[ CAS No. 192061-82-8 ] {[proInfo.proName]}

Name: 192061-82-8|1-(4-Hydroxyindolin-1-yl)ethanone|95%
Brand: Ambeed
SKU: A142610
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Quality Control of [ 192061-82-8 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 192061-82-8 ]

SDS Specification

Alternatived Products of [ 192061-82-8 ]

Product Details of [ 192061-82-8 ]

CAS No. :	192061-82-8	MDL No. :	MFCD11559066
Formula :	C₁₀H₁₁NO₂	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	MOCNHZXRXZCZKR-UHFFFAOYSA-N
M.W :	177.20	Pubchem ID :	19598465
Synonyms :

Calculated chemistry of [ 192061-82-8 ]

Physicochemical Properties

Num. heavy atoms :	13
Num. arom. heavy atoms :	6
Fraction Csp3 :	0.3
Num. rotatable bonds :	1
Num. H-bond acceptors :	2.0
Num. H-bond donors :	1.0
Molar Refractivity :	53.47
TPSA :	40.54 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) :	-6.7 cm/s

Lipophilicity

Log Po/w (iLOGP) :	1.58
Log Po/w (XLOGP3) :	0.96
Log Po/w (WLOGP) :	0.92
Log Po/w (MLOGP) :	1.14
Log Po/w (SILICOS-IT) :	1.41
Consensus Log Po/w :	1.2

Druglikeness

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

Water Solubility

Log S (ESOL) :	-1.82
Solubility :	2.69 mg/ml ; 0.0152 mol/l
Class :	Very soluble
Log S (Ali) :	-1.4
Solubility :	7.08 mg/ml ; 0.0399 mol/l
Class :	Very soluble
Log S (SILICOS-IT) :	-2.04
Solubility :	1.6 mg/ml ; 0.00906 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	0.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	1.65

Safety of [ 192061-82-8 ]

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 [ 192061-82-8 ]

* 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.

Downstream synthetic route of [ 192061-82-8 ]

[ 192061-82-8 ] Synthesis Path-Downstream 1~9

1
4-acetoxy-1-acetylindoline [ No CAS ]
[ 192061-82-8 ]

Yield	Reaction Conditions	Operation in experiment
82%		l-Acetyl-4-hydroxyindoline. A solution of 4-acetoxy-l-acetylindoline (8.77g, 40 mmol) in MeOH (250 mL) was treated with 2 M aq. NaOH (22 mL, 44 mmol), stirred at room temperature for 0.75 h, diluted with water (100 mL) and concentrated. The residue was acidified to pH 3 with 2 M aq. HCl and the precipitate was filtered, washed with water and dried under vacuum. The filtrate was extracted with EtOAc and the organic phase was <n="21"/>washed with saturated aq. NaHCO3 and brine, dried and evaporated to give more solid. The combined solids were recrystallised (EtOAc) to give 17 as white crystals (5.75 g, 82%), NMR (
82%		A solution of 27 (8.77g, 40 mmol) in MEOH (250 mL) was treated with 2 M aq. NAOH (22 mL, 44 mmol), stirred at room temperature for 0.75 h, diluted with water (100 mL) and concentrated. The residue was acidified to pH 3 with 2 M aq. HC1 and the precipitate was filtered, washed with water and dried under vacuum. The filtrate was extracted with EtOAc and the organic phase was washed with saturated aq. NAHCO3 and brine, dried and evaporated to give more solid. The combined solids were recrystallised (EtOAc) to give 28 as white crystals (5.75 g, 82%), mp 230-231oC ; (Found: C, 67. 80 ; H, 6. 26; N, 7.86 ; Calcd. for CLOH11N02 : C, 67.78 ; H, 6. 26 ; N, 7. 90%) ; IR: VMAX/CM~1 3150, 1630, 1610,1295 ; 1H NMR: (90 MHz, CDCl3 + DMSO-d6) 9.10 (1H, br s), 7.57 (1H, d, J = 8 Hz), 6.93 (1H, t, J = 8 Hz), 6.48 (1H, d, J = 8 Hz), 4.05 (2H, t, J = 8 Hz), 3.04 (2H, t, J = 8 Hz) and 2.16 (3H, S).

