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Structure of 1873-88-7
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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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CAS No. : | 1873-88-7 |
Formula : | C7H22O2Si3 |
M.W : | 222.50 |
SMILES Code : | C[Si](C)(C)O[SiH](C)O[Si](C)(C)C |
MDL No. : | MFCD00048000 |
InChI Key : | SWGZAKPJNWCPRY-UHFFFAOYSA-N |
Pubchem ID : | 6327366 |
GHS Pictogram: |
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Signal Word: | Danger |
Hazard Statements: | H225-H315-H319-H335 |
Precautionary Statements: | P210-P302+P352-P305+P351+P338 |
Class: | 3 |
UN#: | 1993 |
Packing Group: | Ⅱ |
Num. heavy atoms | 12 |
Num. arom. heavy atoms | 0 |
Fraction Csp3 | 1.0 |
Num. rotatable bonds | 4 |
Num. H-bond acceptors | 2.0 |
Num. H-bond donors | 0.0 |
Molar Refractivity | 61.87 |
TPSA ? Topological Polar Surface Area: Calculated from |
18.46 Ų |
Log Po/w (iLOGP)? iLOGP: in-house physics-based method implemented from |
3.57 |
Log Po/w (XLOGP3)? XLOGP3: Atomistic and knowledge-based method calculated by |
3.45 |
Log Po/w (WLOGP)? WLOGP: Atomistic method implemented from |
2.54 |
Log Po/w (MLOGP)? MLOGP: Topological method implemented from |
0.96 |
Log Po/w (SILICOS-IT)? SILICOS-IT: Hybrid fragmental/topological method calculated by |
-2.54 |
Consensus Log Po/w? Consensus Log Po/w: Average of all five predictions |
1.6 |
Log S (ESOL):? ESOL: Topological method implemented from |
-3.13 |
Solubility | 0.165 mg/ml ; 0.000743 mol/l |
Class? Solubility class: Log S scale |
Soluble |
Log S (Ali)? Ali: Topological method implemented from |
-3.52 |
Solubility | 0.0674 mg/ml ; 0.000303 mol/l |
Class? Solubility class: Log S scale |
Soluble |
Log S (SILICOS-IT)? SILICOS-IT: Fragmental method calculated by |
-2.39 |
Solubility | 0.904 mg/ml ; 0.00406 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 |
Yes |
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 |
-5.21 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 |
0.0 |
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) |
4.28 |
* 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 |
---|---|---|
96% | With dihydrogen hexachloroplatinate; at 75 - 85℃; for 2h; | Into a 500 mL round bottom flask equipped with a temperature controller, heating mantel, and condenser 3-ethenyl-7-oxabicyclo[4.I.Ojheptane (57.8 grams, 0.47 mole) was added. The solution was stirred with a magnetic stirrer and heated to 75C. Chloroplatinic acid (20 ppm) was added followed by the slow addition of 1,1,1,3,5,5,5- heptmethyltrisiloxane (100 g, 0.45 mol) via an addition fbnnel. The exotherm was not allowed to go above 85C. After the addition the reaction was held at 75C for 2 hours.resulting product was distilled through a 6 inch Vigreux column under a 0.9 torr vacuum. The product, 3-[bis-(trimethylsiloxy)methylsi lanyl-ethyl}-7- oxabicyclo[4.l.0]heptane, evolved between 110 and 120 C. The pure product (151.1 grams, 96% yield) was a clear colorless fluid. |
96% | With dihydrogen hexachloroplatinate; at 75 - 85℃; | Into a 500 mL round bottom flask equipped with a temperature controller, heating mantel, and condenser 3- ethenyl-7-oxabicyclo [ 4.1.0 ] heptane (57.8 grams, 0.47 mole) was added. The solution was stirred with a magnetic stirrer and heated to 75C. Chloroplatinic acid (20 ppm) was added followed by the slow addition of 1,1,1,3,5,5,5- heptmethyltrisiloxane (100 g, 0.45 mole) via an addition funnel. The exotherm was not allowed to go above 85C. After the addition the reaction was held at 75C for 2 hours. The resulting product was distilled through a 6 inch Vigreux column under a 0.9 torr vacuum. The product, 3- [bis- ( trimethylsiloxy) methylsilanyl-ethyl ] -7- oxabicyclo [ 4.1.0 ] eptane, evolved between 110 and 120 C . The pure product (151.1 grams, 96% yield) was a clear colorless fluid . |
