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Chemical Structure| 123387-53-1 Chemical Structure| 123387-53-1

Structure of 123387-53-1

Chemical Structure| 123387-53-1

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Product Details of [ 123387-53-1 ]

CAS No. :123387-53-1
Formula : C14H19NO2
M.W : 233.31
SMILES Code : O=C(N1CCCC2=C1C=CC=C2)OC(C)(C)C
English Name :tert-Butyl 3,4-dihydroquinoline-1(2H)-carboxylate
MDL No. :MFCD19684135
InChI Key :GVSRWAIRQCMAHG-UHFFFAOYSA-N
Pubchem ID :10633398

Safety of [ 123387-53-1 ]

Computational Chemistry of [ 123387-53-1 ] Show Less

Physicochemical Properties

Num. heavy atoms 17
Num. arom. heavy atoms 6
Fraction Csp3 0.5
Num. rotatable bonds 3
Num. H-bond acceptors 2.0
Num. H-bond donors 0.0
Molar Refractivity 72.18
TPSA ?

Topological Polar Surface Area: Calculated from
Ertl P. et al. 2000 J. Med. Chem.

29.54 Ų

Lipophilicity

Log Po/w (iLOGP)?

iLOGP: in-house physics-based method implemented from
Daina A et al. 2014 J. Chem. Inf. Model.

3.11
Log Po/w (XLOGP3)?

XLOGP3: Atomistic and knowledge-based method calculated by
XLOGP program, version 3.2.2, courtesy of CCBG, Shanghai Institute of Organic Chemistry

3.06
Log Po/w (WLOGP)?

WLOGP: Atomistic method implemented from
Wildman SA and Crippen GM. 1999 J. Chem. Inf. Model.

2.99
Log Po/w (MLOGP)?

MLOGP: Topological method implemented from
Moriguchi I. et al. 1992 Chem. Pharm. Bull.
Moriguchi I. et al. 1994 Chem. Pharm. Bull.
Lipinski PA. et al. 2001 Adv. Drug. Deliv. Rev.

2.8
Log Po/w (SILICOS-IT)?

SILICOS-IT: Hybrid fragmental/topological method calculated by
FILTER-IT program, version 1.0.2, courtesy of SILICOS-IT, http://www.silicos-it.com

2.43
Consensus Log Po/w?

Consensus Log Po/w: Average of all five predictions

2.88

Water Solubility

Log S (ESOL):?

ESOL: Topological method implemented from
Delaney JS. 2004 J. Chem. Inf. Model.

-3.28
Solubility 0.123 mg/ml ; 0.000528 mol/l
Class?

Solubility class: Log S scale
Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly

Soluble
Log S (Ali)?

Ali: Topological method implemented from
Ali J. et al. 2012 J. Chem. Inf. Model.

-3.35
Solubility 0.105 mg/ml ; 0.00045 mol/l
Class?

Solubility class: Log S scale
Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly

Soluble
Log S (SILICOS-IT)?

SILICOS-IT: Fragmental method calculated by
FILTER-IT program, version 1.0.2, courtesy of SILICOS-IT, http://www.silicos-it.com

-3.47
Solubility 0.0791 mg/ml ; 0.000339 mol/l
Class?

Solubility class: Log S scale
Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly

Soluble

Pharmacokinetics

GI absorption?

Gatrointestinal absorption: according to the white of the BOILED-Egg

High
BBB permeant?

BBB permeation: according to the yolk of the BOILED-Egg

Yes
P-gp substrate?

P-glycoprotein substrate: SVM model built on 1033 molecules (training set)
and tested on 415 molecules (test set)
10-fold CV: ACC=0.72 / AUC=0.77
External: ACC=0.88 / AUC=0.94

No
CYP1A2 inhibitor?

Cytochrome P450 1A2 inhibitor: SVM model built on 9145 molecules (training set)
and tested on 3000 molecules (test set)
10-fold CV: ACC=0.83 / AUC=0.90
External: ACC=0.84 / AUC=0.91

Yes
CYP2C19 inhibitor?

Cytochrome P450 2C19 inhibitor: SVM model built on 9272 molecules (training set)
and tested on 3000 molecules (test set)
10-fold CV: ACC=0.80 / AUC=0.86
External: ACC=0.80 / AUC=0.87

Yes
CYP2C9 inhibitor?

