[ CAS No. 69976-81-4 ] {[proInfo.proName]}

Name: 69976-81-4|1-(3-Hydroxy-2-methylphenyl)ethanone|95%
Brand: Ambeed
SKU: A319384
Rating: 91 (22 reviews)

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2D 3D

Structure of 69976-81-4 * Storage: {[proInfo.prStorage]}

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Quality Control of [ 69976-81-4 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 69976-81-4 ]

SDS Specification

Alternatived Products of [ 69976-81-4 ]

Product Details of [ 69976-81-4 ]

CAS No. :	69976-81-4	MDL No. :	MFCD13689052
Formula :	C₉H₁₀O₂	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	ZGMOESHBYCGMDS-UHFFFAOYSA-N
M.W :	150.17	Pubchem ID :	22082814
Synonyms :

Calculated chemistry of [ 69976-81-4 ]

Physicochemical Properties

Num. heavy atoms :	11
Num. arom. heavy atoms :	6
Fraction Csp3 :	0.22
Num. rotatable bonds :	1
Num. H-bond acceptors :	2.0
Num. H-bond donors :	1.0
Molar Refractivity :	43.63
TPSA :	37.3 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) :	-6.07 cm/s

Lipophilicity

Log Po/w (iLOGP) :	1.67
Log Po/w (XLOGP3) :	1.62
Log Po/w (WLOGP) :	1.9
Log Po/w (MLOGP) :	1.44
Log Po/w (SILICOS-IT) :	2.14
Consensus Log Po/w :	1.76

Druglikeness

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

Water Solubility

Log S (ESOL) :	-2.13
Solubility :	1.12 mg/ml ; 0.00742 mol/l
Class :	Soluble
Log S (Ali) :	-2.02
Solubility :	1.45 mg/ml ; 0.00965 mol/l
Class :	Soluble
Log S (SILICOS-IT) :	-2.53
Solubility :	0.446 mg/ml ; 0.00297 mol/l
Class :	Soluble

Medicinal Chemistry

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

Safety of [ 69976-81-4 ]

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 [ 69976-81-4 ]

* 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 [ 69976-81-4 ]
Downstream synthetic route of [ 69976-81-4 ]

[ 69976-81-4 ] Synthesis Path-Upstream 1~3

1
[ 24487-92-1 ]
[ 69976-81-4 ]

Reference： [1] Angewandte Chemie - International Edition, 2016, vol. 55, # 27, p. 7766 - 7771[2] Angew. Chem., 2016, vol. 128, p. 7897 - 7902,6
[3] Journal of Medicinal Chemistry, 2009, vol. 52, # 20, p. 6433 - 6446
[4] Patent: EP2287173, 2011, A1, . Location in patent: Page/Page column 40

2
[ 603-80-5 ]
[ 917-54-4 ]
[ 69976-81-4 ]

Reference： [1] Patent: US2012/225876, 2012, A1, . Location in patent: Page/Page column 53-54

3
[ 55289-06-0 ]
[ 69976-81-4 ]

Reference： [1] Angewandte Chemie - International Edition, 2016, vol. 55, # 27, p. 7766 - 7771[2] Angew. Chem., 2016, vol. 128, p. 7897 - 7902,6

[ 69976-81-4 ] Synthesis Path-Downstream 1~15

2
[ 69976-81-4 ]
[ 1192215-69-2 ]

Reference： [1]Journal of Medicinal Chemistry,2009,vol. 52,p. 6433 - 6446

3
[ 24487-92-1 ]
[ 69976-81-4 ]

Yield	Reaction Conditions	Operation in experiment
		(2) The compound obtained in (1) mentioned above (840 mg) was dissolved in methylene chloride (10 ml), a solution of boron tribromide in methylene chloride (5.6 ml) was slowly added dropwise to the solution under ice cooling, and the resulting mixture was stirred at the same temperature for 2 hours. Methanol was added dropwise to the reaction mixture until fuming ceased, and then the resulting mixture was concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography (hexane:ethyl acetate = 10:1 to 5:1) to obtain a hydroxy compound (96.5 mg).

