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Chemical Structure| 89343-06-6 Chemical Structure| 89343-06-6
Chemical Structure| 89343-06-6

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CAS No.: 89343-06-6

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Product Details of [ 89343-06-6 ]

CAS No. :89343-06-6
Formula : C11H22Si
M.W : 182.38
SMILES Code : CC([Si](C(C)C)(C#C)C(C)C)C
MDL No. :MFCD00075452
InChI Key :KZGWPHUWNWRTEP-UHFFFAOYSA-N
Pubchem ID :2734682

Safety of [ 89343-06-6 ]

GHS Pictogram:
Signal Word:Danger
Hazard Statements:H225-H315-H319
Precautionary Statements:P501-P240-P210-P233-P243-P241-P242-P264-P280-P370+P378-P337+P313-P305+P351+P338-P362+P364-P303+P361+P353-P332+P313-P403+P235
Class:3
UN#:1993
Packing Group:Ⅲ

Calculated chemistry of [ 89343-06-6 ] Show Less

Physicochemical Properties

Num. heavy atoms 12
Num. arom. heavy atoms 0
Fraction Csp3 0.82
Num. rotatable bonds 3
Num. H-bond acceptors 0.0
Num. H-bond donors 0.0
Molar Refractivity 61.02
TPSA ?

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

0.0 ?2

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

4.73
Log Po/w (WLOGP)?

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

3.92
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.

4.06
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

1.91
Consensus Log Po/w?

Consensus Log Po/w: Average of all five predictions

3.55

Water Solubility

Log S (ESOL):?

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

-3.75
Solubility 0.0322 mg/ml ; 0.000177 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.

-4.46
Solubility 0.00633 mg/ml ; 0.0000347 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

-2.54
Solubility 0.532 mg/ml ; 0.00292 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

 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

 No
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

 No
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.

-4.05 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

 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

2.0 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)

 3.78

Application In Synthesis [ 89343-06-6 ]

* 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 [ 89343-06-6 ]