96% | With dihydrogen hexachloroplatinate; at 75 - 85℃; for 2h; | Temperature controller, 500 ml round bottom flask 3-ethenyl-7-oxabicyclo[4.1.0]heptane(57.8 g, 0.47 mole) with a heating mantle and condenser were added. The solution is stirred with a magnetic stirrer, it was heated to 75 . It is added chloroplatinic acid (20 ppm), 1,1,1,3,5,5,5-heptamethyltrisiloxane(100 grams, 0.45 moles) after the was added slowly by addition funnel. Exotherm was not exceed 85 C.. After the addition, the reaction was carried out for 2 hours at 75 C.. Resulting product was distilled through a Vigreux column 15.24 cm (6 inches) under a vacuum of 0.9 Torr. Is the product 3-[bis(trimethylsiloxy)methylsilanylethyl]-7-oxabicyclo[4.1.0]heptane was released between 110 ~ 120 . Pure product (151.1 g, 96% yield) was a clear, colorless liquid. |
94% | C13H28N2OPtSi2; In xylene; at 70℃; for 4h;Product distribution / selectivity; | Preparation of Preparation of silane compound by hydrosilylation of (CH 3 ) 3 Si-O-Si(CH 3 )(H)-OSi(CH 3 ) 3 and 3-vinyl-7-oxabicyclo[4.1.0]heptane (/) ) A catalyst described in Table 1 (15 ppm (6.4×10-7 mol) of platinum included in the catalyst) was dissolved in xylene and added to a 25 mL 2-necked round-bottom flask equipped with a nitrogen gas inlet tube and a cooling tube. After adding (CH3)3Si-O-Si(CH3)(H)-OSi(CH3)3 (5.38 g, 24.2 mmol) and dodecane (0.38 g, 2.2 mmol) as internal standard, the mixture was heated to 70 ºC while stirring. Then, 3-vinyl-7-oxabicyclo[4.1.0]heptane ( , 3.00 g, 24.2 mmol) was added thereto dropwisely at a rate of 1 mL/min using a syringe. Thereafter, the progress of reaction was monitored by gas chromatography.The hydrosilylation reaction of Preparation Example 7 was performed according to Scheme 10. Reaction condition and yield of the produced silane compound are given in Table 8.[Scheme 10]Used catalyst amount (ppm) Reaction condition Remaining 3-vinyl-7-oxabicyclo[4.1.0]heptane (%) Yield (%) Temp. (ºC) Time (hr) Comp. Ex. 1 15 70 4 - 92 Ex. 1 15 4 - 94 3-vinyl-7-oxabicyclo[4.1.0]heptane (/) ) A catalyst described in Table 1 (15 ppm (6.4×10-7 mol) of platinum included in the catalyst) was dissolved in xylene and added to a 25 mL 2-necked round-bottom flask equipped with a nitrogen gas inlet tube and a cooling tube. After adding (CH3)3Si-O-Si(CH3)(H)-OSi(CH3)3 (5.38 g, 24.2 mmol) and dodecane (0.38 g, 2.2 mmol) as internal standard, the mixture was heated to 70 ºC while stirring. Then, 3-vinyl-7-oxabicyclo[4.1.0]heptane ( , 3.00 g, 24.2 mmol) was added thereto dropwisely at a rate of 1 mL/min using a syringe. Thereafter, the progress of reaction was monitored by gas chromatography.The hydrosilylation reaction of Preparation Example 7 was performed according to Scheme 10. Reaction condition and yield of the produced silane compound are given in Table 8.[Scheme 10]Used catalyst amount (ppm) Reaction condition Remaining 3-vinyl-7-oxabicyclo[4.1.0]heptane (%) Yield (%) Temp. (ºC) Time (hr) Comp. Ex. 1 15 70 4 - 92 Ex. 1 15 4 - 94 |
C13H28N2OPtSi2; In dodecane; xylene; at 70℃; for 4h;Inert atmosphere;Product distribution / selectivity; | A catalyst described in Table 1 (15 ppm (6.4×10-7 mol) of platinum included in the catalyst) was dissolved in xylene and added to a 25 mL 2-necked round-bottom flask equipped with a nitrogen gas inlet tube and a cooling tube. After adding (CH3)3Si-O-Si(CH3)(H)-OSi(CH3)3 (5.38 g, 24.2 mmol) and dodecane (0.38 g, 2.2 mmol) as internal standard, the mixture was heated to 70 C. while stirring. Then, 3-vinyl-7-oxabicyclo[4.1.0]heptane 3.00 g, 24.2 mmol) was added thereto dropwisely at a rate of 1 mL/min using a syringe. Thereafter, the progress of reaction was monitored by gas chromatography.The hydrosilylation reaction of Preparation Example 7 was performed according to Scheme 10. Reaction condition and yield of the produced silane compound are given in Table 8. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
