[ CAS No. 3336-49-0 ] {[proInfo.proName]}

Name: 3336-49-0|Isoquinolin-4-ol|95%
Brand: Ambeed
SKU: A297984
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Quality Control of [ 3336-49-0 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 3336-49-0 ]

SDS Specification

Alternatived Products of [ 3336-49-0 ]

Product Details of [ 3336-49-0 ]

CAS No. :	3336-49-0	MDL No. :	MFCD00234514
Formula :	C₉H₇NO	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	DXTUTXYCHFWRQC-UHFFFAOYSA-N
M.W :	145.16	Pubchem ID :	18750
Synonyms :

Calculated chemistry of [ 3336-49-0 ]

Physicochemical Properties

Num. heavy atoms :	11
Num. arom. heavy atoms :	10
Fraction Csp3 :	0.0
Num. rotatable bonds :	0
Num. H-bond acceptors :	2.0
Num. H-bond donors :	1.0
Molar Refractivity :	43.77
TPSA :	33.12 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) :	-5.94 cm/s

Lipophilicity

Log Po/w (iLOGP) :	1.45
Log Po/w (XLOGP3) :	1.75
Log Po/w (WLOGP) :	1.94
Log Po/w (MLOGP) :	0.92
Log Po/w (SILICOS-IT) :	2.01
Consensus Log Po/w :	1.61

Druglikeness

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

Water Solubility

Log S (ESOL) :	-2.52
Solubility :	0.443 mg/ml ; 0.00305 mol/l
Class :	Soluble
Log S (Ali) :	-2.06
Solubility :	1.26 mg/ml ; 0.00866 mol/l
Class :	Soluble
Log S (SILICOS-IT) :	-3.1
Solubility :	0.115 mg/ml ; 0.000791 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	0.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	1.11

Safety of [ 3336-49-0 ]

Signal Word:	Warning	Class:	N/A
Precautionary Statements:	P261-P280-P305+P351+P338	UN#:	N/A
Hazard Statements:	H302-H315-H319-H332-H335	Packing Group:	N/A
GHS Pictogram:

Application In Synthesis of [ 3336-49-0 ]

* 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 [ 3336-49-0 ]
Downstream synthetic route of [ 3336-49-0 ]

[ 3336-49-0 ] Synthesis Path-Upstream 1~2

1
[ 3336-49-0 ]
[ 25475-67-6 ]

Reference： [1] Chemical and Pharmaceutical Bulletin, 1959, vol. 7, p. 501,504

2
[ 3336-49-0 ]
[ 1532-91-8 ]

Reference： [1] Journal of the American Chemical Society, 1958, vol. 80, p. 3443,3448

[ 3336-49-0 ] Synthesis Path-Downstream 1~73

1
[ 1532-72-5 ]
[ 3336-49-0 ]
[ 491-30-5 ]

Reference： [1]Pharmaceutical Bulletin,1957,vol. 5,p. 606,609

2
[ 23687-25-4 ]
[ 3336-49-0 ]

Reference： [1]Pharmaceutical Bulletin,1955,vol. 3,p. 454,458

3
[ 3336-49-0 ]
[ 108-24-7 ]
[ 58245-97-9 ]

Reference： [1]Synthetic Communications,2004,vol. 34,p. 137 - 149
[2]Journal of Organic Chemistry,1956,vol. 21,p. 1337,1340

4
[ 3336-49-0 ]
[ 98-88-4 ]
[ 66612-90-6 ]

Reference： [1]Journal of Organic Chemistry,1956,vol. 21,p. 1337,1340

5
[ 3336-49-0 ]
[ 98-59-9 ]
[ 1532-82-7 ]

Reference： [1]Pharmaceutical Bulletin,1955,vol. 3,p. 454,458

6
[ 3336-49-0 ]
[ 98-59-9 ]
4-hydroxy-2-(toluene-4-sulfonyl)-isoquinolinium; chloride [ No CAS ]
[ 114252-85-6 ]

Reference： [1]Pharmaceutical Bulletin,1955,vol. 3,p. 454,458

7
[ 3336-49-0 ]
[ 98-59-9 ]
[ 114252-85-6 ]

Reference： [1]Pharmaceutical Bulletin,1955,vol. 3,p. 454,458

8
[ 3336-49-0 ]
[ 1532-91-8 ]

