Alternatived Products of [ 30290-78-9 ]
Product Details of [ 30290-78-9 ]
CAS No. : 30290-78-9
MDL No. : MFCD20331711
Formula :
C15 H15 N
Boiling Point :
-
Linear Structure Formula : -
InChI Key : YUEVNAMKBJHWDG-UHFFFAOYSA-N
M.W :
209.29
Pubchem ID : 12209396
Synonyms :
Calculated chemistry of [ 30290-78-9 ]
Physicochemical Properties
Num. heavy atoms :
16
Num. arom. heavy atoms :
12
Fraction Csp3 :
0.2
Num. rotatable bonds :
1
Num. H-bond acceptors :
0.0
Num. H-bond donors :
1.0
Molar Refractivity :
70.83
TPSA :
12.03 Ų
Pharmacokinetics
GI absorption :
High
BBB permeant :
Yes
P-gp substrate :
Yes
CYP1A2 inhibitor :
Yes
CYP2C19 inhibitor :
No
CYP2C9 inhibitor :
No
CYP2D6 inhibitor :
Yes
CYP3A4 inhibitor :
No
Log Kp (skin permeation) :
-4.91 cm/s
Lipophilicity
Log Po/w (iLOGP) :
2.44
Log Po/w (XLOGP3) :
3.75
Log Po/w (WLOGP) :
3.06
Log Po/w (MLOGP) :
3.47
Log Po/w (SILICOS-IT) :
3.61
Consensus Log Po/w :
3.27
Druglikeness
Lipinski :
0.0
Ghose :
None
Veber :
0.0
Egan :
0.0
Muegge :
1.0
Bioavailability Score :
0.55
Water Solubility
Log S (ESOL) :
-3.99
Solubility :
0.0215 mg/ml ; 0.000103 mol/l
Class :
Soluble
Log S (Ali) :
-3.7
Solubility :
0.0422 mg/ml ; 0.000202 mol/l
Class :
Soluble
Log S (SILICOS-IT) :
-5.57
Solubility :
0.000562 mg/ml ; 0.00000269 mol/l
Class :
Moderately soluble
Medicinal Chemistry
PAINS :
0.0 alert
Brenk :
0.0 alert
Leadlikeness :
2.0
Synthetic accessibility :
2.37
Application In Synthesis of [ 30290-78-9 ]
* 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 [ 30290-78-9 ]
1
[ 605-03-8 ]
[ 64-17-5 ]
[ 30290-78-9 ]
2
[ 605-03-8 ]
[ 30290-78-9 ]
Reference:
[1]Chemische Berichte,1895,vol. 28,p. 1042
[2]Pharmaceutical Chemistry Journal,1980,vol. 14,p. 532 - 538
Khimiko-Farmatsevticheskii Zhurnal,1980,vol. 14,p. 38 - 43
[3]Patent: DE79385,
Fortschr. Teerfarbenfabr. Verw. Industriezweige,vol. 4,p. 1142
3
[ 30290-78-9 ]
[ 108-24-7 ]
1-acetyl-4-phenyl-1,2,3,4-tetrahydro-quinoline
[ No CAS ]
4
[ 30290-78-9 ]
[ 74-88-4 ]
[ 27623-83-2 ]
5
[ 30290-78-9 ]
1-nitroso-4-phenyl-1,2,3,4-tetrahydro-quinoline
[ No CAS ]
Yield Reaction Conditions Operation in experiment
With sodium nitrite in saurer Loesung;
With sodium nitrite in saurer Loesung;
6
[ 30290-78-9 ]
[ 111663-92-4 ]
Yield Reaction Conditions Operation in experiment
Benzoylieren, nach Schotten-Baumann;
7
[ 4888-33-9 ]
[ 30290-78-9 ]
Yield Reaction Conditions Operation in experiment
With ethanol; sodium
With diisobutylaluminium hydride In toluene for 5h; Reflux;
Reference:
[1]Perold; v.Reiche
[Journal of the American Chemical Society, 1957, vol. 79, p. 465]
[2]Chisholm, David R.; Zhou, Garr-Layy; Pohl, Ehmke; Valentine, Roy; Whiting, Andrew
[Beilstein Journal of Organic Chemistry, 2016, vol. 12, p. 1851 - 1862]
8
[ 30290-78-9 ]
[ 79-04-9 ]
[ 76061-90-0 ]
Yield Reaction Conditions Operation in experiment
84.3%
for 0.666667h; Heating;
Reference:
[1]Shvedov, V. I.; Vasil'eva, V. F.; Korsakova, I. Ya.; Galitsina, V. A.; Medvedev, B. A.; et al.
