Structure of 67191-35-9
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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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Search for reports by entering the product batch number.
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Search for reports by entering the product batch number.
Batch number can be found on the product's label following the word 'Batch'.
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CAS No. : | 67191-35-9 |
Formula : | C11H14O |
M.W : | 162.23 |
SMILES Code : | CC(C)OC1=CC=CC=C1C=C |
MDL No. : | MFCD20384496 |
InChI Key : | SXCKVSZTZAMSRS-UHFFFAOYSA-N |
Pubchem ID : | 5461811 |
GHS Pictogram: |
![]() |
Signal Word: | Warning |
Hazard Statements: | H315-H319-H335 |
Precautionary Statements: | P261-P305+P351+P338 |
Num. heavy atoms | 12 |
Num. arom. heavy atoms | 6 |
Fraction Csp3 | 0.27 |
Num. rotatable bonds | 3 |
Num. H-bond acceptors | 1.0 |
Num. H-bond donors | 0.0 |
Molar Refractivity | 52.64 |
TPSA ? Topological Polar Surface Area: Calculated from |
9.23 Ų |
Log Po/w (iLOGP)? iLOGP: in-house physics-based method implemented from |
2.73 |
Log Po/w (XLOGP3)? XLOGP3: Atomistic and knowledge-based method calculated by |
3.47 |
Log Po/w (WLOGP)? WLOGP: Atomistic method implemented from |
3.01 |
Log Po/w (MLOGP)? MLOGP: Topological method implemented from |
2.96 |
Log Po/w (SILICOS-IT)? SILICOS-IT: Hybrid fragmental/topological method calculated by |
3.15 |
Consensus Log Po/w? Consensus Log Po/w: Average of all five predictions |
3.06 |
Log S (ESOL):? ESOL: Topological method implemented from |
-3.2 |
Solubility | 0.101 mg/ml ; 0.000625 mol/l |
Class? Solubility class: Log S scale |
Soluble |
Log S (Ali)? Ali: Topological method implemented from |
-3.35 |
Solubility | 0.0732 mg/ml ; 0.000451 mol/l |
Class? Solubility class: Log S scale |
Soluble |
Log S (SILICOS-IT)? SILICOS-IT: Fragmental method calculated by |
-3.4 |
Solubility | 0.0652 mg/ml ; 0.000402 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) |
Yes |
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) |
Yes |
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 |
-4.83 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 |
2.0 |
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 |
0.0 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) |
1.65 |
* 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 |
---|---|---|
With copper(l) chloride; | EXAMPLE 1 Metathesis by Ethenolysis of Methyl Oleate Catalyzed by a Type 3 Complex (FIG. 1) in an Ionic Liquid; 1 ml of 3-butyl-1,2-dimethylimidazolium bis-triflylamide with formula [BMMI]+[N(CF3SO2)2]- pre-dried overnight at 80° C., 148 mg of methyl oleate (source: Fluka, with a purity higher than 98percent) and 15 mg of the complex with formula Cl2Ru(CH-o-O-iPrC6H4)PCy3 (synthesized by reacting the 1st generation Grubbs complex with formula Cl2Ru(CHC6H5)(PCy3)2 with 1-isopropoxy-2-vinylbenzene in the presence of CuCl), this corresponding to 5percent molar of catalyst with respect to methyl oleate, were introduced, in an inert atmosphere of argon, into an autoclave reactor provided with an agitation system and a pressure sensor. The autoclave was then placed under vacuum and pressurized to obtain a pressure of 10 bars (1 MPa) of ethylene (origin: Alphagas, quality N25). The temperature was kept constant at 20° C. The medium was stirred at ambient temperature for 2 hours, then the excess ethylene was slowly purged by returning to atmosphere pressure at a temperature not exceeding 20° C. and the autoclave was again placed under an atmosphere of argon. The products were separated from the ionic liquid by adding 2 to 3 ml of heptane distilled over CaH2 and degassed. An aliquot (100 mul) of the extracted solution was passed through a short silica column (2 cm) eluted with diethyl ether. It was analyzed by gas phase chromatography (ZB-1 column, 100percent dimethylpolysiloxane, 30 metres, helium vector gas 2 ml/min, temperature programming: 60° C. then 5° C./min to 220° C.) coupled to a mass spectrometer. The methyl oleate conversion was 95percent. It was calculated using decane as an internal reference. The reaction products were composed of 1-decene (fraction A) and methyl decenoate (fraction B). The presence of 1-decene isomers was not detected. Homo-metathesis products were present in trace amounts and could not be quantified. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
