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Chemistry
Organic Building Blocks
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ethynylphenyl
Tetrakis(4-ethynylphenyl)methane
Chemistry
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[ CAS No. 177991-01-4 ] {[proInfo.proName]}

,{[proInfo.pro_purity]}
Cat. No.: {[proInfo.prAm]}
Chemical Structure| 177991-01-4
Chemical Structure| 177991-01-4
Structure of 177991-01-4 * Storage: {[proInfo.prStorage]}
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Quality Control of [ 177991-01-4 ]

COA NMR CNMR HPLC LC-MS

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SDS Specification
Alternatived Products of [ 177991-01-4 ]

Product Details of [ 177991-01-4 ]

CAS No. :177991-01-4 MDL No. :MFCD24873189
Formula : C33H20 Boiling Point : -
Linear Structure Formula :- InChI Key :JGUCYLISNORQFW-UHFFFAOYSA-N
M.W : 416.51 Pubchem ID :12157742
Synonyms :

Calculated chemistry of [ 177991-01-4 ]

Physicochemical Properties

Num. heavy atoms : 33
Num. arom. heavy atoms : 24
Fraction Csp3 : 0.03
Num. rotatable bonds : 4
Num. H-bond acceptors : 0.0
Num. H-bond donors : 0.0
Molar Refractivity : 136.49
TPSA : 0.0 Ų

Pharmacokinetics

GI absorption : Low
BBB permeant : No
P-gp substrate : Yes
CYP1A2 inhibitor : No
CYP2C19 inhibitor : Yes
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -3.2 cm/s

Lipophilicity

Log Po/w (iLOGP) : 5.29
Log Po/w (XLOGP3) : 7.95
Log Po/w (WLOGP) : 6.31
Log Po/w (MLOGP) : 8.68
Log Po/w (SILICOS-IT) : 9.45
Consensus Log Po/w : 7.54

Druglikeness

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

Water Solubility

Log S (ESOL) : -7.71
Solubility : 0.00000821 mg/ml ; 0.0000000197 mol/l
Class : Poorly soluble
Log S (Ali) : -7.8
Solubility : 0.00000659 mg/ml ; 0.0000000158 mol/l
Class : Poorly soluble
Log S (SILICOS-IT) : -10.23
Solubility : 0.0000000242 mg/ml ; 0.0000000001 mol/l
Class : Insoluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 1.0 alert
Leadlikeness : 2.0
Synthetic accessibility : 2.95

Safety of [ 177991-01-4 ]

Signal Word:Warning Class:
Precautionary Statements:P261-P280-P301+P312-P302+P352-P305+P351+P338 UN#:
Hazard Statements:H302-H315-H319-H335 Packing Group:
GHS Pictogram:

Application In Synthesis of [ 177991-01-4 ]

* 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 [ 177991-01-4 ]

