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[ CAS No. 1268524-71-5 ] {[proInfo.proName]}

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Cat. No.: {[proInfo.prAm]}
Chemical Structure| 1268524-71-5
Chemical Structure| 1268524-71-5
Structure of 1268524-71-5 * Storage: {[proInfo.prStorage]}
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Product Details of [ 1268524-71-5 ]

CAS No. :1268524-71-5 MDL No. :MFCD22124456
Formula : C23H25ClN4O2S Boiling Point : -
Linear Structure Formula :- InChI Key :DNVXATUJJDPFDM-QGZVFWFLSA-N
M.W : 456.99 Pubchem ID :49871818
Synonyms :
(−)-JQ1

Calculated chemistry of [ 1268524-71-5 ]

Physicochemical Properties

Num. heavy atoms : 31
Num. arom. heavy atoms : 16
Fraction Csp3 : 0.39
Num. rotatable bonds : 5
Num. H-bond acceptors : 5.0
Num. H-bond donors : 0.0
Molar Refractivity : 128.62
TPSA : 97.61 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : No
P-gp substrate : No
CYP1A2 inhibitor : No
CYP2C19 inhibitor : Yes
CYP2C9 inhibitor : Yes
CYP2D6 inhibitor : No
CYP3A4 inhibitor : Yes
Log Kp (skin permeation) : -5.64 cm/s

Lipophilicity

Log Po/w (iLOGP) : 4.17
Log Po/w (XLOGP3) : 4.85
Log Po/w (WLOGP) : 4.83
Log Po/w (MLOGP) : 3.63
Log Po/w (SILICOS-IT) : 6.6
Consensus Log Po/w : 4.81

Druglikeness

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

Water Solubility

Log S (ESOL) : -5.78
Solubility : 0.000757 mg/ml ; 0.00000166 mol/l
Class : Moderately soluble
Log S (Ali) : -6.63
Solubility : 0.000106 mg/ml ; 0.000000232 mol/l
Class : Poorly soluble
Log S (SILICOS-IT) : -7.64
Solubility : 0.0000103 mg/ml ; 0.0000000226 mol/l
Class : Poorly soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 2.0
Synthetic accessibility : 4.64

Safety of [ 1268524-71-5 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P280-P305+P351+P338 UN#:N/A
Hazard Statements:H302 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 1268524-71-5 ]

* 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 [ 1268524-71-5 ]
  • Downstream synthetic route of [ 1268524-71-5 ]

