[ CAS No. 22246-05-5 ] {[proInfo.proName]}

Name: 22246-05-5|7-Hydroxy-3,4-dihydro-2H-isoquinolin-1-one|98%
Brand: Ambeed
SKU: A239110
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Quality Control of [ 22246-05-5 ]

COA NMR CNMR HPLC LC-MS

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SDS Specification

Alternatived Products of [ 22246-05-5 ]

Product Details of [ 22246-05-5 ]

CAS No. :	22246-05-5	MDL No. :	MFCD04114872
Formula :	C₉H₉NO₂	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	CZORCICKCUXXCZ-UHFFFAOYSA-N
M.W :	163.17	Pubchem ID :	44203201
Synonyms :

Calculated chemistry of [ 22246-05-5 ]

Physicochemical Properties

Num. heavy atoms :	12
Num. arom. heavy atoms :	6
Fraction Csp3 :	0.22
Num. rotatable bonds :	0
Num. H-bond acceptors :	2.0
Num. H-bond donors :	2.0
Molar Refractivity :	48.23
TPSA :	49.33 Å²

Pharmacokinetics

GI absorption :	High
BBB permeant :	No
P-gp substrate :	No
CYP1A2 inhibitor :	No
CYP2C19 inhibitor :	No
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-6.67 cm/s

Lipophilicity

Log Po/w (iLOGP) :	1.3
Log Po/w (XLOGP3) :	0.88
Log Po/w (WLOGP) :	0.3
Log Po/w (MLOGP) :	0.84
Log Po/w (SILICOS-IT) :	1.61
Consensus Log Po/w :	0.99

Druglikeness

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

Water Solubility

Log S (ESOL) :	-1.78
Solubility :	2.73 mg/ml ; 0.0167 mol/l
Class :	Very soluble
Log S (Ali) :	-1.5
Solubility :	5.16 mg/ml ; 0.0316 mol/l
Class :	Very soluble
Log S (SILICOS-IT) :	-2.58
Solubility :	0.426 mg/ml ; 0.00261 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	0.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	1.41

Safety of [ 22246-05-5 ]

Signal Word:	Warning	Class:	N/A
Precautionary Statements:	P280-P305+P351+P338-P310	UN#:	N/A
Hazard Statements:	H302-H315-H319-H332-H335	Packing Group:	N/A
GHS Pictogram:

Application In Synthesis of [ 22246-05-5 ]

* 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 [ 22246-05-5 ]
Downstream synthetic route of [ 22246-05-5 ]

[ 22246-05-5 ] Synthesis Path-Upstream 1~6

1
[ 22246-04-4 ]
[ 22246-05-5 ]

Yield	Reaction Conditions	Operation in experiment
81%	With boron tribromide In dichloromethane at -78 - 20℃; Inert atmosphere	Under a nitrogen atmosphere, Intermediate 157 (19 g, 107 mmol) was dissolved in DCM (250 mL) and cooled to -78°C. Boron tribromide (1M in DCM, 430 mL, 430 mmol) was added dropwise to the resulting suspension within 1.5 h. After 30 min, the cooling bath was removed and the reaction mixture was allowed to warm to r. , then stirred overnight. The reaction mixture was quenched by careful dropwise addition of MeOH (114 mL, 2.81 mol) and the resulting solution was stirred for 1.5 h, then concentrated in vacuo. The residue was coevaporated from MeOH and crystallized from water, then filtered, washed with water and dried, to afford the title compound (14.6 g, 81percent). δ_Η (300 MHz, DMSO-de) 9.47 (s, IH), 7.83 (s, IH), 7.25 (d, J2.7 Hz, IH), 7.09 (d, J8.2 Hz, IH), 6.85 (dd, J 8.1, 2.7 Hz, IH), 3.31 (td, J 6.6, 2.8 Hz, 2H), 2.76 (t, J 6.6 Hz, 2H)
80%	With boron tribromide In dichloromethane at 20℃; Cooling with ice	Intermediate 19:[0136] BBr₃ (4.75 mL, 47.5 mmol, in CH₂C1₂) was added to a cold solution (ice-bath) of intermediate 18 (3.36 g, 18.98 mmol) in CH₂C1₂ (100 mL). The mixture was then warmed to rt and stirred overnight. Water was carefully added dropwise to quench the reaction. EtOAc was added and the mixture was washed with water, brine, dried over anhydrous MgS0₄, filtered and concentrated to afford 7-hydroxy-3,4-dihydroisoquinolin-l(2H)-one (intermediate 19) (2.46 g, 80percent) as a white solid, mp: 201-203°C.

