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[ CAS No. 41024-91-3 ] {[proInfo.proName]}

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Chemical Structure| 41024-91-3
Chemical Structure| 41024-91-3
Structure of 41024-91-3 * Storage: {[proInfo.prStorage]}
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Product Details of [ 41024-91-3 ]

CAS No. :41024-91-3 MDL No. :MFCD00012204
Formula : C24H34O10S2 Boiling Point : -
Linear Structure Formula :- InChI Key :BUHGDYPBQWWWQS-UHFFFAOYSA-N
M.W :546.65 Pubchem ID :361968
Synonyms :
Pentaethylene glycol di(p-toluenesulfonate)

Calculated chemistry of [ 41024-91-3 ]

Physicochemical Properties

Num. heavy atoms : 36
Num. arom. heavy atoms : 12
Fraction Csp3 : 0.5
Num. rotatable bonds : 19
Num. H-bond acceptors : 10.0
Num. H-bond donors : 0.0
Molar Refractivity : 131.86
TPSA : 140.42 Ų

Pharmacokinetics

GI absorption : Low
BBB permeant : No
P-gp substrate : Yes
CYP1A2 inhibitor : No
CYP2C19 inhibitor : Yes
CYP2C9 inhibitor : Yes
CYP2D6 inhibitor : Yes
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -7.99 cm/s

Lipophilicity

Log Po/w (iLOGP) : 5.28
Log Po/w (XLOGP3) : 2.32
Log Po/w (WLOGP) : 4.64
Log Po/w (MLOGP) : 1.7
Log Po/w (SILICOS-IT) : 3.46
Consensus Log Po/w : 3.48

Druglikeness

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

Water Solubility

Log S (ESOL) : -3.68
Solubility : 0.113 mg/ml ; 0.000207 mol/l
Class : Soluble
Log S (Ali) : -4.91
Solubility : 0.00676 mg/ml ; 0.0000124 mol/l
Class : Moderately soluble
Log S (SILICOS-IT) : -7.8
Solubility : 0.00000874 mg/ml ; 0.000000016 mol/l
Class : Poorly soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 1.0 alert
Leadlikeness : 2.0
Synthetic accessibility : 4.28

Safety of [ 41024-91-3 ]

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 [ 41024-91-3 ]

* 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 [ 41024-91-3 ]
  • Downstream synthetic route of [ 41024-91-3 ]

[ 41024-91-3 ] Synthesis Path-Upstream   1~4

  • 1
  • [ 4792-15-8 ]
  • [ 98-59-9 ]
  • [ 41024-91-3 ]
YieldReaction ConditionsOperation in experiment
8.1 mg With sodium hydroxide In tetrahydrofuran; water for 3 h; Inert atmosphere Triglycol dichloride (10.8g, 57.8mmol) was added to a stirred mixture of KOH (7.8g, 139.3mmol) in ethylene glycol (60mL) at room temperature under N2. The reaction mixture was stirred at refluxing temperature for 36h. After cooling to room temperature, the reaction mixture was filtered and concentrated under reduced pressure to yield a viscous oil. To a stirred solution of the above viscous oil and NaOH (4.8g, 120mmol) in THF/H2O (v/v=1/1 40mL) cooled to 0°C under N2 was slowly added portions of p-toluenesulfonyl chloride (22g, 115mmol). After stirring for 3h, water (100mL) was added to the reaction mixture. The product was extracted with CH2Cl2 (20mL×3) and washed with brine (20mL×3). The combined organic layer was dried over MgSO4 and the CH2Cl2 was evaporated off. The crude product was purified by column chromatography (petroleum ether: ethyl acetate=3:1) to give pure product (8.1g) as yellow oil. Yield 27.5percent, 1H NMR (CDCl3, 500MHz) δ 2.44 (3H, s), 3.57 (4H, s), 3.59 (2H, s), 3.67 (2H, t, J=4.8Hz), 4.14 (2H, t, J=4.8Hz), 7.33 (2H, d, J=8.1Hz), 7.78 (2H, d, J=8.2Hz).
Reference: [1] Bioorganic and Medicinal Chemistry, 2007, vol. 15, # 14, p. 4841 - 4856
[2] Journal of Organic Chemistry, 1999, vol. 64, # 18, p. 6870 - 6873
[3] Canadian Journal of Chemistry, 2006, vol. 84, # 10, p. 1273 - 1279
[4] Collection of Czechoslovak Chemical Communications, 1987, vol. 52, # 8, p. 2057 - 2060
[5] Russian Journal of Organic Chemistry, 2012, vol. 48, # 10, p. 1345 - 1352[6] Zh. Org. Khim., 2012, vol. 48, # 10, p. 1350 - 1357,8
[7] Chemical Communications, 2016, vol. 52, # 45, p. 7310 - 7313
[8] Organic Letters, 2018, vol. 20, # 2, p. 369 - 372
[9] Journal of the Chemical Society - Perkin Transactions 1, 1998, # 2, p. 265 - 269
[10] Bulletin of the Chemical Society of Japan, 1990, vol. 63, # 4, p. 1260 - 1262
[11] Bulletin of the Chemical Society of Japan, 1990, vol. 63, # 4, p. 1260 - 1262
[12] Organic and Biomolecular Chemistry, 2006, vol. 4, # 11, p. 2082 - 2087
[13] Journal of Organic Chemistry, 1984, vol. 49, p. 1408 - 1412
[14] Journal of the Chemical Society, Perkin Transactions 2: Physical Organic Chemistry (1972-1999), 1985, p. 607 - 624
[15] Liebigs Annalen der Chemie, 1983, # 5, p. 770 - 801
[16] Journal of Heterocyclic Chemistry, 1994, vol. 31, # 4, p. 1047 - 1052
[17] Journal of Organic Chemistry, 2004, vol. 69, # 11, p. 3928 - 3936
[18] Tetrahedron Letters, 2006, vol. 47, # 48, p. 8563 - 8566
[19] Tetrahedron, 2014, vol. 70, # 50, p. 9545 - 9553
  • 2
  • [ 4792-15-8 ]
  • [ 98-59-9 ]
  • [ 41024-91-3 ]
  • [ 155130-15-7 ]
Reference: [1] Organic Letters, 2002, vol. 4, # 14, p. 2329 - 2332
  • 3
  • [ 112-26-5 ]
  • [ 41024-91-3 ]
Reference: [1] Tetrahedron, 2014, vol. 70, # 50, p. 9545 - 9553
  • 4
  • [ 107-21-1 ]
  • [ 112-26-5 ]
  • [ 98-59-9 ]
  • [ 41024-91-3 ]
Reference: [1] Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999), 1981, p. 449 - 454
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