Cytochrome P450 2C9 inhibitor: SVM model built on 5940 molecules (training set)
and tested on 2075 molecules (test set)
10-fold CV: ACC=0.78 / AUC=0.85
External: ACC=0.71 / AUC=0.81

No
CYP2D6 inhibitor?

Cytochrome P450 2D6 inhibitor: SVM model built on 3664 molecules (training set)
and tested on 1068 molecules (test set)
10-fold CV: ACC=0.79 / AUC=0.85
External: ACC=0.81 / AUC=0.87

No
CYP3A4 inhibitor?

Cytochrome P450 3A4 inhibitor: SVM model built on 7518 molecules (training set)
and tested on 2579 molecules (test set)
10-fold CV: ACC=0.77 / AUC=0.85
External: ACC=0.78 / AUC=0.86

No
Log Kp (skin permeation)?

Skin permeation: QSPR model implemented from
Potts RO and Guy RH. 1992 Pharm. Res.

-5.55 cm/s

Druglikeness

Lipinski?

Lipinski (Pfizer) filter: implemented from
Lipinski CA. et al. 2001 Adv. Drug Deliv. Rev.
MW ≤ 500
MLOGP ≤ 4.15
N or O ≤ 10
NH or OH ≤ 5

0.0
Ghose?

Ghose filter: implemented from
Ghose AK. et al. 1999 J. Comb. Chem.
160 ≤ MW ≤ 480
-0.4 ≤ WLOGP ≤ 5.6
40 ≤ MR ≤ 130
20 ≤ atoms ≤ 70

None
Veber?

Veber (GSK) filter: implemented from
Veber DF. et al. 2002 J. Med. Chem.
Rotatable bonds ≤ 10
TPSA ≤ 140

0.0
Egan?

Egan (Pharmacia) filter: implemented from
Egan WJ. et al. 2000 J. Med. Chem.
WLOGP ≤ 5.88
TPSA ≤ 131.6

0.0
Muegge?

Muegge (Bayer) filter: implemented from
Muegge I. et al. 2001 J. Med. Chem.
200 ≤ MW ≤ 600
-2 ≤ XLOGP ≤ 5
TPSA ≤ 150
Num. rings ≤ 7
Num. carbon > 4
Num. heteroatoms > 1
Num. rotatable bonds ≤ 15
H-bond acc. ≤ 10
H-bond don. ≤ 5

0.0
Bioavailability Score?

Abbott Bioavailability Score: Probability of F > 10% in rat
implemented from
Martin YC. 2005 J. Med. Chem.

0.55

Medicinal Chemistry

PAINS?

Pan Assay Interference Structures: implemented from
Baell JB. & Holloway GA. 2010 J. Med. Chem.

0.0 alert
Brenk?

Structural Alert: implemented from
Brenk R. et al. 2008 ChemMedChem

0.0 alert: heavy_metal
Leadlikeness?

Leadlikeness: implemented from
Teague SJ. 1999 Angew. Chem. Int. Ed.
250 ≤ MW ≤ 350
XLOGP ≤ 3.5
Num. rotatable bonds ≤ 7

No; 1 violation:MW<1.0
Synthetic accessibility?

Synthetic accessibility score: from 1 (very easy) to 10 (very difficult)
based on 1024 fragmental contributions (FP2) modulated by size and complexity penaties,
trained on 12'782'590 molecules and tested on 40 external molecules (r2 = 0.94)

2.36

Application In Synthesis of [ 123387-53-1 ]

* 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 [ 123387-53-1 ]

