Home Cart 0 Sign in  
X

[ CAS No. 5751-52-0 ] {[proInfo.proName]}

,{[proInfo.pro_purity]}
Cat. No.: {[proInfo.prAm]}
3d Animation Molecule Structure of 5751-52-0
Chemical Structure| 5751-52-0
Chemical Structure| 5751-52-0
Structure of 5751-52-0 * Storage: {[proInfo.prStorage]}
Cart0 Add to My Favorites Add to My Favorites Bulk Inquiry Inquiry Add To Cart

Quality Control of [ 5751-52-0 ]

Related Doc. of [ 5751-52-0 ]

Alternatived Products of [ 5751-52-0 ]

Product Details of [ 5751-52-0 ]

CAS No. :5751-52-0 MDL No. :MFCD00218597
Formula : C10H8O3 Boiling Point : -
Linear Structure Formula :- InChI Key :ZIPLCYUNFCYCCT-UHFFFAOYSA-N
M.W : 176.17 Pubchem ID :600605
Synonyms :

Calculated chemistry of [ 5751-52-0 ]

Physicochemical Properties

Num. heavy atoms : 13
Num. arom. heavy atoms : 10
Fraction Csp3 : 0.1
Num. rotatable bonds : 1
Num. H-bond acceptors : 3.0
Num. H-bond donors : 0.0
Molar Refractivity : 48.98
TPSA : 39.44 Ų

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) : -6.12 cm/s

Lipophilicity

Log Po/w (iLOGP) : 2.07
Log Po/w (XLOGP3) : 1.77
Log Po/w (WLOGP) : 1.8
Log Po/w (MLOGP) : 0.53
Log Po/w (SILICOS-IT) : 2.44
Consensus Log Po/w : 1.72

Druglikeness

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

Water Solubility

Log S (ESOL) : -2.55
Solubility : 0.496 mg/ml ; 0.00281 mol/l
Class : Soluble
Log S (Ali) : -2.22
Solubility : 1.07 mg/ml ; 0.00608 mol/l
Class : Soluble
Log S (SILICOS-IT) : -3.74
Solubility : 0.0324 mg/ml ; 0.000184 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 2.49

Safety of [ 5751-52-0 ]

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 [ 5751-52-0 ]

* 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 [ 5751-52-0 ]
  • Downstream synthetic route of [ 5751-52-0 ]

