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[ CAS No. 13682-77-4 ] {[proInfo.proName]}

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Chemical Structure| 13682-77-4
Chemical Structure| 13682-77-4
Structure of 13682-77-4 * Storage: {[proInfo.prStorage]}

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Product Citations

Product Citations

William F. Tracy ; Geraint H. M. Davies ; Lauren N. Grant , et al. DOI:

Abstract: Immunomodulatory imide drugs form the core of many pharmaceutically relevant structures, but Csp2–Csp2 bond formation via metal-catalyzed cross coupling is difficult due to the sensitivity of the glutarimide ring ubiquitous in these structures. We report that replacement of the traditional alkali base with a fluoride source enhances a previously challenging Suzuki–Miyaura coupling on glutarimide-containing compounds with trifluoroborates. These enabling conditions are reactive enough to generate these derivatives in high yields but mild enough to preserve both the glutarimide and its sensitive stereocenter. Experimental and computational data suggest a mechanistically distinct process of π-coordination of the trifluoroborate enabled by these conditions.

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Product Details of [ 13682-77-4 ]

CAS No. :13682-77-4 MDL No. :MFCD02093335
Formula : C2H3BF3K Boiling Point : -
Linear Structure Formula :CH2CHBF3K InChI Key :ZCUMGICZWDOJEM-UHFFFAOYSA-N
M.W : 133.95 Pubchem ID :23679353
Synonyms :

Calculated chemistry of [ 13682-77-4 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 7
Num. arom. heavy atoms : 0
Fraction Csp3 : 0.0
Num. rotatable bonds : 1
Num. H-bond acceptors : 3.0
Num. H-bond donors : 0.0
Molar Refractivity : 19.28
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 : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -5.28 cm/s

Lipophilicity

Log Po/w (iLOGP) : 0.0
Log Po/w (XLOGP3) : 2.59
Log Po/w (WLOGP) : 2.82
Log Po/w (MLOGP) : 1.45
Log Po/w (SILICOS-IT) : 0.45
Consensus Log Po/w : 1.46

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 3.0
Bioavailability Score : 0.55

Water Solubility

Log S (ESOL) : -2.24
Solubility : 0.778 mg/ml ; 0.00581 mol/l
Class : Soluble
Log S (Ali) : -2.24
Solubility : 0.773 mg/ml ; 0.00577 mol/l
Class : Soluble
Log S (SILICOS-IT) : -1.12
Solubility : 10.2 mg/ml ; 0.0759 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 1.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 2.36

Safety of [ 13682-77-4 ]

Signal Word:Danger Class:8
Precautionary Statements:P280-P305+P351+P338-P310 UN#:3261
Hazard Statements:H314 Packing Group:Ⅱ
GHS Pictogram:
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