[ CAS No. 128676-85-7 ] {[proInfo.proName]}

Name: 128676-85-7|2-Chloro-3-iodoquinoline|95%
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SKU: A791048
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Quality Control of [ 128676-85-7 ]

COA NMR CNMR HPLC LC-MS

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SDS Specification

Alternatived Products of [ 128676-85-7 ]

Product Details of [ 128676-85-7 ]

CAS No. :	128676-85-7	MDL No. :	MFCD09999230
Formula :	C₉H₅ClIN	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	VAKSSUOSONRGPR-UHFFFAOYSA-N
M.W :	289.50	Pubchem ID :	14616623
Synonyms :

Calculated chemistry of [ 128676-85-7 ]

Physicochemical Properties

Num. heavy atoms :	12
Num. arom. heavy atoms :	10
Fraction Csp3 :	0.0
Num. rotatable bonds :	0
Num. H-bond acceptors :	1.0
Num. H-bond donors :	0.0
Molar Refractivity :	59.47
TPSA :	12.89 Å²

Pharmacokinetics

GI absorption :	High
BBB permeant :	Yes
P-gp substrate :	No
CYP1A2 inhibitor :	Yes
CYP2C19 inhibitor :	Yes
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-5.37 cm/s

Lipophilicity

Log Po/w (iLOGP) :	2.38
Log Po/w (XLOGP3) :	3.8
Log Po/w (WLOGP) :	3.49
Log Po/w (MLOGP) :	3.26
Log Po/w (SILICOS-IT) :	4.05
Consensus Log Po/w :	3.4

Druglikeness

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

Water Solubility

Log S (ESOL) :	-4.65
Solubility :	0.00655 mg/ml ; 0.0000226 mol/l
Class :	Moderately soluble
Log S (Ali) :	-3.77
Solubility :	0.0497 mg/ml ; 0.000172 mol/l
Class :	Soluble
Log S (SILICOS-IT) :	-5.26
Solubility :	0.00159 mg/ml ; 0.0000055 mol/l
Class :	Moderately soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	2.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	2.06

Safety of [ 128676-85-7 ]

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 [ 128676-85-7 ]

* 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 [ 128676-85-7 ]
Downstream synthetic route of [ 128676-85-7 ]

[ 128676-85-7 ] Synthesis Path-Upstream 1~6

1
[ 612-62-4 ]
[ 128676-85-7 ]

Reference： [1] Heterocycles, 2004, vol. 63, # 3, p. 631 - 639
[2] Tetrahedron, 2007, vol. 63, # 51, p. 12786 - 12790
[3] Bulletin of the Korean Chemical Society, 2016, vol. 37, # 6, p. 958 - 961

2
[ 862249-68-1 ]
[ 128676-85-7 ]

Reference： [1] Journal of Heterocyclic Chemistry, 1989, vol. 26, p. 1589 - 1594

3
[ 335649-85-9 ]
[ 128676-85-7 ]

Reference： [1] Tetrahedron, 2007, vol. 63, # 36, p. 8954 - 8961

4
[ 950856-36-7 ]
[ 128676-85-7 ]

Reference： [1] Tetrahedron, 2007, vol. 63, # 36, p. 8954 - 8961

5
[ 79476-07-6 ]
[ 128676-85-7 ]

Reference： [1] Tetrahedron, 2007, vol. 63, # 36, p. 8954 - 8961

6
[ 580-17-6 ]
[ 128676-85-7 ]

Reference： [1] Tetrahedron, 2007, vol. 63, # 36, p. 8954 - 8961

[ 128676-85-7 ] Synthesis Path-Downstream 1~46

1
[ 862249-68-1 ]
[ 128676-85-7 ]

Reference： [1]Journal of Heterocyclic Chemistry,1989,vol. 26,p. 1589 - 1594

2
[ 128676-85-7 ]
[ 74-89-5 ]
[ 128676-93-7 ]

Reference： [1]Journal of Heterocyclic Chemistry,1989,vol. 26,p. 1589 - 1594
[2]Heterocycles,2004,vol. 63,p. 631 - 639