[ 5751-52-0 ] Synthesis Path-Upstream   1~21

  • 1
  • [ 5751-52-0 ]
  • [ 42327-52-6 ]
Reference: [1] Bioorganic and Medicinal Chemistry Letters, 2018, vol. 28, # 11, p. 2098 - 2102
[2] Applied Organometallic Chemistry, 2011, vol. 25, # 11, p. 804 - 809
[3] Journal of Chemical Research, Miniprint, 1988, # 6, p. 1570 - 1582
  • 2
  • [ 5751-52-0 ]
  • [ 18385-69-8 ]
Reference: [1] Bulletin of the Chemical Society of Japan, 2004, vol. 77, # 3, p. 549 - 552
  • 3
  • [ 552-41-0 ]
  • [ 4637-24-5 ]
  • [ 5751-52-0 ]
YieldReaction ConditionsOperation in experiment
70%
Stage #1: at 100℃; for 0.166667 h;
Stage #2: With hydrogenchloride In dichloromethane; water at 40℃; for 0.5 h;
Example 10A
7-methoxy-4H-1-benzopyran-4-one
1-(2-Hydroxy-4-methoxyphenyl)ethanone (47 g, 283 mmol) was dissolved in N,N-dimethylformamide dimethyl acetal (47 mL, 351 mmol), and the solution was heated to >100° C. in a sand bath for 10 minutes, at which point a solid mass had formed.
The flask was cooled to ambient temperature, and 200 mL of heptanes were added.
The solids were broken up with a spatula and collected by filtration with a frilled funnel.
The solid material was crushed with a pestle and then washed with heptanes.
The solid was then dried on the filter to give about 60 g of the crude intermediate.
This intermediate was dissolved in dichloromethane (1 L) and stirred with 150 mL of concentrated HCl at 40° C. for 30 minutes.
The flask was cooled to ambient temperature, and about 100 mL of water was added.
The layers were separated, and the aqueous layer was extracted with dichloromethane (2*100 mL).
The combined organic extracts were washed with saturated sodium bicarbonate (100 mL) and brine (100 mL) and dried over sodium sulfate.
The mixture was filtered, and the filtrate was concentrated in vacuo to give a solid.
The solid was then precipitated from 500 mL of 1:1 cyclopentyl methyl ether:heptanes to give the title compound (35 g, 70percent yield).
1H NMR (400 MHz, CDCl3) δ ppm 8.11 (d, J=8.9 Hz, 1H), 7.77 (d, J=6.0 Hz, 1H), 6.97 (dd, J=8.9, 2.4 Hz, 1H), 6.84 (d, J=2.4 Hz, 1H), 6.28 (d, J=6.0 Hz, 1H), 3.90 (s, 3H); MS(ESI+) m/z 176.9 (M+H)+.
70%
Stage #1: at 100℃; for 0.166667 h;
Stage #2: With hydrogenchloride In dichloromethane at 40℃; for 0.5 h;
1-(2-Hydroxy-4-methoxyphenyl)ethanone (47 g, 283 mmol) was dissolved in N,N-dimethylformamide dimethyl acetal (47 mL, 351 mmol), and the solution was heated at >100° C. in a sand bath for 10 minutes, at which point a solid mass formed. The flask was cooled to ambient temperature, and 200 mL of heptanes were added. The solids were broken up with a spatula and collected by filtration with a fritted funnel. The solid material was crushed with a pestle and washed with heptanes. The solid was dried on the filter to give about 60 g of the crude intermediate. The intermediate was dissolved in dichloromethane (1 L) and stirred with 150 mL of concentrated HCl at 40° C. for 30 minutes. The flask was cooled to ambient temperature, and about 100 mL of water was added. The layers were separated, and the aqueous layer was extracted with dichloromethane (2×100 mL). The combined organic extracts were washed with saturated sodium bicarbonate (100 mL) and brine (100 mL) and dried over sodium sulfate. The mixture was filtered, and the filtrate was concentrated in vacuo to give a solid. The solid was taken into 500 mL of 1:1 cyclopentyl methyl ether:heptanes and the precipitate was collected to provide the title compound (35 g, 70percent yield). 1H NMR (400 MHz, CDCl3) δ ppm 8.11 (d, J=8.9 Hz, 1H), 7.77 (d, J=6.0 Hz, 1H), 6.97 (dd, J=8.9, 2.4 Hz, 1H), 6.84 (d, J=2.4 Hz, 1H), 6.28 (d, J=6.0 Hz, 1H), 3.90 (s, 3H); MS(ESI+) m/z 176.9 (M+H)+.
Reference: [1] Bioorganic and Medicinal Chemistry Letters, 2018, vol. 28, # 11, p. 2098 - 2102
[2] Patent: US2017/15675, 2017, A1, . Location in patent: Paragraph 0970
[3] Patent: US2017/305891, 2017, A1, . Location in patent: Paragraph 0735
  • 4
  • [ 292638-85-8 ]
  • [ 73220-42-5 ]
  • [ 42059-83-6 ]
  • [ 5751-52-0 ]
YieldReaction ConditionsOperation in experiment
70.5% With copper diacetate; palladium diacetate In dimethyl sulfoxide; N,N-dimethyl-formamide at 100℃; for 6 h; Inert atmosphere; Green chemistry To a solution of 3-iodo-7-methoxy-4H-chromen-4-one (1) (4 mmol) and methyl acrylate (2) (4.8 mmol) in solvent was added catalyst (5 mmol percent) and base (8 mmol). The reaction mixture was stirred via oil heating under nitrogen protection. Then the mixture was poured into 10percent HCl ice-water (300 mL) slowly with stirring. The suspension was filtered through a filter and filter cake was collected and dried. The crude product was purified by chromatography over silica gel to give compound 3 or 4.
