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Chemical Structure| 501-65-5 Chemical Structure| 501-65-5

Structure of 501-65-5

Chemical Structure| 501-65-5

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Product Citations

Product Citations

Deem, Madeleine C. ; Hein, Jason E. ;

Abstract: Online HPLC reaction progress monitoring provides detailed data-rich profiles; however, extracting kinetic information requires UV-visible response factors to determine concentrations from peak areas. If the reaction's overall mass balance is known and some anal. trend for all relevant species can be recorded, it is possible to estimate the absolute response factors of all species using a system of linear equations. We delineate a method using the Microsoft Solver plug-in to convert time course profiles to reagent concentrations without anal. standards

Purchased from AmBeed: ; ; ; ; ; ; ;

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Product Details of [ 501-65-5 ]

CAS No. :501-65-5
Formula : C14H10
M.W : 178.23
SMILES Code : C1(C#CC2=CC=CC=C2)=CC=CC=C1
MDL No. :MFCD00004786
InChI Key :JRXXLCKWQFKACW-UHFFFAOYSA-N
Pubchem ID :10390

Safety of [ 501-65-5 ]

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H302-H315-H319-H335
Precautionary Statements:P261-P301+P312-P302+P352-P304+P340-P305+P351+P338

Computational Chemistry of [ 501-65-5 ] Show Less

Physicochemical Properties

Num. heavy atoms 14
Num. arom. heavy atoms 12
Fraction Csp3 0.0
Num. rotatable bonds 0
Num. H-bond acceptors 0.0
Num. H-bond donors 0.0
Molar Refractivity 58.86
TPSA ?

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

0.0 Ų

Lipophilicity

Log Po/w (iLOGP)?

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

2.85
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

4.78
Log Po/w (WLOGP)?

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

3.17
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.

5.24
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

3.95
Consensus Log Po/w?

Consensus Log Po/w: Average of all five predictions

4.0

Water Solubility

Log S (ESOL):?

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

-4.59
Solubility 0.00457 mg/ml ; 0.0000257 mol/l
Class?

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

Moderately soluble
Log S (Ali)?

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

-4.51
Solubility 0.00549 mg/ml ; 0.0000308 mol/l
Class?

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

Moderately 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

-4.99
Solubility 0.00181 mg/ml ; 0.0000101 mol/l
Class?

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

Moderately soluble

Pharmacokinetics

GI absorption?

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

Low
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

Yes
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.

-3.99 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

1.0
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

2.0
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

1.0 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<2.0
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)

2.25

Application In Synthesis of [ 501-65-5 ]

* 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 [ 501-65-5 ]

