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Chemical Structure| 79060-88-1

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Feliciano-Carmona, Alberto ; Wang, Xiqu ; Hughes, Russell P ; Daugulis, Olafs ; Brookhart, Maurice ;

Abstract: We have prepared cationic palladium complexes possessing a new zwitterionic ligand bis-N,N’−1-(2,4,6-triphenylpyridyl) oxalamide [(N∧N)Pd(Me)(L)]+ [BArF], (BArF = 3,5-(CF3)2C6H3, L = NCMe, CO). The structure of [(N∧N)Pd(Me)(CO)]+ [BArF] was determined by X-ray diffraction analysis. Energy Decomposition Analysis (EDA) indicates this N∧N zwitterionic ligand is more electron-donating relative to bidentate diimine ligands. Low temperature NMR analysis shows the existence of linkage isomers with the N∧N isomer the most stable. Structures were assigned using NMR and DFT analysis. Barriers to interconversion of isomers are ΔG = 10−12 kcal/mol. Kinetics of acetonitrile displacement from [(N∧N)Pd(Me)-(NCCH3)]+ [BArF] by CD3CN, ethylene and t Bu3P were measured and mechanisms of exchange determined. The ethylene complex, [(N∧N)Pd(Me)(C2H4)]+ was generated at −45 °C, and the barrier of migratory insertion was determined at 0 °C (ΔG = 23.4 kcal/mol) and compared to related diimine complexes. The methyl carbonyl complex undergoes migratory insertion in the presence of CO at −70 to −55 °C (ΔG = ca. 15.7 kcal/mol) to yield the acyl carbonyl complex. The neutral bistrimethylsilylmethyl complex, (N∧N)Pd(CH2SiMe3)2 was prepared and characterized by X-ray diffraction analysis. It displays dynamic behavior at very low temperatures in the NMR spectrum (−90 °C, ΔG = 7.9 kcal/mol) which, supported by DFT analysis, is ascribed to rotation of the bulky −CH2SiMe3 groups.

Purchased from AmBeed: ;

Long Li ; Carlin Thompson ; Xuewei Wang ;

Abstract: Paper-based ion-selective optodes (ISOs) allow for low-cost ion measurements using widely accessible optical detectors such as smartphones, representing an attractive analytical platform for medical testing and environmental monitoring. Previously reported paper-based ISOs rely on plasticized PVC membranes or PVC/plasticizer-free adsorption layers containing hydrophobic sensing chemicals. In this paper, we studied a new format of paper-based ISOs, in which a plasticizer phase containing sensing chemicals is deposited onto paper without using a hydrophobic polymer like PVC. Compared to ISOs without plasticizers and polymers, the plasticizer-based ISOs show much higher pH sensitivity when using chromoionophore I and tetrakis[3,5-bis(trifluoromethyl)phenyl]borate as the sensing chemicals. When the sensing layer further contains a solid ionophore with high molecular rigidity, the plasticizer-based ISOs for cations also exhibit enhanced sensitivity than the plasticizer-free ISOs. However, when the ionophore is a liquid at room temperature or has a long chain, the plasticizer-based and plasticizer-free ISOs have comparable responses because the ionophore behaves as a pseudo-plasticizer. Compared to ISOs with both plasticizers and polymers, the elimination of hydrophobic polymers like PVC makes inkjet printing more efficient and preserves the capillary action of the porous paper. By using the newly launched Samba cartridge with smaller nozzles, the plasticizer-based and polymer-free optodes for , , and ions are prepared by inkjet printing for the first time. In an example application, the inkjet-printed plasticizer-based and polymer-free ISOs are used for colorimetric measurements of urine .

Keywords: Ionophore ; Ion-selective optode ; paper ; Inkjet printing ; Colorimetric

Purchased from AmBeed: ;

Chen, Zhi-Hao ; Daugulis, Olafs ; Brookhart, Maurice ;

Abstract: A well-defined Pd complex [(tBuXPhos)Pd(Me)(BArf)] bearing a bulky monophosphine ligand was synthesized and fully characterized. X-ray diffraction anal. shows that the 1,3,5-triisopropylaryl group of the dialkylbiaryl phosphine ligand exhibits a weak η6-interaction with the Pd(II) center. This catalyst exhibits excellent functional group tolerance and polymerizes propargyl esters containing benzoyl and acetyl groups, propargyl Me ether, propargyl alc., benzyl acetylene, and Ph acetylene to yield polymers with Mn values at 5-15 kDa with monomodal mol. weight distributions between ∼1.4 and 2.1.