[ 177991-01-4 ] Synthesis Path-Downstream   1~80

  • 1
  • [ 177991-00-3 ]
  • [ 177991-01-4 ]
Reference： [1]ChemPlusChem,2018,vol. 83,p. 448 - 454
[2]Tetrahedron Letters,1996,vol. 37,p. 3825 - 3828
[3]Tetrahedron,1997,vol. 53,p. 6835 - 6846
[4]Journal of Materials Chemistry,2011,vol. 21,p. 1700 - 1703
[5]Journal of the American Chemical Society,2016,vol. 138,p. 2142 - 2145
[6]Chemical Communications,1999,p. 173 - 174
[7]New Journal of Chemistry,2018,vol. 42,p. 14067 - 14070
[8]Chemical Communications,2016,vol. 52,p. 12602 - 12605
[9]Chemical Communications,2014,vol. 50,p. 13910 - 13913
[10]Tetrahedron,2015,vol. 71,p. 9519 - 9527
[11]Advanced Synthesis and Catalysis,2009,vol. 351,p. 313 - 318
[12]Organic and Biomolecular Chemistry,2009,vol. 7,p. 4734 - 4743
[13]Chemistry - A European Journal,2014,vol. 20,p. 16273 - 16278
[14]Chemical Communications,2021,vol. 57,p. 907 - 910
  • 2
  • [ 177991-01-4 ]
  • [ 220210-61-7 ]
  • [ 220210-65-1 ]
Reference： [1]Chemical Communications,1998,p. 2661 - 2662
  • 3
  • [ 134856-58-9 ]
  • [ 177991-01-4 ]
  • [ 220210-65-1 ]
Reference： [1]Chemistry - A European Journal,2000,vol. 6,p. 4364 - 4370
  • 4
  • [ 177991-01-4 ]
  • 3,4-bis(4-triisopropylsilylethynylphenyl)-2,5-diphenylcyclopentadienone [ No CAS ]
  • C161H100 [ No CAS ]
Reference： [1]Chemistry - A European Journal,2001,vol. 7,p. 4126 - 4133
  • 5
  • [ 13154-24-0 ]
  • [ 177991-01-4 ]
  • triisopropyl-{4-[tris-(4-ethynyl-phenyl)-methyl]-phenylethynyl}-silane [ No CAS ]
  • C51H60Si2 [ No CAS ]
  • C60H80Si3 [ No CAS ]
Reference： [1]Journal of the American Chemical Society,2001,vol. 123,p. 8101 - 8108
  • 6
  • triisopropyl-{4-[tris-(4-ethynyl-phenyl)-methyl]-phenylethynyl}-silane [ No CAS ]
  • [ 177991-01-4 ]
Reference： [1]Journal of the American Chemical Society,2001,vol. 123,p. 8101 - 8108
  • 7
  • C60H80Si3 [ No CAS ]
  • [ 177991-01-4 ]
Reference： [1]Journal of the American Chemical Society,2001,vol. 123,p. 8101 - 8108
  • 8
  • [ 177991-01-4 ]
  • [ 391248-33-2 ]
  • C145H108N8 [ No CAS ]
Reference： [1]Tetrahedron,2003,vol. 59,p. 3925 - 3935
  • 9
  • [ 479-33-4 ]
  • [ 177991-01-4 ]
  • [ 808766-49-6 ]
  • C150H105Cl [ No CAS ]
  • C150H105Cl [ No CAS ]
Reference： [1]Journal of Organic Chemistry,2004,vol. 69,p. 8029 - 8037
  • 10
  • [ 479-33-4 ]
  • [ 177991-01-4 ]
  • [ 808766-54-3 ]
  • C152H111NO3 [ No CAS ]
  • C152H111NO3 [ No CAS ]
Reference： [1]Journal of Organic Chemistry,2004,vol. 69,p. 8029 - 8037
  • 11
  • [ 56754-91-7 ]
  • [ 177991-01-4 ]
  • [ 808766-50-9 ]
  • C151H108N8O3 [ No CAS ]
  • C151H108N8O3 [ No CAS ]
Reference： [1]Journal of Organic Chemistry,2004,vol. 69,p. 8029 - 8037
  • 12
  • [ 177991-01-4 ]
  • [ 189619-39-4 ]
  • [ 808766-49-6 ]
  • C216H225ClSi6 [ No CAS ]
  • C216H225ClSi6 [ No CAS ]
Reference： [1]Journal of Organic Chemistry,2004,vol. 69,p. 8029 - 8037
  • 13
  • [ 177991-01-4 ]
  • [ 189619-39-4 ]
  • [ 808766-54-3 ]
  • C164H111NO3 [ No CAS ]
  • C164H111NO3 [ No CAS ]
Reference： [1]Journal of Organic Chemistry,2004,vol. 69,p. 8029 - 8037
  • 14
  • [ 177991-01-4 ]
  • [ 189619-39-4 ]
  • [ 808766-54-3 ]
  • C218H231NO3Si6 [ No CAS ]
  • C218H231NO3Si6 [ No CAS ]
Reference： [1]Journal of Organic Chemistry,2004,vol. 69,p. 8029 - 8037
  • 15
  • [ 177991-01-4 ]
  • [ 189619-39-4 ]
  • [ 808766-50-9 ]
  • C169H114N2O3 [ No CAS ]
  • C169H114N2O3 [ No CAS ]
Reference： [1]Journal of Organic Chemistry,2004,vol. 69,p. 8029 - 8037
  • 16
  • [ 177991-01-4 ]
  • [ 189619-39-4 ]
  • [ 808766-50-9 ]
  • C223H234N2O3Si6 [ No CAS ]
