4-benzodioxan-6-yl)ethyl)-1,4,9-triazaspiro[5.5]undecane · hydrochloride Under an atmosphere of argon, to a solution of the compound prepared in Example 9 (315 mg) in dichloromethane (5 ml) were added <strong>[2879-20-1]1,4-benzodioxan-6-yl methyl ketone</strong> (285 mg), triethylamine (0.354 ml) and a solution of titanium tetrachloride in dichloromethane (1.0 M, 0.63 ml). The reaction mixture was stirred for 16 hours at room temperature. To the reaction mixture was added a solution of sodium cyanoborohydride (133 mg) in methanol (2 ml). The reaction mixture was stirred for 1 hour at room temperature. To the reaction mixture was added 2N aqueous solution of sodium hydroxide, and was extracted with ethyl acetate. The extract was dried over anhydrous magnesium sulfate and concentrated. The obtained residue was purified by column chromatography on silica gel (Fuji Silysia Chemical Ltd., BW235; chloroform: methanol = 50: 1). The obtained residue was dissolved in methanol. The solution was acidified by adding 1 N hydrochloric acid, and was concentrated to give the compound of the present invention (176 mg) having the following physical data. TLC: Rf 0.46 (chloroform: methanol = 10:1); NMR (CD3OD): delta 7.04 (d, J = 2.1 Hz, 1H), 6.98 (dd, J = 8.4, 2.1 Hz, 1H), 6.92 (d, J = 8.4 Hz, 1H), 4.40 (q, J = 6.9 Hz, 1H), 4.26 (s, 4H), 3.98 (dd, J = 8.1, 4.5 Hz, 1H), 3.82-3.17 (m, 6H), 2.55-2.04 (m, 4H), 1. 87-1.28 (m, 10H), 1.04-0.85 (m, 9H).
		Under an atmosphere of argon, to a solution of the compound prepared in Example 9 (315 mg) in dichloromethane (5 ml) were added <strong>[2879-20-1]1,4-benzodioxan-6-yl methyl ketone</strong> (285 mg), triethylamine (0.354 ml) and a solution of titanium tetrachloride in dichloromethane (1.0 M, 0.63 ml). The reaction mixture was stirred for 16 hours at room temperature. To the reaction mixture was added a solution of sodium cyanoborohydride (133 mg) in methanol (2 ml). The reaction mixture was stirred for 1 hour at room temperature. To the reaction mixture was added 2N aqueous solution of sodium hydroxide, and was extracted with ethyl acetate. The extract was dried over anhydrous magnesium sulfate and concentrated. The obtained residue was purified by column chromatography on silica gel (Fuji Silysia Chemical Ltd., BW235; chloroform : methanol = 50 : 1). The obtained residue was dissolved in methanol. The solution was acidified by adding 1N hydrochloric acid, and was concentrated to give the compound of the present invention (176 mg) having the following physical data. TLC : Rf 0.46 (chloroform : methanol = 10 : 1); NMR (CD3OD) : delta 7.04 (d, J = 2.1 Hz, 1H), 6.98 (dd, J = 8.4, 2.1 Hz, 1H), 6.92 (d, J = 8.4 Hz, 1H), 4.40 (q, J = 6.9 Hz, 1H), 4.26 (s, 4H), 3.98 (dd, J = 8.1, 4.5 Hz, 1H), 3.82-3.17 (m, 6H), 2.55-2.04 (m, 4H), 1.87-1.28 (m, 10H), 1.04-0.85 (m, 9H).

Yield	Reaction Conditions	Operation in experiment
82%	With hydrogenchloride; In ethanol; water;Reflux;	A solution of <strong>[2879-20-1]1-(2,3-dihydrobenzo[b][1,4]dioxin-6-yl)ethanone</strong> (XV) (11 mmol), dimethylamine hydrochloride (14 mmol), paraformaldehyde (16 mmol) and 12 N HCl (2 drops) in ethanol (5 mL) was refluxed overnight. The solution was cooled to room temperature and the ethanol was evaporated under vacuum. The residue was treated with ethyl acetate, heated slightly and sonicated to disperse into fine particles. The solids were filtered and dried at room temperature to produce 1-(2,3-dihydrobenzo[b][1,4]dioxin-6-yl)-3-(dimethylamino)propan-1-one (XVI) as a white solid, (82% yield), 1H NMR (CDCl3, 400 MHz): delta ppm 2.77 (s, 6H), 3.41 (m, 2H), 3.56 (m, 2H), 4.25 (m, 4H), 6.85 (m, 1H), 7.45 (m, 2H).
40.2%		A solution of <strong>[2879-20-1]1-(2,3-dihydrobenzo[b][1,4]dioxin-6-yl)ethanone</strong> (XXXII) (4.68 g, 26.3 mmol), dimethylamine hydrochloride (2.78 g, 34.1 mmol), paraformaldehyde (1.18 g, 39.4 mmol) and 12 N HCl (50 muL) in ethanol (8.0 mL) was refluxed overnight. The solution was cooled to room temperature and the ethanol was evaporated under vacuum. The residue was treated with EtOAc, heated slightly and sonicated to disperse into fine particles. The solids were filtered and dried at room temperature to produce 1-(2,3-dihydrobenzo[b][1,4]dioxin-6-yl)-3-(dimethylamino) propan-1-one hydrochloride as a white solid, (7.73 g, quantitative yield). The solid was cooled in minimum about of water (12 mL) and cooled to 0 C. A 20% aqueous solution of NaOH was added until pH=10. The solution was extracted with DCM, dried and evaporated to produce 1-(2,3-dihydrobenzo[b][1,4]dioxin-6-yl)-3-(dimethylamino) propan-1-one (XXXIII) a colorless oil (2.485 g, 10.6 mmol, 40.2% yield) 1H NMR (CDCl3, 500 MHz): delta ppm 2.77 (s, 6H), 3.41 (m, 2H), 3.56 (m, 2H), 4.25 (m, 4H), 6.85 (m, 1H), 7.45 (m, 2H); ESIMS found C13H17NO3 m/z 236 (M+H).

[ CAS No. 2879-20-1 ] {[proInfo.proName]}

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[ 2879-20-1 ] Synthesis Path-Upstream 1~8

[ 2879-20-1 ] Synthesis Path-Downstream 1~88

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Ketones

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Benzodioxans

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