Reference： [1]Journal of the American Chemical Society,1958,vol. 80,p. 3443,3448

9
[ 3336-49-0 ]
[ 102877-49-6 ]

Reference： [1]Pharmaceutical Bulletin,1955,vol. 3,p. 454,458

10
[ 3336-49-0 ]
[ 36718-46-4 ]

Reference： [1]Chemical and pharmaceutical bulletin,1959,vol. 7,p. 501,504

11
[ 1532-97-4 ]
[ 3336-49-0 ]

Reference： [1]Journal of the American Chemical Society,2016,vol. 138,p. 13493 - 13496
[2]Synthetic Communications,2004,vol. 34,p. 137 - 149
[3]Journal of the American Chemical Society,1947,vol. 69,p. 1946
[4]Organic Letters,2017,vol. 19,p. 3033 - 3036

12
[ 119-65-3 ]
[ 3336-49-0 ]
[ 17999-93-8 ]

Reference： [1]Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry,1993,vol. 32,p. 889 - 891
[2]Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry,1993,vol. 32,p. 889 - 891

13
[ 119-65-3 ]
[ 3336-49-0 ]
[ 17999-93-8 ]
[1,1']Biisoquinolinyl-4-ol [ No CAS ]
1',2',3',4'-Tetrahydro-[3,4']biisoquinolinyl-4-ol [ No CAS ]

Reference： [1]Tetrahedron,1994,vol. 50,p. 9079 - 9096
[2]Tetrahedron,1994,vol. 50,p. 9079 - 9096

14
[ 58245-97-9 ]
[ 3336-49-0 ]

Reference： [1]Chemical and pharmaceutical bulletin,1984,vol. 32,p. 4731 - 4739

15
[ 3336-49-0 ]
[ 4548-45-2 ]
4-hydroxy-2-(5-nitro-2-pyridyl)-isoquinolinium chloride [ No CAS ]

Reference： [1]Journal of Chemical Research, Miniprint,1980,p. 3337 - 3360

16
[ 3336-49-0 ]
[ 15724-88-6 ]
2-<trans-3-(4-chlorophenyl)-3-oxoprop-1-enyl>-4-hydroxyisoquinolinium chloride [ No CAS ]

Reference： [1]Journal of Chemical Research, Miniprint,1980,p. 3337 - 3360

19
[ 7664-93-9 ]
[ 1532-82-7 ]
[ 7732-18-5 ]
[ 3336-49-0 ]
[ 491-30-5 ]

Reference： [1]Pharmaceutical Bulletin,1955,vol. 3,p. 454,458

20
[ 1532-82-7 ]
[ 7732-18-5 ]
furan-2,3,5(4H)-trione pyridine (1:1) [ No CAS ]
[ 3336-49-0 ]
[ 491-30-5 ]

Reference： [1]Pharmaceutical Bulletin,1955,vol. 3,p. 454,458

21
[ 64-17-5 ]
[ 1532-82-7 ]
[ 7732-18-5 ]
KOH-solution [ No CAS ]
[ 3336-49-0 ]
[ 491-30-5 ]

Reference： [1]Pharmaceutical Bulletin,1955,vol. 3,p. 454,458

22
[ 3336-49-0 ]
[ 100-44-7 ]
N-benzyl-4-hydroxyisoquinolinium chloride [ No CAS ]

Reference： [1]Macromolecules,2002,vol. 35,p. 4258 - 4265

23
[ 3336-49-0 ]
[ 265119-58-2 ]
[ 877143-89-0 ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2005,vol. 15,p. 3632 - 3636

24
[ 659729-09-6 ]
[ 3336-49-0 ]
4-(6-(4-(trifluoromethyl)phenyl)pyrimidin-4-yloxy)isoquinoline [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2007,vol. 50,p. 3515 - 3527

25
[ 3336-49-0 ]
1-benzyl-1a,6a-dihydroindeno[1,2-b]azirin-6(1H)-one [ No CAS ]

Reference： [1]Macromolecules,2002,vol. 35,p. 4258 - 4265

26
[ 3336-49-0 ]
[ 70273-45-9 ]

Reference： [1]Synthetic Communications,2004,vol. 34,p. 137 - 149

27
[ 3336-49-0 ]
[ 51641-23-7 ]