  • C223H234N2O3Si6 [ No CAS ]
Reference： [1]Journal of Organic Chemistry,2004,vol. 69,p. 8029 - 8037
  • 17
  • [ 177991-01-4 ]
  • C45H32O5 [ No CAS ]
  • [ 808766-50-9 ]
  • C205H150N2O15 [ No CAS ]
  • C205H150N2O15 [ No CAS ]
Reference： [1]Journal of Organic Chemistry,2004,vol. 69,p. 8029 - 8037
  • 18
  • [ 177991-01-4 ]
  • [ 808766-49-6 ]
  • C66H45Cl [ No CAS ]
  • C66H45Cl [ No CAS ]
Reference： [1]Journal of Organic Chemistry,2004,vol. 69,p. 8029 - 8037
  • 19
  • [ 177991-01-4 ]
  • [ 808766-54-3 ]
  • C68H51NO3 [ No CAS ]
  • C68H51NO3 [ No CAS ]
  • C103H82N2O6 [ No CAS ]
Reference： [1]Journal of Organic Chemistry,2004,vol. 69,p. 8029 - 8037
  • 20
  • [ 177991-01-4 ]
  • [ 808766-50-9 ]
  • C73H54N2O3 [ No CAS ]
  • C73H54N2O3 [ No CAS ]
Reference： [1]Journal of Organic Chemistry,2004,vol. 69,p. 8029 - 8037
  • 21
  • [ 871585-23-8 ]
  • [ 177991-01-4 ]
  • C153H92N8 [ No CAS ]
Reference： [1]Doklady Chemistry,2005,vol. 400,p. 34 - 38
  • 22
  • 2,5-di(methylcarboxy)-3,4-bis(4-triisopropylsilylethynylphenyl)-cyclopentadienone [ No CAS ]
  • [ 177991-01-4 ]
  • C129H84O16 [ No CAS ]
Reference： [1]New Journal of Chemistry,2007,vol. 31,p. 1275 - 1282
[2]ChemPlusChem,2012,vol. 77,p. 102 - 105
  • 23
  • [ 105309-59-9 ]
  • [ 177991-01-4 ]
Reference： [1]Chemical Communications,1999,p. 173 - 174
[2]Chemical Communications,2014,vol. 50,p. 13910 - 13913
[3]Tetrahedron,2015,vol. 71,p. 9519 - 9527
[4]ChemPlusChem,2018,vol. 83,p. 448 - 454
  • 24
  • [ 134080-67-4 ]
  • [ 177991-01-4 ]
Reference： [1]Tetrahedron,1997,vol. 53,p. 6835 - 6846
[2]Tetrahedron Letters,1996,vol. 37,p. 3825 - 3828
  • 25
  • [ 61117-58-6 ]
  • [ 177991-01-4 ]
  • [ 220210-63-9 ]
Reference： [1]Chemical Communications,1998,p. 2661 - 2662
[2]Chemical Communications,1998,p. 2661 - 2662
  • 26
  • [ 1092585-30-2 ]
  • [ 177991-01-4 ]
  • [ 1092585-32-4 ]
Reference： [1]Angewandte Chemie - International Edition,2008,vol. 47,p. 8292 - 8296
  • 27
  • [ 5660-91-3 ]
  • [ 177991-01-4 ]
  • [ 1092585-31-3 ]
Reference： [1]Angewandte Chemie - International Edition,2008,vol. 47,p. 8292 - 8296
  • 28
  • [ 1206518-78-6 ]
  • [ 177991-01-4 ]
  • C109H84N12O4P4 [ No CAS ]
Reference： [1]Advanced Synthesis and Catalysis,2009,vol. 351,p. 313 - 318
  • 29
  • [ 1206518-79-7 ]
  • [ 177991-01-4 ]
  • C109H132N12O4P4 [ No CAS ]
Reference： [1]Advanced Synthesis and Catalysis,2009,vol. 351,p. 313 - 318
  • 30
  • [ 1206518-81-1 ]
  • [ 177991-01-4 ]
  • C133H148N12O4P4 [ No CAS ]
Reference： [1]Advanced Synthesis and Catalysis,2009,vol. 351,p. 313 - 318
  • 31
  • tetrakis[4-(3-hydroxy-3-methyl-1-butyn-1-yl)phenyl]methane [ No CAS ]
  • [ 177991-01-4 ]
Reference： [1]Organic and Biomolecular Chemistry,2009,vol. 7,p. 3549 - 3560
  • 32
  • [ 696-07-1 ]
  • [ 177991-01-4 ]
  • [ 1190592-61-0 ]
Reference： [1]Organic and Biomolecular Chemistry,2009,vol. 7,p. 3549 - 3560
  • 33
  • [ 4016-63-1 ]
  • [ 177991-01-4 ]
  • [ 1190592-64-3 ]
Reference： [1]Organic and Biomolecular Chemistry,2009,vol. 7,p. 3549 - 3560
  • 34
  • [ 2946-39-6 ]
  • [ 177991-01-4 ]
  • [ 1190592-62-1 ]
Reference： [1]Organic and Biomolecular Chemistry,2009,vol. 7,p. 3549 - 3560
  • 35
  • [ 151416-77-2 ]
  • [ 177991-01-4 ]
  • [ 1190592-67-6 ]
Reference： [1]Organic and Biomolecular Chemistry,2009,vol. 7,p. 3549 - 3560
  • 36
  • [ 15717-45-0 ]
  • [ 177991-01-4 ]
  • 8,8',8'',8'''-[methanetetrayl-tetrakis(benzene-4,1-diyl-ethyne-2,1-diyl)]tetrakis(2',3',5'-tri-O-acetylguanosine) [ No CAS ]
Reference： [1]Organic and Biomolecular Chemistry,2009,vol. 7,p. 3549 - 3560
  • 37