Reference： [1] Journal of Medicinal Chemistry, 1997, vol. 40, # 13, p. 2085 - 2101
[2] Patent: WO2016/198400, 2016, A1, . Location in patent: Page/Page column 97
[3] Patent: WO2012/3418, 2012, A2, . Location in patent: Page/Page column 53
[4] Bioorganic and Medicinal Chemistry Letters, 2010, vol. 20, # 1, p. 222 - 227
[5] Molecules, 2016, vol. 21, # 12,

2
[ 91247-71-1 ]
[ 22246-05-5 ]

Reference： [1] Journal of Organic Chemistry, 2012, vol. 77, # 20, p. 9313 - 9328,16
[2] Journal of Organic Chemistry, 2012, vol. 77, # 20, p. 9313 - 9328,16
[3] Patent: WO2016/198400, 2016, A1,

3
[ 62372-08-1 ]
[ 22246-05-5 ]

Reference： [1] Journal of Organic Chemistry, 2012, vol. 77, # 20, p. 9313 - 9328,16
[2] Heterocycles, 2016, vol. 93, # 2, p. 705 - 713

4
[ 55-81-2 ]
[ 22246-05-5 ]

Reference： [1] Journal of Organic Chemistry, 2012, vol. 77, # 20, p. 9313 - 9328,16
[2] Journal of Organic Chemistry, 2012, vol. 77, # 20, p. 9313 - 9328,16
[3] Patent: WO2016/198400, 2016, A1,

5
[ 38480-95-4 ]
[ 22246-05-5 ]

Reference： [1] Molecules, 2016, vol. 21, # 12,

6
[ 13623-25-1 ]
[ 22246-05-5 ]

Reference： [1] Patent: WO2012/3418, 2012, A2,

[ 22246-05-5 ] Synthesis Path-Downstream 1~64

1
[ 22246-04-4 ]
[ 22246-05-5 ]

Yield	Reaction Conditions	Operation in experiment
81%	With boron tribromide; In dichloromethane; at -78 - 20℃;Inert atmosphere;	Under a nitrogen atmosphere, Intermediate 157 (19 g, 107 mmol) was dissolved in DCM (250 mL) and cooled to -78C. Boron tribromide (1M in DCM, 430 mL, 430 mmol) was added dropwise to the resulting suspension within 1.5 h. After 30 min, the cooling bath was removed and the reaction mixture was allowed to warm to r. , then stirred overnight. The reaction mixture was quenched by careful dropwise addition of MeOH (114 mL, 2.81 mol) and the resulting solution was stirred for 1.5 h, then concentrated in vacuo. The residue was coevaporated from MeOH and crystallized from water, then filtered, washed with water and dried, to afford the title compound (14.6 g, 81%). deltaEta (300 MHz, DMSO-de) 9.47 (s, IH), 7.83 (s, IH), 7.25 (d, J2.7 Hz, IH), 7.09 (d, J8.2 Hz, IH), 6.85 (dd, J 8.1, 2.7 Hz, IH), 3.31 (td, J 6.6, 2.8 Hz, 2H), 2.76 (t, J 6.6 Hz, 2H)
80%	With boron tribromide; In dichloromethane; at 20℃;Cooling with ice;	Intermediate 19:[0136] BBr3 (4.75 mL, 47.5 mmol, in CH2C12) was added to a cold solution (ice-bath) of intermediate 18 (3.36 g, 18.98 mmol) in CH2C12 (100 mL). The mixture was then warmed to rt and stirred overnight. Water was carefully added dropwise to quench the reaction. EtOAc was added and the mixture was washed with water, brine, dried over anhydrous MgS04, filtered and concentrated to afford 7-hydroxy-3,4-dihydroisoquinolin-l(2H)-one (intermediate 19) (2.46 g, 80%) as a white solid, mp: 201-203C.

Reference： [1]Journal of Medicinal Chemistry,1997,vol. 40,p. 2085 - 2101
[2]Patent: WO2016/198400,2016,A1 .Location in patent: Page/Page column 97
[3]Patent: WO2012/3418,2012,A2 .Location in patent: Page/Page column 53
[4]Bioorganic and Medicinal Chemistry Letters,2010,vol. 20,p. 222 - 227
[5]Molecules,2016,vol. 21

2
[ 22246-05-5 ]
[ 100-39-0 ]
[ 190604-11-6 ]

Reference： [1]Journal of Medicinal Chemistry,1997,vol. 40,p. 2085 - 2101

Yield	Reaction Conditions	Operation in experiment
67%	With aluminum (III) chloride; In toluene; at 105℃; for 2.0h;	General procedure: The compound 6-methoxy-2,3-dihydro-1-indenone (1.0 g, 6.17 mmol) was placed in a reaction flask and then added with the solvent toluene (20 mL). To the reactor with stirring, aluminum trichloride solids (2.4 g, 18.50mmol) were added and reacted at 105 C for 2 hours. After TLC monitored the completion of the reaction, the solvent was removed by concentration, and the reaction solution was added with water and extracted with ethyl acetate. The organic phases were combined, washed with saturated saline solution, dried and concentrated to afford a crude product, which was purified by column chromatography to afford the product 25-1 (420 mg, 46%).