[ 501-65-5 ] Synthesis Path-Downstream   1~35

  • 3
  • [ 88-67-5 ]
  • [ 501-65-5 ]
  • [ 3469-20-3 ]
  • 5
  • [ 32993-05-8 ]
  • [ 501-65-5 ]
  • [ 1227476-15-4 ]
  • (η5-C5H5)Ru(phenylazophenyl)(PPh3) [ No CAS ]
  • [ 3469-20-3 ]
  • 7
  • [ 19591-17-4 ]
  • [ 501-65-5 ]
  • [ 3469-20-3 ]
  • [ 1239-56-1 ]
  • 8
  • [ 501-65-5 ]
  • [ 161117-84-6 ]
  • [ 3469-20-3 ]
  • 9
  • [ 501-65-5 ]
  • [ 161117-84-6 ]
  • [ 3469-20-3 ]
  • [ 138343-96-1 ]
  • 10
  • [ 501-65-5 ]
  • [ 212063-19-9 ]
  • [ 3469-20-3 ]
  • 11
  • [ 103-84-4 ]
  • [ 501-65-5 ]
  • [ 3469-20-3 ]
  • [ 1239-56-1 ]
YieldReaction ConditionsOperation in experiment
Preparation of Cyclopalladated Complex I' Into a mixture of 1d (1.25g, 9.28 mmol) and Pd(OAc) (1.0g, 4.46 mmol) was added toluene (15 mL), and the solution was refluxed under a slow stream of nitrogen for 0.5 h. The precipitate from the solution was quickly filtered and washed with fresh solvent to give greenish yellow I'. Then the filtrate was again refluxed for 1.5 h, and the deposited I' was collected. The total yield of I' was 1.21g, 91 percent based on palladium. The decomposed point is 205-208 oC. Spectral data was consistent with the literature that was reported previously.1; To a suspension of I'(0.08 mmol, 49.6 mg) in DMF (2.0 mL) was added 2a (0.15 mmol, 26.1 mg), 2,2'-bipyridine (0.16 mmol, 25.0 mg) and the mixture was stirred at room temperature for a few min. Then the reaction was heated at 120 oC for 3.5 h. On cooling, the mixture was diluted with H2O, and extracted with ethyl ether. The extract was dried over anhydrous Na2SO4 and concentrated under reduced pressure. The residue was purified by flash chromatography on silica gel with petroleum ether/ethyl acetate as eluent to afford the products 3da and 3da' in 49percent and 22percent yields, respectively. The data for 3da: m.p. 132-133 oC (literature2); 1H NMR (300 MHz, CDCl3): 8.46 (d, J = 8.1 Hz, 1H), 7.56 (d, J = 7.2 Hz, 1H), 7.44-7.20 (m, 12H), 2.0 (s, 3H); 13C NMR (75 MHz, CDCl3): 171.6, 136.7, 135.0, 133.0, 132.9, 131.6, 130.7, 130.0, 129.2, 128.6, 128.2, 126.9, 125.5, 123.8, 123.3, 119.5, 116.2, 27.9; IR (neat): 3054, 2962, 2919, 1695, 1611, 1488, 1444, 1368, 1348, 1303, 1221, 1183, 1155, 1128, 1104, 1075, 1022, 977, 930, 810, 777cm-1; MS (70 eV, EI) m/z (percent): 311, 269 (100), 254, 239, 213, 190, 165, 139, 89, 77, 63; HRMS Calcd for C22H17NO: 311.1310, found: 311.1315. The date for 3da': m.p. 114-116 oC (literature3); 1H NMR (300 MHz, CDCl3): 8.24 (brs, 1H), 7.68 (d, J = 7.8 Hz, 1H), 7.46-7.13 (m, 13H); 13C NMR (100 MHz, CDCl3): 135.9, 135.0, 134.1, 132.7, 130.1, 128.7, 128.6, 128.5, 128.1, 127.7, 126.2, 122.7, 120.4, 119.7, 115.0, 110.9; IR (neat): , 3057, 2963, 2923, 2851, 1601, 1553, 1505, 1485, 1456, 1440, 1424, 1371, 1305, 1329, 1262, 1179, 1155, 1095, 1071, 966, 800 cm-1; MS (70 eV, EI) m/z (percent): 269 (100), 254, 239, 226, 213, 190, 165, 133, 120, 106, 89, 77, 63; HRMS Calcd for C20H15N: 269.1204, found: 269.1201.
  • 12
  • [ 62-53-3 ]
  • [ 501-65-5 ]
  • [ 3469-20-3 ]
YieldReaction ConditionsOperation in experiment
92% With sodium iodide dihydrate; rhodium contaminated with carbon; sodium carbonate; In N,N-dimethyl-formamide; at 135℃; for 36h;Schlenk technique; 1) In a pre-dried 50mL Schlenk reaction tube with a magneton, 0.3 mmol of aniline, 0.9 mmol of alkyne, 0.03 mmol of rhodium on carbon, 0.3 mmol of sodium carbonate,0.15mmol sodium iodide dihydrate were added and mixed evenly, 2) After adding 1.0 mL of dimethylformamide, the reaction tube was placed in a preheated 135 °C oil bath and the reaction was blocked for 36 hours; 3) Water and ethyl acetate were added to separate the organic phase, the solvent was removed on a rotary evaporator and passed through a column of silica gel to give the target product as a white solid.