  • [ 1516-60-5 ]
  • [ 177991-01-4 ]
  • [ 1201839-58-8 ]
Reference： [1]Organic and Biomolecular Chemistry,2009,vol. 7,p. 4734 - 4743
  • 38
  • [ 3296-02-4 ]
  • [ 177991-01-4 ]
  • [ 1201839-54-4 ]
Reference： [1]Organic and Biomolecular Chemistry,2009,vol. 7,p. 4734 - 4743
  • 39
  • [ 79410-35-8 ]
  • [ 177991-01-4 ]
  • (S,S,S,S)-4,4',4'',4'''-methanetetrayltetra-4-phenyl-1H-1,2,3-triazole-1-acetic acid [ No CAS ]
Reference： [1]Organic and Biomolecular Chemistry,2009,vol. 7,p. 4734 - 4743
  • 40
  • 3,5-dicarboxyphenyl azide [ No CAS ]
  • [ 177991-01-4 ]
  • 5,5',5'',5'''-((methanetetrayltetrakis(benzene-4,1-diyl))tetrakis(1H-1,2,3-triazole-4,1-diyl))tetraisophthalic acid [ No CAS ]
Reference： [1]Organic and Biomolecular Chemistry,2009,vol. 7,p. 4734 - 4743
  • 41
  • [ 79410-46-1 ]
  • [ 177991-01-4 ]
  • [ 1201839-60-2 ]
Reference： [1]Organic and Biomolecular Chemistry,2009,vol. 7,p. 4734 - 4743
  • 42
  • [ 622-37-7 ]
  • [ 177991-01-4 ]
  • [ 1201839-50-0 ]
Reference： [1]Organic and Biomolecular Chemistry,2009,vol. 7,p. 4734 - 4743
  • 43
  • [Ru(bpy)2(dbpy)]Cl2. [ No CAS ]
  • [ 177991-01-4 ]
  • ([Ru(2,2'-biipyridine)2(HCCC5H3NC5H3NCCH)]Cl2)(x)(C(C6H4CCH)4)(y) [ No CAS ]
Reference： [1]Journal of the American Chemical Society,2011,vol. 133,p. 2056 - 2059
  • 44
  • [ 1268460-61-2 ]
  • [ 177991-01-4 ]
  • ([Ir(2-phenylpyridine(-H))2(HCCC5H3NC5H3NCCH)]Cl)(x)(C(C6H4CCH)4)(y) [ No CAS ]
Reference： [1]Journal of the American Chemical Society,2011,vol. 133,p. 2056 - 2059
  • 45
  • [ 109-04-6 ]
  • [ 177991-01-4 ]
  • [ 1287733-09-8 ]
Reference： [1]European Journal of Organic Chemistry,2011,p. 1743 - 1754
  • 46
  • [ 626-55-1 ]
  • [ 177991-01-4 ]
  • [ 1287733-10-1 ]
Reference： [1]European Journal of Organic Chemistry,2011,p. 1743 - 1754
  • 47
  • [ 10557-85-4 ]
  • [ 177991-01-4 ]
  • [ 1287733-11-2 ]
Reference： [1]European Journal of Organic Chemistry,2011,p. 1743 - 1754
  • 48
  • [ 591-50-4 ]
  • [ 177991-01-4 ]
  • tetrakis[4-(phenylethynyl)phenyl]methane [ No CAS ]
Reference： [1]European Journal of Organic Chemistry,2011,p. 1743 - 1754
  • 49
  • [ 13329-40-3 ]
  • [ 177991-01-4 ]
  • [ 1287733-02-1 ]
Reference： [1]European Journal of Organic Chemistry,2011,p. 1743 - 1754
  • 50
  • [ 696-62-8 ]
  • [ 177991-01-4 ]
  • [ 1287732-98-2 ]
Reference： [1]European Journal of Organic Chemistry,2011,p. 1743 - 1754
  • 51
  • [ 51839-15-7 ]
  • [ 177991-01-4 ]
  • [ 1287733-05-4 ]
Reference： [1]European Journal of Organic Chemistry,2011,p. 1743 - 1754
  • 52
  • [ 51934-41-9 ]
  • [ 177991-01-4 ]
  • [ 1287733-04-3 ]
Reference： [1]European Journal of Organic Chemistry,2011,p. 1743 - 1754
  • 53
  • [ 19524-06-2 ]
  • [ 177991-01-4 ]
  • [ 359647-86-2 ]
Reference： [1]European Journal of Organic Chemistry,2011,p. 1743 - 1754
  • 54
  • [ 127437-29-0 ]
  • [ 177991-01-4 ]
  • octaethyl 5,5',5'',5'''-[methanetetrayltetrakis(4,1-phenyleneethyne-2,1-diyl)]tetraisophthalate [ No CAS ]
Reference： [1]European Journal of Organic Chemistry,2011,p. 1743 - 1754
  • 55
  • [ 630-76-2 ]
  • [ 177991-01-4 ]
Reference： [1]Journal of Materials Chemistry,2011,vol. 21,p. 1700 - 1703
[2]Tetrahedron,2014,vol. 70,p. 4778 - 4783
[3]Chemistry - A European Journal,2014,vol. 20,p. 16273 - 16278
[4]Chemical Communications,2014,vol. 50,p. 13910 - 13913
[5]Tetrahedron,2015,vol. 71,p. 9519 - 9527
[6]Chemical Communications,2017,vol. 53,p. 10576 - 10579
[7]New Journal of Chemistry,2018,vol. 42,p. 14067 - 14070
  • 56
  • [ 64896-47-5 ]
  • [ 177991-01-4 ]
  • C212H136 [ No CAS ]