Reference： [1]Synthetic Communications,2004,vol. 34,p. 137 - 149

28
[ 3336-49-0 ]
4-acetoxy-1,2,3,4-tetrahydroisoquinoline [ No CAS ]

Reference： [1]Synthetic Communications,2004,vol. 34,p. 137 - 149

29
[ 3336-49-0 ]
N-tert-butoxycarbonyl-4-hydroxy-1,2,3,4-tetrahydroisoquinoline [ No CAS ]

Reference： [1]Synthetic Communications,2004,vol. 34,p. 137 - 149

30
[ 3336-49-0 ]
3a,4,10,10a-tetrahydro-4,10-iminobenz<f>azulen-9(1H)-one [ No CAS ]

Reference： [1]Journal of Chemical Research, Miniprint,1980,p. 3337 - 3360

31
[ 3336-49-0 ]
3a,4,10,10a-tetrahydro-11-methyl-4,10-iminobenz<f>azulen-9(1H)-one [ No CAS ]

Reference： [1]Journal of Chemical Research, Miniprint,1980,p. 3337 - 3360

32
[ 3336-49-0 ]
C₁₅H₁₅NO₂ [ No CAS ]

Reference： [1]Journal of Chemical Research, Miniprint,1980,p. 3337 - 3360

33
[ 3336-49-0 ]
[ 75734-45-1 ]

Reference： [1]Journal of Chemical Research, Miniprint,1980,p. 3337 - 3360

34
[ 3336-49-0 ]
11-<trans-1-(4-chlorophenyl)-1-oxoprop-2-en-3-yl>-3a,4,10,10a-tetrahydro-4,10-iminobenz<f>azulen-9(1H)-one [ No CAS ]

Reference： [1]Journal of Chemical Research, Miniprint,1980,p. 3337 - 3360

35
[ 3336-49-0 ]
1,3-ethano-1,2,3,4-tetrahydro-2-(5-nitro-2-pyridyl)-4-oxo-9-endo-phenylisoquinoline [ No CAS ]

Reference： [1]Journal of Chemical Research, Miniprint,1980,p. 3337 - 3360

36
[ 3336-49-0 ]
1,3-ethano-1,2,3,4-tetrahydro-2-(5-nitro-2-pyridyl)-4-oxo-10-endo-phenylisoquinoline [ No CAS ]

Reference： [1]Journal of Chemical Research, Miniprint,1980,p. 3337 - 3360

37
[ 3336-49-0 ]
13-<trans-3-(4-chlorophenyl)-3-oxoprop-1-enyl>-5,5a,12,12a-tetrahydro-6,12-iminodibenz<a,f>azulen-11(6H)-one [ No CAS ]

Reference： [1]Journal of Chemical Research, Miniprint,1980,p. 3337 - 3360

38
[ 3336-49-0 ]
13-<trans-3-(4-chlorophenyl)-3-oxoprop-1-enyl>-4b,11,11a,12-tetrahydro-5,11-iminodibenz<a,g>azulen-10(5H)-one [ No CAS ]

Reference： [1]Journal of Chemical Research, Miniprint,1980,p. 3337 - 3360

39
[ 3336-49-0 ]
C₁₆H₁₈NO⁽¹⁺⁾*I^(1-) [ No CAS ]

Reference： [1]Journal of Chemical Research, Miniprint,1980,p. 3337 - 3360

40
[ 3336-49-0 ]
2-<trans-3-(4-chlorophenyl)-3-oxoprop-1-enyl>-1,3-ethano-1,2,3,4-tetrahydro-4-oxoisoquinoline-10-exo-carbonitrile [ No CAS ]

Reference： [1]Journal of Chemical Research, Miniprint,1980,p. 3337 - 3360

41
[ 3336-49-0 ]
2-<trans-3-(4-chlorophenyl)-3-oxoprop-1-enyl>-1,3-ethano-1,2,3,4-tetrahydro-4-oxoisoquinoline-10-endo-carbonitrile [ No CAS ]

Reference： [1]Journal of Chemical Research, Miniprint,1980,p. 3337 - 3360

42
[ 3336-49-0 ]
2-<trans-3-(4-chlorophenyl)-3-oxoprop-1-enyl>-1,3-ethano-1,2,3,4-tetrahydro-4-oxoisoquinoline-9-exo-carbonitrile [ No CAS ]