4
[ 22246-05-5 ]
[ 190604-13-8 ]

Reference： [1]Journal of Medicinal Chemistry,1997,vol. 40,p. 2085 - 2101

5
[ 22246-05-5 ]
[ 1027583-68-1 ]

Reference： [1]Journal of Medicinal Chemistry,1997,vol. 40,p. 2085 - 2101

6
[ 22246-05-5 ]
[ 1027720-02-0 ]

Reference： [1]Journal of Medicinal Chemistry,1997,vol. 40,p. 2085 - 2101

7
[ 22246-05-5 ]
[ 190604-12-7 ]

Reference： [1]Journal of Medicinal Chemistry,1997,vol. 40,p. 2085 - 2101

8
[ 22246-05-5 ]
[ 190604-14-9 ]

Reference： [1]Journal of Medicinal Chemistry,1997,vol. 40,p. 2085 - 2101

9
[ 22246-05-5 ]
[ 1027994-02-0 ]

Reference： [1]Journal of Medicinal Chemistry,1997,vol. 40,p. 2085 - 2101

10
[ 22246-05-5 ]
[ 1026177-04-7 ]

Reference： [1]Journal of Medicinal Chemistry,1997,vol. 40,p. 2085 - 2101

11
[ 22246-05-5 ]
[ 1027514-28-8 ]

Reference： [1]Journal of Medicinal Chemistry,1997,vol. 40,p. 2085 - 2101

12
[ 22246-05-5 ]
[ 1026846-42-3 ]

Reference： [1]Journal of Medicinal Chemistry,1997,vol. 40,p. 2085 - 2101

13
[ 22246-05-5 ]
[ 190604-49-0 ]

Reference： [1]Journal of Medicinal Chemistry,1997,vol. 40,p. 2085 - 2101

14
[ 22246-05-5 ]
[ 190604-50-3 ]

Reference： [1]Journal of Medicinal Chemistry,1997,vol. 40,p. 2085 - 2101

15
[ 22246-05-5 ]
[ 190604-15-0 ]

Reference： [1]Journal of Medicinal Chemistry,1997,vol. 40,p. 2085 - 2101

16
[ 22246-05-5 ]
(7-{2-[4-(tert-Butoxycarbonylamino-imino-methyl)-phenyl]-ethoxy}-1-oxo-3,4-dihydro-1H-isoquinolin-2-yl)-acetic acid tert-butyl ester [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,1997,vol. 40,p. 2085 - 2101

17
[ 22246-05-5 ]
[ 190604-51-4 ]

Reference： [1]Journal of Medicinal Chemistry,1997,vol. 40,p. 2085 - 2101

18
[ 22246-05-5 ]
[ 190604-52-5 ]

Reference： [1]Journal of Medicinal Chemistry,1997,vol. 40,p. 2085 - 2101

19
[ 22246-05-5 ]
[7-(4-Carbamimidoyl-benzyloxy)-1-oxo-3,4-dihydro-1H-isoquinolin-2-yl]-acetic acid; compound with trifluoro-acetic acid [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,1997,vol. 40,p. 2085 - 2101

20
[ 22246-05-5 ]
[7-(3-Guanidino-propoxy)-1-oxo-3,4-dihydro-1H-isoquinolin-2-yl]-acetic acid [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,1997,vol. 40,p. 2085 - 2101

21
[ 22246-05-5 ]
[7-(4-Guanidino-butoxy)-1-oxo-3,4-dihydro-1H-isoquinolin-2-yl]-acetic acid [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,1997,vol. 40,p. 2085 - 2101

22
[ 22246-05-5 ]
{7-[2-(4-Carbamimidoyl-phenyl)-ethoxy]-1-oxo-3,4-dihydro-1H-isoquinolin-2-yl}-acetic acid [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,1997,vol. 40,p. 2085 - 2101

23
[ 22246-05-5 ]
[ 106-96-7 ]
[ 917884-95-8 ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2010,vol. 20,p. 222 - 227

24
[ 22246-05-5 ]
[ 1262657-59-9 ]

Reference： [1]Chemical Biology and Drug Design,2010,vol. 76,p. 505 - 510

25
[ 22246-05-5 ]
[ 598-31-2 ]
[ 1262657-69-1 ]

Reference： [1]Chemical Biology and Drug Design,2010,vol. 76,p. 505 - 510

26
[ 110-52-1 ]
[ 22246-05-5 ]
[ 1354030-24-2 ]

Yield	Reaction Conditions	Operation in experiment
63%	With potassium carbonate; In ethanol;Reflux;	Intermediate 21:[0139] A mixture of intermediate 19 (196 mg, 1.2 mmol), 1,4-dibromobutane (0.43 mL, 3.6 mmol) and anhydrous K2C03 (166 mg, 1.22 mmol) was dissolved in EtOH (4 mL) and the solution was heated to reflux and stirred overnight. The mixture was diluted with water and extracted with EtOAc. The combined EtOAc layers were washed with water, brine, dried over anhydrous Na2SC>4, concentrated in vacuo and purified by flash chromatography on silica gel column (elution with PE/EtOAc = 3 : 1) to give 7-(4-bromobutoxy)-3,4-dihydroisoquinolin-l(2H)- one (intermediate 21) (230 mg, 63%) as a white solid.