Reference： [1]Chemical Communications,2012,vol. 48,p. 94 - 96
  • 57
  • [ 1431084-98-8 ]
  • [ 177991-01-4 ]
  • C161H92N8O16 [ No CAS ]
Reference： [1]ChemPlusChem,2012,vol. 77,p. 102 - 105
  • 58
  • [ 1431085-01-6 ]
  • [ 177991-01-4 ]
  • C169H92N8 [ No CAS ]
Reference： [1]ChemPlusChem,2012,vol. 77,p. 102 - 105
  • 59
  • [ 1431639-26-7 ]
  • [ 177991-01-4 ]
  • C145H84N16 [ No CAS ]
Reference： [1]ChemPlusChem,2012,vol. 77,p. 102 - 105
  • 60
  • C71H68OSi2 [ No CAS ]
  • [ 177991-01-4 ]
  • C241H132 [ No CAS ]
Reference： [1]ChemPlusChem,2012,vol. 77,p. 102 - 105
  • 61
  • [ 1431639-26-7 ]
  • [ 177991-01-4 ]
  • C217H244N16Si8 [ No CAS ]
Reference： [1]Collection of Czechoslovak Chemical Communications,2012,vol. 77,p. 102 - 105
  • 62
  • C71H68OSi2 [ No CAS ]
  • [ 177991-01-4 ]
  • C313H292Si8 [ No CAS ]
Reference： [1]Collection of Czechoslovak Chemical Communications,2012,vol. 77,p. 102 - 105
  • 63
  • 2,5-di(methylcarboxy)-3,4-bis(4-triisopropylsilylethynylphenyl)-cyclopentadienone [ No CAS ]
  • [ 177991-01-4 ]
  • [ 947595-80-4 ]
Reference： [1]Collection of Czechoslovak Chemical Communications,2012,vol. 77,p. 102 - 105
  • 64
  • [ 1431084-98-8 ]
  • [ 177991-01-4 ]
  • C233H252N8O16Si8 [ No CAS ]
Reference： [1]Collection of Czechoslovak Chemical Communications,2012,vol. 77,p. 102 - 105
  • 65
  • [ 1431085-01-6 ]
  • [ 177991-01-4 ]
  • C241H252N8Si8 [ No CAS ]
Reference： [1]Collection of Czechoslovak Chemical Communications,2012,vol. 77,p. 102 - 105
  • 66
  • [ 1593194-01-4 ]
  • [ 177991-01-4 ]
  • [ 1593194-23-0 ]
YieldReaction ConditionsOperation in experiment
88% With copper(ll) sulfate pentahydrate; sodium ascorbate; triethylamine; tris[(1-benzyl-1H-1,2,3-triazol-4yl)methyl]amine; In tetrahydrofuran; at 23℃; for 16h; 117 mg (0.281 mmol) ethynyl functionalized tetraphenylmethane core 14 and 1.110 g (2.247 mmol) of AB2 azide 3 were dissolved in THF. To the solution were added 56 mg (0.281 mmol)sodium ascorbate, 75 mg (0.140 mmol) TBTA, 3 mL triethylamineand 35 mg (0.140 mmol) CuSO4*5H2O. The solution was stirred at room temperature for 16 h. After adsorption to silica, the solution was purified by column chromatography using firstly hexane and then a mixture of hexane and ethyl acetate (10:1) as eluent to yield 578 mg (88%) of the product as a colorless solid. Rf (hexane/EtOAc10/1)0.72. 1H NMR (300 MHz, THF-d8, 298 K) d 8.93 (s, 4H,Hg), 8.00 (s, 8H, Hi), 7.93 (d, 3JHH8.5 Hz, 8H, Hc), 7.48 (d,3JHH8.5 Hz, 8H, Hd), 2.71 (s, 12H, Hl), 1.19 (m, 168H, HoHp). 13CNMR (75 MHz, THF-d8, 298 K) d 148.67 (C), 147.53 (C), 143.52 (C),136.19 (C), 132.35 (CeH, Cd), 129.89 (C),125.93 (C),125.90 (CeH, Cc),124.16 (CeH, Ci), 119.13 (CeH, Cg), 105.36 (C, Cn), 97.47 (C, Cm), 19.75(CH3, Cl), 19.12 (CH3, Cp), 12.28 (CeH, Co) MALDI-TOF (m/z): calcdfor C149H208N12Si8: 2390.5, found: 2393.4 (and fragments from UV induced decomposition).
Reference： [1]Tetrahedron,2014,vol. 70,p. 3178 - 3184
  • 67
  • 2'-azido-5'-phenyl-1,1':3',1''-terphenyl [ No CAS ]
  • [ 177991-01-4 ]
  • tetrakis(4-(1-(5'-phenyl-[1,1':3',1'’-terphenyl]-20-yl)-1H-1,2,3-triazol-4-yl)phenyl)methane [ No CAS ]
YieldReaction ConditionsOperation in experiment
