Alternatived Products of [ 146744-23-2 ]
Product Details of [ 146744-23-2 ]
CAS No. : 146744-23-2
MDL No. : MFCD24369086
Formula :
C12 H10 O3
Boiling Point :
-
Linear Structure Formula : -
InChI Key : OPAWKBQBXLRPLC-UHFFFAOYSA-N
M.W : 202.21
Pubchem ID : 15437333
Synonyms :
Calculated chemistry of [ 146744-23-2 ]
Physicochemical Properties
Num. heavy atoms :
15
Num. arom. heavy atoms :
10
Fraction Csp3 :
0.08
Num. rotatable bonds :
2
Num. H-bond acceptors :
3.0
Num. H-bond donors :
1.0
Molar Refractivity :
57.47
TPSA :
46.53 Ų
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) :
-6.11 cm/s
Lipophilicity
Log Po/w (iLOGP) :
1.93
Log Po/w (XLOGP3) :
2.01
Log Po/w (WLOGP) :
2.47
Log Po/w (MLOGP) :
2.31
Log Po/w (SILICOS-IT) :
2.34
Consensus Log Po/w :
2.21
Druglikeness
Lipinski :
0.0
Ghose :
None
Veber :
0.0
Egan :
0.0
Muegge :
0.0
Bioavailability Score :
0.55
Water Solubility
Log S (ESOL) :
-2.72
Solubility :
0.384 mg/ml ; 0.0019 mol/l
Class :
Soluble
Log S (Ali) :
-2.61
Solubility :
0.492 mg/ml ; 0.00243 mol/l
Class :
Soluble
Log S (SILICOS-IT) :
-3.58
Solubility :
0.0532 mg/ml ; 0.000263 mol/l
Class :
Soluble
Medicinal Chemistry
PAINS :
0.0 alert
Brenk :
1.0 alert
Leadlikeness :
1.0
Synthetic accessibility :
1.42
Safety of [ 146744-23-2 ]
Application In Synthesis of [ 146744-23-2 ]
* 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 [ 146744-23-2 ]
1
[ 582-17-2 ]
[ 108-24-7 ]
[ 146744-23-2 ]
Yield Reaction Conditions Operation in experiment
With sodium hydroxide at 50 - 60℃;
2
[ 146744-23-2 ]
[ 98-88-4 ]
2-acetoxy-7-benzoyloxy-naphthalene
[ No CAS ]
Yield Reaction Conditions Operation in experiment
With pyridine
3
[ 108-05-4 ]
[ 582-17-2 ]
[ 22472-26-0 ]
[ 146744-23-2 ]
Yield Reaction Conditions Operation in experiment
In tetrahydrofuran; cyclohexane at 40℃; for 12h; Chromobacterium viscosum lipase immobilized on Celite; Yield given. Yields of byproduct given;
4
[ 582-17-2 ]
[ 6548-96-5 ]
[ 146744-23-2 ]
[ 55154-12-6 ]
Yield Reaction Conditions Operation in experiment
With borate buffer; azoniacyclophane CP66 In 1,4-dioxane at 25℃;
5
[ 22472-26-0 ]
[ 582-17-2 ]
[ 146744-23-2 ]
Yield Reaction Conditions Operation in experiment
45%
With lipase of Pseudomonas sp; water In various solvent(s) at 25℃; for 1h;
6
[ 146744-23-2 ]
[ 77-78-1 ]
[ 3469-26-9 ]
7
[ 146744-23-2 ]
2-hydroxy-7-acetoxy-1-nitronaphthalene
[ No CAS ]
Yield Reaction Conditions Operation in experiment
58%
With 4-nitro-4-methyl-2,3,5,6-tetrabromo-2,5-cyclohexadien-1-one In diethyl ether at 20℃; for 3h;
With 4-nitro-4-methyl-2,3,5,6-tetrabromo-2,5-cyclohexadien-1-one In diethyl ether
Reference:
[1]Yu, Younong; Singh, Sudhir K.; Liu, Angela; Li, Tsai-Kun; Liu, Leroy F.; LaVoie, Edmond J.