Purchased from AmBeed: ;

George F. Riegel ; Keiji Takashige ; Alex Lovstedt ; Steven R. Kass ;

Abstract: Several charge-containing TADDOL salts were synthesized and used as organocatalysts in asymmetric Diels–Alder and hetero-Diels–Alder reactions. Their catalytic activity was found to exceed that of a noncharged analog while maintaining or improving upon the enantioselectivity. The enhanced activities of the TADDOL salts enabled them to act as presumed hydrogen bond donor catalysts in the Diels–Alder and hetero-Diels–Alder reactions of 1,3-cyclohexadiene with methyl vinyl ketone at 40°C and 2-phenoxy-1,3-butadiene with ethyl glyoxylate at room temperature, respectively. Given the ionic nature of these charge-activated catalysts, it also proved possible to recycle and reuse the TADDOL without chromatography or the need for a recrystallization.

Purchased from AmBeed:

Alternative Products

Product Details of [ 79060-88-1 ]

CAS No. :79060-88-1
Formula : C32H12BF24Na
M.W : 886.20
SMILES Code : FC(C1=CC(C(F)(F)F)=CC([B-](C2=CC(C(F)(F)F)=CC(C(F)(F)F)=C2)(C3=CC(C(F)(F)F)=CC(C(F)(F)F)=C3)C4=CC(C(F)(F)F)=CC(C(F)(F)F)=C4)=C1)(F)F.[Na+]
MDL No. :MFCD00043323
InChI Key :LTGMONZOZHXAHO-UHFFFAOYSA-N
Pubchem ID :23681909

Safety of [ 79060-88-1 ]

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H315-H319-H335
Precautionary Statements:P261-P305+P351+P338

Computational Chemistry of [ 79060-88-1 ] Show Less

Physicochemical Properties

Num. heavy atoms 58
Num. arom. heavy atoms 24
Fraction Csp3 0.25
Num. rotatable bonds 12
Num. H-bond acceptors 24.0
Num. H-bond donors 0.0
Molar Refractivity 150.07
TPSA ?

Topological Polar Surface Area: Calculated from
Ertl P. et al. 2000 J. Med. Chem.

0.0 Ų

Lipophilicity

Log Po/w (iLOGP)?

iLOGP: in-house physics-based method implemented from
Daina A et al. 2014 J. Chem. Inf. Model.

0.0
Log Po/w (XLOGP3)?

XLOGP3: Atomistic and knowledge-based method calculated by
XLOGP program, version 3.2.2, courtesy of CCBG, Shanghai Institute of Organic Chemistry

14.17
Log Po/w (WLOGP)?

WLOGP: Atomistic method implemented from
Wildman SA and Crippen GM. 1999 J. Chem. Inf. Model.

20.43
Log Po/w (MLOGP)?

MLOGP: Topological method implemented from
Moriguchi I. et al. 1992 Chem. Pharm. Bull.
Moriguchi I. et al. 1994 Chem. Pharm. Bull.
Lipinski PA. et al. 2001 Adv. Drug. Deliv. Rev.

11.02
Log Po/w (SILICOS-IT)?

SILICOS-IT: Hybrid fragmental/topological method calculated by
FILTER-IT program, version 1.0.2, courtesy of SILICOS-IT, http://www.silicos-it.com

13.7
Consensus Log Po/w?

Consensus Log Po/w: Average of all five predictions

11.86

Water Solubility

Log S (ESOL):?

ESOL: Topological method implemented from
Delaney JS. 2004 J. Chem. Inf. Model.

-13.78
Solubility 0.0 mg/ml ; 0.0 mol/l
Class?

Solubility class: Log S scale
Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly

Insoluble
Log S (Ali)?

Ali: Topological method implemented from
Ali J. et al. 2012 J. Chem. Inf. Model.

-14.26
Solubility 0.0 mg/ml ; 0.0 mol/l
Class?