[ 89343-06-6 ] Synthesis Path-Downstream   1~26

  • 1
  • [ 54523-47-6 ]
  • [ 89343-06-6 ]
  • [ 325834-46-6 ]
  • 2
  • [ 145691-59-4 ]
  • [ 89343-06-6 ]
  • [ 945867-08-3 ]
  • 3
  • [ 689291-89-2 ]
  • [ 89343-06-6 ]
  • [ 1038395-11-7 ]
YieldReaction ConditionsOperation in experiment
94% With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; triethylamine; at 20℃; for 24.0833h;Inert atmosphere; Compound 12 (1.62 g, 5.20 mmol), triisopropylsilylacetylene (1.15 mL, 0.950 g, 5.20 mmol), PdCl2(PPh3)2 (46 mg, 0.065 mmol), and CuI (25 mg, 0.13 mmol) were added to Et3N (20 mL). The solution was bubbled with N2 at rt for 5 min and then stirred at rt and under N2 protection for 24 h. After the reaction was completed as checked by TLC analysis, the solvent was removed by rotary evaporation. The resulting residue was diluted with CHCl3. The mixture was filtered through a MgSO4 pad. The solution obtained was sequentially washed with HCl (aq 10%) and brine. The organic layer was dried over MgSO4 and concentrated under vacuum to give crude 23, which was further purified by silica flash column chromatography (hexanes/CH2Cl2, 4:1) to yield compound 23 (1.78 g, 4.87 mmol, 94%) as a colorless oil. IR (KBr) 2944, 2891, 2866, 2736, 2156, 1695, 1582, 1469, 1383 cm-1; 1H NMR (CDCl3, 500 MHz) δ 10.53 (s, 1H), 8.05 (d, J=2.0 Hz, 1H), 7.67 (dd, J=8.5, 1.5 Hz, 1H), 7.47 (d, J=8.0 Hz, 1H), 1.15 (s, 21H); 13C NMR (CDCl3, 125 MHz) δ 190.4, 137.5, 136.7, 135.4, 130.1, 125.9, 123.4, 101.1, 100.9, 18.8, 11.4; HRMS (CI) m/z calcd for C18H25BrOSi 364.0858, found 365.1071 [M+H]+.
  • 4
  • [ 19955-99-8 ]
  • [ 89343-06-6 ]
  • [ 1115020-88-6 ]
  • 5
  • [ 2622-63-1 ]
  • [ 89343-06-6 ]
  • (E)-1-methyl-2-[2-(2-triisopropylsilylvinyl)phenyl]-1H-benzimidazole [ No CAS ]
  • 6
  • [ 1006-68-4 ]
  • [ 89343-06-6 ]
  • [ 1187772-47-9 ]
  • 7
  • [ 145691-59-4 ]
  • [ 89343-06-6 ]
  • [ 1239921-54-0 ]
  • 8
  • [ 89343-06-6 ]
  • [ 211029-67-3 ]
  • [ 1244029-72-8 ]
  • 9
  • [ 4949-69-3 ]
  • [ 89343-06-6 ]
  • [ 1307853-94-6 ]
  • 10
  • [ 626-44-8 ]
  • [ 89343-06-6 ]
  • [ 867017-53-6 ]
  • 11
  • [ 16618-68-1 ]
  • [ 89343-06-6 ]
  • [ 1610450-12-8 ]
YieldReaction ConditionsOperation in experiment
430 mg With copper(l) iodide; tetrakis(triphenylphosphine) palladium(0); triethylamine; In N,N-dimethyl-formamide; at 80℃; for 1h; (i) 3-Methoxy-5-((triisopropylsilyl)ethvnyl)aniline Pd(PPh3)4 (286 mg, 0.247 mmol) was added to a degassed suspension of 3-bromo-5- methoxyaniline (500 mg, 2.475 mmol), Cu(l) iodide (47.1 mg, 0.247 mmol), and ethynyltriisopropylsilane (0.833 mL, 3.71 mmol) in TEA (3 mL) and DMF (3 mL). Heated at 80C (block temp.) for 1 h then partitioned between ethyl acetate (20 mL) and saturated NH4CI solution (20 mL). The organics were separated, and washed with 20%w/w NaCI solution, separated, dried (MgS04) filtered and solvents evaporated. The crude product was purified by chromatography on the Companion (12 g column, 10% EtOAc:isohexane to 40%) to afford the sub-title compound (430 mg) as a clear brown oil. 1 H NMR (400 MHz, CDCI3) delta 6.44 (s, 1 H), 6.43 (s, 1 H), 6.20 (t, 1 H), 3.76 (s, 3H), 3.68 (s, 2H), 1.12 (s, 21 H). LCMS m/z 304 (M+H)+ (ES+)
  • 12
  • [ 42237-85-4 ]
  • [ 89343-06-6 ]
  • 3-amino-5-((triisopropylsilyl)ethynyl)benzoic acid [ No CAS ]
YieldReaction ConditionsOperation in experiment
45.5 g With copper(l) iodide; tetrakis(triphenylphosphine) palladium(0); triethylamine; In N,N-dimethyl-formamide; at 90℃; for 2h; Pd(PPh3)4 (9.36 g, 8.10 mmol) was added to a degassed suspension of <strong>[42237-85-4]3-amino-5-bromobenzoic acid</strong> (50 g, 231 mmol), CuI (1.499 g, 7.87 mmol), and ethynylriisopropylsilane (80 mL, 356 mmol) in Et3N (300 mL) and DMF (300 mL). The mixture was heated to 90 C. for 2 h. The mixture was cooled and carefully poured into ice-cold HCl (2.0M aq.) (1100 mL, 2200 mmol) and diluted with diethyl ether (500 mL). The biphasic mixture was filtered to remove palladium residues. The layers of the filtrate were separated and the aqueous phase was extracted with a further portion of diethyl ether (300 mL). The organic phases were combined and washed with 20% brine (2*300 mL), 40% brine (300 mL), dried (MgSO4), filtered and concentrated in vacuo affording a pale orange solid. The solid was recrystallised in acetonitrile (250 mL) and collected by filtration, washing with fresh acetonitrile (2*30 mL) affording the product as a yellow solid. The solid was slurried in hexane (250 mL) for 5 h then filtered, washing with more hexane to afford the sub-title compound (45.5 g) as a pale yellow solid. 1H NMR (400 MHz, DMSO-d6) delta: 12.87 (bs, 1H), 7.18 (t, 1H), 7.10 (t, 1H), 6.86 (t, 1H), 5.54 (bs, 2H), 1.10 (s, 21H). LCMS m/z 318 (M+H)+ (ES+); 316 (M-H)- (ES-)