[Bioorganic and Medicinal Chemistry, 2003, vol. 11, # 7, p. 1475 - 1491]
[2]Location in patent: scheme or table
Arnatt, Christopher K.; Zhang, Yan
[Tetrahedron Letters, 2012, vol. 53, # 13, p. 1592 - 1594]
8
[ 101597-25-5 ]
[ 146744-23-2 ]
3,3,10,10-tetrakis(4-methoxyphenyl)-3H,10H-naphtho[2,1-b;7,8-b']dipyran
[ No CAS ]
9-acetoxy-[3,3-bis(4-methoxyphenyl)]-3H-naphtho[2,1-b]pyran
[ No CAS ]
Yield Reaction Conditions Operation in experiment
1: 77%
2: 23%
Stage #1: 1,1-bis(4-methoxyphenyl)-2-propyn-1-ol; 2-acetoxy-7-hydroxynaphthalene In toluene for 0.75h; Heating;
Stage #2: With aluminum oxide In toluene for 4h; Heating; Further stages.;
9
[ 582-17-2 ]
[ 146744-23-2 ]
Yield Reaction Conditions Operation in experiment
Multi-step reaction with 2 steps
1: pyridine
2: 45 percent / lipase of Pseudomonas sp.; water / various solvent(s) / 1 h / 25 °C
10
[ 582-17-2 ]
[ 108-24-7 ]
[ 22472-26-0 ]
[ 146744-23-2 ]
Yield Reaction Conditions Operation in experiment
1: 64%
2: 28%
With pyridine hydrogenfluoride In dichloromethane at 27℃; for 2h;
11
[ 146744-23-2 ]
(E)-4-acetoxy-2-carboxycinnamic acid
[ No CAS ]
Yield Reaction Conditions Operation in experiment
84%
With oxone In water; acetonitrile at 20℃; for 10h;
12
[ 146744-23-2 ]
[ 4049-33-6 ]
2-(7-hydroxynaphthyl)-β-D-xylopyranoside
[ No CAS ]
Yield Reaction Conditions Operation in experiment
With boron trifluoride diethyl etherate In dichloromethane
Reference:
[1]Thorsheim, Karin; Persson, Andrea; Siegbahn, Anna; Tykesson, Emil; Westergren-Thorsson, Gunilla; Mani, Katrin; Ellervik, Ulf
[Glycoconjugate Journal, 2016, vol. 33, # 2, p. 245 - 257]
13
[ 146744-23-2 ]
[ 4049-33-6 ]
C21 H22 O9
[ No CAS ]
Yield Reaction Conditions Operation in experiment
With boron trifluoride diethyl etherate In dichloromethane
Reference:
[1]Thorsheim, Karin; Persson, Andrea; Siegbahn, Anna; Tykesson, Emil; Westergren-Thorsson, Gunilla; Mani, Katrin; Ellervik, Ulf
[Glycoconjugate Journal, 2016, vol. 33, # 2, p. 245 - 257]
14
3-bromo-1-iodosylbenzene
[ No CAS ]
[ 146744-23-2 ]
7-(2-bromo-4-iodophenoxy)naphthalen-2-yl acetate
[ No CAS ]
Yield Reaction Conditions Operation in experiment
73%
Stage #1: 3-bromo-1-iodosylbenzene With 3-chloro-benzenecarboperoxoic acid In dichloromethane at 25℃; for 2h; Schlenk technique;
Stage #2: 2-acetoxy-7-hydroxynaphthalene With butyric acid In tetrahydrofuran; dichloromethane at 70℃; for 0.166667h; Schlenk technique;
15
[ 146744-23-2 ]
8-(2-(diphenylphosphoryl)phenyl)-7-hydroxynaphthalen-2-yl acetate
[ No CAS ]
Yield Reaction Conditions Operation in experiment
Multi-step reaction with 2 steps
1.1: triethylamine; 2-chloro-1,3-dimethylimidazolinium chloride; sodium azide / tetrahydrofuran; acetonitrile / 0.33 h / -20 °C
2.1: bis[dichloro(pentamethylcyclopentadienyl)iridium(III)]; silver hexafluoroantimonate; mesitylenecarboxylic acid / 1,2-dichloro-ethane / 0.33 h / 60 °C / Molecular sieve; Inert atmosphere; Sealed tube
2.2: 12 h / Molecular sieve; Inert atmosphere; Sealed tube
16
[ 146744-23-2 ]
7-acetoxy-1-diazo-2(1H)-naphthalenone
[ No CAS ]
Yield Reaction Conditions Operation in experiment
With sodium azide; 2-chloro-1,3-dimethylimidazolinium chloride; triethylamine In tetrahydrofuran; acetonitrile at -20℃; for 0.333333h;
With sodium azide; 2-chloro-1,3-dimethylimidazolinium chloride; triethylamine In tetrahydrofuran; acetonitrile for 0.333333h;
Reference:
[1]Liu, Zhong; Wu, Ji-Qiang; Yang, Shang-Dong
[Organic Letters, 2017, vol. 19, # 19, p. 5434 - 5437]
[2]Ghosh, Bidhan; Samanta, Rajarshi
[Chemical Communications, 2019, vol. 55, # 48, p. 6886 - 6889]
17
[ 582-17-2 ]
[ 75-36-5 ]
[ 146744-23-2 ]
Yield Reaction Conditions Operation in experiment
70%
With triethylamine In dichloromethane at 0 - 25℃; for 6h;
Reference:
[1]Chen, Ye-Hui; Li, Heng-Hui; Li, Shaoyu; Tan, Bin; Xiang, Shao-Hua; Zhang, Xiao
[Angewandte Chemie - International Edition, 2020, vol. 59, # 28, p. 11374 - 11378][Angew. Chem.]