[ 123387-53-1 ] Synthesis Path-Downstream   1~14

  • 1
  • [ 212560-94-6 ]
  • [ 123387-53-1 ]
YieldReaction ConditionsOperation in experiment
at 165℃;
Multi-step reaction with 2 steps 1: 28 percent / benzene / 18 h / 165 °C 2: 96 percent / toluene / 24 h / 165 °C
  • 2
  • [ 212560-94-6 ]
  • [ 123387-53-1 ]
  • [ 226710-76-5 ]
YieldReaction ConditionsOperation in experiment
1: 33% 2: 28% In benzene at 165℃; for 18h;
  • 3
  • [ 226710-76-5 ]
  • [ 123387-53-1 ]
YieldReaction ConditionsOperation in experiment
96% In toluene at 165℃; for 24h;
  • 4
  • [ 123387-53-1 ]
  • [ 179898-00-1 ]
YieldReaction ConditionsOperation in experiment
82% With tert.-butylhydroperoxide; sodium hydrogencarbonate In decane; 1,2-dichloro-ethane at 40℃; for 16h;
75% With tert.-butylhydroperoxide; Rh2(cap)4; sodium hydrogencarbonate In 1,2-dichloro-ethane at 40℃; for 16h; tert-butyl 4-oxo-3,4-dihydroquixnoline-1(2H)-carboxylate To a 50 mL round bottom flask charged with tert-butyl3,4-dihydroquinoline-1(2II)- carboxylate (I 9,4.28 mmol), dirhodium tetracaprolactamate (140 mg, 0.21 mmol) and sodium bicarbonate (179 mg2.l4 mmol) was added anhydrous DCE (16 mL). tert-butyl hydrogen peroxide (4.28 mL,21.4 mmol) was added and the reaction placed on a pre-heated hot plate (40 'C), fitted with a septum and an empty balloon and mixed for 12 h. The following day more catalyst and tert-butyl hydrogen peroxide were added (0.005 and 5 equiv, respectively) and the reaction was allowed to mix for an additional 4 h. The reaction was cooled to ambient temperature then filtered through a short plug of silica gel eluting with DCM (125 mL). The solution was concentrated and then purified by silica gel chromatography to afford tert-butyl4- oxo-3,4-dihydroquinoline-l(2ll)-carboxylate (785 mg, 75o/o) as a colorless oil. LCMS m/2248 [M+H]+.
73% With tert.-butylhydroperoxide; C56H53ClN3P2Ru(1+)*F6P(1-) In benzene at 25℃; for 18h; Inert atmosphere; Schlenk technique;
49% With potassium permanganate; magnesium sulfate In water; acetone for 48h;
48% With glucose dehydrogenase; D-glucose; cytochrome P450 enzyme CYP102A1 R47L/Y51F/I263A/E267V/I401P mutant; C21H25N7O17P3(3-)*2H(1+)*Na(1+) In aq. phosphate buffer; ethanol at 20℃; for 36h; Enzymatic reaction;
With potassium permanganate In acetone at 25℃; for 36h;
71 % With Ethyl 2-mercaptopropionate; 4CzIPN; water In acetonitrile at 20℃; Irradiation; Schlenk technique; Inert atmosphere; Sealed tube;