[Pharmaceutical Chemistry Journal, 1980, vol. 14, # 8, p. 532 - 538][Khimiko-Farmatsevticheskii Zhurnal, 1980, vol. 14, # 8, p. 38 - 43]
9
[ 100-42-5 ]
[ 622-79-7 ]
[ 30290-78-9 ]
Yield Reaction Conditions Operation in experiment
With trifluorormethanesulfonic acid 1.) C6 H6 , from 0 deg C to RT, 10 min, 2.) benzene, RT, 1 h; Yield given. Multistep reaction;
11
1-acetyl-4-phenyl-1,2,3,4-tetrahydro-quinoline
[ No CAS ]
[ 30290-78-9 ]
12
[ 7647-01-0 ]
[ 605-03-8 ]
[ 64-17-5 ]
[ 7732-18-5 ]
[ 30290-78-9 ]
13
[ 87374-48-9 ]
[ 30290-78-9 ]
Yield Reaction Conditions Operation in experiment
7 % Chromat.
In acetonitrile at 20℃; for 0.5h; Photolysis;
14
[ 30290-78-9 ]
[ 76061-98-8 ]
Yield Reaction Conditions Operation in experiment
Multi-step reaction with 2 steps
1: 84.3 percent / 0.67 h / Heating
2: 62 percent / ethanol / 2 h
Reference:
[1]Shvedov, V. I.; Vasil'eva, V. F.; Korsakova, I. Ya.; Galitsina, V. A.; Medvedev, B. A.; et al.
[Pharmaceutical Chemistry Journal, 1980, vol. 14, # 8, p. 532 - 538][Khimiko-Farmatsevticheskii Zhurnal, 1980, vol. 14, # 8, p. 38 - 43]
15
[ 30290-78-9 ]
[ 76061-83-1 ]
Yield Reaction Conditions Operation in experiment
Multi-step reaction with 3 steps
1: 84.3 percent / 0.67 h / Heating
2: urotropine, NaI / ethanol / 24 h / Ambient temperature
3: 84 percent / ethanol / 0.67 h / Heating
Reference:
[1]Shvedov, V. I.; Vasil'eva, V. F.; Korsakova, I. Ya.; Galitsina, V. A.; Medvedev, B. A.; et al.
[Pharmaceutical Chemistry Journal, 1980, vol. 14, # 8, p. 532 - 538][Khimiko-Farmatsevticheskii Zhurnal, 1980, vol. 14, # 8, p. 38 - 43]
16
[ 30290-78-9 ]
[ 695143-00-1 ]
Yield Reaction Conditions Operation in experiment
Multi-step reaction with 2 steps
1: 84.3 percent / 0.67 h / Heating
2: urotropine, NaI / ethanol / 24 h / Ambient temperature
Reference:
[1]Shvedov, V. I.; Vasil'eva, V. F.; Korsakova, I. Ya.; Galitsina, V. A.; Medvedev, B. A.; et al.
[Pharmaceutical Chemistry Journal, 1980, vol. 14, # 8, p. 532 - 538][Khimiko-Farmatsevticheskii Zhurnal, 1980, vol. 14, # 8, p. 38 - 43]
17
[ 2983-48-4 ]
[ 30290-78-9 ]
Yield Reaction Conditions Operation in experiment
Multi-step reaction with 2 steps
1: conc. aq. HCl / butan-1-ol / 9 h
2: Na, n-butanol / Heating
Reference:
[1]Shvedov, V. I.; Vasil'eva, V. F.; Korsakova, I. Ya.; Galitsina, V. A.; Medvedev, B. A.; et al.
