Structure of 2136-75-6
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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. : | 2136-75-6 |
| Formula : | C20H17OP |
| M.W : | 304.32 |
| SMILES Code : | C1=CC=C(C=C1)P(=CC=O)(C2=CC=CC=C2)C3=CC=CC=C3 |
| MDL No. : | MFCD00006994 |
| InChI Key : | CQCAYWAIRTVXIY-UHFFFAOYSA-N |
| Pubchem ID : | 75051 |
| GHS Pictogram: |
|
| Signal Word: | Warning |
| Hazard Statements: | H315-H319-H335 |
| Precautionary Statements: | P302+P352-P305+P351+P338 |
| Num. heavy atoms | 22 |
| Num. arom. heavy atoms | 18 |
| Fraction Csp3 | 0.0 |
| Num. rotatable bonds | 4 |
| Num. H-bond acceptors | 1.0 |
| Num. H-bond donors | 0.0 |
| Molar Refractivity | 97.28 |
| TPSA ? Topological Polar Surface Area: Calculated from |
26.88 Ų |
| Log Po/w (iLOGP)? iLOGP: in-house physics-based method implemented from |
0.0 |
| Log Po/w (XLOGP3)? XLOGP3: Atomistic and knowledge-based method calculated by |
3.59 |
| Log Po/w (WLOGP)? WLOGP: Atomistic method implemented from |
2.98 |
| Log Po/w (MLOGP)? MLOGP: Topological method implemented from |
4.41 |
| Log Po/w (SILICOS-IT)? SILICOS-IT: Hybrid fragmental/topological method calculated by |
5.44 |
| Consensus Log Po/w? Consensus Log Po/w: Average of all five predictions |
3.28 |
| Log S (ESOL):? ESOL: Topological method implemented from |
-4.33 |
| Solubility | 0.0142 mg/ml ; 0.0000468 mol/l |
| Class? Solubility class: Log S scale |
Moderately soluble |
| Log S (Ali)? Ali: Topological method implemented from |
-3.84 |
| Solubility | 0.0439 mg/ml ; 0.000144 mol/l |
| Class? Solubility class: Log S scale |
Soluble |
| Log S (SILICOS-IT)? SILICOS-IT: Fragmental method calculated by |
-7.53 |
| Solubility | 0.00000909 mg/ml ; 0.0000000299 mol/l |
| Class? Solubility class: Log S scale |
Poorly 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 |
-5.61 cm/s |
| Lipinski? Lipinski (Pfizer) filter: implemented from |
1.0 |
| 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 |
2.0 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) |
4.09 |
* 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.

[ 2136-75-6 ]
[ 21204-67-1 ]
[ 13937-08-1 ]
[ 16583-06-5 ]
[ 2136-75-6 ]

| Yield | Reaction Conditions | Operation in experiment |
|---|---|---|
| In N,N-dimethyl-formamide; at 25℃; | General procedure: The reaction mixture of aldehyde (0.5mmol) and 2-(triphenylphosphoranylidene)acetaldehyde (0.51mmol) in DMF (0.5mL) was stirred for 1-4 days and detected with TLC. The reaction mixture was extracted with dichloromethane (10mL×3). The combined organic extracts were rinsed with brine (5mL×3) and dried over anhydrous magnesium sulfate, and the volatile components were evaporated under vacuum to give the crude product, which was subjected to the PTLC purification using hexanes/ethyl acetate (1/1, v/v) as eluent to give the respective product. All intermediates were directly used for the next step reaction after confirming with their 1H NMR data. The 1H NMR data for the sixteen known (E)-3-aryl-2-propenals (33, 34, 36, 37, 39-46, 48, 49, 56, 57) are in consistent with those reported in the literature. |
| Yield | Reaction Conditions | Operation in experiment |
|---|---|---|
| 46% | In N,N-dimethyl-formamide; at 25℃; | General procedure: The reaction mixture of aldehyde (0.5mmol) and 2-(triphenylphosphoranylidene)acetaldehyde (0.51mmol) in DMF (0.5mL) was stirred for 1-4days and detected with TLC. The reaction mixture was extracted with dichloromethane (10mL×3). The combined organic extracts were rinsed with brine (5mL×3) and dried over anhydrous magnesium sulfate, and the volatile components were evaporated under vacuum to give the crude product, which was subjected to the PTLC purification using hexanes/ethyl acetate (1/1, v/v) as eluent to give the respective product. All intermediates were directly used for the next step reaction after confirming with their 1H NMR data. The 1H NMR data for the sixteen known (E)-3-aryl-2-propenals (33, 34, 36, 37, 39-46, 48, 49, 56, 57) are in consistent with those reported in the literature. |
| Yield | Reaction Conditions | Operation in experiment |
|---|---|---|
| 60% | In toluene; for 17h;Reflux; | Into a 1L dry single-mouth flask, add <strong>[19955-99-8]3-vinylbenzaldehyde</strong> (13.2g, 0.10 mol), (formylmethylene)triphenylphosphine (33.5g, 0.11mmol) and toluene (200 ml). Reflux the reaction system for 17 hours then concentrated. The crude product is purified by column chromatography (eluant: petroleum ether/ethyl acetate of the volume ratio: 100/1 to 80/20) to obtain a yellow solid (9.6g, yield: 60%) |
| Yield | Reaction Conditions | Operation in experiment |
|---|---|---|
| In dichloromethane; | A suspension of 2-chlorobenzaldehyde (200 mg, 1.428 mmol) in dichloromethane was degassed with ISh for 15 minutes at room temperature, following which 2-(triphenyl- 5- phosphanylidene)acetaldehyde (433 mg, 1.428 mmol) was added and the resulting reaction mixture stirred overnight. The crude reaction mixture was concentrated in vacuo and passed through a silica plug using 2% ethyl acetate in hexane as an eluent. |
| Yield | Reaction Conditions | Operation in experiment |
|---|---|---|
| In acetonitrile; at 20℃; for 24h; | 5-Methyl-1,3,4-thiadiazole-2-carbaldehyde (700 g) was dissolved in ACN (10 ml) and (formylmethylene)triphenylphosphorane (1.8 g) was added with stirring. After stirring for 24 h at RT the solution was concentrated in vacuo. The residue was purified by flash chromatography on silica gel (25 g; 0 % to 100 % EA in heptane in 8 min). The compound containing fractions were combined and the solvent was removed in vacuo to yield 293 mg of the title compound containing some residual triphenylphosphine oxide (13 %). LC/MS: m/z = 155.1 [M+H]+; tR: 0.52 min (LC/MS-method D). 1H N MR (600 MHz, DMSO-d6) δ ppm 9.77 (1 H), 8.05 (1 H), 6.92 (1 H), 2.80 (3 H). | |
| In acetonitrile; at 20℃; for 24h; | 5-Methyl-1,3,4-thiadiazole-2-carbaldehyde (700 g) was dissolved in ACN (10 ml) and (formylmethylene)triphenylphosphorane (1.8 g) was added with stirring. After stirring for 24 h at RT the solution was concentrated in vacuo. The residue was purified by flash chromatography on silica gel (25 g; 0 % to 100 % EA in heptane in 8 min). The compound containing fractions were combined and the solvent was removed in vacuo to yield 293 mg of the title compound containing some residual triphenylphosphine oxide (13 %). LC/MS: m/z = 155.1 [M+H]+; tR: 0.52 min (LC/MS-method D). 1H N MR (600 MHz, DMSO-d6) δ ppm 9.77 (1 H), 8.05 (1 H), 6.92 (1 H), 2.80 (3 H). |