  • 5
  • [ 229496-36-0 ]
  • [ 123387-53-1 ]
YieldReaction ConditionsOperation in experiment
81% With caesium carbonate; 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl In toluene at 100℃; for 24h;
  • 6
  • [ 56267-47-1 ]
  • [ 123387-53-1 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: 81 percent / tetrabutylammonium bromide; aq. NaOH / CH2Cl2 / 18 h / Heating 2: 33 percent / benzene / 18 h / 165 °C
Multi-step reaction with 3 steps 1: 81 percent / tetrabutylammonium bromide; aq. NaOH / CH2Cl2 / 18 h / Heating 2: 28 percent / benzene / 18 h / 165 °C 3: 96 percent / toluene / 24 h / 165 °C
  • 7
  • [ 4248-19-5 ]
  • [ 181717-14-6 ]
  • [ 123387-53-1 ]
YieldReaction ConditionsOperation in experiment
78% With copper(l) iodide; caesium carbonate; N,N`-dimethylethylenediamine In tetrahydrofuran at 80℃; for 16h; Inert atmosphere;
  • 8
  • [ 38857-88-4 ]
  • [ 123387-53-1 ]
  • [ 1588564-16-2 ]
YieldReaction ConditionsOperation in experiment
59% In benzene for 12h; Reflux;
In benzene for 12h; Reflux; Bis(2,2,2-trichloroethyl) 1-{1-(t-butoxycarbonyl)-1,2,3,4-tetrahydroquinolin-2(1H)-yl}hydrazine-1,2-dicarboxylate (41l) 40l (0.233 g, 1.0 mmol) was dissolved in benzene (3.3 mL), 23e (0.457 g, 1.2 mmol) was added, and stirred at reflux for 12 h. After cooled to room temperature, the solvent was removed under reduced pressure. Purification by column chromatography (n-hexane : EtOAc = 10 : 1 v /v) gave 41l (0.358 g, 58%) as colorless crystals. 1HNMR (400 MHz, CDCl3) δ 1.12~1.40 (m, 2H), 1.80~2.10 (br, 1H), 2.20 (s, 3H), 2.40~2.80 (m, 2H),4.30~5.00 (m, 4H), 6.30~6.65 (br, 1H), 6.95~7.30 (br, 5H). 13CNMR (100 MHz, CDCl3) δ 23.00, 25.60,29.61, 67.50~69.00 (br), 74.84, 75.57, 125.34, 126.20, 126.90, 127.07, 133.00~137.30 (br),137.50~139.00 (br), 151.00~153.00 (br), 171.81. IR (KBr) 3290, 2979, 1775, 1734, 752, 717 cm-1.FABMS (NBA) m/z: 613.8 (C20H2435Cl537ClN3O6: [M+H]+), 611.8 (C20H2435Cl6N3O6: [M+H]+), 557.8,513.8, 232.1, 176.0, 132.0 (100%). HR-MS calcd. for C20H2435Cl6N3O6 ([M+H]+) 611.9796, found.611.9784.
  • 9
  • [ 123387-53-1 ]
  • [ 1680191-85-8 ]
YieldReaction ConditionsOperation in experiment
73% Stage #1: tert-butyl 1,2,3,4-tetrahydroquinoline-1-carboxylate With N,N,N,N,-tetramethylethylenediamine; sec.-butyllithium In diethyl ether at -78℃; for 3h; Stage #2: With 1,2-Diiodoethane In diethyl ether at -78 - 20℃; for 19h; tert-Butyl 8-iodo-3,4-dihydroquinoline-l(2H)-carboxylate A similar procedure to that described in Peter Beak, Won-Koo Lee Tetrahedron Letters 1989, 30, 1197-1200 was used: sec- Butyllithium (0.51 mL, 0.71 mmol) was added to a -78 °C solution of tert- vXy 3,4- dihydroquinoline-l(2H)-carboxylate (139 mg, 0.59 mmol) and Ν,Ν,Ν',Ν'- tetramethylethylenediamine (TMEDA, 0.2 mL, 1.33 mmol) in diethyl ether (1.2 mL). After 3 h, a solution of 1 ,2-diiodoethane (201 mg, 0.71 mL) in 1 mL diethyl ether was added by cannula and the reaction was allowed to warm to room temperature. After 19 h, the mixture was partitioned between 20 mL 0 and 20 mL diethyl ether. The aqueous layer was further extracted with 20 mL diethyl ether and the combined ether solution was dried (Na2S04), filtered and evaporated. Purification of the residue by flash chromatography on silica gel using a Combiflash unit by Teledyne Isco (0% ethyl acetate/hexanes 40%) gave the title compound (154 mg, 73%).
66% Stage #1: tert-butyl 1,2,3,4-tetrahydroquinoline-1-carboxylate With tert.-butyl lithium Stage #2: With iodine