18
[ 74-96-4 ]
[ 146744-23-2 ]
7-acetyloxy-2-ethoxynaphthalene
[ No CAS ]
Yield Reaction Conditions Operation in experiment
With potassium carbonate In acetone for 24h; Reflux;
Reference:
[1]Chen, Ye-Hui; Li, Heng-Hui; Li, Shaoyu; Tan, Bin; Xiang, Shao-Hua; Zhang, Xiao
[Angewandte Chemie - International Edition, 2020, vol. 59, # 28, p. 11374 - 11378][Angew. Chem.]
19
[ 146744-23-2 ]
[ 106-94-5 ]
C15 H16 O3
[ No CAS ]
Yield Reaction Conditions Operation in experiment
With potassium carbonate In acetone for 24h; Reflux;
Reference:
[1]Chen, Ye-Hui; Li, Heng-Hui; Li, Shaoyu; Tan, Bin; Xiang, Shao-Hua; Zhang, Xiao
[Angewandte Chemie - International Edition, 2020, vol. 59, # 28, p. 11374 - 11378][Angew. Chem.]
20
[ 109-65-9 ]
[ 146744-23-2 ]
C16 H18 O3
[ No CAS ]
Yield Reaction Conditions Operation in experiment
With potassium carbonate In acetone for 24h; Reflux;
Reference:
[1]Chen, Ye-Hui; Li, Heng-Hui; Li, Shaoyu; Tan, Bin; Xiang, Shao-Hua; Zhang, Xiao
[Angewandte Chemie - International Edition, 2020, vol. 59, # 28, p. 11374 - 11378][Angew. Chem.]
21
[ 146744-23-2 ]
[ 100-39-0 ]
[ 1257230-84-4 ]
Yield Reaction Conditions Operation in experiment
With potassium carbonate In acetone for 24h; Reflux;
Reference:
[1]Chen, Ye-Hui; Li, Heng-Hui; Li, Shaoyu; Tan, Bin; Xiang, Shao-Hua; Zhang, Xiao
[Angewandte Chemie - International Edition, 2020, vol. 59, # 28, p. 11374 - 11378][Angew. Chem.]
22
[ 146744-23-2 ]
(R)-2-chloro-3-(7-ethoxy-2-hydroxynaphthalen-1-yl)cyclohexa-2,5-diene-1,4-dione
[ No CAS ]
Yield Reaction Conditions Operation in experiment
Multi-step reaction with 3 steps
1.1: potassium carbonate / acetone / 24 h / Reflux
2.1: potassium hydroxide / tetrahydrofuran; water / 24 h / 25 °C / Inert atmosphere
3.1: (R)-3,3'-bis(2,4,6-triisopropylphenyl)binol phosphoric acid / 1,2-dichloro-ethane / 72 h / -32 °C / Inert atmosphere
3.2: 0.5 h / -32 °C / Inert atmosphere
Reference:
[1]Chen, Ye-Hui; Li, Heng-Hui; Li, Shaoyu; Tan, Bin; Xiang, Shao-Hua; Zhang, Xiao
[Angewandte Chemie - International Edition, 2020, vol. 59, # 28, p. 11374 - 11378][Angew. Chem.]
23
[ 146744-23-2 ]
(R)-2-chloro-3-(2-hydroxy-7-propoxynaphthalen-1-yl)cyclohexa-2,5-diene-1,4-dione
[ No CAS ]
Yield Reaction Conditions Operation in experiment
Multi-step reaction with 3 steps
1.1: potassium carbonate / acetone / 24 h / Reflux
2.1: potassium hydroxide / tetrahydrofuran; water / 24 h / 25 °C / Inert atmosphere
3.1: (R)-3,3'-bis(2,4,6-triisopropylphenyl)binol phosphoric acid / 1,2-dichloro-ethane / 72 h / -32 °C / Inert atmosphere
3.2: 0.5 h / -32 °C / Inert atmosphere
Reference:
[1]Chen, Ye-Hui; Li, Heng-Hui; Li, Shaoyu; Tan, Bin; Xiang, Shao-Hua; Zhang, Xiao
[Angewandte Chemie - International Edition, 2020, vol. 59, # 28, p. 11374 - 11378][Angew. Chem.]