Reference： [1]Patent: WO2008/94922,2008,A1 .Location in patent: Page/Page column 19-20
[2]Patent: WO2004/85394,2004,A1 .Location in patent: Page 25-26

Yield	Reaction Conditions	Operation in experiment
		Preference is more particularly given, among these N-substituted 4-hydroxyindoline derivatives, to: 4-hydroxy-1-N-(beta-hydroxyethyl)indoline, 4-hydroxy-1-N-(beta-hydroxypropyl)indoline, 1-N-acetyl-4-hydroxyindoline, 1-N-(beta,gamma-dihydroxypropyl)-4-hydroxyindoline, 4-hydroxy-1-N-(beta-hydroxyethyl)-5-methylindoline, 1-N-(gamma-dimethylaminopropyl)-4-hydroxyindoline,
		Preference is more particularly given, among these new N-substituted 4-hydroxyindoline derivatives of formula (I'), to: 4-hydroxy-1-N-(beta-hydroxyethyl)indoline, 4-hydroxy-1-N-(beta-hydroxypropyl)indoline, 1-N-acetyl-4-hydroxyindoline, 1-N-(beta,gamma-dihydroxypropyl)-4-hydroxyindoline, 4-hydroxy-1-N-(beta-hydroxyethyl)-5-methylindoline, 1-N-(gamma-dimethylaminopropyl)-4-hydroxyindoline,

3
[ 192061-82-8 ]
[ 96-32-2 ]
[ 737816-56-7 ]

Yield	Reaction Conditions	Operation in experiment
90%		Methyl (l-acetylindolin-4-yloxy)acetate . A suspension of K2CO3 (6.64 g, 48 mmol) in acetone (250 mL) was mixed with l-acetyl-4-hydroxyindoline (5.67 g, 32 mmol). After 15 min, methyl bromoacetate (7.34 g, 48 mmol) was added and the mixture was heated under reflux for 4 h. The solid was filtered, washed with acetone and the filtrate was evaporated, to give methyl (l-acetylindolin-4-yloxy)acetate as white crystals (7.19 g, 90%), NMR (delta,): 7.88 (IH, d, J= 8 Hz), 7.14 (IH, t, J= 8 Hz), 6.44 (IH, d, J= 8 Hz), 4.66 (2H, s), 4.08 (2H, t, J= 8.5 Hz), 3.79 (3H, s), 3.20 (2H, t, J= 8.5 Hz) and 2.21 (s, 3H).
90%		A suspension of anhydrous K2CO3 (6.64 g, 48 mmol) in acetone (250 mL) was mixed with 28 (5.67 g, 32 mmol). After 15 min, methyl bromoacetate (7.34 g, 48 mmol) was added and the mixture was heated under reflux for 4 h. The solid was filtered, washed with acetone and the filtrate was evaporated, then re-evaporated from toluene to give 29 as white crystals (7.19 g, 90%), mp 129-131oC (from EtOAc-petroleum ether); (Found: C, 62.33 ; H, 6. 06 ; N, 5.54 ; Calcd. for C13HL5NO4 : C, 62.64 ; H, 6.07 ; N, 5. 62%) ; IR: TX/CM 1770, 1660,1605, 1440,1230, 1125; 1H NMR: (500 MHz) # 7. 88 (1H, d, J = 8 Hz), 7.14 (1H, t, J = 8 Hz), 6.44 (1H, d, J = 8 Hz), 4.66 (2H, s), 4.08 (2H, t, J = 8.5 Hz), 3.79 (3H, s), 3.20 (2H, t, J = 8.5 Hz) and 2.21 (s, 3H).

Reference： [1]Patent: WO2008/94922,2008,A1 .Location in patent: Page/Page column 20
[2]Patent: WO2004/85394,2004,A1 .Location in patent: Page 26

4
[ 192061-82-8 ]
1-(4-(tert-butyldimethylsilyloxy)-5-nitroindolin-1-yl)ethanone [ No CAS ]