40% With copper(ll) sulfate pentahydrate; sodium ascorbate; triethylamine; tris[(1-benzyl-1H-1,2,3-triazol-4yl)methyl]amine; In tetrahydrofuran; at 23℃; for 16h; 10 mg (0.024 mmol) ethynyl functionalized tetraphenylmethane core 14 and 67 mg (0.192 mmol) bulky azide 5 were dissolved in THF. To the solution were added 5 mg (0.024 mmol) sodium ascorbate, 6 mg (0.012 mmol) TBTA, 0.5 mL triethylamine and 3 mg (0.012 mmol) CuSO4*5H2O. The solution was stirred at room temperature for 16 h, where upon a yellow-white suspension was obtained.The suspension was purified by column chromatography using firstly a 4:1 mixture of hexane and ethyl acetate and then methylene chloride as eluent to yield 0.017 g (40%) of the compound as a white solid. 1H NMR (700 MHz, CD2Cl2, 298 K) d 7.79 (s,8H, Hj), 7.75 (d, 3JHH7.7 Hz, 8H, Hm), 7.51 (t, 3JHH7.5 Hz, 8H, Hn),7.49 (s, 4H, Hg), 7.49 (d, 3JHH8.4 Hz, 8H, Hc), 7.44 (t, 3JHH7.4 Hz,4H, Ho), 7.28 (m, 24H, HqHs), 7.24 (d, 3JHH8.4 Hz, 8H, Hd), 7.23(m, 16H, Hr). 13C NMR (75 MHz, CD2Cl2, 298 K) d 146.98 (C), 146.87(C), 143.63 (C), 141.10 (C), 140.00 (C), 138.41 (C), 132.53 (C), 131.52(CeH, Cd), 129.61 (CeH, Cn), 129.37 (CeH, Cj), 128.98 (CeH, Cr),128.87 (CeH, CoCq), 128.64 (C), 128.37 (CeH, Cs), 127.86 (CeH,Cm), 125.59 (CeH, Cc), 123.74 (CeH, Cg) FDMS (m/z): calcd forC129H88N12: 1805.7, found: no signal due to UV laser induced decomposition.
Reference： [1]Tetrahedron,2014,vol. 70,p. 3178 - 3184
  • 68
  • [ 105309-59-9 ]
  • [ 1066-54-2 ]
  • [ 177991-01-4 ]
Reference： [1]Tetrahedron,2014,vol. 70,p. 4778 - 4783
[2]Chemical Communications,2017,vol. 53,p. 10576 - 10579
  • 69
  • [ 121129-63-3 ]
  • [ 177991-01-4 ]
  • [ 1616282-37-1 ]
YieldReaction ConditionsOperation in experiment
20% With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; triethylamine; In tetrahydrofuran; at 40℃; for 24h;Inert atmosphere; 2-Iodo-tetrathiafulvalene (7, 33mg, 0.1mmol), Pd(PPh3)2Cl2 (2mg, 0.0034mmol), CuI (1mg, 0.0057mmol), and <strong>[177991-01-4]tetrakis(4-ethynylphenyl)methane</strong> (3, 14mg, 0.017mmol) were dissolved in the mixture of 4mL of NEt3 and 4mL of THF. Then the mixture was degassed with N2. After stirring at 40C over 24h under N2 atmosphere, the mixture was cooled to room temperature and the solvent was evaporated, the residue was dissolved in dichloromethane and filtered. Purification by column chromatography on silica gel (hexane/dichloromethane 5:1 to 2:1, v/v, as eluent) followed by recrystallization from ethanol gave T1 (5mg) in 20% yield as a yellow solid. FT-IR (ν) 3070, 2964, 2923, 2198, 1629, 1492, 1384cm-1; 1H NMR (400MHz, CDCl3) δ 7.35 (d, J=8.0Hz, 8H), 7.12 (d, J=8.0Hz, 8H), 6.54 (s, 4H), 6.33 (s, 8H); 13C NMR (100MHz, CDCl3) δ 146.4, 131.3, 131.0, 124.9, 120.4, 119.3, 119.0, 116.1, 113.4, 93.1, 81.2, 58.9; HRMS (ESI): calcd for C57H28S16, 1223.7722 [M]+, found: 1223.7725.
Reference： [1]Tetrahedron,2014,vol. 70,p. 4778 - 4783
  • 70
  • [ 62-53-3 ]
  • [ 177991-01-4 ]
Reference： [1]Chemistry - A European Journal,2014,vol. 20,p. 16273 - 16278
[2]Chemical Communications,2017,vol. 53,p. 10576 - 10579
  • 71
  • [ 76-83-5 ]
  • [ 177991-01-4 ]
Reference： [1]Chemistry - A European Journal,2014,vol. 20,p. 16273 - 16278
  • 72
  • [ 177991-01-4 ]
  • 1,3-dimethyl 5-azidoisophthalate [ No CAS ]
  • octamethyl 5,5',5'',5'''-((methanetetrayltetrakis(benzene-4,1-diyl))tetrakis(1H-1,2,3-triazole-4,1-diyl))tetraisophthalate [ No CAS ]
Reference： [1]Journal of the American Chemical Society,2016,vol. 138,p. 2142 - 2145
  • 73
  • [ 76-83-5 ]
  • [ 62-53-3 ]
  • [ 177991-01-4 ]
Reference： [1]Chemical Communications,2016,vol. 52,p. 12881 - 12884
  • 74
  • [ 630-76-2 ]
  • [ 1066-54-2 ]
  • [ 177991-01-4 ]
Reference： [1]Chemical Communications,2016,vol. 52,p. 12881 - 12884
  • 75
  • [ 76-84-6 ]
  • [ 177991-01-4 ]
Reference： [1]Chemical Communications,2017,vol. 53,p. 10576 - 10579
  • 76
  • [ 134080-67-4 ]
  • [ 1066-54-2 ]
  • [ 177991-01-4 ]