[Pharmaceutical Chemistry Journal, 1980, vol. 14, # 8, p. 532 - 538][Khimiko-Farmatsevticheskii Zhurnal, 1980, vol. 14, # 8, p. 38 - 43]
18
[ 30290-78-9 ]
4-phenyl-3,4-dihydro-2<i>H</i>-quinolin-6-one oxime
[ No CAS ]
Yield Reaction Conditions Operation in experiment
Multi-step reaction with 2 steps
1: sodium nitrite / in saurer Loesung
2: glacial acetic acid; alcoholic hydrochloric acid / 30 °C
Multi-step reaction with 2 steps
1: sodium nitrite / in saurer Loesung
2: hydrogenchloride; acetic acid / 30 °C
19
[ 3056-73-3 ]
[ 30290-78-9 ]
Yield Reaction Conditions Operation in experiment
Multi-step reaction with 2 steps
1: concentrated aqueous hydriodic acid
2: ethanol; sodium
Multi-step reaction with 2 steps
1: Polyphosphoric acid / 0.17 h / 120 °C
2: diisobutylaluminium hydride / toluene / 5 h / Reflux
Reference:
[1]Perold; v.Reiche
[Journal of the American Chemical Society, 1957, vol. 79, p. 465]
[2]Chisholm, David R.; Zhou, Garr-Layy; Pohl, Ehmke; Valentine, Roy; Whiting, Andrew
[Beilstein Journal of Organic Chemistry, 2016, vol. 12, p. 1851 - 1862]
20
[ 14371-10-9 ]
[ 30290-78-9 ]
Yield Reaction Conditions Operation in experiment
Multi-step reaction with 2 steps
1: sodium tris(acetoxy)borohydride; acetic acid / 1,2-dichloro-ethane / 20 °C
2: polyphosphoric acid / 100 °C / Inert atmosphere
Multi-step reaction with 2 steps
1: acetic acid; sodium tris(acetoxy)borohydride / 1,2-dichloro-ethane / 15 h / Inert atmosphere
2: polyphosphoric acid / 6 h / 100 °C
Reference:
[1]Rao Lingam, V.S. Prasada; Thomas, Abraham; Mukkanti, Khagga; Gopalan, Balasubramanian
[Synthetic Communications, 2011, vol. 41, # 12, p. 1809 - 1828]
[2]Jung, Dahyeon; Kim, Min Hye; Kim, Jinho
[Organic Letters, 2016, vol. 18, # 24, p. 6300 - 6303]
21
[ 92573-86-9 ]
[ 30290-78-9 ]
Yield Reaction Conditions Operation in experiment
71%
With polyphosphoric acid at 100℃; Inert atmosphere;
With polyphosphoric acid at 100℃; for 6h;
Reference:
[1]Location in patent: experimental part
Rao Lingam, V.S. Prasada; Thomas, Abraham; Mukkanti, Khagga; Gopalan, Balasubramanian
[Synthetic Communications, 2011, vol. 41, # 12, p. 1809 - 1828]
[2]Jung, Dahyeon; Kim, Min Hye; Kim, Jinho
[Organic Letters, 2016, vol. 18, # 24, p. 6300 - 6303]
22
[ 62-53-3 ]
[ 30290-78-9 ]
Yield Reaction Conditions Operation in experiment
Multi-step reaction with 2 steps
1: sodium tris(acetoxy)borohydride; acetic acid / 1,2-dichloro-ethane / 20 °C
2: polyphosphoric acid / 100 °C / Inert atmosphere
Multi-step reaction with 3 steps
1.1: dichloromethane / 0.5 h
1.2: 4 h / 20 °C
2.1: Polyphosphoric acid / 0.17 h / 120 °C
3.1: diisobutylaluminium hydride / toluene / 5 h / Reflux
Multi-step reaction with 2 steps
1: acetic acid; sodium tris(acetoxy)borohydride / 1,2-dichloro-ethane / 15 h / Inert atmosphere
2: polyphosphoric acid / 6 h / 100 °C
Reference:
[1]Rao Lingam, V.S. Prasada; Thomas, Abraham; Mukkanti, Khagga; Gopalan, Balasubramanian
[Synthetic Communications, 2011, vol. 41, # 12, p. 1809 - 1828]
[2]Chisholm, David R.; Zhou, Garr-Layy; Pohl, Ehmke; Valentine, Roy; Whiting, Andrew
[Beilstein Journal of Organic Chemistry, 2016, vol. 12, p. 1851 - 1862]
[3]Jung, Dahyeon; Kim, Min Hye; Kim, Jinho
[Organic Letters, 2016, vol. 18, # 24, p. 6300 - 6303]
23
[ 30290-78-9 ]
[ 605-03-8 ]
Yield Reaction Conditions Operation in experiment
92%
With diethylazodicarboxylate; In chloroform; toluene; at 20℃; for 12h;
General procedure: To a 10 mL round bottom flask equipped with a magnetic stir bar, 1,2,3,4-tetrahydroquinoline (0.5 mmol), DEAD solution 40 wt% in toluene (2.2 eq, 1.1 mmol, 0.5 mL), and CHCl3 (1.0 mL) was added. The reaction mixture was stirred at room temperature for 12 h. The mixture was concentrated on rotary evaporator. The residue was purified by column chromatography with EtOAc:hexane (1:5) to give quinolines. In case of 2f and 2m, the product spot was close to the spot of the remained DEAD. To eliminate the remained DEAD, 1 equivalent of PPh3 was added after the reaction and the reaction mixture was stirred.[19] After 10 min, the reaction mixture was concentrated on rotary evaporator. The residue was purified by column chromatography with CHCl3:hexane (1:1) to give quinolines.
70%
With 4-tert-Butylcatechol; oxygen; In water; at 20℃; for 20h;Green chemistry;
General procedure: N-heterocycle substrate (0.2 mmol), Na-AMO (20 mg, 10 mol%), catechol Q-2 (3.3 mg, 0.02 mmol) was added into a reaction tube. The reaction tube was filled and protected with oxygen using a O2 balloon, then H2O was added into the reaction tube with a syringe. The reaction was allowed to react at room temperature for 20 h. After completion of reaction, the resulting mixture was filtered, washed with EtOAc and extracted by EtOAc. The organic phases were combined, washed with brine and dried with Na2SO4. Next, organic solution was concentrated under reduced vacuum to give the crude product. Finally, the product was purified by silica gel chromatography to yield the pure product.
Reference:
[1]Organic Letters,2016,vol. 18,p. 6300 - 6303
[2]Journal of the American Chemical Society,2014,vol. 136,p. 11910 - 11913
[3]Synthetic Communications,2018,vol. 48,p. 1291 - 1298
[4]Tetrahedron Letters,2020,vol. 61
[5]Organic Letters,2018,vol. 20,p. 6436 - 6439
[6]Catalysis science and technology,2020,vol. 10,p. 360 - 371
24
[ 100-42-5 ]
[ 50-00-0 ]
[ 30290-78-9 ]
copper(II) tetrafluroborate hexahydrate
[ No CAS ]
C48 H38 N2 (2+) *2BF4 (1-)
[ No CAS ]
Yield Reaction Conditions Operation in experiment
87%
In nitromethane at 100℃; for 24h; Sealed tube; Inert atmosphere; Schlenk technique;
Reference:
[1]Chen, Wei-Chen; Gandeepan, Parthasarathy; Tsai, Chia-Hung; Luo, Ching-Zong; Rajamalli, Pachaiyappan; Cheng, Chien-Hong