Reference： [1]Journal of Chemical Research, Miniprint,1980,p. 3337 - 3360

43
[ 3336-49-0 ]
2-<trans-3-(4-chlorophenyl)-3-oxoprop-1-enyl>-1,3-ethano-1,2,3,4-tetrahydro-4-oxoisoquinoline-9-endo-carbonitrile [ No CAS ]

Reference： [1]Journal of Chemical Research, Miniprint,1980,p. 3337 - 3360

44
[ 3336-49-0 ]
14-<trans-3-(4-chlorophenyl)-3-oxoprop-1-enyl>-6b,7,13,13a-tetrahydro-7,13-iminobenzo<4,5>cyclohept<1,2-a>acenaphtylen-12-one, endo-isomer [ No CAS ]

Reference： [1]Journal of Chemical Research, Miniprint,1980,p. 3337 - 3360

45
[ 3336-49-0 ]
14-<trans-3-(4-chlorophenyl)-3-oxoprop-1-enyl>-6b,7,13,13a-tetrahydro-7,13-iminobenzo<4,5>cyclohept<1,2-a>acenaphtylen-12-one, exo-isomer [ No CAS ]

Reference： [1]Journal of Chemical Research, Miniprint,1980,p. 3337 - 3360

46
[ 3336-49-0 ]
10-<trans-3-(4-chlorophenyl)-3-oxoprop-1-enyl>-6,7,8,9,-tetrahydro-9-oxo-5H-5,8-iminobenzocycloheptene-6,7-endo-N-phenyldicarboximide [ No CAS ]

Reference： [1]Journal of Chemical Research, Miniprint,1980,p. 3337 - 3360

47
[ 3336-49-0 ]
10-<trans-3-(4-chlorophenyl)-3-oxoprop-1-enyl>-6,7,8,9,-tetrahydro-9-oxo-5H-5,8-iminobenzocycloheptene-6,7-exo-N-phenyldicarboximide [ No CAS ]

Reference： [1]Journal of Chemical Research, Miniprint,1980,p. 3337 - 3360

48
[ 1532-72-5 ]
KNO₃ [ No CAS ]
[ 3336-49-0 ]

49
2-isoquinolinio-acetylcyanomethylide [ No CAS ]
[ 3336-49-0 ]

50
[ 96284-58-1 ]
[ 3336-49-0 ]

Reference： [1]Chemical and pharmaceutical bulletin,1984,vol. 32,p. 4731 - 4739
[2]Chemical and pharmaceutical bulletin,1984,vol. 32,p. 4731 - 4739
[3]Chemical and pharmaceutical bulletin,1984,vol. 32,p. 4731 - 4739
[4]Chemical and pharmaceutical bulletin,1984,vol. 32,p. 4731 - 4739
[5]Chemical and pharmaceutical bulletin,1984,vol. 32,p. 4731 - 4739
[6]Chemical and pharmaceutical bulletin,1984,vol. 32,p. 4731 - 4739

51
[ 3336-49-0 ]
2-methyl-4-(toluene-4-sulfonyloxy)-isoquinolinium; iodide [ No CAS ]

Reference： [1]Pharmaceutical Bulletin,1955,vol. 3,p. 454,458

52
[ 3336-49-0 ]
[ 114252-85-6 ]

Reference： [1]Pharmaceutical Bulletin,1955,vol. 3,p. 454,458

53
[ 3336-49-0 ]
[ 25475-67-6 ]

Reference： [1]Chemical and pharmaceutical bulletin,1959,vol. 7,p. 501,504

54
[ 3336-49-0 ]
4-chloroisoquinoline N-oxide [ No CAS ]

Reference： [1]Journal of the American Chemical Society,1958,vol. 80,p. 3443,3448

55
[ 3336-49-0 ]
[ 101860-70-2 ]

Reference： [1]Chemical and pharmaceutical bulletin,1959,vol. 7,p. 501,504
[2]Patent: US2003/125561,2003,A1

56
[ 3336-49-0 ]
[ 109311-02-6 ]

Reference： [1]Chemical and pharmaceutical bulletin,1959,vol. 7,p. 501,504

57
[ 3336-49-0 ]
[ 108127-93-1 ]

Reference： [1]Chemical and pharmaceutical bulletin,1959,vol. 7,p. 501,504

58
[ 3336-49-0 ]
[ 66729-00-8 ]