Reference： [1]Patent: WO2012/3418,2012,A2 .Location in patent: Page/Page column 54-55
[2]Journal of Medicinal Chemistry,2012,vol. 55,p. 7141 - 7153

27
[ 13623-25-1 ]
[ 22246-05-5 ]

Reference： [1]Patent: WO2012/3418,2012,A2

28
[ 22246-05-5 ]
[ 109-64-8 ]
[ 1354030-22-0 ]

Yield	Reaction Conditions	Operation in experiment
63%	With potassium carbonate; In ethanol;Reflux;	Intermediate 20:[0137] A mixture of intermediate 19 (326 mg, 2 mmol), 1,3-dibromopropane (0.62 mL, 6 mmol) and anhydrous K2C03 (276 mg, 2 mmol) was dissolved in 4 mL of EtOH and the solution was heated to reflux and stirred overnight. The mixture was diluted with water and extracted with EtOAc. The combined EtOAc layers were washed with water, brine, dried over anhydrous Na2S04, concentrated in vacuo and purified by flash chromatography on silica gel column (elution with PE EtOAc = 5:1) to give 7-(3-bromopropoxy)-3,4-dihydroisoquinolin-l(2H)-one (intermediate 20) (360 mg, 63%) as a white solid.

Reference： [1]Patent: WO2012/3418,2012,A2 .Location in patent: Page/Page column 53
[2]Journal of Medicinal Chemistry,2012,vol. 55,p. 7141 - 7153

29
(1E)-N-hydroxy-6-methoxy-2,3-dihydro-1H-inden-1-imine [ No CAS ]
[ 22246-05-5 ]

Reference： [1]Patent: WO2012/3418,2012,A2

30
[ 22246-05-5 ]
[ 1354030-55-9 ]

Reference： [1]Patent: WO2012/3418,2012,A2
[2]Journal of Medicinal Chemistry,2012,vol. 55,p. 7141 - 7153

31
[ 22246-05-5 ]
[ 1354030-67-3 ]

Reference： [1]Patent: WO2012/3418,2012,A2
[2]Journal of Medicinal Chemistry,2012,vol. 55,p. 7141 - 7153

32
[ 22246-05-5 ]
[ 1354030-69-5 ]

Reference： [1]Patent: WO2012/3418,2012,A2

33
[ 22246-05-5 ]
[ 1354030-23-1 ]

Reference： [1]Patent: WO2012/3418,2012,A2
[2]Journal of Medicinal Chemistry,2012,vol. 55,p. 7141 - 7153

34
[ 22246-05-5 ]
[ 1354030-25-3 ]

Reference： [1]Patent: WO2012/3418,2012,A2

35
(1E)-6-methoxy-N-[(methylsulfonyl)oxy]-2,3-dihydro-1H-inden-1-imine [ No CAS ]
[ 22246-05-5 ]

Reference： [1]Patent: WO2012/3418,2012,A2

36
[ 91247-71-1 ]
[ 22246-05-5 ]

Reference： [1]Journal of Organic Chemistry,2012,vol. 77,p. 9313 - 9328,16
[2]Journal of Organic Chemistry,2012,vol. 77,p. 9313 - 9328,16
[3]Patent: WO2016/198400,2016,A1

37
[ 62372-08-1 ]
[ 22246-05-5 ]

Reference： [1]Journal of Organic Chemistry,2012,vol. 77,p. 9313 - 9328,16
[2]Heterocycles,2016,vol. 93,p. 705 - 713

38
[ 55-81-2 ]
[ 22246-05-5 ]

Reference： [1]Journal of Organic Chemistry,2012,vol. 77,p. 9313 - 9328,16
[2]Journal of Organic Chemistry,2012,vol. 77,p. 9313 - 9328,16
[3]Patent: WO2016/198400,2016,A1

39
[ 75-30-9 ]
[ 22246-05-5 ]
7-isopropoxy-3,4-dihydroisoquinolin-1(2H)-one [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2016,vol. 59,p. 8306 - 8325

40
[ 22246-05-5 ]
[ 1616285-68-7 ]

Reference： [1]Journal of Medicinal Chemistry,2016,vol. 59,p. 8306 - 8325

41
[ 38480-95-4 ]
[ 22246-05-5 ]