3
[ 81290-20-2 ]
[ 128676-85-7 ]
[ 25199-86-4 ]

Reference： [1]European Journal of Organic Chemistry,2003,p. 1559 - 1568

4
[ 612-62-4 ]
[ 128676-85-7 ]

Reference： [1]Heterocycles,2004,vol. 63,p. 631 - 639
[2]Tetrahedron,2007,vol. 63,p. 12786 - 12790
[3]Bulletin of the Korean Chemical Society,2016,vol. 37,p. 958 - 961

5
[ 128676-85-7 ]
[ 100-46-9 ]
[ 668459-13-0 ]

Reference： [1]Heterocycles,2004,vol. 63,p. 631 - 639

6
[ 5049-61-6 ]
[ 128676-85-7 ]
pyrazino[2',1':2,3]imidazo[4,5-b]quinoline [ No CAS ]
2-chloro-N-(pyrazin-2-yl)quinolin-3-amine [ No CAS ]

Reference： [1]Tetrahedron,2007,vol. 63,p. 8954 - 8961

7
[ 5469-70-5 ]
[ 128676-85-7 ]
pyridazino[6',1':2,3]imidazo[4,5-b]quinoline [ No CAS ]

Reference： [1]Tetrahedron,2007,vol. 63,p. 8954 - 8961

8
[ 335649-85-9 ]
[ 128676-85-7 ]

Reference： [1]Tetrahedron,2007,vol. 63,p. 8954 - 8961

9
[ 504-29-0 ]
[ 128676-85-7 ]
pyrido[2',1':2,3]imidazo[4,5-b]quinoline [ No CAS ]

Reference： [1]Tetrahedron,2007,vol. 63,p. 8954 - 8961

10
[ 504-29-0 ]
[ 128676-85-7 ]
pyrido[2',1':2,3]imidazo[4,5-b]quinoline [ No CAS ]
2-chloro-N-(pyridin-2-yl)quinolin-3-amine [ No CAS ]

Reference： [1]Tetrahedron,2007,vol. 63,p. 8954 - 8961

11
[ 504-29-0 ]
[ 128676-85-7 ]
pyrido[2',1':2,3]imidazo[4,5-b]quinoline [ No CAS ]
N,N'-di(pyridin-2-yl)quinoline-2,3-diamine [ No CAS ]

Reference： [1]Tetrahedron,2007,vol. 63,p. 8954 - 8961

12
[ 580-22-3 ]
[ 128676-85-7 ]
diquino[1,2-a:3',2'-d]imidazole [ No CAS ]

Reference： [1]Tetrahedron,2007,vol. 63,p. 8954 - 8961

13
[ 1532-84-9 ]
[ 128676-85-7 ]
isoquino[1',2':2,3]imidazo[4,5-b]quinoline [ No CAS ]

Reference： [1]Tetrahedron,2007,vol. 63,p. 8954 - 8961

14
[ 128676-85-7 ]
[ 1066-54-2 ]
2-chloro-3-[2-(trimethylsilyl)ethynyl]quinoline [ No CAS ]

Reference： [1]Tetrahedron,2007,vol. 63,p. 12786 - 12790

15
[ 950856-36-7 ]
[ 128676-85-7 ]

Reference： [1]Tetrahedron,2007,vol. 63,p. 8954 - 8961

16
[ 79476-07-6 ]
[ 128676-85-7 ]

Reference： [1]Tetrahedron,2007,vol. 63,p. 8954 - 8961

17
[ 580-17-6 ]
[ 128676-85-7 ]

Reference： [1]Tetrahedron,2007,vol. 63,p. 8954 - 8961

18
[ 128676-85-7 ]
1,2-dimethyl-1H-pyrrolo[2,3-b]quinoline [ No CAS ]

Reference： [1]Heterocycles,2004,vol. 63,p. 631 - 639

19
[ 128676-85-7 ]
1-benzyl-2-methyl-1H-pyrrolo[2,3-b]quinoline [ No CAS ]

Reference： [1]Heterocycles,2004,vol. 63,p. 631 - 639

20
[ 128676-85-7 ]
[ 590371-95-2 ]