91% | With Amberlyst 15-A resin; In dichloromethane; at 40℃; for 1.25h;Inert atmosphere; | A flame-dried Schlenk reaction flask is charged with a stir bar and put under an Ar atmosphere. 923 mg [Dichloro-(3-phenyl-1H-inden-1-ylidene)-bis-(tricyclohexyl-phosphine)-ruthenium(II)] 2a (1.0 mmol; Umicore AG & Co KG, Hanau), 173 mg 2-isopropoxystyrene (1.05 mmol; 1.05 equiv.; Aldrich) and 1026 mg Amberlyst 15-A resin in dry form (4.0 mmol, 4 equiv.; Rohm and Haas Co., Philadelphia, USA) are loaded into the reaction flask and 25 mL dichloromethane (DCM) is added. The reaction is stirred at 40 C. for 75 minutes and the solution colored from red to brown. Subsequently, the reaction mixture is sent through a Pasteur pipette equipped with a cotton plug to remove the Amberlyst resin. Evaporation of all volatiles, suspending the residue in 20 mL n-hexane and subsequent filtration and drying of the precipitate in vacuo afforded 548 mg of the desired compound 3a (yield: 91%) |
74% | With copper chloride (I); In dichloromethane; at 40℃; for 2h;Schlenk technique; Inert atmosphere; | In an oven dried Schlenk under Ar, were placed Dichloro(3-phenyl-1 H-inden-1 -ylidene) bis(tricyclohexylphosphine)ruthenium(ll) (M1 , HG1 Chemical Formula: C28H45CI2OPRU purchased from Umicore) complex (2.0 g, 2.2 mmol, 1 Molecular Weight: 600,61 equiv) and CuCI (236.0 mg, 2.4 mmol, 1.1 equiv). A solution of 2- isopropoxystyrene (synthesized from salicylaldehyde by alkylation and Wittig olefination following a previously reported procedure)1 (390.0 mg, 2.4 mmol, 1.1 equiv) in DCM (6 ml.) was added, then DCM was added to obtain 50 ml. solution. The resulting mixture was stirred for 2 h at 40C. The reaction was monitored by TLC (Pentane:Acetone 9:1) until the complete disappearance of M1. DCM was evaporated under reduced pressure and the solid was taken in Acetone (HPLC grade) and filtered through celite pad until the undesired solid became whitish. Volatiles were removed under vacuum and the obtained solid was dissolved in CHCI3 and filtered off. The filtrate was evaporated and the solid was dissolved in warm Et20 and the catalyst was precipitated with Pentane (3 times). The mixture was filtered off and the brown solid was collected (955 mg, 74% yield). Analytical data were consistent with the previously reported data. |
73% | With copper chloride (I); In dichloromethane; at 40℃; for 2h;Inert atmosphere; Schlenk technique; | In an oven dried Schlenk under Ar, were placed Dichloro(3-phenyl-1H-inden-1-ylidene) bis(tricyclohexylphosphine)ruthenium(II) (M1, purchased from Umicore) complex (2.0 g, 2.17 mmol, 1 equiv) and CuCl (236.0 mg, 2.38 mmol, 1.1 equiv). A solution of 2-isopropoxystyrene (synthesized from salicylaldehyde by alkylation and Wittig olefination following a previously reported procedure)1 (390.0 mg, 2.40 mmol, 1.1 equiv) in DCM (6 mL) was added, then DCM was added to obtain 50 mL of solution. The resulting mixture was stirred for 2 h at 40C. The reaction was monitored by TLC (Pentane:Acetone 9:1) until the complete disappearance of M1. DCM was evaporated under reduced pressure and the solid was taken up in Acetone (HPLC grade) and filtered through a celite pad until the undesired solid became whitish. Volatiles were removed under vacuum and the solid obtained was dissolved in CHCl3 and filtered off. The filtrate was evaporated, the solid was dissolved in warm Et2O and the complex was precipitated with Pentane (3 times). The mixture was filtered off and the brown solid was collected (955 mg, 73% yield). |
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