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[ CAS No. 39746-00-4 ] {[proInfo.proName]}

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Chemical Structure| 39746-00-4
Chemical Structure| 39746-00-4
Structure of 39746-00-4 * Storage: {[proInfo.prStorage]}
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Product Details of [ 39746-00-4 ]

CAS No. :39746-00-4 MDL No. :MFCD00674102
Formula : C15H16O5 Boiling Point : -
Linear Structure Formula :- InChI Key :OBRRYUZUDKVCOO-FVCCEPFGSA-N
M.W : 276.28 Pubchem ID :2724454
Synonyms :

Calculated chemistry of [ 39746-00-4 ]

Physicochemical Properties

Num. heavy atoms : 20
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.47
Num. rotatable bonds : 4
Num. H-bond acceptors : 5.0
Num. H-bond donors : 1.0
Molar Refractivity : 69.59
TPSA : 72.83 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : No
P-gp substrate : No
CYP1A2 inhibitor : No
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -6.94 cm/s

Lipophilicity

Log Po/w (iLOGP) : 2.09
Log Po/w (XLOGP3) : 1.47
Log Po/w (WLOGP) : 1.16
Log Po/w (MLOGP) : 1.69
Log Po/w (SILICOS-IT) : 1.62
Consensus Log Po/w : 1.61

Druglikeness

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

Water Solubility

Log S (ESOL) : -2.44
Solubility : 1.01 mg/ml ; 0.00366 mol/l
Class : Soluble
Log S (Ali) : -2.61
Solubility : 0.684 mg/ml ; 0.00248 mol/l
Class : Soluble
Log S (SILICOS-IT) : -2.56
Solubility : 0.759 mg/ml ; 0.00275 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 1.0 alert
Leadlikeness : 0.0
Synthetic accessibility : 3.48

Safety of [ 39746-00-4 ]

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 [ 39746-00-4 ]

* 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 [ 39746-00-4 ]
  • Downstream synthetic route of [ 39746-00-4 ]

[ 39746-00-4 ] Synthesis Path-Upstream   1~4

  • 1
  • [ 39746-01-5 ]
  • [ 39746-00-4 ]
YieldReaction ConditionsOperation in experiment
69% With sodium tetrahydroborate In methanol; dichloromethane at 0℃; for 0.416667 h; To a suspension of sodium borohydride (650 mg, 17.1 mmol) in methanol (20 mL) at 0° C. (bath temperature) was added a solution of (3aR,4R,5R,6aS)-5-(benzoyloxy)hexahydro-2H-cyclopenta[b]furan-2-one-4-carboxaldehyde (1) (available from Cayman Chemical Company, Ann Arbor, Mich.) (3.5 g, 12.8 mmol) as a solution in 1:1 methanol:methylene chloride (40 mL). After 25 min, saturated citric acid was added cautiously (60 mL), the mixture was extracted with ethyl acetate (3.x.40 mL), the combined organic layers were washed with water (2.x.80 mL) and saturated brine (2.x.80 mL), dried (magnesium sulfate), filtered, and concentrated to afford 2 (2.43 g, 69percent).
Reference: [1] Patent: US6353000, 2002, B1, . Location in patent: Page column 10
[2] Journal of Pharmacology and Experimental Therapeutics, 1999, vol. 290, # 3, p. 1278 - 1284
[3] Patent: US6353014, 2002, B1, . Location in patent: Page column 18
  • 2
  • [ 101208-17-7 ]
  • [ 39746-00-4 ]
YieldReaction ConditionsOperation in experiment
6.01 kg With hydrogenchloride In water; acetonitrile at 45℃; for 3.5 h; Industrial scale Add 30L of pyridine to the reactor with the filter element at the bottom, add (a) 4kg (leq) of the Corey lactone diol while stirring, add 7.13kg (1. leq) of triphenylchloromethane, and control the temperature at 20°C for 12h to complete In the reaction, 2.82 L (1.05 eq) of benzoyl chloride was added dropwise and the reaction was allowed to proceed at a controlled temperature of 30° C. for 4.5 h to complete the reaction; 44 L of pure water was added to the reaction vessel and stirred for 2 h to obtain a suspension. Nitrogen gas was introduced into the reaction vessel and passed through the reactor. The bottom of the filter will be suspended hydraulic filter, and then add isopropanol 40L to the reaction vessel, heated to reflux for 1h, the liquid pressure filter to obtain a solid powder; add 60L acetonitrile to the reaction vessel, add 30L of 3mol/L hydrochloric acid aqueous solution dropwise, control Temperature 45 ° C reaction 3.5h to complete reaction, the reaction system was cooled to 10 ° C, was added saturated aqueous sodium carbonate and neutralization reaction to ΡΗ = 7; the solvent acetonitrile in the reaction vessel was distilled off, and the resulting crude product was obtained by pressure filtration; 40K n-propyl ether was added to the reaction vessel, and the mixture was heated to reflux for 3 h, and then pressed and dried to give the product (-) Corey lactone benzoate, 6.4 Kg, a yield of 93.59percent, and a purity of 99.03percent.
Reference: [1] Patent: US2013/184476, 2013, A1, . Location in patent: Paragraph 0115
[2] Patent: CN107935975, 2018, A, . Location in patent: Paragraph 0111; 0115; 0125; 0129; 0134; 0135; 0141
  • 3
  • [ 58707-50-9 ]
  • [ 39746-00-4 ]
Reference: [1] Revue Roumaine de Chimie, 2014, vol. 59, # 10, p. 845 - 853
  • 4
  • [ 32233-40-2 ]
  • [ 39746-00-4 ]
Reference: [1] Revue Roumaine de Chimie, 2014, vol. 59, # 10, p. 845 - 853
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