Reference： [1]European Journal of Organic Chemistry,2003,p. 1559 - 1568

21
[ 128676-85-7 ]
3-trifluoromethyl-2-quinolinecarboxylic acid [ No CAS ]

Reference： [1]European Journal of Organic Chemistry,2003,p. 1559 - 1568

22
[ 612-62-4 ]
imidazole silver [ No CAS ]
[ 128676-85-7 ]

Reference： [1]Journal of Heterocyclic Chemistry,1989,vol. 26,p. 1589 - 1594

Yield	Reaction Conditions	Operation in experiment
		Step 1 Synthesis of 2-chloro-3-iodo-quinoline (Intermediate A) A suspension of 3-(2-chloro)-quinolineboronic acid (5.05 g, 24.3 mmol, 1 equiv, prepared by the method of Marsais, F; Godard, A.; Queguiner, G. J. Heterocyclic Chem. 1989, 26, 1589-1594) and N-iodosuccinimide (5.48 g, 24.4 mmol, 1.00 equiv) in acetonitrile (300 mL) was stirred at 23 C. in the dark for 20 hours. The reaction mixture was concentrated to dryness, and the resulting yellow solid was partitioned between saturated aqueous sodium bicarbonate solution and dichloromethane. The organic layer was washed with water, then dried over magnesium sulfate and concentrated to give 2-chloro-3-iodo-quinoline (intermediate A) as a pale yellow solid. 1H NMR (400 MHz, CDCl3) delta8.67 (s, 1H), 7.99 (br d, 1H, J=8.4 Hz), 7.75 (br t, 1H, J=7.7 Hz), 7.72 (br d, 1H, J=7.8 Hz), 7.57 (br t, 1H, J=7.6 Hz).
		Step 1 Synthesis of 2-chloro-3-iodo-quinoline (Intermediate 10-A) A suspension of 3-(2-chloro)-quinolineboronic acid (5.05 g, 24.3 mmol, 1 equiv, prepared by the method of Marsais, F; Godard, A.; Queguiner, G. J. Heterocyclic Chem. 1989, 26, 1589-1594) and N-iodosuccinimide (5.48 g, 24.4 mmol, 1.00 equiv) in acetonitrile (300 mL) was stirred at 23 C. in the dark for 20 h. The reaction mixture was concentrated to dryness, and the resulting yellow solid was partitioned between saturated aqueous sodium bicarbonate solution and dichioromethane. The organic layer was washed with water, then dried over magnesium sulfate and concentrated to give 2-chloro-3-iodo-quinoline (intermediate 10-A) as a pale yellow solid. 1H NMR (400 MHz, CDCl3) delta8.67 (s, 1H), 7.99 (br d, 1H, J=8.4 Hz), 7.75 (br t, 1H, J=7.7 Hz), 7.72 (br d, 1H, J=7.8 Hz), 7.57 (br t, 1H, J=7.6 Hz).
		2-chloro-3-iodo-quinoline (1-2) A suspension of 3-(2-chloro)-quinolineboronic acid (1-1, 5.05 g, 24.3 mmol, 1 equiv, prepared by the method of Marsais, F; Godard, A.; Queguiner, G. J. Heterocyclic Chem. 1989, 26, 1589-1594) and N-iodosuccinimide (5.48 g, 24.4 mmol, 1.00 equiv) in acetonitrile (300 mL) was stirred at 23 C. in the dark for 20 hours. The reaction mixture was concentrated to dryness, and the resulting yellow solid was partitioned between saturated aqueous sodium bicarbonate solution and dichloromethane. The organic layer was washed with water, then dried over magnesium sulfate and concentrated to give 2-chloro-3-iodo-quinoline as a pale yellow solid. 1H NMR (400 MHz, CDCl3) delta 8.67 (s, 1H), 7.99 (br d, 1H, J=8.4 Hz), 7.75 (br t, 1H, J=7.7 Hz), 7.72 (br d, 1H, J=7.8 Hz), 7.57 (br t, 1H, J=7.6 Hz).