45.5 g With copper(l) iodide; tetrakis(triphenylphosphine) palladium(0); triethylamine; In N,N-dimethyl-formamide; at 90℃; for 2h; Pd(PPh3)4 (9.36 g, 8.10 mmol) was added to a degassed suspension of <strong>[42237-85-4]3-amino-5-bromobenzoic acid</strong> (50 g, 231 mmol), Cul (1.499 g, 7.87 mmol), and ethynyltriisopropylsilane(80 mL, 356 mmol) in Et3N (300 mL) and DMF (300 mL). The mixture was heated to 90C for2h. The mixture was cooled and carefully poured into ice-cold HCI (2.OM aq.) (1100 mL, 2200mmol) and diluted with diethyl ether (500 mL). The biphasic mixture was filtered to remove palladium residues. The layers of the filtrate were separated and the aqueous phase was extracted with a further portion of diethyl ether (300 mL). The organic phases were combined and washed with 20% brine (2 x 300 mL), 40% brine (300 mL), dried (MgSO4), filtered and concentrated in vacuo affording a pale orange solid. The solid was recrystallised inacetonitrile (250 mL) and collected by filtration, washing with fresh acetonitrile (2 x 30 mL) affording the product as a yellow solid. The solid was slurried in hexane (250 mL) for 5h then filtered, washing with more hexane to afford the sub-title compound (45.5 g) as a pale yellow solid.1H NMR (400 MHz, DMSO-d6) O: 12.87 (bs, 1H), 7.18 (t, 1H), 7.10 (t, 1H), 6.86 (t, 1H), 5.54(bs, 2H), 1.10 (5, 21H).LCMS mlz 318 (M+H) (ES); 316 (M-H (ES)
45.5 g With copper(l) iodide; tetrakis(triphenylphosphine) palladium(0); triethylamine; In N,N-dimethyl-formamide; at 90℃; for 2h;Inert atmosphere; (i) 3-Amino-5-((triisopropylsilyl)ethynyl)benzoic acidPd(PPh3)4 (9.36 g, 8.10 mmol) was added to a degassed suspension of <strong>[42237-85-4]3-amino-5-bromobenzoic acid</strong> (50 g, 231 mmol), Cul (1.499 g, 7.87 mmol) and ethynyltriisopropylsilane(80 mL, 356 mmcl) in Et3N (300 mL) and DMF (300 mL). The mixture was heated to 90 Cfor2 h. The mixture was cooled and carefully poured into ice-cold HCI (2.0 M aq.) (1100 mL,2200 mmol) and diluted with diethyl ether (500 mL). The biphasic mixture was filtered to remove palladium residues. The layers of the filtrate were separated and the aqueous phase was extracted with a further portion of diethyl ether (300 mL). The organic phases were combined and washed with 20% brine (2 x 300 mL), 40% brine (300 mL), dried (MgSO4),filtered and concentrated in vacuo affording a pale orange solid. The solid was recrystallised in acetonitrile (250 mL) and collected by filtration, washing with fresh acetonitrile (2 x 30 mL) affording the product as a yellow solid. The solid was slurried in hexane (250 mL) for 5 h then filtered, washing with more hexane to afford the sub-title compound (45.5 g) as a pale yellow solid.1H NMR (400 MHz, DMSO-d6) O: 12.87 (bs, iH), 7.18 (t, iH), 7.10 (t, IH), 6.86 (t, IH), 5.54 (bs, 2H), 1.10 (s, 21H).LCMS m/z 318 (M+H) (ES); 316 (M-H) (ES-)
45.5 g With copper(l) iodide; tetrakis(triphenylphosphine) palladium(0); In triethylamine; N,N-dimethyl-formamide; at 90℃; for 2h;Inert atmosphere; (i) 3-Amino-5-((triisopropylsilyl)ethvnyl)benzoic acidPd(PPh3)4(9 36 g, 8.10 mmol) was added to a degassed suspension of <strong>[42237-85-4]3-amino-5-bromobenzoic acid</strong> (50 g, 231 mmol), Cul (1.499 g, 7.87 mmol), and ethynyltriisopropylsilane (80 mL, 356 mmol) in triethylamine (300 mL) and DMF (300 mL). The mixture was heated to 90C for 2h. The mixture was cooled and carefully poured into ice-cold HCI (2.0M aq.) (1 100 mL, 2200 mmol) and diluted with diethyl ether (500 mL). The biphasic mixture was filtered to remove palladium residues. The layers of the filtrate were separated and the aqueous phase was extracted with a further portion of diethyl ether (300 mL). The organic phases were combined and washed with 20% brine (2 x 300 mL), 40% brine (300 mL), dried (MgS04), filtered and concentrated in vacuo affording a pale orange solid. The solid was recrystallised in acetonitrile (250 mL) and collected by filtration, washing with fresh acetonitrile (2 x 30 mL) affording the product as a yellow solid. The solid was slurried in hexane (250 mL) for 5h then filtered, washing with more hexane to afford the sub-title compound (45.5 g) as a pale yellow solid.1H NMR (400 MHz, DMSO-de) delta: 12.87 (bs, 1 H), 7.18 (t, 1 H), 7.10 (t, 1 H), 6.86 (t, 1 H), 5.54 (bs, 2H), 1.10 (s, 21 H). LCMS m/z 318 (M+H)+(ES+); 316 (M-H)"(ES")

