[ CAS No. 501-65-5 ] {[proInfo.proName]}

Name: 501-65-5|Diphenylacetylene|98%
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DV 2D 3D

3d Animation Molecule Structure of 501-65-5

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Quality Control of [ 501-65-5 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 501-65-5 ]

SDS Specification

Alternatived Products of [ 501-65-5 ]

Product Details of [ 501-65-5 ]

CAS No. :	501-65-5	MDL No. :	MFCD00004786
Formula :	C₁₄H₁₀	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	JRXXLCKWQFKACW-UHFFFAOYSA-N
M.W :	178.23	Pubchem ID :	10390
Synonyms :

Calculated chemistry of [ 501-65-5 ]

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 :	0.0 Å²

Pharmacokinetics

GI absorption :	Low
BBB permeant :	Yes
P-gp substrate :	No
CYP1A2 inhibitor :	Yes
CYP2C19 inhibitor :	Yes
CYP2C9 inhibitor :	Yes
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-3.99 cm/s

Lipophilicity

Log Po/w (iLOGP) :	2.85
Log Po/w (XLOGP3) :	4.78
Log Po/w (WLOGP) :	3.17
Log Po/w (MLOGP) :	5.24
Log Po/w (SILICOS-IT) :	3.95
Consensus Log Po/w :	4.0

Druglikeness

Lipinski :	1.0
Ghose :	None
Veber :	0.0
Egan :	0.0
Muegge :	2.0
Bioavailability Score :	0.55

Water Solubility

Log S (ESOL) :	-4.59
Solubility :	0.00457 mg/ml ; 0.0000257 mol/l
Class :	Moderately soluble
Log S (Ali) :	-4.51
Solubility :	0.00549 mg/ml ; 0.0000308 mol/l
Class :	Moderately soluble
Log S (SILICOS-IT) :	-4.99
Solubility :	0.00181 mg/ml ; 0.0000101 mol/l
Class :	Moderately soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	1.0 alert
Leadlikeness :	2.0
Synthetic accessibility :	2.25

Safety of [ 501-65-5 ]

Signal Word:	Warning	Class:	N/A
Precautionary Statements:	P261-P301+P312-P302+P352-P304+P340-P305+P351+P338	UN#:	N/A
Hazard Statements:	H302-H315-H319-H335	Packing Group:	N/A
GHS Pictogram:

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.

Upstream synthesis route of [ 501-65-5 ]
Downstream synthetic route of [ 501-65-5 ]

[ 501-65-5 ] Synthesis Path-Upstream 1~15

1
[ 106-47-8 ]
[ 501-65-5 ]
[ 52598-02-4 ]

Yield	Reaction Conditions	Operation in experiment
90%	With Cp*Rh(H₂O)3(OTf)2; oxygen; acetic anhydride In pentan-1-ol at 100℃; for 24 h;	The 4-aminochlorobenzene 1j (76.5 mg, 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. 0μL, 0 . 6mmol), adding 2.0 ml in tertiary amyl alcohol , oxygen (1atm), 100 degrees reaction 24 hours after stop the reaction, add NaOH (48 mg, 1 . 2mmol) and methanol 2 ml after stirring one hour, column chromatography to obtain pure product 5-chloro-2,3-diphenyl indole 3ja. The product is white solid, yield 90percent.

Reference： [1] Chemical Communications, 2014, vol. 50, # 33, p. 4331 - 4334
[2] Patent: CN105218426, 2016, A, . Location in patent: Paragraph 0039; 0040

2
[ 873-38-1 ]
[ 501-65-5 ]
[ 52598-02-4 ]

Yield	Reaction Conditions	Operation in experiment
55%	With 2 mol% Pd/C; sodium carbonate In N,N-dimethyl-formamide at 140℃; for 144 h; Inert atmosphere	aryl bromide (1 mmol), alkyne (3 mmol), Na₂CO₃ (3 mmol), Pd/C (2 mo lpercent) and DMF (2 mL) were introduced in a sealed tube. The reactor was placed under stirring in a preheated oil bath at 120 °C or 140 °C after being flushed by argon. The reaction completion was monitored by GC. After cooling to room temperature, the reaction mixture was filtered through a celite pad, which was washed with EtOAc (100 mL). The resulting organic layer was then washed with Na₂CO₃ (2 .x. 40 mL) and brine (40 mL). The organic layer was dried over Na₂SO₄ and the solvent was removed under reduced pressure. If necessary (for the silylated compounds), the crude product could be fully deprotected by treatment with HCl 1 M before being purified by flash chromatography on silica.