24
[ 146744-23-2 ]
(R)-2-(7-butoxy-2-hydroxynaphthalen-1-yl)-3-chlorocyclohexa-2,5-diene-1,4-dione
[ No CAS ]
Yield Reaction Conditions Operation in experiment
Multi-step reaction with 3 steps
1.1: potassium carbonate / acetone / 24 h / Reflux
2.1: potassium hydroxide / tetrahydrofuran; water / 24 h / 25 °C / Inert atmosphere
3.1: (R)-3,3'-bis(2,4,6-triisopropylphenyl)binol phosphoric acid / 1,2-dichloro-ethane / 72 h / -32 °C / Inert atmosphere
3.2: 0.5 h / -32 °C / Inert atmosphere
Reference:
[1]Chen, Ye-Hui; Li, Heng-Hui; Li, Shaoyu; Tan, Bin; Xiang, Shao-Hua; Zhang, Xiao
[Angewandte Chemie - International Edition, 2020, vol. 59, # 28, p. 11374 - 11378][Angew. Chem.]
25
[ 146744-23-2 ]
(R)-2-(7-(benzyloxy)-2-hydroxynaphthalen-1-yl)-3-chlorocyclohexa-2,5-diene-1,4-dione
[ No CAS ]
Yield Reaction Conditions Operation in experiment
Multi-step reaction with 3 steps
1.1: potassium carbonate / acetone / 24 h / Reflux
2.1: potassium hydroxide / tetrahydrofuran; water / 24 h / 25 °C / Inert atmosphere
3.1: (R)-3,3'-bis(2,4,6-triisopropylphenyl)binol phosphoric acid / 1,2-dichloro-ethane / 72 h / -32 °C / Inert atmosphere
3.2: 0.5 h / -32 °C / Inert atmosphere
Reference:
[1]Chen, Ye-Hui; Li, Heng-Hui; Li, Shaoyu; Tan, Bin; Xiang, Shao-Hua; Zhang, Xiao
[Angewandte Chemie - International Edition, 2020, vol. 59, # 28, p. 11374 - 11378][Angew. Chem.]
26
[ 146744-23-2 ]
[ 57944-44-2 ]
Yield Reaction Conditions Operation in experiment
Multi-step reaction with 2 steps
1: potassium carbonate / acetone / 24 h / Reflux
2: potassium hydroxide / tetrahydrofuran; water / 24 h / 25 °C / Inert atmosphere
Reference:
[1]Chen, Ye-Hui; Li, Heng-Hui; Li, Shaoyu; Tan, Bin; Xiang, Shao-Hua; Zhang, Xiao
[Angewandte Chemie - International Edition, 2020, vol. 59, # 28, p. 11374 - 11378][Angew. Chem.]
27
[ 146744-23-2 ]
7-propoxy-2-naphthol
[ No CAS ]
Yield Reaction Conditions Operation in experiment
Multi-step reaction with 2 steps
1: potassium carbonate / acetone / 24 h / Reflux
2: potassium hydroxide / tetrahydrofuran; water / 24 h / 25 °C / Inert atmosphere
Reference:
[1]Chen, Ye-Hui; Li, Heng-Hui; Li, Shaoyu; Tan, Bin; Xiang, Shao-Hua; Zhang, Xiao
[Angewandte Chemie - International Edition, 2020, vol. 59, # 28, p. 11374 - 11378][Angew. Chem.]
28
[ 146744-23-2 ]
[ 79044-34-1 ]
Yield Reaction Conditions Operation in experiment
Multi-step reaction with 2 steps
1: potassium carbonate / acetone / 24 h / Reflux
2: potassium hydroxide / tetrahydrofuran; water / 24 h / 25 °C / Inert atmosphere
Reference:
[1]Chen, Ye-Hui; Li, Heng-Hui; Li, Shaoyu; Tan, Bin; Xiang, Shao-Hua; Zhang, Xiao
[Angewandte Chemie - International Edition, 2020, vol. 59, # 28, p. 11374 - 11378][Angew. Chem.]
29
[ 146744-23-2 ]
[ 118495-07-1 ]
Yield Reaction Conditions Operation in experiment
Multi-step reaction with 2 steps
1: potassium carbonate / acetone / 24 h / Reflux
2: potassium hydroxide / tetrahydrofuran; water / 24 h / 25 °C / Inert atmosphere
Reference:
[1]Chen, Ye-Hui; Li, Heng-Hui; Li, Shaoyu; Tan, Bin; Xiang, Shao-Hua; Zhang, Xiao
[Angewandte Chemie - International Edition, 2020, vol. 59, # 28, p. 11374 - 11378][Angew. Chem.]