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Structure of N,N-Diethylformamide
CAS No.: 617-84-5
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The BI-3802 was designed by Boehringer Ingelheim and could be obtained free of charge through the Boehringer Ingelheim open innovation portal opnMe.com, associated with its negative control.
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Tonsel-White, Elizabeth A ;
Abstract: The synthesis of two cobalt(II) complexes: the novel complex [Co(phen)3]2[Co(pytc)2]•16.25H2O 1 and the previously reported [Co(bpy)3](OH)2•7H2O 2, along with a cobalt(II/III)-containing MOF, Co-PPF2, previously reported as well, was achieved. These complexes were characterized by elemental analysis, X-ray crystallography, microscopy, conductivity measurements, TGA, SEM, CV , and UV-visible , and FTIR spectroscopies. From the CV scan rates, diffusion coefficients for complexes 1 and 2 were determined to be 1.0 × 10−6 cm2 s-1 and 4.8 × 10−7 cm2 s-1. Electrocatalytic studies with complexes 1 and 2 revealed insights into the mechanistic aspects of hydrogen evolution and the influence of acid strength on catalytic performance utilizing p-cyanoanilinium tetrafluoroborate, p-toluenesulfonic acid monohydrate, trifluoroacetic acid, and acetic acid by using DMSO and DMF:H2O (90:10, v/v). Under homogeneous photocatalytic conditions, the maximum turnover frequency (TOFmax) for complex 1 was 1118 min-1 in DMF:H2O (90:10, v/v) and 1038 min-1 in DMF:H2O (50:50, v/v), with turnover numbers (TON) of 41 and 16, respectively. Meanwhile, under heterogeneous photocatalytic conditions, Co-PPF2 exhibited a TOFmax of 2361 min-1 and a TON of 60 in DMF:H2O (50:50, v/v). The reduction of sodium bromate (NaBrO3) by [Co(dmgBF2)2(OH2)2] (where dmgBF2 = difluoroboryldimethylglyoximato) was investigated in hydrochloric and nitric acids. Analytical studies were carried out via gravimetric analysis and UV-visible spectrophotometry. In the gravimetric analysis, a 0.100 M AgNO3 solution was added to the HCl-acidified reaction mixture, forming a precipitate of AgX (X = halide). The gravimetric analysis proved that sodium bromate was reduced to from quantitative amounts of sodium bromide in the presence of hydrochloric acid. Through simulated stoichiometric calculations, the amount of AgBr that precipitated gave a yield of 98 ± 1%. Biochar was used to sequester the complex from the reaction mixture and to neutralize the acidic media. The UV-visible data confirmed the sequestration of the complex from the reaction mixture after exposure to the biochar. The collected pH data proved a direct relationship between pH and the amount of biochar used in the form of a titration curve. These findings demonstrate the efficiency of using biochar in the sequestration and neutralization process.
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CAS No. : | 617-84-5 |
Formula : | C5H11NO |
M.W : | 101.15 |
SMILES Code : | O=CN(CC)CC |
MDL No. : | MFCD00003287 |
InChI Key : | SUAKHGWARZSWIH-UHFFFAOYSA-N |
Pubchem ID : | 12051 |
GHS Pictogram: |
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Signal Word: | Danger |
Hazard Statements: | H225-H315-H319-H335 |
Precautionary Statements: | P261-P305+P351+P338 |
Class: | 3 |
UN#: | 1993 |
Packing Group: | Ⅲ |
Num. heavy atoms | 7 |
Num. arom. heavy atoms | 0 |
Fraction Csp3 | 0.8 |
Num. rotatable bonds | 3 |
Num. H-bond acceptors | 1.0 |
Num. H-bond donors | 0.0 |
Molar Refractivity | 29.63 |
TPSA ? Topological Polar Surface Area: Calculated from |
20.31 Ų |
Log Po/w (iLOGP)? iLOGP: in-house physics-based method implemented from |
1.67 |
Log Po/w (XLOGP3)? XLOGP3: Atomistic and knowledge-based method calculated by |
0.47 |
Log Po/w (WLOGP)? WLOGP: Atomistic method implemented from |
0.48 |
Log Po/w (MLOGP)? MLOGP: Topological method implemented from |
0.89 |
Log Po/w (SILICOS-IT)? SILICOS-IT: Hybrid fragmental/topological method calculated by |
0.06 |
Consensus Log Po/w? Consensus Log Po/w: Average of all five predictions |
0.72 |
Log S (ESOL):? ESOL: Topological method implemented from |
-0.57 |
Solubility | 27.5 mg/ml ; 0.272 mol/l |
Class? Solubility class: Log S scale |
Very soluble |
Log S (Ali)? Ali: Topological method implemented from |
-0.47 |
Solubility | 34.6 mg/ml ; 0.342 mol/l |
Class? Solubility class: Log S scale |
Very soluble |
Log S (SILICOS-IT)? SILICOS-IT: Fragmental method calculated by |
-0.67 |
Solubility | 21.5 mg/ml ; 0.213 mol/l |
Class? Solubility class: Log S scale |
Soluble |
GI absorption? Gatrointestinal absorption: according to the white of the BOILED-Egg |
High |
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) |
No |
CYP1A2 inhibitor? Cytochrome P450 1A2 inhibitor: SVM model built on 9145 molecules (training set) |
No |
CYP2C19 inhibitor? Cytochrome P450 2C19 inhibitor: SVM model built on 9272 molecules (training set) |
No |
CYP2C9 inhibitor? Cytochrome P450 2C9 inhibitor: SVM model built on 5940 molecules (training set) |
No |
CYP2D6 inhibitor? Cytochrome P450 2D6 inhibitor: SVM model built on 3664 molecules (training set) |
No |
CYP3A4 inhibitor? Cytochrome P450 3A4 inhibitor: SVM model built on 7518 molecules (training set) |
No |
Log Kp (skin permeation)? Skin permeation: QSPR model implemented from |
-6.58 cm/s |
Lipinski? Lipinski (Pfizer) filter: implemented from |
0.0 |
Ghose? Ghose filter: implemented from |
None |
Veber? Veber (GSK) filter: implemented from |
0.0 |
Egan? Egan (Pharmacia) filter: implemented from |
0.0 |
Muegge? Muegge (Bayer) filter: implemented from |
1.0 |
Bioavailability Score? Abbott Bioavailability Score: Probability of F > 10% in rat |
0.55 |
PAINS? Pan Assay Interference Structures: implemented from |
0.0 alert |
Brenk? Structural Alert: implemented from |
1.0 alert: heavy_metal |
Leadlikeness? Leadlikeness: implemented from |
No; 1 violation:MW<1.0 |
Synthetic accessibility? Synthetic accessibility score: from 1 (very easy) to 10 (very difficult) |
1.0 |
* 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.