Reference： [1]Angewandte Chemie - International Edition,2016,vol. 55,p. 7766 - 7771
Angew. Chem.,2016,vol. 128,p. 7897 - 7902,6
[2]Journal of Medicinal Chemistry,2009,vol. 52,p. 6433 - 6446
[3]Patent: EP2287173,2011,A1 .Location in patent: Page/Page column 40

4
[ 69976-81-4 ]
[ 107-15-3 ]
[ 1196732-39-4 ]

Yield	Reaction Conditions	Operation in experiment
		(3) The compound obtained in (2) mentioned above (90 mg) was dissolved in methanol (1 ml), ethylenediamine (0.32 ml) was added to the solution, and the resulting mixture was stirred at room temperature overnight and at 50C for 2 hours. Sodium borohydride (22.7 mg) was added to the reaction mixture at room temperature, and the resulting mixture was stirred at the same temperature for 3 hours. 2 N Hydrochloric acid was added to the reaction mixture, the resulting mixture was washed with chloroform, and then the aqueous layer was made alkaline with 5 N aqueous sodium hydroxide, and concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography (chloroform:methanol:28% aqueous ammonia = 10:1:0.1 to 5:1:0.1) to obtain the title compound (21.1 mg). 1H-NMR, (600 MHz, CDCl3) delta (ppm): 1.31 (d, J=6.88Hz, 3H), 2.22 (s, 3H), 2.48-2.54 (m, 1H), 2.56-2.62 (m, 1H), 2.74-2.79 (m, 2H), 4.06 (q, J=6.42Hz, 1H), 6.64 (d, J=7.79Hz, 1H), 6.99-7.03 (m, 1H), 7.03-7.08 (m, 1H)

Reference： [1]Patent: EP2287173,2011,A1 .Location in patent: Page/Page column 40

5
[ 603-80-5 ]
[ 917-54-4 ]
[ 69976-81-4 ]

Yield	Reaction Conditions	Operation in experiment
		To a solution of 3-hydroxy-2-methylbenzoic acid (1.00 g) in THF (6.6 mL) at -78 C. was added methyllithium (21.7 mL, 1M ether solution), and then the mixture was stirred at room temperature overnight. The reaction mixture was diluted with 1M hydrochloric acid, extracted with ethyl acetate, dehydrated with sodium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (eluent: hexane/ethyl acetate=7/1) to give Compound II (584 mg).

Reference： [1]Patent: US2012/225876,2012,A1 .Location in patent: Page/Page column 53-54

6
[ 194222-05-4 ]
[ 69976-81-4 ]
[ 1307255-35-1 ]

Yield	Reaction Conditions	Operation in experiment
	With di-isopropyl azodicarboxylate; triphenylphosphine; In toluene; at 20℃;	To a mixture of Compound III (200 mg), Compound IV (247 mg), triphenylphosphine (349 mg) and toluene (7 mL) was added diisopropyl azodicarboxylate (264 muL), and the mixture was stirred at room temperature overnight. The reaction solution was washed successively with 1M aqueous sodium hydroxide solution, 1M hydrochloric acid, and brine. The organic layers were combined, and dried over sodium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (eluent: hexane/ethyl acetate=6/1) to give the title compound IV (377 mg).1H-NMR (CDCl3) delta 1.48 (s, 9H), 1.85-2.16 (m, 8H), 2.33 (s, 3H), 2.56 (s, 3H), 4.16-4.32 (m, 2H), 4.59-4.66 (m, 1H), 6.76-6.85 (m, 1H), 7.08-7.22 (m, 2H)

Reference： [1]Patent: US2012/225876,2012,A1 .Location in patent: Page/Page column 53-54

7
[ 69976-81-4 ]
[ 76911-01-8 ]
1-(3-(hex-5-yn-1-yloxy)-2-methylphenyl)ethanone [ No CAS ]