[ 1268524-71-5 ] Synthesis Path-Upstream   1~14

  • 1
  • [ 1068-57-1 ]
  • [ 1268524-71-5 ]
  • [ 1268524-70-4 ]
YieldReaction ConditionsOperation in experiment
82 % ee at 20 - 90℃; for 2 h; In a 500mL two neck round-bottomed flask equipped with a magnetic stir bar was dissolved amide 5 (3.40g, 8.13mmol) in THF (60mL) and cooled to −78°C. While stirring at −78°C, potassium tert-butoxide (1.0M solution in THF, 8.95mL, 8.94mmol, 1.10equiv) was added. The reaction mixture was warmed to −10°C and stirred for 30min. The reaction mixture was cooled to −78°C and diphenyl chlorophosphate (2.02mL, 9.76mmol) was added to the reaction mixture. The resulting mixture was warmed to −10°C and stirred at this temperature for 45min. Acetylhydrazide (0.90, 12.20mmol, 1.50equiv) was added to the reaction mixture. The reaction mixture was stirred at room temperature. After 1h, 1-butanol (70mL) was added to the reaction mixture, which was heated to 90°C. After 1h, all solvents were removed under reduce pressure. The residue was dissolved in CH2Cl2 and washed with saturated aq. NaHCO3, brine, dried over anhydrous Na2SO4 and concentrated in vacuo to obtain crude (+)-JQ1, which was purified by flash column chromatography on silica gel (0–100percent ethyl acetate in hexanes) to afford (+)-JQ1 (3.04g, 82percent) as a white solid and with a 91:9 er (determined with Supercritical Fluid Chromatography (SFC) using the CHIRALPAK AS-H column, CO2–EtOH (3:1), 210nm, tR (R-enantiomer) 1.62min, tR (S-enantiomer) 3.51min). This product was further purified by preparative SFC using a CHIRALPAK AS-H column to obtain (+)-JQ1 (S-enantiomer) with >99percent ee. The spectral data of (+)-JQ1 matched with those described in the literature6 with the exception of the optical rotation. [α]D22 +41 (c 0.50, CHCl3), (Lit. [α]D22 +55 (c 0.50, CHCl3);12 (−)-JQ1: >99percent ee, [α]D22 −39 (c 0.55, CHCl3), (Lit. [α]D22 −55 (c 0.50, CHCl3).6
Reference: [1] Tetrahedron Letters, 2015, vol. 56, # 23, p. 3454 - 3457
  • 2
  • [ 71989-14-5 ]
  • [ 1268524-71-5 ]
  • [ 1268524-70-4 ]
Reference: [1] Tetrahedron Letters, 2015, vol. 56, # 23, p. 3454 - 3457
[2] Tetrahedron Letters, 2015, vol. 56, # 23, p. 3454 - 3457
  • 3
  • [ 50508-66-2 ]
  • [ 1268524-71-5 ]
  • [ 1268524-70-4 ]
Reference: [1] Tetrahedron Letters, 2015, vol. 56, # 23, p. 3454 - 3457
[2] Tetrahedron Letters, 2015, vol. 56, # 23, p. 3454 - 3457
  • 4
  • [ 1268524-65-7 ]
  • [ 1268524-71-5 ]
  • [ 1268524-70-4 ]
Reference: [1] Tetrahedron Letters, 2015, vol. 56, # 23, p. 3454 - 3457
[2] Tetrahedron Letters, 2015, vol. 56, # 23, p. 3454 - 3457
  • 5
  • [ 1268524-66-8 ]
  • [ 1268524-71-5 ]
  • [ 1268524-70-4 ]
Reference: [1] Tetrahedron Letters, 2015, vol. 56, # 23, p. 3454 - 3457
  • 6
  • [ 1268524-67-9 ]
  • [ 1268524-71-5 ]
  • [ 1268524-70-4 ]
Reference: [1] Tetrahedron Letters, 2015, vol. 56, # 23, p. 3454 - 3457
  • 7
  • [ 1268524-69-1 ]
  • [ 1268524-71-5 ]
  • [ 1268524-70-4 ]
Reference: [1] Tetrahedron Letters, 2015, vol. 56, # 23, p. 3454 - 3457
  • 8
  • [ 1068-57-1 ]
  • [ 1268524-71-5 ]
  • [ 1268524-70-4 ]
YieldReaction ConditionsOperation in experiment
82 % ee at 20 - 90℃; for 2 h; In a 500mL two neck round-bottomed flask equipped with a magnetic stir bar was dissolved amide 5 (3.40g, 8.13mmol) in THF (60mL) and cooled to −78°C. While stirring at −78°C, potassium tert-butoxide (1.0M solution in THF, 8.95mL, 8.94mmol, 1.10equiv) was added. The reaction mixture was warmed to −10°C and stirred for 30min. The reaction mixture was cooled to −78°C and diphenyl chlorophosphate (2.02mL, 9.76mmol) was added to the reaction mixture. The resulting mixture was warmed to −10°C and stirred at this temperature for 45min. Acetylhydrazide (0.90, 12.20mmol, 1.50equiv) was added to the reaction mixture. The reaction mixture was stirred at room temperature. After 1h, 1-butanol (70mL) was added to the reaction mixture, which was heated to 90°C. After 1h, all solvents were removed under reduce pressure. The residue was dissolved in CH2Cl2 and washed with saturated aq. NaHCO3, brine, dried over anhydrous Na2SO4 and concentrated in vacuo to obtain crude (+)-JQ1, which was purified by flash column chromatography on silica gel (0–100percent ethyl acetate in hexanes) to afford (+)-JQ1 (3.04g, 82percent) as a white solid and with a 91:9 er (determined with Supercritical Fluid Chromatography (SFC) using the CHIRALPAK AS-H column, CO2–EtOH (3:1), 210nm, tR (R-enantiomer) 1.62min, tR (S-enantiomer) 3.51min). This product was further purified by preparative SFC using a CHIRALPAK AS-H column to obtain (+)-JQ1 (S-enantiomer) with >99percent ee. The spectral data of (+)-JQ1 matched with those described in the literature6 with the exception of the optical rotation. [α]D22 +41 (c 0.50, CHCl3), (Lit. [α]D22 +55 (c 0.50, CHCl3);12 (−)-JQ1: >99percent ee, [α]D22 −39 (c 0.55, CHCl3), (Lit. [α]D22 −55 (c 0.50, CHCl3).6
Reference: [1] Tetrahedron Letters, 2015, vol. 56, # 23, p. 3454 - 3457
  • 9
  • [ 71989-14-5 ]
  • [ 1268524-71-5 ]
  • [ 1268524-70-4 ]
Reference: [1] Tetrahedron Letters, 2015, vol. 56, # 23, p. 3454 - 3457
[2] Tetrahedron Letters, 2015, vol. 56, # 23, p. 3454 - 3457
  • 10
  • [ 50508-66-2 ]
  • [ 1268524-71-5 ]
  • [ 1268524-70-4 ]
Reference: [1] Tetrahedron Letters, 2015, vol. 56, # 23, p. 3454 - 3457
[2] Tetrahedron Letters, 2015, vol. 56, # 23, p. 3454 - 3457
  • 11
  • [ 1268524-65-7 ]
  • [ 1268524-71-5 ]
  • [ 1268524-70-4 ]
Reference: [1] Tetrahedron Letters, 2015, vol. 56, # 23, p. 3454 - 3457
[2] Tetrahedron Letters, 2015, vol. 56, # 23, p. 3454 - 3457
  • 12
  • [ 1268524-66-8 ]
  • [ 1268524-71-5 ]
  • [ 1268524-70-4 ]
Reference: [1] Tetrahedron Letters, 2015, vol. 56, # 23, p. 3454 - 3457
  • 13
  • [ 1268524-67-9 ]
  • [ 1268524-71-5 ]
  • [ 1268524-70-4 ]
Reference: [1] Tetrahedron Letters, 2015, vol. 56, # 23, p. 3454 - 3457
  • 14
  • [ 1268524-69-1 ]
  • [ 1268524-71-5 ]
  • [ 1268524-70-4 ]
Reference: [1] Tetrahedron Letters, 2015, vol. 56, # 23, p. 3454 - 3457
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