84% With Cp*Rh(H2O)3(OTf)2; oxygen; acetic anhydride; In pentan-1-ol; at 100℃; for 24h; The aniline 1a (55. 0muL, 0 . 6mmol), 1, 2-diphenyl 2a (71.3 mg, 0 . 4mmol), Cp*Rh (H2O)3(OTf)2(11.8 mg, 5mol percent), acetic anhydride (59. 0muL, 0 . 6mmol), adding 2.0 ml in tertiary amyl alcohol , oxygen (1atm), 100oC reaction 24 hours after stop the reaction, add NaOH (48 mg, 1 . 2mmol) and methanol 2 ml after stirring one hour, column chromatography get the pure product 2,3-diphenyl indole 3aa. The product is white solid, yield 70percent.
  • 13
  • [ 62-53-3 ]
  • [ 501-65-5 ]
  • [ 3469-20-3 ]
  • [ 1646-67-9 ]
  • 14
  • [ 501-65-5 ]
  • [ 36719-71-8 ]
  • [ 3469-20-3 ]
  • 15
  • [ 19591-17-4 ]
  • [ 501-65-5 ]
  • [ 3469-20-3 ]
YieldReaction ConditionsOperation in experiment
90% With lithium hydroxide monohydrate; C24H23N3O3PdS; In N,N-dimethyl-formamide; at 130℃; for 20h; General procedure: The 25 mL RB-flask was charged with 2-haloamines (1 mmol), diphenylacetylene (1.5 mmol), LiOH·H2O (4 mmol) and catalyst (0.001 molpercent of 5 in 2 mL N,N-dimethylformamide). The reaction mixture was stirred at 130 °C for 20 h. The reaction mixture was cooled to room temperature, diluted with ethyl acetate (20 mL) and washed with brine water. The combined organic phase was dried over anhydrous Na2SO4. After removal of the solvent, the residue was subjected to column chromatography on silica gel using ethyl acetate and hexane to afford the indole product in high purity. In case of 2-bromoanilines, 0.1 molpercent of catalyst 5 was applied.
  • 17
  • C8H9(2)HN2O [ No CAS ]
  • [ 501-65-5 ]
  • [ 3469-20-3 ]
  • C20H14(2)HN [ No CAS ]
  • 20
  • [ 4165-61-1 ]
  • [ 62-53-3 ]
  • [ 501-65-5 ]
  • [ 3469-20-3 ]
  • 4,5,6,7-tetradeuterium-2,3-diphenyl-1H-indole [ No CAS ]
  • 21
  • [ 5369-19-7 ]
  • [ 501-65-5 ]
  • [ 1594135-25-7 ]
  • 22
  • [ 103-84-4 ]
  • [ 501-65-5 ]
  • [ 3469-20-3 ]
  • 23
  • [ 62830-55-1 ]
  • [ 501-65-5 ]
  • [ 405924-38-1 ]
  • 24
  • [ 5926-51-2 ]
  • [ 501-65-5 ]
  • C17H11BrO2 [ No CAS ]
  • 25
  • [ 501-65-5 ]
  • [ 1137-96-8 ]
  • [ 3469-20-3 ]
YieldReaction ConditionsOperation in experiment
40% With silver hexafluoroantimonate; dichloro(pentamethylcyclopentadienyl)rhodium (III) dimer; zinc trifluoromethanesulfonate; Trimethylacetic acid; In 1,2-dichloro-ethane; at 80℃; for 15h;Sealed tube; Inert atmosphere; General procedure: Nitrones (0.2 mmol), diarylacetylenes (0.3 mmol), [Cp*RhCl2]2 (4 molpercent), AgSbF6 (16 molpercent), PivOH (2.0 equiv)and ethyl acetate (2 mL) were charged into the sealed tube. The reaction mixture was stirred at 80 °C for 15 h. After cooled to room temperature, the solvent was removed under reduced pressure and the residue was purified by silica gel chromatography using triethylamine/PE or PE/EA to afford compounds 3.
  • 26
  • [ 501-65-5 ]
  • [ 36719-71-8 ]
  • [ 3469-20-3 ]
  • 27
  • [ 13438-50-1 ]
  • [ 501-65-5 ]
  • 1,2-diphenylcyclopenta[cd]fluoranthene [ No CAS ]
  • 28
  • [ 52512-27-3 ]
  • [ 501-65-5 ]
  • [ 3469-20-3 ]
  • 29
  • [ 100-65-2 ]
  • [ 501-65-5 ]
  • [ 3469-20-3 ]
  • 30
  • [ 3585-93-1 ]
  • [ 501-65-5 ]
  • [ 5782-11-6 ]
  • [ 3469-20-3 ]
  • 32
  • [ 13438-50-1 ]
  • [ 501-65-5 ]
  • 13H-indeno[1,2-b]fluoranthene [ No CAS ]
  • 33
  • [ 456-14-4 ]
  • [ 501-65-5 ]
  • 6-fluoro-3,4-diphenylisoquinolin-1-amine [ No CAS ]
  • 34
  • [ 1173707-01-1 ]
  • [ 501-65-5 ]
  • 1-(6-fluoro-2,3-diphenyl-1H-indol-1-yl)ethanone [ No CAS ]
  • 35
  • [ 20197-92-6 ]
  • [ 501-65-5 ]
  • 8-amino-5,6-dimethoxy-3,4-diphenyl-1H-isochromen-1-one [ No CAS ]
 

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