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[ CAS No. 6315-52-2 ] {[proInfo.proName]}

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Chemical Structure| 6315-52-2
Chemical Structure| 6315-52-2
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Product Details of [ 6315-52-2 ]

CAS No. :6315-52-2 MDL No. :MFCD00008549
Formula : C16H18O6S2 Boiling Point : -
Linear Structure Formula :- InChI Key :LZIPBJBQQPZLOR-UHFFFAOYSA-N
M.W : 370.44 Pubchem ID :228289
Synonyms :

Calculated chemistry of [ 6315-52-2 ]

Physicochemical Properties

Num. heavy atoms : 24
Num. arom. heavy atoms : 12
Fraction Csp3 : 0.25
Num. rotatable bonds : 7
Num. H-bond acceptors : 6.0
Num. H-bond donors : 0.0
Molar Refractivity : 89.06
TPSA : 103.5 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : No
P-gp substrate : No
CYP1A2 inhibitor : Yes
CYP2C19 inhibitor : Yes
CYP2C9 inhibitor : Yes
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -6.49 cm/s

Lipophilicity

Log Po/w (iLOGP) : 3.06
Log Po/w (XLOGP3) : 2.92
Log Po/w (WLOGP) : 4.58
Log Po/w (MLOGP) : 3.02
Log Po/w (SILICOS-IT) : 1.97
Consensus Log Po/w : 3.11

Druglikeness

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

Water Solubility

Log S (ESOL) : -3.88
Solubility : 0.0483 mg/ml ; 0.000131 mol/l
Class : Soluble
Log S (Ali) : -4.75
Solubility : 0.00652 mg/ml ; 0.0000176 mol/l
Class : Moderately soluble
Log S (SILICOS-IT) : -5.78
Solubility : 0.00062 mg/ml ; 0.00000167 mol/l
Class : Moderately soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 1.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 3.19

Safety of [ 6315-52-2 ]

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 [ 6315-52-2 ]

* 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 [ 6315-52-2 ]
  • Downstream synthetic route of [ 6315-52-2 ]