Solubility class: Log S scale
Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly

Insoluble
Log S (SILICOS-IT)?

SILICOS-IT: Fragmental method calculated by
FILTER-IT program, version 1.0.2, courtesy of SILICOS-IT, http://www.silicos-it.com

-16.38
Solubility 0.0 mg/ml ; 4.17e-17 mol/l
Class?

Solubility class: Log S scale
Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly

Insoluble

Pharmacokinetics

GI absorption?

Gatrointestinal absorption: according to the white of the BOILED-Egg

Low
BBB permeant?

BBB permeation: according to the yolk of the BOILED-Egg

No
P-gp substrate?

P-glycoprotein substrate: SVM model built on 1033 molecules (training set)
and tested on 415 molecules (test set)
10-fold CV: ACC=0.72 / AUC=0.77
External: ACC=0.88 / AUC=0.94

Yes
CYP1A2 inhibitor?

Cytochrome P450 1A2 inhibitor: SVM model built on 9145 molecules (training set)
and tested on 3000 molecules (test set)
10-fold CV: ACC=0.83 / AUC=0.90
External: ACC=0.84 / AUC=0.91

No
CYP2C19 inhibitor?

Cytochrome P450 2C19 inhibitor: SVM model built on 9272 molecules (training set)
and tested on 3000 molecules (test set)
10-fold CV: ACC=0.80 / AUC=0.86
External: ACC=0.80 / AUC=0.87

No
CYP2C9 inhibitor?

Cytochrome P450 2C9 inhibitor: SVM model built on 5940 molecules (training set)
and tested on 2075 molecules (test set)
10-fold CV: ACC=0.78 / AUC=0.85
External: ACC=0.71 / AUC=0.81

No
CYP2D6 inhibitor?

Cytochrome P450 2D6 inhibitor: SVM model built on 3664 molecules (training set)
and tested on 1068 molecules (test set)
10-fold CV: ACC=0.79 / AUC=0.85
External: ACC=0.81 / AUC=0.87

No
CYP3A4 inhibitor?

Cytochrome P450 3A4 inhibitor: SVM model built on 7518 molecules (training set)
and tested on 2579 molecules (test set)
10-fold CV: ACC=0.77 / AUC=0.85
External: ACC=0.78 / AUC=0.86

No
Log Kp (skin permeation)?

Skin permeation: QSPR model implemented from
Potts RO and Guy RH. 1992 Pharm. Res.

-1.65 cm/s

Druglikeness

Lipinski?

Lipinski (Pfizer) filter: implemented from
Lipinski CA. et al. 2001 Adv. Drug Deliv. Rev.
MW ≤ 500
MLOGP ≤ 4.15
N or O ≤ 10
NH or OH ≤ 5

2.0
Ghose?

Ghose filter: implemented from
Ghose AK. et al. 1999 J. Comb. Chem.
160 ≤ MW ≤ 480
-0.4 ≤ WLOGP ≤ 5.6
40 ≤ MR ≤ 130
20 ≤ atoms ≤ 70

None
Veber?

Veber (GSK) filter: implemented from
Veber DF. et al. 2002 J. Med. Chem.
Rotatable bonds ≤ 10
TPSA ≤ 140

1.0
Egan?

Egan (Pharmacia) filter: implemented from
Egan WJ. et al. 2000 J. Med. Chem.
WLOGP ≤ 5.88
TPSA ≤ 131.6

1.0
Muegge?

Muegge (Bayer) filter: implemented from
Muegge I. et al. 2001 J. Med. Chem.
200 ≤ MW ≤ 600
-2 ≤ XLOGP ≤ 5
TPSA ≤ 150
Num. rings ≤ 7
Num. carbon > 4
Num. heteroatoms > 1
Num. rotatable bonds ≤ 15
H-bond acc. ≤ 10
H-bond don. ≤ 5

4.0
Bioavailability Score?

Abbott Bioavailability Score: Probability of F > 10% in rat
implemented from
Martin YC. 2005 J. Med. Chem.

0.17

Medicinal Chemistry

PAINS?

Pan Assay Interference Structures: implemented from
Baell JB. & Holloway GA. 2010 J. Med. Chem.

0.0 alert
Brenk?