  • 13
  • [ 42237-85-4 ]
  • [ 89343-06-6 ]
  • 3-((4-((4-((tert-butoxycarbonyl)amino)naphthalen-1-yl)oxy)pyridin-2-yl)amino)-5-((triisopropylsilyl)ethynyl)benzoic acid [ No CAS ]
  • 14
  • [ 626-44-8 ]
  • [ 89343-06-6 ]
  • 1,3,5-tris(triisopropylsilylethynyl)benzene [ No CAS ]
  • 15
  • [ 303-49-1 ]
  • [ 89343-06-6 ]
  • N,N-dimethyl-3-(3-((triisopropylsilyl)ethynyl)-10,11-dihydro-5H-dibenzo[b,f]azepine-5-yl)propane-1-amine [ No CAS ]
YieldReaction ConditionsOperation in experiment
87% With chloro[2-(dicyclohexylphosphino)-3,6-dimethoxy-2?,4?,6?-tri-1-propyl-1,1?-biphenyl][2-(2-aminoethyl)phenyl]palladium(II); caesium carbonate; In acetonitrile; at 85℃; for 7h; In a glove box with argon atmosphere <strong>[303-49-1]clomipramin</strong>e (100.0 mg, 0.285 mmol, 1 equiv), (triisopropylsilyl)acetylene (104.0 mg, 0.569 mmol, 2 equiv), Cs2CO3 (0.231 g, 0.712 mmol, 2.5 equiv), acetonitrile (1 mL) and XPhos-precatalyst PdG1 (6.31 mg, 0.0085 mmol, 3%) were all mixed in a vial. Subsequently the vial was closed, removed from the glove box and the reaction mixture was stirred in a preheated heating block at 85 C. After 7 h the reaction was allowed to cool to room temperature, diluted with NaHCO3 10% (10 mL) and extracted with ethyl acetate. The combined organic phases were dried over MgSO4, filtered and evaporated. The crude product was purified by flash column chromatography (Dichloromethane followed by 5% methanol in dichloromethane) to yield compound 26 as brown oil (128.1 mg, 87%). Rf (5% methanol in dichloromethane) 0.41. 1H NMR (400 MHz, CDCl3): delta 7.20-6.87 (m, 7H) 3.77 (t, 2H, J = 8.0 Hz) 3.12 (s, 4H) 2.48 (t, 2H, J = 7.4 Hz) 2.27 (d, 6H) 1.82 (quint. 2H, J = 8 Hz) 1.13 (s, 21H, (triisopropylsilyl)). 13C NMR (100 MHz, CDCl3): delta 148.5 148.3, 135.2, 135.0, 130.6-120.8, 107.9 90.1, 57.8, 49.1, 45.4, 33.0, 32.4, 25.7, 19.4, 12.0. MS
  • 16
  • [ 443-82-3 ]
  • [ 89343-06-6 ]
  • [ 106-51-4 ]
  • 1,11-difluoro-6,13-bis[(triisopropylsilyl)ethynyl]pentacene [ No CAS ]
  • 1,8-difluoro-6,13-bis[(triisopropylsilyl)ethynyl]pentacene [ No CAS ]
  • 17
  • [ 443-82-3 ]
  • [ 89343-06-6 ]
  • [ 106-51-4 ]
  • C44H54F2O2Si2 [ No CAS ]
  • C44H54F2O2Si2 [ No CAS ]
  • 18
  • [ 89343-06-6 ]
  • [ 175278-00-9 ]
  • triisopropyl((2-(trifluoromethoxy)phenyl)ethynyl)silane [ No CAS ]
YieldReaction ConditionsOperation in experiment
68% With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; triethylamine; at 30℃; for 1h;Inert atmosphere; Sealed tube; General procedure: For example, synthesis of 1,2-diphenylethyne, 3a. To an oven-dried 5 mL microwave vessel was added Pd(PPh3)2Cl2 (3.5 mg, 0.005 mmol, 2 mol %) and CuI (1.9 mg, 0.01 mmol, 4 mol %). The vessel was then capped and purged with N2 before addition of Cyrene (0.5 mL, 0.5 M), Et3N (38 muL, 0.275 mmol, 1.1 equiv), iodobenzene (27.9 