Reference： [1]Chemical and pharmaceutical bulletin,1959,vol. 7,p. 501,504

59
[ 3336-49-0 ]
[ 100306-33-0 ]
[ 695229-11-9 ]

Yield	Reaction Conditions	Operation in experiment
50%	With 4,4-(dimethyl-1,1-dioxido-1,2,5-thiadiazolidin-2-yl)-triphenyl phosphonium; In toluene; at 20℃; for 18.0h;	Add 4, 4-(DIMETHYL-1, 1-DIOXIDO-1, 2,5-thiadiazolidin-2-yl)-triphenyl phosphonium (790 mg, 2.0 mmol, 1.3 equiv.) to a stirred solution of (R)- (+)-3-chloro-1-phenyl-1-propanol (404 mg, 1.54 mmol, 1 equiv. ) and <strong>[3336-49-0]isoquinolin-4-ol</strong> (293 mg, 2.0 mmol, 1.3 equiv. , prepared as described in Tetrahedron, 1963, 19, 827-832) in dry toluene (15 mL) and stir at room temperature for 18 hr. Add ethyl acetate, water, and brine, separate the layers, and extract the aqueous layer with ethyl acetate (3 times). Wash the combined organic extracts with brine (2 times), dry over anhydrous magnesium sulfate, filter, and concentrate under reduced pressure. Purification by medium pressure liquid chromatography eluting with 0-20% ethyl acetate in hexanes affords the title compound as a pale yellow oil (229 mg, 50%): ON (CDC13, 400 MHz) : 2.32-2. 42 (m, 1H), 2.66-2. 71 (m, 1H), 3. 64-3. 72 (m, 1H), 3.82-3. 91 (m, 1H), 5.67 (dd, 1H, J = 9,5 Hz), 7.25-7. 37 (m, 3H), 7.40-7. 46 (m, 2H), 7.62 (ddd, 1H, J = 7,7, 2 Hz), 7.73 (ddd, 1H, J = 7,7, 1 Hz), 7.91 (d, 1H, J= 8 HZ), 7.93 (s, 1H), 8.33 (dd, 1H, J= 8,1 Hz), 8.83 (s, 1H)

Reference： [1]Patent: WO2004/43931,2004,A1 .Location in patent: Page 51-52

60
[ 3336-49-0 ]
[ 100306-34-1 ]
[ 695229-34-6 ]

Yield	Reaction Conditions	Operation in experiment
47%	With 4,4-(dimethyl-1,1-dioxido-1,2,5-thiadiazolidin-2-yl)-triphenyl phosphonium; In toluene; at 20℃; for 18h;	Add 4, 4- (DIMETHYL-1, 1-DIOXIDO-1, 2,5-thiadiazolidin-2-yl)-triphenyl phosphonium (547 mg, 1.4 mmol, 1.2 equiv. Prepared as described in J. Org. Chem. 1994, 59, 2289. ) to a stirred solution of (S)- (-)-3-CHLORO-L-PHENYL-L-PROPANOL (306 mg, 1.17 mmol, 1 equiv. ) and <strong>[3336-49-0]isoquinolin-4-ol</strong> (206 mg, 1.42 mmol, 1.2 equiv. prepared as described in Tetrahedron, 1963, 19, 827-832) in dry toluene (11 ML) and stir at room temperature for 18 hr. Add ethyl acetate, water, and brine, separate the layers, and extract the aqueous layer with ethyl acetate (3 times). Wash the combined organic extracts with brine (2 times), dry over anhydrous magnesium sulfate, filter, and concentrate under reduced pressure. Purification by medium pressure liquid chromatography eluting with 0-50% ethyl acetate in hexanes affords the title compound as a pale yellow oil (163 mg, 47%): ON (CDC13, 400 MHz) : 2.32-2. 42 (m, 1H), 2.66-2. 71 (m, 1H), 3.64-3. 72 (m, 1H), 3.82-3. 91 (m, 1H), 5.67 (dd, 1H, J = 9,5 Hz), 7.25-7. 37 (m, 3H), 7.40-7. 46 (m, 2H), 7.62 (ddd, 1H, J= 7,7, 2 Hz), 7.73 (ddd, 1H, J = 7,7, 1 Hz), 7.91 (d, 1H, J= 8 Hz), 7.93 (s, 1H), 8.33 (dd, 1H, J = 8,1 Hz), 8.83 (s, 1H)