Structural Alert: implemented from
Brenk R. et al. 2008 ChemMedChem

1.0 alert: heavy_metal
Leadlikeness?

Leadlikeness: implemented from
Teague SJ. 1999 Angew. Chem. Int. Ed.
250 ≤ MW ≤ 350
XLOGP ≤ 3.5
Num. rotatable bonds ≤ 7

No; 1 violation:MW<3.0
Synthetic accessibility?

Synthetic accessibility score: from 1 (very easy) to 10 (very difficult)
based on 1024 fragmental contributions (FP2) modulated by size and complexity penaties,
trained on 12'782'590 molecules and tested on 40 external molecules (r2 = 0.94)

4.59

Application In Synthesis of [ 79060-88-1 ]

* 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.

  • Downstream synthetic route of [ 79060-88-1 ]

[ 79060-88-1 ] Synthesis Path-Downstream   1~9

  • 1
  • [ 179268-55-4 ]
  • [ 79060-88-1 ]
  • [ 13406-29-6 ]
  • [ 849519-15-9 ]
  • 2
  • chloro(1,5-cyclooctadiene)rhodium(I) dimer [ No CAS ]
  • [ 133463-88-4 ]
  • [ 79060-88-1 ]
  • [Rh(1,5-COD)((S,S)-4,4'-dibenzyl-2,2'-bis(2-oxazoline))](BAr(F))) [ No CAS ]
  • 3
  • [ 72287-26-4 ]
  • [ 79060-88-1 ]
  • [Pd(1,1'-bis(diphenylphosphino)ferrocene)(μ-Cl)]2[tetrakis(3,5-bis(trifluoromethyl)phenyl)borate]2 [ No CAS ]
  • 4
  • [ 215788-65-1 ]
  • [ 79060-88-1 ]
  • [Pd(dippf)(μ-Cl)]2[tetrakis(3,5-bis(trifluoromethyl)phenyl)borate]2 [ No CAS ]
  • 5
  • [ 79060-88-1 ]
  • [ 55894-18-3 ]
  • allyltributylphosphonium tetrakis-(3,5-bis(trifluoromethyl)phenyl)borate [ No CAS ]
  • 6
  • [ 15471-17-7 ]
  • [Mo{N-2,6-(Me2)C6H3}(CHCMe2Ph)(1,3-dimesitylimidazolin-2-ylidene)(OTf)(OC6F5)] [ No CAS ]
  • [ 79060-88-1 ]
  • [Mo(N-2,6-(Me2)C6H3)(CHCMe2Ph)(1,3-dimesitylimidazolin-2-ylidene)(OC6F5)(pyridiniumpropanesulfonate)][tetrakis(3,5-bis(trifluoromethyl)phenyl)borate] [ No CAS ]
  • 7
  • [ 6832-21-9 ]
  • [ 79060-88-1 ]
  • C11H17N*C32H12BF24(1-)*H(1+) [ No CAS ]
  • 8
  • [ 142-08-5 ]
  • [ 13938-94-8 ]
  • [ 79060-88-1 ]
  • [Rh(PPh3)2(2-pyridone)(CO)][tetrakis(3,5-bis(trifluoromethyl)phenyl)borate] [ No CAS ]
  • 9
  • [ 63060-94-6 ]
  • [ 79060-88-1 ]
  • C11H15NO2*C32H12BF24(1-)*H(1+) [ No CAS ]
YieldReaction ConditionsOperation in experiment
62% In chloroform; at 35℃; for 24h; General procedure: A mixture of amino acid ester hydrochloride (1.0 equiv., 100 mg) and sodiumtetrakis [3,5-bis(trifluoromethyl)phenyl] borate (NaBArF) (1.1 equiv.) was added tochloroform (40 mL) in a 100 mL round-bottom flask. This was then stirred at 35 for 24h. The progress of the reaction was monitored by taking an aliquot from the clear solution.The anion exchange reaction was deemed complete when no further precipitation(AgCl) was observed upon addition of an aqueous solution of AgNO3 to the aliquot. Theresulting white precipitate was removed by filtering twice. The solvent of the filtrate wassubjected to rotary evaporation under reduced pressure. The resultant yellow viscoussolid was dried in a vacuum at 45 for two days, to generate the target products.
 

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Technical Information

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