[ 6315-52-2 ] Synthesis Path-Upstream   1~12

  • 1
  • [ 56187-04-3 ]
  • [ 6315-52-2 ]
  • [ 52667-89-7 ]
Reference: [1] Organic and Biomolecular Chemistry, 2018, vol. 16, # 40, p. 7503 - 7512
[2] Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 2002, vol. 41, # 2, p. 372 - 375
[3] Journal of the American Chemical Society, 2010, vol. 132, # 49, p. 17366 - 17369
[4] Chemical Communications, 2010, vol. 46, # 10, p. 1640 - 1642
[5] Chemistry of Heterocyclic Compounds (New York, NY, United States), 1990, vol. 26, # 3, p. 346 - 349[6] Khimiya Geterotsiklicheskikh Soedinenii, 1990, # 3, p. 401 - 404
[7] Journal of the Chinese Chemical Society, 2004, vol. 51, # 5 B, p. 1201 - 1208
[8] Synthetic Communications, 2006, vol. 36, # 11, p. 1569 - 1573
[9] Dalton Transactions, 2016, vol. 45, # 23, p. 9412 - 9418
[10] Australian Journal of Chemistry, 1984, vol. 37, # 5, p. 959 - 970
[11] Journal of the Chemical Society. Perkin Transactions 2, 1998, # 1, p. 83 - 88
[12] Journal of the American Chemical Society, 2012, vol. 134, # 10, p. 4683 - 4693
[13] Chemistry - A European Journal, 2018, vol. 24, # 41, p. 10434 - 10442
  • 2
  • [ 6315-52-2 ]
  • [ 52601-80-6 ]
  • [ 52667-89-7 ]
YieldReaction ConditionsOperation in experiment
76% at 100℃; for 3 h; A solution of bis(p-toluenesulfonyl)ethylene glycol (59.5 g, 0.16 mol) in DMF (300 ml) is added dropwise, over a period of 3 hours, to a solution of the disodium salt of tris(p-toluenesulfonyl)diethylenetriamine (98 g, 0.16 mol) in DMF (950 ml) at 100° C. Heating is halted and distilled water (575 ml) is added. A precipitate is immediately formed. After filtration and drying under vacuum, the macrocyclic compound is obtained in the form of a white solid (71.8 g, yield 76percent). Characteristics: 1H NMR (200 MHz, CDCl3) δ 7.67 (d, 6H), 7.29 (d, 6H), 3.39 (s, 12H), 2.41 (s, 9H).
Reference: [1] Patent: US2007/218010, 2007, A1, . Location in patent: Page/Page column 14; 19
  • 3
  • [ 107-21-1 ]
  • [ 98-59-9 ]
  • [ 42772-85-0 ]
  • [ 6315-52-2 ]
Reference: [1] Tetrahedron, 1987, vol. 43, # 19, p. 4271 - 4276
[2] Liebigs Annalen der Chemie, 1981, # 10, p. 1774 - 1784
[3] Organic Letters, 2002, vol. 4, # 14, p. 2329 - 2332
[4] Polymer, 2011, vol. 52, # 18, p. 3879 - 3886
  • 4
  • [ 107-21-1 ]
  • [ 98-59-9 ]
  • [ 6315-52-2 ]
YieldReaction ConditionsOperation in experiment
83% at 0 - 20℃; for 2.5 h; 19.8 g (0.3 mol) of ethylene glycol are dissolved in 150 ml of distilled pyridine and then the solution is cooled with an ice bath. p-Toluenesulfonyl chloride (123 g, 0.65 mol) is added slowly with mechanical stirring. The temperature must remain below 20° C. during the addition. When approximately 90 g have been added, stirring becomes difficult and the mixture is diluted with 200 ml of pyridine. The reaction mixture is left stirring for 2 h 30. An aqueous HCl solution (12N HCl (170 ml) in ice (500 ml)) is added. The solid formed during this addition is filtered off. This solid is dissolved in refluxing methanol (250 ml) and then the new precipitate formed after returning to ambient temperature is filtered off. Finally, the white solid obtained is dried under vacuum and the pure product is obtained (92.4 g, yield 83percent). Characteristics: 1H NMR (200 MHz, CDCl3) δ 7.71 (d, 2H), 7.31 (d, 2H), 4.16 (s, 2H), 2.43 (s, 3H)
83% With triethylamine In tetrahydrofuran for 16.0833 h; Inert atmosphere Triethylamine (5.04 mL, 35.9 mmol) was added to a solution of ethylene glycol (1.000mL, 17.93mmol) in THF (10mL) under an Argon atmosphere. p-toluenesulfonyl chloride (7.18g, 37.7mmol) was dissolved in THF (5 mL) and added dropwise to the solution over 5 minutes. The reaction was stirred for 16 hours and worked-up by extraction with water (30 mL) and DCM (30 mL). The organic solvent was removed under reduced pressure and the product was recrystallized from EtOAc. A white crystalline precipitate was collected by filtration and dried in vacuo, (5.52 g, 14.89 mmol, 83 percent yield).