[RSC Advances, 2016, vol. 6, # 68, p. 63390 - 63397]
25
[ 30290-78-9 ]
[ 605-03-8 ]
C30 H20 N2
[ No CAS ]
26
[ 102-92-1 ]
[ 30290-78-9 ]
Yield Reaction Conditions Operation in experiment
Multi-step reaction with 3 steps
1.1: dichloromethane / 0.5 h
1.2: 4 h / 20 °C
2.1: Polyphosphoric acid / 0.17 h / 120 °C
3.1: diisobutylaluminium hydride / toluene / 5 h / Reflux
27
[ 30290-78-9 ]
4-phenyl-[6]quinolylamine
[ No CAS ]
Yield Reaction Conditions Operation in experiment
Multi-step reaction with 3 steps
1: sodium nitrite / in saurer Loesung
2: hydrogenchloride; acetic acid / 30 °C
28
[ 30290-78-9 ]
[ 586-96-9 ]
2-((1H-indol-3-yl)(phenyl)methyl)aniline
[ No CAS ]
Yield Reaction Conditions Operation in experiment
57%
With 4-nitro-benzoic acid In toluene for 18h; Inert atmosphere;
29
[ 30290-78-9 ]
[ 932-98-9 ]
2-((5-chloro-1H-indol-3-yl)(phenyl)methyl)aniline
[ No CAS ]
Yield Reaction Conditions Operation in experiment
51%
With 4-nitro-benzoic acid In toluene for 18h; Inert atmosphere;
30
[ 30290-78-9 ]
[ 3623-23-2 ]
2-((5-bromo-1H-indol-3-yl)(phenyl)methyl)aniline
[ No CAS ]
Yield Reaction Conditions Operation in experiment
50%
With 4-nitro-benzoic acid In toluene for 18h; Inert atmosphere;
31
[ 30290-78-9 ]
[ 555-16-8 ]
[ 126-81-8 ]
10,10-dimethyl-7-(4-nitrophenyl)-3-phenyl-2,3,7,9,10,11-hexahydro-1H,8H-pyrido[3,2,1-de]acridin-8-one
[ No CAS ]
Yield Reaction Conditions Operation in experiment
60%
With 2,4 dichlorobenzoic acid In toluene at 130℃; for 2h; Microwave irradiation; diastereoselective reaction;
32
[ 50-00-0 ]
[ 30290-78-9 ]
propargyl ether mycophenolate
[ No CAS ]
mycophenoyl methyl ester-7-(butynyloxy-(4-phenyltetrahydroquinoline))
[ No CAS ]
Yield Reaction Conditions Operation in experiment
72%
With copper(l) iodide In 1,4-dioxane at 120℃; for 1h;
1.4 General procedure for synthesis of new propargylamine mycophenolate derivatives (6a-6aa).
General procedure: To the solution of propargylether mycophenolate 3 (100 mg, 0.2685 mmol) in dioxane (1.5mL) was added CuI (0.5 equiv.), HCHO (5.0 equiv) and amine (1.1 equiv). The resultingsolution was stirred at 120 oC for 1 hour. After TLC indicated that the reaction was complete.The reaction mixture was then filtered through a celite and eluted with EtOAc (30.0 mL). Thefiltrate was concentrated in vacuo, the crude residue was then purified by flash columnchromatography.
33
[ 121194-51-2 ]
[ 605-03-8 ]
[ 30290-78-9 ]
4‐phenyl‐1,2‐dihydroquinoline
[ No CAS ]
Yield Reaction Conditions Operation in experiment
1: 25%
2: 56%
3: 7%
With Echavarren's catalyst In dichloromethane at 80℃; for 0.5h; Sealed tube; Inert atmosphere;
Reference:
[1]Arcadi, Antonio; Calcaterra, Andrea; Fabrizi, Giancarlo; Fochetti, Andrea; Goggiamani, Antonella; Iazzetti, Antonia; Marrone, Federico; Marsicano, Vincenzo; Mazzoccanti, Giulia; Serraiocco, Andrea
[Molecules, 2021, vol. 26, # 11]