Reference： [1]Patent: WO2004/43931,2004,A1 .Location in patent: Page 46

61
[ 3336-49-0 ]
[ 32433-41-3 ]

Yield	Reaction Conditions	Operation in experiment
	With hydrogenchloride; bromine; In sodium hydroxide;	c 3-Bromo-<strong>[3336-49-0]4-hydroxyisoquinoline</strong> 6.0 g (41 mmol) of <strong>[3336-49-0]4-hydroxyisoquinoline</strong> are dissolved in 50 ml of 10% strength sodium hydroxide solution, giving a yellowish brown color. The reaction mixture is cooled to -5 C. using an ice/common salt mixture. A mixture comprising 6.6 g (2.1 ml, 41 mmol) of bromine dissolved in 50 ml of 10% strength sodium hydroxide solution is added dropwise to this solution over a period of 1 hour. During this period, the temperature of the reaction solution must never exceed 0 C. After this time, the coolant is removed and the reaction solution is stirred at room temperature for another 3 hours. The reaction solution is then cooled to -10 C. The reaction solution is then brought to a pH of 3 with 2N hydrochloric acid, during which the temperature of the reaction solution never exceeds -5 to 0 C. This gives the crude product as a light yellow solid. The crude product is recrystallized from 180 ml of ethyl acetate. Yield 4.40 g (49.5%)--melting point 164 C.

Reference： [1]Patent: US5266700,1993,A

62
[ 1532-72-5 ]
[ 3336-49-0 ]

Yield	Reaction Conditions	Operation in experiment
10.6 g (48.4%)	With sulfuric acid; sodium carbonate; acetic acid; In chloroform; water;	b 4-Hydroxyisoquinoline (cf. E. Ochai, M. Tkebara, Pharm. Bull. 3 (1956), 454) 21.8 g (150 mmol) of isoquinoline N-oxide are dissolved in 400 ml of chloroform, thoroughly dried over magnesium sulfate and filtered. To this solution are added 31.2 g (164 mmol) of freshly recrystallized p-toluenesulfonic chloride, which dissolves with the evolution of heat. A solution of 20 g of sodium carbonate in 450 ml of water is added with vigorous stirring. This solution is stirred at room temperature for 15 hours. The organic phase is separated off, dried and the solvent is distilled off. 440 ml of 5M sulfuric acid are added to the red, oily residue obtained, and the entire mixture is heated to boiling for 24 hours. The cooled solution is neutralized with solid sodium carbonate, and the resulting light brown precipitate is filtered off. Yield 10.6 g (48.4%)--melting point 207 C. (from acetone/acetic acid (6:1), dec.)

Reference： [1]Patent: US5266700,1993,A

63
[ 3336-49-0 ]
[ 845654-95-7 ]
[ 1190841-34-9 ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2009,vol. 19,p. 5250 - 5255

64
[ 3336-49-0 ]
[ 101774-33-8 ]

Yield	Reaction Conditions	Operation in experiment
8.5 mg	With Escherichia coli BL21-CodonPlus (DE3)-RIL/pJZ54;Enzymatic reaction;	General procedure: Thirty milligrams of 1 was fed into the IPTG induced fermentation broth of E. coli BL21-CodonPlus (DE3)-RIL/pJZ54 that expresses Rdc2. The culture was maintained at 28 C with shaking at 250 rpm for 36 h. The ethyl acetate extract of the broth was fractionated on a Sephadex LH-20 (20 g) column eluted with methanol to give 14 fractions, 5 mL each. Fractions 3-6 were combined and further separated by reverse-phase HPLC (Eclipse XDB-C18 column, 5 mum, 4.6 × 150 mm) with isocratic elution of 25% acetonitrile in H2O (each containing 0.1% TFA) for 20 min at a flow rate of 1 mL/min to yield 8.5 mg of 1a. Similarly, 30 mg of 2 was also incubated with E. coli BL21-CodonPlus (DE3)-RIL/pJZ54 under the same conditions. The ethyl acetate extract was fractionated on a Diaion HP-20 (30 g) column eluted with a stepwise gradient of isopropanol-water (0:100, 20:80, 40:60, 60:40, 80:20, 100:0, each 250 mL) to give 6 fractions. Further separation of fraction 3 by reverse-phase HPLC with isocratic elution of 10% acetonitrile in H2O (each containing 0.1% TFA) over 20 min at a flow rate of 1 mL/min afforded 11.4 mg of 2a in pure form.