Reference： [1] Tetrahedron Letters, 2011, vol. 52, # 16, p. 1916 - 1918

3
[ 501-65-5 ]
[ 52598-02-4 ]

Reference： [1] ACS Catalysis, 2016, vol. 6, # 4, p. 2705 - 2709

4
[ 1073-70-7 ]
[ 501-65-5 ]
[ 52598-02-4 ]

Reference： [1] Advanced Synthesis and Catalysis, 2014, vol. 356, # 7, p. 1571 - 1576
[2] Chemistry - A European Journal, 2014, vol. 20, # 8, p. 2352 - 2356

5
[ 62499-16-5 ]
[ 501-65-5 ]
[ 52598-02-4 ]

Reference： [1] Angewandte Chemie - International Edition, 2013, vol. 52, # 22, p. 5795 - 5798[2] Angew. Chem., 2013, p. 5999

6
[ 501-65-5 ]
[ 6947-29-1 ]
[ 52598-02-4 ]

Reference： [1] Angewandte Chemie - International Edition, 2013, vol. 52, # 47, p. 12426 - 12429[2] Angew. Chem., 2013, vol. 125, # 47, p. 12652 - 12656,4

7
[ 501-65-5 ]
[ 52598-02-4 ]

Reference： [1] Advanced Synthesis and Catalysis, 2015, vol. 357, # 13, p. 2944 - 2950

8
[ 106-49-0 ]
[ 106-47-8 ]
[ 501-65-5 ]
[ 36804-50-9 ]
[ 52598-02-4 ]

Reference： [1] Chemical Communications, 2014, vol. 50, # 33, p. 4331 - 4334

9
[ 1417717-04-4 ]
[ 501-65-5 ]
[ 52598-02-4 ]

Reference： [1] Angewandte Chemie - International Edition, 2016, vol. 55, # 9, p. 3208 - 3211[2] Angew. Chem., 2016, vol. 128, # 9, p. 3261 - 3265,5

10
[ 150-68-5 ]
[ 501-65-5 ]
[ 52598-02-4 ]

Reference： [1] Chemical Communications, 2014, vol. 50, # 95, p. 14964 - 14967

11
[ 501-65-5 ]
[ 21650-51-1 ]
[ 52598-02-4 ]

Reference： [1] Zeitschrift fuer Naturforschung, Teil B: Anorganische Chemie, Organische Chemie, 1983, vol. 38, # 2, p. 251 - 252

12
[ 591-51-5 ]
[ 501-65-5 ]
[ 1607-57-4 ]

Yield	Reaction Conditions	Operation in experiment
37%	Stage #1: With dmap; n-butyllithium; zirconocene dichloride In tetrahydrofuran; hexane at 20℃; for 1 h; Inert atmosphere Stage #2: at 20℃; for 12 h; Inert atmosphere	General procedure: To a solution of Cp₂ZrCl₂ (1.2 mmol, 351 mg) in 5 mL THF, n-BuLi (2.4 mmol, 1.5 mL, 1.6 M in hexane) was added at−78 °C and the mixture was stirred for 1 h at the same temperature. To this solution, 4-dimethylaminopyridine (DMAP, 122 mg, 1.0 mmol) was added. The resulting mixture was warmed to room temperature and stirred for 1 h. Diphenylacetylene (1.0 mmol, 178 mg) was added and the mixture was stirred for 1 h at the same temperature. Subsequently, PhLi (2.0 mmol) was added and the solution was stirred for 12 h at room temperature. Then TCQ (2.0 mmol) was added and stirred for another 12 h to afford alkenylzirconocene 4a. The mixture was quenched with HCl solution to afford product 3a in 62percent isolated yield.

Reference： [1] Beilstein Journal of Organic Chemistry, 2014, vol. 10, p. 528 - 534

13
[ 589-87-7 ]
[ 501-65-5 ]
[ 98-80-6 ]
[ 34699-28-0 ]

Reference： [1] European Journal of Organic Chemistry, 2008, # 14, p. 2417 - 2422

14
[ 501-65-5 ]
[ 14647-23-5 ]
[ 992-04-1 ]

Reference： [1] Journal of Organometallic Chemistry, 1986, vol. 312, p. 399 - 416

15
[ 98-88-4 ]
[ 2644-70-4 ]
[ 103-30-0 ]
[ 103-29-7 ]
[ 501-65-5 ]

Reference： [1] Ber., 1893, vol. 26, p. 867
[2] , Gmelin Handbook: NH4: MVol.2, 12, page 532 - 552,

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Yield	Reaction Conditions	Operation in experiment
98%	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.
86%	With potassium carbonate; In N,N-dimethyl-formamide; at 100℃; for 30h;	General procedure: The 25 mL RB-flask was charged with 2-iodoaniline (1 mmol), diphenylacetylene (1.5 mmol), K2CO3 (2 mmol) and PS-tsu-Pd(II) complex (3) (0.005 mmol) in DMF (2 mL). The reaction mixture was stirred at 100 °C for 30 h. After completion of the reaction, the reaction mixture was cooled to room temperature and filtered to recover the catalyst. Then the experimental procedure was same as above.