		Step A Preparation of 2-chloro-3-iodo-quinoline (Intermediate A) A suspension of 3-(2-chloro)-quinolineboronic acid (5.05 g, 24.3 mmol, 1 equiv, prepared by the method of Marsais, F; Godard, A.; Queguiner, G. J. Heterocyclic Chem. 1989, 26, 1589-1594) and N-iodosuccinimide (5.48 g, 24.4 mmol, 1.00 equiv) in acetonitrile (300 mL) was stirred at 23 C. in the dark for 20 h. The reaction mixture was concentrated to dryness and the resulting yellow solid was partitioned between saturated aqueous sodium bicarbonate solution and dichloromethane. The organic layer was washed with water, then dried over magnesium sulfate and concentrated to give 2-chloro-3-iodo-quinoline (intermediate A) as a pale yellow solid. 1H NMR (400 MHz, CDCl3) delta8.67 (s, 1H), 7.99 (br d, 1H, J=8.4 Hz), 7.75 (br t, 1H, J=7.7 Hz), 7.72 (br d, 1H, J=7.8 Hz), 7.57 (br t, 1H, J=7.6 Hz).
		2-Chloro-3-iodo-quinoline (1-2) A suspension of 3-(2-chloro)-quinolineboronic acid (1-1, 5.05 g, 24.3 mmol, 1 equiv, prepared by the method of Marsais, F; Godard, A.; Queguiner, G. J. Heterocyclic Chem. 1989, 26, 1589-1594) and N-iodosuccinimide (5.48 g, 24.4 mmol, 1.00 equiv) in acetonitrile (300 mL) was stirred at 23 C. in the dark for 20 h. The reaction mixture was concentrated to dryness, and the resulting yellow solid was partitioned between saturated aqueous sodium bicarbonate solution and dichloromethane. The organic layer was washed with water, then dried over magnesium sulfate and concentrated to give 2-chloro-3-iodo-quinoline as a pale yellow solid. 1H NMR (400 MHz, CDCl3) delta8.67 (s, 1H), 7.99 (br d, 1H, J=8.4 Hz), 7.75 (br t, 1H, J=7.7 Hz), 7.72 (br d, 1H, J=7.8 Hz), 7.57 (br t, 1H, J=7.6 Hz).
		Step 1: Synthesis of 2-chloro-3-iodo-quinoline (Intermediate A) A suspension of 3-(2-chloro)-quinolineboronic acid (5.05 g, 24.3 mmol, 1 equiv, prepared by the method of Marsais, F; Godard, A.; Queguiner, G. J. Heterocyclic Chem. 1989, 26, 1589-1594) and N-iodosuccinimide (5.48 g, 24.4 mmol, 1.00 equiv) in acetonitrile (300 mL) was stirred at 23 C. in the dark for 20 hours. The reaction mixture was concentrated to dryness, and the resulting yellow solid was partitioned between saturated aqueous sodium bicarbonate solution and dichloromethane. The organic layer was washed with water, then dried over magnesium sulfate and concentrated to give 2-chloro-3-iodo-quinoline (intermediate A) as a pale yellow solid. 1H NMR (400 MHz, CDCl3) delta8.67 (s, 1H), 7.99 (br d, 1H, J=8.4 Hz), 7.75 (br t, 1H, J=7.7 Hz), 7.72 (br d, 1H, J=7.8 Hz), 7.57 (br t, 1H, J=7.6 Hz).