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2013,vol. 23,p. 1001 - 1003

65
[ 3336-49-0 ]
N-(4-fluorophenyl)-2-(4-hydroxycyclohexyl)acetamide [ No CAS ]
[ 76-05-1 ]
N-(4-fluorophenyl)-2-(cis-4-(isoquinolin-4-yloxy)cyclohexyl)acetamide trifluoroacetate [ No CAS ]
N-(4-fluorophenyl)-2-(trans-4-(isoquinolin-4-yloxy)cyclohexyl)acetamide trifluoroacetate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
		To a vial containing Intermediate 3 IB (200 mg, 0.80 mmol, 1.0 equiv.) and 4- isoquinolinol (170 mg, 1.2 mmol, 1.5 equiv.) was added toluene followed by cyanomethylenetributylphosphorane (0.31 mL, 1.2 mmol, 1.5 equiv.), dropwise. The reaction was stirred at 60 C for 16 h before concentrating. The crude residue was purified by silica gel chromatography (0% to 100% EtOAc in hexanes) to afford a mixture containing Examples 31 and 32, which was further purified by preparative reverse-phase HPLC (PHENOMENEX Gemini-NX, 10mu, CI 8, 11 OA, 250 30 mm, 20 mL/min, eluting with 0% to 100% acetonitrile in water with 0.1% TFA gradient over first 30 min of 40 min run) to afford Example 31 (czs-diastereomer, first eluting) as the TFA salt. 1H NMR (400 MHz; CDC13): delta 8.87 (s, 1H) 8.22 (d, J = 8.0 Hz, 1H) 8.07 (s, 1H) 7.94 (d, J = 8.0 Hz, 1H) 7.56-7.73 (m, 2H) 7.42-7.52 (m, 2H) 7.39 (br. s., 1H) 6.95-7.06 (m, 2H) 4.85 (br. s., 1H) 2.33 (d, J = 7.0 Hz, 2H) 2.22 (d, J = 13.1 Hz, 2H) 2.11 (s, 1H) 1.66-1.79 (m, 4H) 1.51-1.66 (m, 2H). m/z 379.2 (M+H)+. [0298] Further elution of the previous preparative reverse-phase HPLC afforded Example 32 (trans-diastereomer, second eluting) as the TFA salt. 1H NMR (400 MHz; CDCls): delta 8.86 (s, 1H) 8.19-8.25 (m, 1H) 8.09 (s, 1H) 7.93 (d, J = 8.0 Hz, 1H) 7.69 (ddd, J = 8.3, 7.0, 1.3 Hz, 1H) 7.57-7.63 (m, 1H) 7.45-7.54 (m, 2H) 6.94-7.07 (m, 2H) 4.37- 4.51 (m, 1H) 2.24-2.40 (m, 3H) 1.96-2.09 (m, 4H) 1.57-1.72 (m, 2H) 1.17-1.31 (m, 2H). m/z 379.2 (M+H)+.

Reference： [1]Patent: WO2016/73770,2016,A1 .Location in patent: Paragraph 0297-0298

66
[ 55270-33-2 ]
[ 3336-49-0 ]

Reference： [1]Journal of the American Chemical Society,2016,vol. 138,p. 13493 - 13496

67
[ 1532-91-8 ]
[ 3336-49-0 ]

Reference： [1]Journal of the American Chemical Society,2016,vol. 138,p. 13493 - 13496

68
[ 685103-98-4 ]
[ 3336-49-0 ]

Reference： [1]Chemical Science,2017,vol. 8,p. 1551 - 1559

69
[ 3336-49-0 ]
[ 100-51-6 ]
C₁₆H₁₃NO [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
90%	With triphenylphosphine; diethylazodicarboxylate; In tetrahydrofuran; toluene; at 20 - 30℃;Inert atmosphere;	General procedure: PPh3 (89 mg, 0.34 mmole, 2 eq) and the quinolinol or isoquinolinol (25 mg, 0.17 mmole, 1 eq) werecombined in a glass vial and purged with nitrogen. THF (700 muL) was then added followed by benzylalcohol (44 muL, 0.34 mmole, 2 eq). A 40% by weight solution of DEAD in toluene (170 muL, 0.34 mmole, 1eq) was then added dropwise to keep the reaction temperature below 30 oC. The reaction mixture wasshaken at room temperature overnight and then purified on a Waters preparative LC/MS system with agradient of 0 to 60% MeCN-H2O to give the desired product with yields ranging from 50% to 98%. Ininstances where the isomers were not able to be separated, the percentage ratio was determined by 1H NMR.Purified products were characterized by 1H and 13C NMR.