Reference: [1] Tetrahedron, 2012, vol. 68, # 47, p. 9777 - 9787
  • 5
  • [ 73220-33-4 ]
  • [ 5751-52-0 ]
Reference: [1] Organic and Biomolecular Chemistry, 2012, vol. 10, # 4, p. 890 - 894
[2] Chemical Communications, 2012, vol. 48, # 24, p. 2985 - 2987
  • 6
  • [ 73220-33-4 ]
  • [ 5751-52-0 ]
YieldReaction ConditionsOperation in experiment
0.854 g With hydrogenchloride In dichloromethane; water for 1 h; Reflux The enamine was dissolved in dichloromethane (40 mL) and treated with HCl (4 mL) at reflux for one hour. The aqueous layer was removed and extracted with 3 x 40mL of dichloromethane. The combined extracts were washed with saturated aqueous sodium bicarbonate and dried over sodium sulfate, then filtered and the solvent removed under reduced pressure to give title compound (0.854 g, 4.85 mmol, 64.4 percent yield) as pale yellow crystals. 1H NMR (400 MHz, DMSO-d6) δ 8.22 (d, J = 6.0 Hz, 1H), 7.94 (d, J = 8.9 Hz, 1H), 7.13 (d, J = 2.4 Hz, 1H), 7.06 (dd, J = 8.9, 2.4 Hz, 1H), 6.27 (d, J = 6.0 Hz, 1H), 3.90 (s, 3H); MS (ESI+) m/z 177 (M+H)+.
Reference: [1] Journal of Medicinal Chemistry, 2018, vol. 61, # 4, p. 1436 - 1449
[2] Patent: WO2016/69757, 2016, A1, . Location in patent: Page/Page column 127-128
[3] Journal of Chemical Sciences, 2018, vol. 130, # 12,
  • 7
  • [ 94719-81-0 ]
  • [ 5751-52-0 ]
Reference: [1] Journal of Medicinal Chemistry, 2010, vol. 53, # 2, p. 660 - 668
[2] Bulletin of the Chemical Society of Japan, 2004, vol. 77, # 3, p. 549 - 552
[3] Tetrahedron, 2012, vol. 68, # 47, p. 9777 - 9787
  • 8
  • [ 73220-33-4 ]
  • [ 62437-99-4 ]
  • [ 5751-52-0 ]
  • [ 814257-48-2 ]
  • [ 1345865-40-8 ]
YieldReaction ConditionsOperation in experiment
48% at 60℃; for 2 h; General procedure: The hydrazines (method 2) or hydrazine hydrochlorides (method 1) (2 mmol) were added in one portion to a stirred solution of the appropriate compound 11 (2 mmol) in acidified EtOH [10 mL containing 0.17 mL of HCl 37percent (method 2)] or EtOH [10 mL (method 1)]. The resulting solution was stirred for 2 h at 60 °C.
Reference: [1] European Journal of Medicinal Chemistry, 2011, vol. 46, # 11, p. 5293 - 5309
  • 9
  • [ 59887-89-7 ]
  • [ 74-88-4 ]
  • [ 5751-52-0 ]
Reference: [1] Journal of Heterocyclic Chemistry, 2015, vol. 52, # 2, p. 562 - 572
  • 10
  • [ 552-41-0 ]
  • [ 109-94-4 ]
  • [ 5751-52-0 ]
Reference: [1] Chemische Berichte, 1917, vol. 50, p. 917
[2] Journal of Chemical Research, Miniprint, 1988, # 6, p. 1570 - 1582
[3] Journal of Medicinal Chemistry, 1995, vol. 38, # 16, p. 3174 - 3186
[4] Chemistry - An Asian Journal, 2015, vol. 10, # 3, p. 540 - 543
  • 11
  • [ 206054-94-6 ]
  • [ 5751-52-0 ]
Reference: [1] Journal of Chemical Research - Part S, 1998, # 2, p. 88 - 89
  • 12
  • [ 552-41-0 ]
  • [ 5751-52-0 ]
Reference: [1] Chemical Communications, 2012, vol. 48, # 24, p. 2985 - 2987
[2] Tetrahedron, 2012, vol. 68, # 47, p. 9777 - 9787
[3] European Journal of Medicinal Chemistry, 2013, vol. 62, p. 158 - 167
[4] Patent: WO2016/69757, 2016, A1,
[5] Journal of Medicinal Chemistry, 2018, vol. 61, # 4, p. 1436 - 1449
[6] Journal of Chemical Sciences, 2018, vol. 130, # 12,
  • 13
  • [ 288-32-4 ]
  • [ 80930-46-7 ]
  • [ 5751-52-0 ]
  • [ 80930-35-4 ]
Reference: [1] Journal of Heterocyclic Chemistry, 1984, vol. 21, p. 311 - 315
  • 14
  • [ 552-41-0 ]
  • [ 122-51-0 ]
  • [ 5751-52-0 ]
Reference: [1] Chemistry - A European Journal, 2013, vol. 19, # 1, p. 74 - 77
  • 15
  • [ 6133-29-5 ]
  • [ 5751-52-0 ]
Reference: [1] Journal of Chemical Research - Part S, 1998, # 2, p. 88 - 89
  • 16
  • [ 42327-52-6 ]
  • [ 5751-52-0 ]
Reference: [1] Journal of Chemical Research - Part S, 1998, # 2, p. 88 - 89
  • 17
  • [ 89-84-9 ]
  • [ 5751-52-0 ]
Reference: [1] Journal of Heterocyclic Chemistry, 2015, vol. 52, # 2, p. 562 - 572
  • 18
  • [ 94719-82-1 ]
  • [ 5751-52-0 ]
Reference: [1] European Journal of Medicinal Chemistry, 2013, vol. 62, p. 158 - 167
  • 19
  • [ 552-41-0 ]
  • [ 5751-52-0 ]
  • [ 814257-48-2 ]
Reference: [1] European Journal of Medicinal Chemistry, 2011, vol. 46, # 11, p. 5293 - 5309
  • 20
  • [ 5751-52-0 ]
  • [ 98-80-6 ]
  • [ 22395-22-8 ]
Reference: [1] Organic and Biomolecular Chemistry, 2012, vol. 10, # 36, p. 7305 - 7312
[2] Chemical Communications, 2012, vol. 48, # 24, p. 2985 - 2987
  • 21
  • [ 5751-52-0 ]
  • [ 98-80-6 ]
  • [ 22395-22-8 ]
  • [ 21785-09-1 ]
Reference: [1] Organic and Biomolecular Chemistry, 2012, vol. 10, # 36, p. 7305 - 7312
Same Skeleton Products
Historical Records