YieldReaction ConditionsOperation in experiment
72% With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; triethylamine; In N,N-dimethyl-formamide; at 35℃; for 15h;Inert atmosphere; In a 500 mL three-necked round-bottomed flask was added tetrakis(4-iodophenyl)methane (17; 10.86 g, 13.19 mmol), PdCl2(PPh3)2 (1.85 g, 2.63 mmol), CuI (501 mg, 2.63 mmol), ethynyltrimethylsilane (2; 18.6 mL, 131.90 mmol), anhyd DMF (180 mL), and Et3N (20 mL) under N2 atmosphere. The reaction mixture was stirred for 15 h at 35 C, after this time the mixture was filtered and the filter cake was saved. The filtrate was diluted with Et2O (200 mL), washed with aq 10% HCl (100 mL), followed by H2O (2 200 mL) and brine (3 200 mL). The organic phase was dried (anhyd Na2SO4) and concentrated. The crude material was purified by column chromatography (PE/CH2Cl2 0:1) to give the tetrakis[4-(trimethylsilylethynyl)phenyl]methane, which was combined with the filter cake; yield: 7.5 g (80%); pale yellow solid. 1H NMR (300 MHz, CDCl3): = 7.34-7.31 (d, J = 8.4 Hz, 8 H), 7.05-7.02 (d, J = 8.4 Hz, 8 H), 0.23 (s, 36 H).21 In a 500 mL one-neck round bottom flask a mixture of tetrakis[4-(trimethylsilylethynyl)phenyl]methane (7.5 g, 10.65 mmol), aq 1 N NaOH (85 mL), and THF (200 mL) was stirred for 1 h at RT. The mixture was concentrated to remove the THF and extracted with CH2Cl2 (200 mL). The organic phase was washed with H2O (100 mL) and brine (100 mL). The organic layer was dried (anhyd Na2SO4) and con-This document was downloaded for personal use only.The resulting residue was purified by column chromatography (PE/toluene 15:1) to afford 18; yield: 3.23 g (72%); pale yellow solid. 1H NMR (300 MHz, CDCl3): = 7.40-7.37 (d, J = 8.4 Hz, 8 H), 7.13-7.10 (d, J = 8.4 Hz, 8 H), 3.06 (s, 4 H). 13C NMR (100 MHz, CDCl3): = 146.2, 131.6, 130.7, 120.2, 83.1, 77.6, 64.7.21
Reference： [1]Synthesis,2022,vol. 54,p. 1643 - 1651
  • 77
  • [ 917081-96-0 ]
  • [ 177991-01-4 ]
  • C105H68N8O12 [ No CAS ]
YieldReaction ConditionsOperation in experiment
37% With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; triethylamine; In tetrahydrofuran; at 60℃; for 7h;Inert atmosphere; 1,1',1'',1'''-([Methanetetrayltetrakis(benzene-4,1-diyl)]-tetrakis(ethyne-2,1-diyl)}tetrakis(benzene-4,1-diyl))tetrakis[5-methylpyrimidine-2,4(1H,3H)-dione] (19) To a solution of <strong>[177991-01-4]tetrakis(4-ethynylphenyl)methane</strong> (18; 700 mg, 1.68 mmol), 7 (3.47 g, 8.06 mmol), PdCl2(PPh3)2 (58.8 mg, 0.084 mmol), and CuI (32 mg, 0.168 mmol) in anhyd THF (120 mL) was added Et3N (9.3 mL, 67.20 mmol) at RT. The reaction mixture was stirred at 60 C for 7 h under N2. The mixture was directly evaporated and the residue was subjected to column chromatography (CH2Cl2/EtOAc 10:1) to afford the protected thymine tetramer as a white solid (1.02 g, 37%).The protected thymine tetramer (1.02 g, 0.63 mmol) from above was dissolved in MeOH (30 mL) and hydrazine hydrate (1.2 mL, 25.0 mmol) was added. The mixture was stirred at 100 C for 9 h. The mixture was cooled to RT and filtered. The precipitate was dried in vacuo; yield: 682 mg (33% over 2 steps); white powder; mp: 263-265 C. 1H NMR (300 MHz, DMSO-d6): = 11.36 (br, 1 H), 7.66 (s, 1 H), 7.64 (s, 2 H), 7.60-7.57 (d, J = 8.4 Hz, 1 H), 7.50-7.47 (d, J = 8.4 Hz, 2 H), 7.24- 7.22 (d, J = 8.4 Hz, 2 H), 1.81 (s, 3 H). 13C NMR (125 MHz, DMSO-d6): = 164.1, 150.0, 145.8, 140.7, 138.9, 131.9, 131.1, 130.6, 127.0, 121.6, 120.1, 109.5, 89.6, 88.8, 64.3, 11.7.HR-MALDI: m/z [M + H]+ calcd for C77H53N8O8: 1217.3981; found: 1217.3971.