muL, 0.25 mmol, 1 equiv), and phenylacetylene (28.8 muL, 0.263 mmol, 1.05 equiv). The reaction mixture was heated to 30 C and maintained at this temperature with stirring for 1 h before the vessel was vented, and decapped. The solution was then diluted with EtOAc (10 mL), and washed with water (2× 20 mL) and brine (2 × 20 mL). The organics were then passed through a hydrophobic frit and concentrated under reduced pressure to give a yellow oil, which was purified by flash chromatography (silica gel, 0-5% Et2O in petroleum ether) to afford the title compound as a white solid (44.5 mg, quant.).
  • 19
  • [ 63927-22-0 ]
  • [ 89343-06-6 ]
  • [ 2937-50-0 ]
  • C24H32BrNO2Si [ No CAS ]
  • 20
  • [ 39795-60-3 ]
  • [ 89343-06-6 ]
  • 4-[4-[(triisopropylsilyl)ethynyl]phenyl]pyridine [ No CAS ]
  • 21
  • [ 39795-60-3 ]
  • [ 89343-06-6 ]
  • 2-phenyl-4-[4-[(triisopropylsilyl)ethynyl]phenyl]pyridine [ No CAS ]
  • 22
  • [ 40000-20-2 ]
  • [ 89343-06-6 ]
  • 5-(triisopropylsilylethynyl)-1,10-phenanthroline [ No CAS ]
  • 23
  • [ 20101-92-2 ]
  • [ 89343-06-6 ]
  • 2-(4-chloro-2-((triisopropylsilyl)ethynyl)phenyl)acetamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
75% With bis[dichloro(pentamethylcyclopentadienyl)iridium(III)]; silver(I) acetate; sodium acetate; silver(I) triflimide; In 1,2-dichloro-ethane; at 120℃; under 760.051 Torr;Schlenk technique; Inert atmosphere; Phenylacetamide compound 1b (34.0 mg, 0.20 mmol) was sequentially added to a 15 mL Schlenk reaction tube under an atmosphere of atmospheric pressure.Trivalent ruthenium catalyst [Cp*IrCl2] 2 (1.60 mg, 0.002 mmol), bistrifluoromethanesulfonimide silver salt (3.9 mg, 0.01 mmol), sodium acetate (2.5 mg, 0.03 mmol),Silver acetate (10.0 mg, 0.06 mmol), and finally a solution of alkynyl compound 2a (20 muL, 0.30 mmol) in 1,2-dichloroethane (DCE, 1 mL) was charged into the reactor with a syringe.The reaction was carried out at a temperature of 120 C for 24 h. After completion of the reaction, the mixture was cooled to room temperature, suction filtered over Celite, and evaporated.The crude product was chromatographed on the prepared silica gel plate, and the selected developing solvent or eluent was petroleum ether and ethyl acetate in a volume ratio of 10:1.The product 2-(4-chloro-2-((triisopropyl)ethynyl)phenyl)acetamide (3b) was obtained, 52.3 mg, yield 75%, purity 95%.
  • 24
  • [ 615-37-2 ]
  • [ 89343-06-6 ]
  • [ 51997-51-4 ]
  • 1-((9H-carbazol-4-yl)oxy)-3-(3-methyl-2-((triisopropylsilyl)ethynyl)phenyl)propan-2-ol [ No CAS ]
  • 25
  • [ 89343-06-6 ]
  • [ 166599-84-4 ]
  • (benzofuran-4-ylethynyl)triisopropylsilane [ No CAS ]
  • 26
  • [ 2734-70-5 ]
  • [ 89343-06-6 ]
  • (E)-1-(2,6-dimethoxyphenyl)-2-((triisopropylsilyl)ethynyl)diazene [ No CAS ]
 

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