Related Functional Groups of
[ 5751-52-0 ]

Ethers

Chemical Structure| 1157-39-7

[ 1157-39-7 ]

4',7-Dimethoxyisoflavone

Similarity: 0.96

Chemical Structure| 131-57-7

[ 131-57-7 ]

(2-Hydroxy-4-methoxyphenyl)(phenyl)methanone

Similarity: 0.92

Chemical Structure| 829-20-9

[ 829-20-9 ]

1-(2,4-Dimethoxyphenyl)ethanone

Similarity: 0.92

Chemical Structure| 22395-22-8

[ 22395-22-8 ]

7-Methoxy-2-phenyl-4H-chromen-4-one

Similarity: 0.91

Chemical Structure| 579-74-8

[ 579-74-8 ]

1-(2-Methoxyphenyl)ethanone

Similarity: 0.90

Ketones

Chemical Structure| 6320-42-9

[ 6320-42-9 ]

7-Hydroxy-2-methyl-4H-chromen-4-one

Similarity: 0.98

Chemical Structure| 1157-39-7

[ 1157-39-7 ]

4',7-Dimethoxyisoflavone

Similarity: 0.96

Chemical Structure| 90-47-1

[ 90-47-1 ]

9H-Xanthen-9-one

Similarity: 0.94

Chemical Structure| 131-57-7

[ 131-57-7 ]

(2-Hydroxy-4-methoxyphenyl)(phenyl)methanone

Similarity: 0.92

Chemical Structure| 829-20-9

[ 829-20-9 ]

1-(2,4-Dimethoxyphenyl)ethanone

Similarity: 0.92

Related Parent Nucleus of
[ 5751-52-0 ]

Other Aromatic Heterocycles

Chemical Structure| 6320-42-9

[ 6320-42-9 ]

7-Hydroxy-2-methyl-4H-chromen-4-one

Similarity: 0.98

Chemical Structure| 1157-39-7

[ 1157-39-7 ]

4',7-Dimethoxyisoflavone

Similarity: 0.96

Chemical Structure| 90-47-1

[ 90-47-1 ]

9H-Xanthen-9-one

Similarity: 0.94

Chemical Structure| 22395-22-8

[ 22395-22-8 ]

7-Methoxy-2-phenyl-4H-chromen-4-one

Similarity: 0.91

Chemical Structure| 6665-86-7

[ 6665-86-7 ]

7-Hydroxy-2-phenyl-4H-chromen-4-one

Similarity: 0.91