Reference： [1]Synthesis,2022,vol. 54,p. 1643 - 1651
  • 78
  • [ 917081-91-5 ]
  • [ 177991-01-4 ]
  • C117H112N20O16 [ No CAS ]
YieldReaction ConditionsOperation in experiment
1.3 g With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; triethylamine; In tetrahydrofuran; at 60℃; for 2.5h;Inert atmosphere; 7,7',7'',7'''-([Methanetetrayltetrakis(benzene-4,1-diyl)]-tetrakis(ethyne-2,1-diyl)}tetrakis(benzene-4,1-diyl))tetrakis(7Himidazo[4,5-d]pyrimidin-4-amine) (20) To a solution of <strong>[177991-01-4]tetrakis(4-ethynylphenyl)methane</strong> (18; 500 mg, 1.2 mmol), 10 (3.09 g, 5.76 mmol), PdCl2(PPh3)2 (42 mg, 0.06 mmol), and CuI (22 mg, 0.12 mmol) in anhyd THF (100 mL) was added Et3N (6.6 mL, 48 mmol) at RT. The reaction mixture was stirred at 60 C for 2.5 h under N2. The mixture was directly evaporated and the residue was subjected to column chromatography (CH2Cl2/MeOH 20:1) to afford the protected adenine as a white solid (1.3 g). The protected adenine (1.3 g, 0.63 mmol) from above was dissolved in MeOH (30 mL) and KOH (1.05 g, 18.9 mmol) was added. The mixture was stirred at 70 C for 36 h. The mixture was cooled to RT and filtered. The precipitate was washed with THF and dried in vacuo; yield: 478 mg (31%, over 2 steps); light yellow solid; mp > 300 C. 1H NMR (300 MHz, DMSO-d6): = 8.68 (s, 1 H), 8.23 (s, 1 H), 8.07- 8.04 (d, J = 8.1 Hz, 2 H), 7.77-7.75 (d, J = 8.1 Hz, 2 H), 7.60-7.59 (d, J = 4.8 Hz, 2 H), 7.42 (s, 2 H), 7.24 (br, 2 H). 13C NMR (125 MHz, DMSO-d6): = 156.3, 153.2, 149.0, 139.3, 132.5, 131.2, 130.7, 122.5, 120.8, 120.3, 119.3, 89.7, 89.0.HR-MALDI: m/z [M + H]+ calcd C77H49N20: 1253.4444; found: 1253.4429.
Reference： [1]Synthesis,2022,vol. 54,p. 1643 - 1651
  • 79
  • [ 917081-91-5 ]
  • [ 177991-01-4 ]
  • C126H124N20O16 [ No CAS ]
YieldReaction ConditionsOperation in experiment
544 mg With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; triethylamine; In tetrahydrofuran; at 60℃; for 2.5h;Inert atmosphere; 7,7',7'',7'''-([Adamantane-1,3,5,7-tetrayltetrakis(benzene-4,1-diyl)] tetrakis(ethyne-2,1-diyl)}tetrakis(benzene-4,1-diyl))tetrakis(7H-imidazo[4,5-d]pyrimidin-4-amine) (25) To a solution of <strong>[177991-01-4]tetrakis(4-ethynylphenyl)methane</strong> (23; 536 mg, 1.0 mmol), 10 (2.57 g, 4.8 mmol), PdCl2(PPh3)2 (35 mg, 0.05 mmol), and CuI (19 mg, 0.1 mmol) in anhyd THF (100 mL) was added Et3N (5.5 mL, 40.0 mmol) at RT. The reaction mixture was stirred at 60 C for 2.5 h under N2. The mixture was directly evaporated and the residue was subjected to column chromatography (CH2Cl2/MeOH 20:1-10:1) to afford the protected adenine as a light yellow solid (2.06 g). The protected adenine (2.06 g, 1.16 mmol) from above was dissolved in MeOH (30 mL) and solid KOH (1.62 g, 29.0 mmol) was added. The mixture was stirred at 70 C for 36 h. The mixture was cooled to RT and filtered. The precipitate was washed with THF and dried in vacuo; yield: 544 mg (42%, over 2 steps); brownish yellow solid; mp > 300 C. 1H NMR (300 MHz, DMSO-d6): = 8.68 (s, 1 H), 8.24 (s, 1 H), 8.07- 8.04 (d, J = 7.2 Hz, 2 H), 7.78-7.75 (d, J = 7.8 Hz, 2 H), 7.68 (s, 2 H), 7.60-7.58 (d, J = 6.6 Hz, 2 H), 7.41 (s, 2 H). 13C NMR (125 MHz, DMSO-d6): = 156.4, 153.2, 150.4, 149.0, 139.3, 132.4, 131.3, 125.8, 122.5, 121.1, 119.6, 119.4, 90.4, 88.3, 45.6.
Reference： [1]Synthesis,2022,vol. 54,p. 1643 - 1651
  • 80
  • [ 28425-04-9 ]
  • [ 177991-01-4 ]
  • C81H136Cl4P8Pd4 [ No CAS ]
Reference： [1]Chemical Science,2022,vol. 13,p. 1111 - 1118

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