24
potassium phosphate [ No CAS ]
[ 335649-61-1 ]
[ 128676-85-7 ]
tert-butyl 5-[tert-butyl(dimethyl)silyl]oxy}-2-(2-chloro-3-quinolinyl)-1H-indole-1-carboxylate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	tetrakis(triphenylphosphine) palladium(0); In 1,4-dioxane; dichloromethane; water; ethyl acetate;	tert-butyl 5-[tert-butyl(dimethyl)silyl]oxy}-2-(2-chloro-3-quinolinyl)-1H-indole-1-carboxylate (1-7) A deoxygenated mixture of 1-(tert-butoxycarbonyl)-5-[tert-butyl (dimethyl)silyl]oxy}-1H-indol-2-ylboronic acid (1-6, 4.10 g, 10.5 mmol, 1 equiv), <strong>[128676-85-7]2-chloro-3-iodo-quinoline</strong> (1-2, 3.64 g, 12.6 mmol, 1.20 equiv), potassium phosphate (6.67 g, 31.4 mmol, 3.00 equiv), and tetrakis(triphenylphosphine)palladium (0.605 g, 0.524 mmol, 0.050 equiv) in dioxane (100 mL) was heated at 90 C. for 20 hours. The reaction mixture was cooled, then partitioned between a mixture of water and ethyl acetate. The organic layer was separated, washed with brine, dried over magnesium sulfate, and concentrated. The residue was purified by flash column chromatography (20% dichloromethane in hexanes, grading to 90% dichloromethane in hexanes) to give tert-butyl 5-[tert-butyl(dimethyl)silyl]oxy}-2-(2-chloro-3-quinolinyl)-1H-indole-1-carboxylate (1-7) as a tan-colored foam. 1H NMR (400 MHz, CDCl3) delta 8.16 (s, 1H), 8.15 (d, 1H, J=9.0 Hz), 8.07 (d, 1H, J=8.2 Hz), 7.86 (d, 1H, J=7.8 Hz), 7.77 (br t, 1H, J=8.4 Hz), 7.60 (br t, 1H, J=8.1 Hz), 7.03 (d, 1H, J=2.4 Hz), 6.92 (dd, 1H, J=9.0, 2.4 Hz), 6.55 (s, 1H), 1.26 (s, 9H), 1.02 (s, 9H), 0.23 (s, 6H).

Reference： [1]Patent: US2002/72526,2002,A1

25
[ 128676-85-7 ]
[ 59-31-4 ]
[ 335649-85-9 ]

Yield	Reaction Conditions	Operation in experiment
94%	In water; acetic acid;	3-Iodo-1H-quinolin-2-one (3-5) The <strong>[128676-85-7]2-chloro-3-iodoquinoline</strong> (30.0 g) was weighed into a 250 mL flask and suspended in of 50% aqueous acetic acid (125 mL). The mixture was heated to 100 C and allowed to reflux for 16 h to completion by TLC analysis of the crude reaction mixture. The mixture was allowed to cool to ambient temperature followed by dilution with 200 mL of water. The resulting a suspension of the desired product was isolated by vacuum filtration follows by washing with water (50 mL). The water and traces of acetic acid were removed under vacuum for 5 h to afford the desired quinolinone as a tan powder (5-5, 26.5 g, 94%); 1H NMR (500 MHz, CDCl3) delta 12.13 (br s, 1H), 8.71 (s, 1H), 7.65 (d, 1H, J=7.5 Hz), 7.54 (m, 1H), 7.31 (d, 1H, J=8.0 Hz), 7.20 (m, 1H).
	In water; acetic acid;	3-Iodo-1H-quinolin-2-one (1-6) The <strong>[128676-85-7]2-chloro-3-iodoquinoline</strong> (1-5, 30.0 g) was weighed into a 250 mL flask and suspended in of 50% aqueous acetic acid (125 mL). The mixture was heated to 100 C. and allowed to reflux for 16 hours to completion by TLC analysis of the crude reaction mixture. The mixture was allowed to cool to ambient temperature followed by dilution with 200 mL of water. The resulting suspension of the desired product was isolated by vacuum filtration follows by washing with water (50 mL). The water and traces of acetic acid were removed under vacuum for 5 hours to afford the desired quinolinone as a tan powder (1-6). 1H NMR (500 MHz, CDCl3) delta 12.13 (br s, 1H), 8.71 (s, 1H), 7.65 (d, 1H, J=7.5 Hz), 7.54 (m, 1H), 7.31 (d, 1H, J=8.0 Hz), 7.20 (m, 1H).
	In water; acetic acid;	3-Iodo-1H-quinolin-2-one (5-5) The <strong>[128676-85-7]2-chloro-3-iodoquinoline</strong> (1-2, 30.0 g) was weighed into a 250 mL flask and suspended in of 50% aqueous acetic acid (125 mL). The mixture was heated to 100 C. and allowed to reflux for 16 h to completion by TLC analysis of the crude reaction mixture. The mixture was allowed to cool to ambient temperature followed by dilution with 200 mL of water. The resulting a suspension of the desired product was isolated by vacuum filtration follows by washing with water (50 mL). The water and traces of acetic acid were removed under vacuum for 5 h to afford the desired quinolinone as a tan powder (5-5); 1H NMR (500 MHz, CDCl3) delta12.13 (br s, 1H), 8.71 (s, 1H), 7.65 (d, 1H, J=7.5 Hz), 7.54 (m, 1H), 7.31 (d, 1H, J=8.0 Hz), 7.20 (m, 1H).