Yield	Reaction Conditions	Operation in experiment
91%	With 1,1'-bis-(diphenylphosphino)ferrocene; [Pd(eta(5)-C5H5)Fe(eta(5)-C5H3-C(CH3)=N-C6H4-4-CH3)Cl(P(C6H5)3)]; potassium carbonate; In N,N-dimethyl-formamide; at 100℃; for 24h;Inert atmosphere;	General procedure: o-Halobenzaldehyde (0.25 mmol), diphenylacetylene (0.50 mmol), palladacycle (1 mol percent), additive (0.25 mmol), and K2CO3 (0.50 mmol) were dissolved in DMF (1.50 mL) in a 10 mL vial under air and heated at 100 °C for 24 h. After the reaction was complete (monitored by TLC), the mixture was diluted with CH2Cl2 (10 mL), filtered through a pad of Celite, and washed multiple times with CH2Cl2. The combined organic layer was dried over anhydrous Na2SO4, filtered, and evaporated under reduced pressure and the residue was purified by flash chromatography on silica gel (ethyl acetate/hexane) to afford the pure product.
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.
70%	With 2 mol% Pd/C; sodium carbonate; In N,N-dimethyl-formamide; at 140℃; for 72h;Inert atmosphere;	aryl bromide (1 mmol), alkyne (3 mmol), Na2CO3 (3 mmol), Pd/C (2 mo lpercent) and DMF (2 mL) were introduced in a sealed tube. The reactor was placed under stirring in a preheated oil bath at 120 °C or 140 °C after being flushed by argon. The reaction completion was monitored by GC. After cooling to room temperature, the reaction mixture was filtered through a celite pad, which was washed with EtOAc (100 mL). The resulting organic layer was then washed with Na2CO3 (2 .x. 40 mL) and brine (40 mL). The organic layer was dried over Na2SO4 and the solvent was removed under reduced pressure. If necessary (for the silylated compounds), the crude product could be fully deprotected by treatment with HCl 1 M before being purified by flash chromatography on silica.

Yield	Reaction Conditions	Operation 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.

Yield	Reaction Conditions	Operation in experiment
45%	With [RhCl2(p-cymene)]2; potassium acetate; sodium carbonate; In toluene; at 100℃; for 24.0h;Inert atmosphere; Sealed tube;	General procedure: A 25mL sealed tube was charged with aromatic ketones 1(0.2 mmol, 2.0 equiv), diphenylacetylene 2a (0.1 mmol, 1.0 equiv),[RuCl2(p-cymene)]2 (0.015 mmol, 15 molpercent), KOAc (0.2 mmol, 2.0equiv), Na2CO3 (0.2 mmol, 2.0 equiv) and PhMe (0.5 mL). The vialwas evacuated and filled with N2 atmosphere, and stirred at 100 Cfor 24 h. After being cooled to room temperature, the mixture wasevaporated under reduced pressure. The residue was purified byflash column chromatography on silica gel, eluting with petroleumether to afford the desired products 4.
35%	With [ruthenium(II)(eta6-1-methyl-4-isopropyl-benzene)(chloride)(mu-chloride)]2; potassium acetate; sodium carbonate; In toluene; at 100℃; for 24.0h;Sealed tube;	Diphenylacetylene (18 mg, 0.1 mmol) was added to a 25 mL sealed tube with magnetite, corresponding to the aromatic ketone(0.2 mmol), catalyst [RuCl 2 (p-cymene)] 2 (9 mg, 15percent mol), 0.5 mL toluene, followed by the addition of dry sodium carbonate(21 mg, 0.2 mmol) and potassium acetate (19 mg, 0.2 mmol), purged nitrogen three times, reacted at 100°C for 24 hours, and then passed through a column Chromatographic separation (eluent: petroleum ether) gave the target compound. Characterized as follows.3-Isobutyl-1,2-diphenylnaphthalene: Yield: 35percent

[ CAS No. 501-65-5 ] {[proInfo.proName]}

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