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
85% | General procedure: To the N,N-diethylformamide (1ml) was added dropwise phenyl chloroformate (3.5equiv). The mixture was stirred for 10min at room temperature. Then <strong>[33332-28-4]6-chloro-2-aminopyrazine</strong> (1mmol) was introduced to the mixture. After 5min at 45°C, the mixture was basified with K2CO3(aq), extracted with ethyl acetate and washed with water. The organic layer was dried over MgSO4, filtered, and concentrated. The residue was purified by column chromatography to give the product. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
64% | In ethanol; water; at 110.0℃; for 24h;Autoclave; | 2.1.1 Synthesis of [Mn3(L)(HCOO)3(DEF)3] (1) A mixture of MnCl2·4H2O (20.2 mg, 0.1 mmol) and H3L (38.3 mg, 0.1 mmol) in 5 mL DEF/EtOH/H2O (5:3:2, v: v:v) was sealed in a 20 mL Teflon-lined stainless vessel and subjected to 110 C for 24 h, and then cooled to room temperature. Yellow block-shaped crystals of 1 were obtained in 64% yield based on MnCl2·4H2O. Elem anal. Calcd for C39H48Mn3N4O15: C, 47.91; H, 4.95; N, 5.73; Found: C, 47.79; H, 4.74; N, 5.67. IR (cm-1): 1650w, 1617vs, 1598m, 1549vw, 1395s, 1309m, 1271w, 1169w, 1130w, 999w, 827w, 784m, 715w, 666w, 656w. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
91% | With hydrogenchloride; 2,4,6-tripropyl-1,3,5,2,4,6-trioxatriphosphinane-2,4,6-trioxide; In 1,4-dioxane; at 120℃; for 22h; | General procedure: A 20 mL Radleys Carousel screw-capped glass tube was charged with carboxylic acid (2 mmol, 1.0 equiv), DMF (1.2 mL), T3P in DMF 50%(1.28 mL, 1.4 g, 1.1 equiv) and HCl (4 M in dioxane, 0.25 mL, 1.0mmol, 0.5 equiv) at r.t. The mixture was heated to 130 C (ca. 120 C internal) and stirred until the conversion according to LC-MS or TLCwas ?95%. The solution was quenched at 10 C with aq half-saturated Na2CO3 (5 mL; caution: gas evolution) and extracted with i-PrOAc (10mL and 2 × 5 mL or until no product was present in the aqueousphase). Combined organic phases were dried over MgSO4 and concentratedunder reduced pressure. The crude product was purified bychromatography on silica gel as described below. N,N-Diethyl-3-methylbenzamide (20) The reaction was performed according to the general procedure withN,N-diethylformamide using m-toluic acid as starting material. Afterwork-up, the crude material was absorbed on Celite, concentrated todryness and purified by chromatography on silica gel (50 g IsoluteSPE column, Flash Si II; heptane-EtOAc, 4:1 to 1:2) to give 20.Yield: 347 mg (91%); yellow oil.1H NMR (500 MHz, CDCl3): delta = 7.26-7.29 (m, 1 H), 7.19 (m, 2 H), 7.14-7.16 (m, 1 H), 3.54 (br s, 2 H), 3.26 (br s, 2 H), 2.37 (s, 3 H), 1.25 (br s,3 H), 1.11 (br s, 3 H).13C NMR (125 MHz, CDCl3): delta = 171.48, 138.23, 137.29, 129.78,128.23, 126.94, 123.16, 43.28, 39.16, 21.42, 14.26, 12.96. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
61% | With water; calcium chloride; at 100.0℃; for 72h;Autoclave; | H3NTB (0.043 g, 0.115 mmol), CaCl2 (0.034 g, 0.30 mmol), N,N-diethyl-formamide (6.2 g) and H2O (0.9 g) weremixed and the mixture was stirred for half an hour. The resulting homogeneous mixture was then transferred to a 25 mL Teflonlinedstainless steel autoclave and heated at 100 C for three days. Block colorless crystals were obtained upon cooling themixture to room temperature as described above. Yield: 61% based on H3BTB used. Analytically found for compound 2(C57H69Ca3N5O21), %: C 53.23, H 5.64, N 5.29. Calculated, %: C 53.47, H. 5.43, N 5.47. FT-IR (cm-1): 3279 (w), 2921 (m),2848 (m), 1621 (s), 1541 (m), 1428 (s), 1391 (s), 1359 (s), 1200 (w), 1023 (w), 899 (w), 801 (w), 772 (s), 716 (m). |