Reference： [1]Patent: US2002/72526,2002,A1
[2]Patent: US2002/72526,2002,A1
[3]Patent: US6306874,2001,B1

26
[ 335649-84-8 ]
[ 497-19-8 ]
[ 128676-85-7 ]
tert-butyl 5-([tert-butyl(dimethyl)silyl]oxy}methyl)-2-(2-chloro-3-quinolinyl)-1H-indole-1-carboxylate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With lithium chloride;tetrakis(triphenylphosphine) palladium(0); In 1,4-dioxane; hexane; ethyl acetate;	tert-butyl 5-([tert-butyl(dimethyl)silyl]oxy}methyl)-2-(2-chloro-3-quinolinyl)-1H-indole-1-carboxylate (7-1) 1-(tert-butoxycarbonyl)-5-([tert-butyl(dimethyl)silyl]oxy}methyl)-1H-indol-2-ylboronic acid (5-4, 5.60 g, 13.8 mmol, 2.00 equiv) was added in 4 equal portions over 8 hours to a deoxygenated solution of <strong>[128676-85-7]2-chloro-3-iodoquinoline</strong> (1-2, 2.00 g, 6.91 mmol, 1 equiv), lithium chloride (0.878 g, 20.7 mmol, 3.00 equiv), tetrakis(triphenylphosphine)palladium (0.400 g, 0.346 mmol, 0.0500 equiv), and aqueous sodium carbonate solution (2M, 10.4 mL, 20.7 mmol, 3.00 equiv) in dioxane (50 mL) at 80 C., and the resulting mixture was heated an additional 12 h. The reaction mixture was cooled then partitioned between brine and ethyl acetate (2*200 mL). The combined organic layers were dried over sodium sulfate and concentrated. The residue was purified by flash column chromatography (100% hexane initially, grading to 50% EtOAc in hexane) to provide tert-butyl 5-([tert-butyl(dimethyl)silyl]oxy}methyl)-2-(2-chloro-3-quinolinyl)-1H-indole-1-carboxylate (7-1) as a colorless oil. 1H NMR (500 MHz, CDCl3) delta8.25 (d, 1H, J=8.0 Hz), 8.18 (s, 1H), 8.07 (d, 1H, J=8.2 Hz), 7.87 (d, 1H, J=8.0 Hz), 7.77 (br t, 1H, J=8.0 Hz), 7.61 (br t, 1H, J=8.0 Hz), 7.58 (s, 1H), 7.45 (d, 1H, J=8.0 Hz), 6.65 (s, 1H), 4.87 (s, 2H), 1.27 (s, 9H), 0.97 (s, 9H), 0.13 (s, 6H).

Reference： [1]Patent: US6306874,2001,B1

27
C₁₆H₁₉NO₂ [ No CAS ]
[ 128676-85-7 ]
((1S,2S)-4-iodo-1-methyl-1,2-dihydroimidazo[1,2-a]quinolin-2-yl)diphenylmethanol [ No CAS ]

Reference： [1]Organic Letters,2015,vol. 17,p. 4988 - 4991

28
C₁₆H₁₉NO₂ [ No CAS ]
[ 128676-85-7 ]
(2S,3R)-2-((3-iodoquinolin-2-yl)amino)-1,1-diphenylbutane-1,3-diol [ No CAS ]

Reference： [1]Organic Letters,2015,vol. 17,p. 4988 - 4991

29
[ 128676-85-7 ]
[ 908850-62-4 ]