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Type | HazMat fee for 500 gram (Estimated) |
Excepted Quantity | USD 0.00 |
Limited Quantity | USD 15-60 |
Inaccessible (Haz class 6.1), Domestic | USD 80+ |
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Structure of 5394-63-8
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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. : | 5394-63-8 |
Formula : | C7H10O3 |
M.W : | 142.15 |
SMILES Code : | O=C1OC(C)(C)OC(C)=C1 |
MDL No. : | MFCD00040468 |
InChI Key : | XFRBXZCBOYNMJP-UHFFFAOYSA-N |
Pubchem ID : | 79368 |
GHS Pictogram: |
![]() ![]() ![]() |
Signal Word: | Danger |
Hazard Statements: | H315-H319-H361-H373-H225 |
Precautionary Statements: | P501-P260-P202-P240-P210-P233-P201-P243-P241-P242-P264-P280-P370+P378-P308+P313-P337+P313-P305+P351+P338-P362+P364-P303+P361+P353-P332+P313-P403+P235-P405 |
Class: | 3 |
UN#: | 1993 |
Packing Group: | Ⅱ |
Num. heavy atoms | 10 |
Num. arom. heavy atoms | 0 |
Fraction Csp3 | 0.57 |
Num. rotatable bonds | 0 |
Num. H-bond acceptors | 3.0 |
Num. H-bond donors | 0.0 |
Molar Refractivity | 35.58 |
TPSA ? Topological Polar Surface Area: Calculated from |
35.53 Ų |
Log Po/w (iLOGP)? iLOGP: in-house physics-based method implemented from |
1.95 |
Log Po/w (XLOGP3)? XLOGP3: Atomistic and knowledge-based method calculated by |
1.19 |
Log Po/w (WLOGP)? WLOGP: Atomistic method implemented from |
1.2 |
Log Po/w (MLOGP)? MLOGP: Topological method implemented from |
0.65 |
Log Po/w (SILICOS-IT)? SILICOS-IT: Hybrid fragmental/topological method calculated by |
1.4 |
Consensus Log Po/w? Consensus Log Po/w: Average of all five predictions |
1.28 |
Log S (ESOL):? ESOL: Topological method implemented from |
-1.47 |
Solubility | 4.81 mg/ml ; 0.0338 mol/l |
Class? Solubility class: Log S scale |
Very soluble |
Log S (Ali)? Ali: Topological method implemented from |
-1.53 |
Solubility | 4.17 mg/ml ; 0.0294 mol/l |
Class? Solubility class: Log S scale |
Very soluble |
Log S (SILICOS-IT)? SILICOS-IT: Fragmental method calculated by |
-1.24 |
Solubility | 8.27 mg/ml ; 0.0582 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 |
-6.32 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 |
0.56 |
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) |
3.18 |
* 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 |
---|---|---|
Sodium hydroxide (1.06 g, 26. 5 mmol) was added to a solution of <strong>[24835-08-3]2-nitrobenzylamine hydrochloride</strong> (5.0 g, 26.5 mmol) in a mixed solvent comprising 20 ml of methanol and 2 ml of water, followed by stirring at room temperature for 30 minutes. Then, the reaction solution was concentrated under reduced pressure, toluene was added to the resulting residue, followed by azeotropic water separation under reduced pressure to distill the solvent off. To the resulting residue, 100 ml of m-xylene and 2,2,6-trimethyl-1,3-dioxin-4-one (3.77 g, 26.5 mmol) were added, followed by reflux under heating with stirring for 1 hour with azeotropic water separation with a dean-stark apparatus. After the reaction, ethyl acetate and water were added, and the organic layer was separated, dried with saturated aqueous sodium chloride and over anhydrous sodium sulfate and concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography (n-hexane/ethyl acetate=9/1 to 1/1) to obtain 2.27 g of the desired product. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
31% | In 5,5-dimethyl-1,3-cyclohexadiene; for 4h;Reflux; Inert atmosphere; | To a solution of Boc-amino acetone3 17 (4.21 g, 24.3 mmol) in xylenes (24 mL) was added 2,2,6-trimethyl-4H-1,3-dioxin-4-one 18 (7.1 mL, 48.6 mmol). The reaction was heated to reflux (130 C) for 4 h, was cooled to 23 C and concentrated under reduced pressure to afford crude beta-ketoamide. Purification by flash column chromatography (CH2Cl2:Et2O 90:10) provided mixed fractions of beta-ketoamide and alpha,beta-unsaturated lactam 19. alpha,beta-Unsaturated lactam 19 was isolated (1.37, 24%) as a yellow oil. The mixed fractions were re-subjected to flash column chromatography (CH2Cl2:Et2O 90:10) which provided alpha,beta-unsaturated lactam 19 (1.78 g, 31%) for a combined yield of 3.15 g (55%) of a yellow oil. To a solution of alpha,beta-unsaturated lactam 19 (1.40 g, 6.0 mmol) in toluene (120 mL) was added DIBAL-H in hexanes (12 mL, 1.0 M solution, 12 mmol) at -78 C. The reaction was stirred for 4 h, quenched with EtOAc (10 mL)and Rochelle?s salt (20 mL) at -78 C, and allowed to warm to 23 C while stirring vigorously overnight. The solution was diluted with CH2Cl2 (300 mL) and poured over Celite. The organic extracts were separated and washed with brine (60 mL), dried over Na2SO4, decanted, and concentrated under reduced pressure. Purification by flash column chromatography (hexanes:EtOAc 40:60) delivered allylic alcohol (408 mg, 28%) as an orange oil. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
31% | In para-xylene; at 150℃; for 4h;Inert atmosphere; | From Boc-aminoacetone 42: To a solution of Boc-aminoacetone 42(4.21 g, 24.3 mmol) in p-xylene (24 mL) was added dioxinone 43 (7.1mL, 48.6 mmol). The reaction was heated to reflux (150 C) for 4 h,cooled to 23 C, and concentrated under reduced pressure to afford the crude beta-keto amide. Purification by flash column chromatography (CH2Cl2-Et2O, 90:10) provided mixed fractions of beta-keto amideand unsaturated Boc-lactam 40. Unsaturated Boc-lactam 40was isolated (1.37 g, 24%) as a yellow oil. The mixed fractions were re-introduced to flash column chromatography (CH2Cl2-Et2O, 90:10), whichprovided an additional amount of lactam 40(1.78 g, 31%) as a yellow oil; combined total yield: 3.15 g (55%). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
99% | In 5,5-dimethyl-1,3-cyclohexadiene; at 150℃; for 0.166667h;Inert atmosphere; | To a round-bottomed flask was added 42 (10.6 g, 61.0 mmol), dioxinone 43 (8.9 mL, 61.0 mmol), and xylenes (61 mL), and heated to 150 C for 10 min. The reaction was allowed to cool and the mixture was concentrated under reduced pressure to give beta-keto amide 41 as a brown solid; yield: 15.54 g (60.4 mmol, 99%). |
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