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[ CAS No. 23152-99-0 ] {[proInfo.proName]}

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Chemical Structure| 23152-99-0
Chemical Structure| 23152-99-0
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Product Citations

Product Citations

Krzysztof Kuciński ; Grzegorz Hreczycho ; DOI:

Abstract: Commercially available and inexpensive potassium bis(trimethylsilyl)amide (KHMDS) serves as an efficient transition metal-free catalyst for the catalytic sp C?H silylation of several terminal alkynes including two pharmaceuticals. Overall, the presented system allows the synthesis of various attractive silylacetylenes under mild conditions, making this approach an environmentally benign and sustainable alternative to existing synthetic solutions.

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Product Details of [ 23152-99-0 ]

CAS No. :23152-99-0 MDL No. :MFCD03839988
Formula : C11H12 Boiling Point : -
Linear Structure Formula :(CH3)2CHC6H4CCH InChI Key :CODCGGILXPHCLE-UHFFFAOYSA-N
M.W : 144.21 Pubchem ID :637501
Synonyms :

Calculated chemistry of [ 23152-99-0 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 11
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.27
Num. rotatable bonds : 1
Num. H-bond acceptors : 0.0
Num. H-bond donors : 0.0
Molar Refractivity : 48.96
TPSA : 0.0 ?2

Pharmacokinetics

GI absorption : Low
BBB permeant : Yes
P-gp substrate : No
CYP1A2 inhibitor : No
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : Yes
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -4.35 cm/s

Lipophilicity

Log Po/w (iLOGP) : 2.7
Log Po/w (XLOGP3) : 3.98
Log Po/w (WLOGP) : 2.87
Log Po/w (MLOGP) : 4.68
Log Po/w (SILICOS-IT) : 3.46
Consensus Log Po/w : 3.54

Druglikeness

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

Water Solubility

Log S (ESOL) : -3.58
Solubility : 0.038 mg/ml ; 0.000264 mol/l
Class : Soluble
Log S (Ali) : -3.68
Solubility : 0.03 mg/ml ; 0.000208 mol/l
Class : Soluble
Log S (SILICOS-IT) : -3.28
Solubility : 0.0759 mg/ml ; 0.000526 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 1.0 alert
Leadlikeness : 2.0
Synthetic accessibility : 1.6

Safety of [ 23152-99-0 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P305+P351+P338 UN#:N/A
Hazard Statements:H315-H319-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 23152-99-0 ]

* 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 [ 23152-99-0 ]

[ 23152-99-0 ] Synthesis Path-Downstream   1~16

  • 1
  • [ 667-49-2 ]
  • [ 23152-99-0 ]
  • [ 75599-92-7 ]
  • [ 75599-95-0 ]
  • 2
  • [ 667-49-2 ]
  • [ 23152-99-0 ]
  • 1,4,4-Trifluoro-2-(4-isopropyl-phenyl)-cyclobut-2-enecarbonyl fluoride [ No CAS ]
  • 2,2,3,4-Tetrafluoro-6-(4-isopropyl-phenyl)-2H-pyran [ No CAS ]
  • 3
  • [ 23152-99-0 ]
  • [ 99255-51-3 ]
  • [ 99255-60-4 ]
  • 4
  • [ 23152-99-0 ]
  • [ 128217-88-9 ]
  • p-HS-C6H4-X (X=Br or F) [ No CAS ]
  • 4-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-2-[4-(4-isopropyl-phenylethynyl)-benzenesulfonyl]-butyric acid <i>tert</i>-butyl ester [ No CAS ]
  • 5
  • [ 926008-95-9 ]
  • [ 23152-99-0 ]
  • C21H18N3Cl [ No CAS ]
  • 6
  • [ 23152-99-0 ]
  • [ 544-92-3 ]
  • 3-(4-isopropylphenyl)propynenitrile [ No CAS ]
  • 10
  • [ 23152-99-0 ]
  • 4-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-2-[4-(4-isopropyl-phenylethynyl)-benzenesulfonyl]-butyric acid [ No CAS ]
  • 11
  • [ 23152-99-0 ]
  • 4,6-diamino-5-(1,2-bis(4-isopropylphenyl)ethenyl)pyrimidine [ No CAS ]
  • 12
  • [ 23152-99-0 ]
  • 4-amino-5,6-(bis-4-(2-propyl)phenyl)-7-(4-dimethylaminophenyl)pyrido[2.3-d]pyrimidine [ No CAS ]
  • 13
  • [ 23152-99-0 ]
  • C19H18NS(1+)*BF4(1-) [ No CAS ]
  • 14
  • [ 122-03-2 ]
  • [ 23152-99-0 ]
  • 15
  • [ 23152-99-0 ]
  • [ 54290-22-1 ]
  • [ 79135-52-7 ]
YieldReaction ConditionsOperation in experiment
11.40 g (87%) dichlorobis(triphenylphosphine)palladium[II]; copper(I) iodide; In triethylamine; The crude 4-isopropylphenylacetylene was dissolved in triethylamine (100 mL). 4-iodoisopropylbenzene (12.3 g, 50 mmol), dichlorobis(triphenylphosphine)palladium(II) (0.70 g, 1 mmol), and copper(I) iodide (1.5 g) were added. The reaction was stirred at room temperature for 2 days, heated to reflux for 1 hour, cooled, diluted with hexanes, and filtered. The filtrate was evaporated under reduced pressure. The residue was filtered through a pad of silica gel with hexanes, and the solvent was evaporated to give 11.40 g (87%) of 1,2-bis(4-(2-propyl)phenyl)acetylene.
  • 16
  • [ 1118-02-1 ]
  • [ 23152-99-0 ]
  • N-hydroxy-N-[4-[4-(1-methylethyl)phenyl]-3-butyn-2-yl]urea [ No CAS ]
YieldReaction ConditionsOperation in experiment
Example 22 Preparation of N-Hydroxy-N-[4-[4-(1-methylethyl)phenyl]-3-butyn-2-yl]urea The title compound was prepared according to the procedure of Example 15 using p-isopropylphenylacetylene instead of p-bromophenylacetylene in step (a), and using trimethylsilyl isocyanate instead of methyl isocyanate in step (d). m.p. 154-156 C.; NMR (300 MHz, DMSO-d6), 1.18 (6H, d, J=7 Hz), 1.35 (3H, d, J=7 Hz), 2.89 (1H, m), 5.12 (1H, q, J=7 Hz), 6.55 (2H, s), 7.22 (2H, d, J=7 Hz), 7.31 (2H, d, J=7 Hz), 9.31 (1H, s); MS (M+1)+ 247, (M+NH4)+ 264. Analysis calc'd for C14 H18 N2 O2: C, 68.26; H, 7.36; N, 11.37. Found: C, 67.80, H, 7.27; N, 11.17.
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