58% Stage #1: tert-butyl 1,2,3,4-tetrahydroquinoline-1-carboxylate With N,N,N,N,-tetramethylethylenediamine; sec.-butyllithium In diethyl ether; hexane at -78℃; for 1h; Stage #2: With iodine In diethyl ether; hexane at -78℃; for 0.75h; General procedure: To a solution of N-tert-butyl 2-methylindoline-1-carboxylate (4.00 g, 17.1 mmol) and tetramethylethylenediamine (4.34 mL, 29.1 mmol) in Et2O (82 mL) was added 1.03 M sec-BuLi in hexane (34.3mL, 34.3 mmol) at -78 °C and the mixture was stirred for 1 h at the same temperature. To the mixture was added a solution of iodine (6.09 g, 24.0 mmol) in Et2O (46 mL) dropwise at -78 °C and stirred for 45 min at the same temperature. The mixture was warm up to room temperature and stirred overnight. The mixture was extracted with Et2O and the extract was washed with sat. NH4Cl and sat. Na2S2O3. After drying the extract over MgSO4, the filtrate was concentrated under reduced pressure to leave a residue, which was purified by column chromatography over silica gel with n-hexane-EtOAc(14:1) to give S1 (4.61 g, 75%).
  • 10
  • [ 123387-53-1 ]
  • [ 1038731-97-3 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1.1: sec.-butyllithium; N,N,N,N,-tetramethylethylenediamine / diethyl ether / 3 h / -78 °C 1.2: 19 h / -78 - 20 °C 2.1: hydrogenchloride / 1,4-dioxane / 1 h / 20 °C
Multi-step reaction with 2 steps 1.1: sec.-butyllithium; N,N,N,N,-tetramethylethylenediamine / hexane; diethyl ether / 1 h / -78 °C 1.2: 0.75 h / -78 °C 2.1: trifluoroacetic acid / dichloromethane / 2 h / 0 - 20 °C
Multi-step reaction with 2 steps 1: tert.-butyl lithium 2: hydrogenchloride / 1,4-dioxane / 1 h / 20 °C
  • 11
  • [ 635-46-1 ]
  • [ 24424-99-5 ]
  • [ 123387-53-1 ]
YieldReaction ConditionsOperation in experiment
94% In tetrahydrofuran at 60℃; for 20h; Schlenk technique;
89% With dmap In dichloromethane at 20℃; for 16h;
84% Stage #1: 1,2,3,4-tetrahydroquinoline With sodium hydride In tetrahydrofuran; mineral oil for 1.5h; Inert atmosphere; Reflux; Stage #2: di-<i>tert</i>-butyl dicarbonate In tetrahydrofuran; mineral oil for 48h; Reflux; Inert atmosphere;
70% Stage #1: 1,2,3,4-tetrahydroquinoline With sodium hydride Stage #2: di-<i>tert</i>-butyl dicarbonate In tetrahydrofuran for 24h; Reflux;
14% With triethylamine In tetrahydrofuran at 20 - 32℃; for 4h;
13% With dmap; triethylamine In acetonitrile at 20 - 55℃; tert-Butyl 3,4-dihydroquinoline-l(2H)-carboxylate Di-tert-butyl dicarbonate (1.181 g, 5.4 mmol) was added to a solution of 1,2,3, 4-tetrahydroquino line (626 mg, 4.7 mmol), triethylamine (1.3 mL, 9.3 mmol) and DMAP (112 mg, 0.19 mmol) in CH3CN (15 mL). The reaction was stirred for 1.5 h at room temperature and then was heated overnight at 55 °C. The solution was allowed to cool to room temperature and then was evaporated. The residue was partitioned between 25 mL ethyl acetate and 25 mL 1 M HCl. The ethyl acetate solution was further washed with 1 M HCl (2 x 25 mL) and 25 mL brine and then was dried (Na2S04), filtered and evaporated. Purification of the residue by flash chromatography on silica gel using a Combiflash unit by Teledyne Isco (0% ethyl acetate/hexanes -> 40%) gave the title compound (139 mg, 13%).
With triethylamine In dichloromethane for 10h; Reflux;
With triethylamine In dichloromethane at 40℃; for 24h; Inert atmosphere; Glovebox;
With dmap; triethylamine In dichloromethane at 0 - 20℃;
With dmap In dichloromethane at 0 - 20℃; for 24h;
83 % With dmap; triethylamine In methanol at 0 - 20℃; Inert atmosphere;
46 % With dmap In dichloromethane at 0 - 20℃;
With dmap In tetrahydrofuran at 20℃; Inert atmosphere; Glovebox; Schlenk technique;