Reference： [1]Heterocycles,2017,vol. 94,p. 1305 - 1313

70
2C₉H₆NO^(1-)*Cu⁽²⁺⁾*5H₂O [ No CAS ]
[ 3336-49-0 ]

Yield	Reaction Conditions	Operation in experiment
	With sodiumsulfide nonahydrate; In ethanol; at 40℃; for 20.0h;	General procedure: The hydrolysis reaction was as follows: The mixture ofbromoisoquinoline (11.2 g, 50.5 mmol), hydrated CuSO4 (5 g,20.l mmol), copper bronze (4.1 g, 64.1 mmol), and NaOH (31.3g, 757.5 mmol) in water (17 mL) was heated in an autoclaveat 210C for 12 h. After cooling to room temperature, themixure was filtered and the solid cake was washed with water,the combined filtrate was adjusted to pH 6 with hydrochloricacid to precipitate the solid (i4-i8)2Cu.5H2O. The Na2S.9H2O (5 g, 24.5 mmol) was add to a solutionof (i4-i8)2Cu.5H2O (21.75 g 49 mmol) in 200 mL EtOH, andstirred at 40C for 20 h and then filtered. Removal of excess ofsolvent afforded solid, the solid to water (500 mL), and adjustedto pH 6 with hydrochloric acid to give i4-i8 as off-white solid.

Reference： [1]Indian Journal of Heterocyclic Chemistry,2017,vol. 27,p. 65 - 70

71
[ 1532-72-5 ]
[ 3336-49-0 ]

Yield	Reaction Conditions	Operation in experiment
4.8 g (60.4%)	With p-toluenesulfonyl chloride; In chloroform; for 1.0h;	2. 4-Hydroxyisoquinoline To a solution of isoquinoline-N-oxide (7.93 g, 54.63 mmol) in chloroform (160 mL) was added portionwise p-toluenesulfonyl chloride (19.66 g, 103.1 mmol). After the mixture had been refluxed for one hour solvent was removed with a rotary evaporator, and the dense solution was dissolved in methanol (100 mL). After a few minutes, a white solid precipitated. After standing overnight filtration gave 4.8 g (60.4%) of the hydroxy compound, mp 223-224 C.

Reference： [1]Patent: US2003/125561,2003,A1

72
[ 3336-49-0 ]
[ 366003-94-3 ]

Reference： [1]Patent: US2003/125561,2003,A1

73
[ 3336-49-0 ]
[ 36718-46-4 ]

Yield	Reaction Conditions	Operation in experiment
1.43 g (36.4%)	With sulfuric acid; potassium nitrate; at 50 - 55℃; for 0.5h;	3. 3-Nitro-<strong>[3336-49-0]4-hydroxyisoquinoline</strong> To a solution of 3 g (20.6 mmol) of 4-hydrocyisoquinoline dissolved in 14 mL of conc. H2SO4 there was added 2.4 g of KNO3 during 30 min. while keeping the temperature between 50-55 C. The mixture was maintained at this temperature for 3 hours after which the reaction mixture was poured onto crushed ice. The yellow precipitate was collected, washed with water and recrystallized from ethanol to give 1.43 g (36.4%) of the nitroquinoline as yellow needles: mp 170-171 C. (lit mp 173 C.); 1H-NMR (DMSO-d6 200 MHz) delta 8.80 (s, 1H), 8.64 (d, 1H), 8.36 (d, 1H), 8.0 (dd, 1H), 7.61 (dd, 1H); IR (KBr) 2408 (broad, OH), 1569 (s, NO2), 1488 (s, NO2) cm-1

Reference： [1]Patent: US2003/125561,2003,A1

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H413	May cause long-lasting harmful effects to aquatic life
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[ CAS No. 3336-49-0 ] {[proInfo.proName]}

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[ 3336-49-0 ] Synthesis Path-Upstream 1~2

[ 3336-49-0 ] Synthesis Path-Downstream 1~73

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Alcohols

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Isoquinolines

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