hexahydro-2H-oxepin-2-one; Karstedt platinum catalyst; at 70℃;Conversion of starting material; | 21.48 g (173 mmol) of VCMX and the organic compound (see table 1 below) are charged to a 100 ml reactor. [0095] The reaction mixture is heated to 70 C. with stirring. 5.5 mul (10 ppm) of a solution of Karstedt catalyst containing 10% of platinum are added to the reactor and 35 g (157.3 mmol) of heptamethyl-hydrotrisiloxane are subsequently run in dropwise onto the VCMX. [0096] At the end of the addition, the degree of conversion of the SiH units is measured. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
C19H35N2OPtSi2; In toluene; at 70℃; for 10h; | 21.48 g (173 mmol) of 4-vinylcyclohexene oxide (VCMX) are placed in a 100 ml reactor. The reaction mixture is heated to 70 C. with agitation. 20 mul (10 ppm) of a solution of the catalytic metal complex (XXI) at 2.68% for platinum in toluene are added to the reactor and 35 g (157.3 mmol) of heptamethylhydrotrisiloxane are then poured dropwise, over 3 hours, onto the VCMX. [0247] After reaction for 5 hours, the degree of transformation of the SiH units is 99.5%, and 0.5% of the epoxide functions have disappeared. After reaction for 7 hours, the degree of transformation of the SiH units is 99.8%, and 1% of the epoxide functions have disappeared. The viscosity of the reaction crude at 25 C. is measured: v=6 mPa/s. | |
Karstedt platinum catalyst; In toluene; at 70℃; for 10h; | 21.48 g (173 mmol) of 4-vinylcyclohexene oxide (VCMX) are placed in a 100 ml reactor. The reaction mixture is heated at 70 C. with agitation. 5.5 mul (10 ppm) of a solution of Karstedt catalyst at 10% for platinum are added to the reactor and 35 g (157.3 mmol) of heptamethylhydrosiloxane are then poured dropwise, over 3 hours, onto the VCMX. [0250] After reaction for 5 hours, the degree of transformation of the SiH units is 99%, but 12% of the epoxide functions have disappeared. After reaction for 7 hours, the degree of transformation of the SiH units is 99.3%, and 23% of the epoxide functions have disappeared. The viscosity of the reaction crude at 25 C. is measured: v=38 mPa/s. [0251] The viscosity value for the oil of example 3 is 6 times higher than that of example 2, which means that some of the epoxide functions present in the medium have polymerized during the hydrosilylation reaction in the presence of the Karstedt catalyst. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With platinum(0)-1,3-divinyl-1,1,3,3-tetramethyldisiloxane complex; In toluene; at 100℃; for 24h;Green chemistry; | General procedure: A silane and an appropriate alkyne were placed in a 25cm3 round bottom flask equipped with a stirrer and a glass stopper. The reagents were dissolved in toluene or THF and Karstedt?s catalyst was added. Subsequently, the reaction mixture was heated to 60C or 100C, depending on the reaction. Samples of the reaction mixture were collected in intervals, and the conversion of SiH was determined by 1H NMR and GC-MS. Then the reactions were repeated in determined reaction time, and the resulting mixtures were isolated by the evaporation of the solvent under vacuum. Products were characterized by 1H, 13C, 29Si NMR, GC-MS analysis. The platinum residue was removed by filtration of petroleum ether solution through silica gel. After evaporation of solvents, the products were dried for 6h under vacuum. Isolated products were characterized by 1H, 13C, 29Si NMR, GC-MS. For new compounds, elemental analysis was performed as well. |