80% at -30 - -18℃; for 48 - 72 h; (1) Add 17 g of toluenesulfonyl chloride (TsCl) (F.W.=190.65, 0.089 mol) into conical flask (A) with 20 ml of pyridine.(2) Add 1.1 ml of ethylene glycol (F.W.=62.07, 0.018 mol) into conical flask (B) with 30 ml of pyridine.(3) Pour solution of conical flask (A) into conical flask (B) under the temperature of dry ice-acetone bath (-30° C. approximately) and then put the flask under -18° C. promptly for react two to three days.(4) After complete reaction, pour the reactant in conical flask (B) into 500 ml beaker with ice water and cracked ice; white solid substance will appear after stirring.(5) Add optimal 1N HCl into beaker above-mentioned and adjust pH to 67.(6) Filter and collect white solid substance, then re-crystallize in mixture of methylene chloride and normal hexane to yield 80percent of 5.33 g ethylene glycol-1,2-ditosylate.
80% at -30 - -18℃; for 48 - 72 h; Cooling with acetone-dry ice 1. Preparation of ethylene glycol-1,2-ditosylate(1) Add 17 g of toluenesulfonyl chloride (TsCl) (F.W.=190.65, 0.089 mol) into conical flask (A) with 20 ml of pyridine.(2) Add 1.1 ml of ethylene glycol (F.W.=62.07, 0.018 mol) into conical flask (B) with 30 ml of pyridine.(3) Pour solution of conical flask (A) into conical flask (B) under the temperature of dry ice-acetone bath (-30° C. approximately) and then put the flask under -18° C. promptly for react two to three days.(4) After complete reaction, pour the reactant in conical flask (B) into 500 ml beaker with ice water and cracked ice; white solid substance will appear after stirring.(5) Add optimal 1N HCl into beaker above-mentioned and adjust pH to 67.(6) Filter and collect white solid substance, then re-crystallize in mixture of methylene chloride and normal hexane to yield 80percent of 5.33 g ethylene glycol-1,2-ditosylate.
80% at -30 - 18℃; for 72 h; Cooling with acetone-dry ice Example 1. The synthetic method of 18F-labeled precursor t-BOC-(O-tosyloxyethyl)-L-Tyr-OBzl 1. Preparation of ethylene glycol-1,2-ditosylate (1) Add 17g of toluenesulfonyl chloride (TsCl)(F.W.=190.65 , 0.089 mol) into conical flask (A) with 20 ml of pyridine. (2) Add 1.1 ml of ethylene glycol (F.W.=62.07 , 0.018 mol) into conical flask (B) with 30 ml of pyridine. (3) Pour solution of conical flask (A) into conical flask (B) under the temperature of dry ice-acetone bath (-30°C approximately) and then put the flask under -18°C promptly for react two to three days. (4) After complete reaction, pour the reactant in conical flask (B) into 500 ml beaker with ice water and cracked ice; white solid substance will appear after stirring. (5) Add optimal 1N HCl into beaker above-mentioned and adjust pH to 6~7. (6) Filter and collect white solid substance, then re-crystallize in mixture of methylene chloride and normal hexane to yield 80percent of 5.33g ethylene glycol-1,2-ditosylate.
26.85 g With sodium hydroxide In tetrahydrofuran; water at 20℃; 5 g (80.55 mmol) of ethylene glycol and 33.78 g (177.21 mmol) of 4-toluenesulfonyl chloride were dissolved in 100 ml of tetrahydrofuran and stirred. Then, 11.27 g (281.93 mol) of sodium hydroxide was dissolved in a minimum amount of water, and the mixture was stirred at room temperature. After completion of the reaction, diethyl ether and water were added to separate the layers, and the mixture was concentrated under reduced pressure to obtain 26.85 g (72.49 mmol) of the title compound represented by the formula (III).

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  • 5
  • [ 4124-41-8 ]
  • [ 107-21-1 ]
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  • 6
  • [ 74-85-1 ]
  • [ 108164-35-8 ]
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  • 7
  • [ 16836-95-6 ]
  • [ 106-93-4 ]
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  • 8
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  • 9
  • [ 6192-52-5 ]
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  • 10
  • [ 75-21-8 ]
  • [ 98-59-9 ]
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  • 11
  • [ 6315-52-2 ]
  • [ 6052-10-4 ]
Reference: [1] Journal of Heterocyclic Chemistry, 1998, vol. 35, # 1, p. 209 - 215
  • 12
  • [ 6315-52-2 ]
  • [ 383-50-6 ]
Reference: [1] Journal of Labelled Compounds and Radiopharmaceuticals, 2016, vol. 59, # 3, p. 103 - 108
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