References: [1]Piña, Jeanette; Aguirre, Lupita S.; Litwiller, Levi T.; Ly, Hai T.; Crockett, Michael P.; Thomas, Andy A. [Chemistry - A European Journal, 2025, vol. 31, # 29].
[2]Zhang, Shanxue; Li, Yufeng; Wang, Tao; Li, Ming; Wen, Lirong; Guo, Weisi [Organic Letters, 2022, vol. 24, # 8, p. 1742 - 1746].
[3]Poon, Jia-Fei; Yan, Jiajie; Singh, Vijay P.; Gates, Paul J.; Engman, Lars [Chemistry - A European Journal, 2016, vol. 22, # 36, p. 12891 - 12903].
[4]Noël-Duchesneau, Ludovik; Maddaluno, Jacques; Durandetti, Muriel [ChemCatChem, 2019, vol. 11, # 16, p. 4154 - 4160].
[5]Li, Yushu; Wong, Luet L. [Angewandte Chemie - International Edition, 2019, vol. 58, # 28, p. 9551 - 9555][Angew. Chem., 2019, vol. 131, # 28, p. 9651 - 9655,5].
[6]Current Patent Assignee: ALLERGAN - WO2015/48553, 2015, A1 Location in patent: Page/Page column 15; 32.
[7]Zhou, Xiaojian; Zheng, Daijun; Cui, Baodong; Han, Wenyong; Chen, Yongzheng [Tetrahedron, 2015, vol. 71, # 29, p. 4738 - 4744].
[8]Sun, Ming-Xue; Wang, Yao-Feng; Xu, Bao-Hua; Ma, Xin-Qi; Zhang, Suo-Jiang [Organic and Biomolecular Chemistry, 2018, vol. 16, # 11, p. 1971 - 1975].
[9]Wakaki, Takayuki; Sakai, Kentaro; Enomoto, Takafumi; Kondo, Mio; Masaoka, Shigeyuki; Oisaki, Kounosuke; Kanai, Motomu [Chemistry - A European Journal, 2018, vol. 24, # 32, p. 8051 - 8055].
[10]Dong, Jianyang; Xia, Qing; Lv, Xueli; Yan, Changcun; Song, Hongjian; Liu, Yuxiu; Wang, Qingmin [Organic Letters, 2018, vol. 20, # 18, p. 5661 - 5665].
[11]Ryan, Michelle-Rose; Lynch, Denis; Collins, Stuart G.; Maguire, Anita R. [Organic Process Research and Development, 2024, vol. 28, # 5, p. 1946 - 1963].
[12]Zachmann, Ashley K. Z.; Drappeau, Justine A.; Liu, Shubin; Alexanian, Erik J. [Angewandte Chemie - International Edition, 2024, vol. 63, # 29][Angew. Chem., 2024, vol. 136, # 29].
[13]Dong, Kun; Wu, Tianbao; Wang, Minyan; Lin, Luqing [Angewandte Chemie - International Edition, 2024, vol. 63, # 43][Angew. Chem., 2024, vol. 136, # 43].
  • 12
  • [ 123387-53-1 ]
  • [ 932398-74-8 ]
YieldReaction ConditionsOperation in experiment
95% With glucose dehydrogenase; D-glucose; cytochrome P450 enzyme CYP102A1 R47L/Y51F/I263A/E267V/I401P mutant; C21H25N7O17P3(3-)*2H(1+)*Na(1+) In aq. phosphate buffer; ethanol at 20℃; for 16h; Enzymatic reaction;
Multi-step reaction with 2 steps 1: potassium permanganate / acetone / 36 h / 25 °C 2: sodium tetrahydroborate / methanol / 0.5 h / 25 °C
  • 13
  • [ 77129-69-2 ]
  • [ 123387-53-1 ]
  • [ 2024584-14-1 ]
YieldReaction ConditionsOperation in experiment
363 mg Stage #1: tert-butyl 1,2,3,4-tetrahydroquinoline-1-carboxylate With N,N,N,N,-tetramethylethylenediamine; sec.-butyllithium In diethyl ether at -78℃; for 2h; Inert atmosphere; Stage #2: dibutyl ditelluride In diethyl ether at 20℃; Inert atmosphere; Stage #3: With trifluoroacetic acid In diethyl ether; dichloromethane for 0.5h; Inert atmosphere;
  • 14
  • [ 851076-20-5 ]
  • [ 123387-53-1 ]
  • [ 2024584-15-2 ]
YieldReaction ConditionsOperation in experiment
320 mg Stage #1: tert-butyl 1,2,3,4-tetrahydroquinoline-1-carboxylate With N,N,N,N,-tetramethylethylenediamine; sec.-butyllithium In diethyl ether at -78℃; for 2h; Inert atmosphere; Stage #2: di-n-hexadecyl ditelluride In diethyl ether at 20℃; Inert atmosphere; Stage #3: With trifluoroacetic acid In diethyl ether; dichloromethane for 0.5h; Inert atmosphere;
 

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Related Parent Nucleus of
[ 123387-53-1 ]

Tetrahydroquinolines

Chemical Structure| 944906-95-0

A181669 [944906-95-0]

tert-Butyl 4-amino-3,4-dihydroquinoline-1(2H)-carboxylate

Similarity: 0.93

Chemical Structure| 351324-70-4

A333439 [351324-70-4]

tert-Butyl 7-amino-3,4-dihydroquinoline-1(2H)-carboxylate

Similarity: 0.92

Chemical Structure| 327044-56-4

A175266 [327044-56-4]

tert-Butyl 6-hydroxy-3,4-dihydroquinoline-1(2H)-carboxylate

Similarity: 0.91

Chemical Structure| 1187932-64-4

A219947 [1187932-64-4]

tert-Butyl 7-bromo-3,4-dihydroquinoline-1(2H)-carboxylate

Similarity: 0.86

Chemical Structure| 1123169-45-8

A424289 [1123169-45-8]

tert-Butyl 6-bromo-3,4-dihydroquinoline-1(2H)-carboxylate

Similarity: 0.85